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Acetaminophen
Also known as: Paracetamol, 4-acetamidophenol, 103-90-2, Tylenol, N-(4-hydroxyphenyl)acetamide, Apap
Molecular Formula
C8H9NO2
Molecular Weight
151.16  g/mol
InChI Key
RZVAJINKPMORJF-UHFFFAOYSA-N
FDA UNII
362O9ITL9D

Analgesic antipyretic derivative of acetanilide. It has weak anti-inflammatory properties and is used as a common analgesic, but may cause liver, blood cell, and kidney damage.
1 2D Structure

Acetaminophen

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
N-(4-hydroxyphenyl)acetamide
2.1.2 InChI
InChI=1S/C8H9NO2/c1-6(10)9-7-2-4-8(11)5-3-7/h2-5,11H,1H3,(H,9,10)
2.1.3 InChI Key
RZVAJINKPMORJF-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC(=O)NC1=CC=C(C=C1)O
2.2 Other Identifiers
2.2.1 UNII
362O9ITL9D
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Acamol

2. Acephen

3. Acetaco

4. Acetamidophenol

5. Acetominophen

6. Algotropyl

7. Anacin 3

8. Anacin-3

9. Anacin3

10. Apap

11. Datril

12. Hydroxyacetanilide

13. N-(4-hydroxyphenyl)acetanilide

14. N-acetyl-p-aminophenol

15. P-acetamidophenol

16. P-hydroxyacetanilide

17. Panadol

18. Paracetamol

19. Tylenol

2.3.2 Depositor-Supplied Synonyms

1. Paracetamol

2. 4-acetamidophenol

3. 103-90-2

4. Tylenol

5. N-(4-hydroxyphenyl)acetamide

6. Apap

7. Panadol

8. N-acetyl-p-aminophenol

9. 4'-hydroxyacetanilide

10. Acetaminofen

11. Datril

12. P-hydroxyacetanilide

13. P-acetamidophenol

14. Algotropyl

15. Lonarid

16. Naprinol

17. Doliprane

18. Injectapap

19. Acamol

20. Acenol

21. Anelix

22. Multin

23. P-acetaminophenol

24. Abensanil

25. Acetagesic

26. Acetalgin

27. Biocetamol

28. Clixodyne

29. Gelocatil

30. Liquagesic

31. Pyrinazine

32. Servigesic

33. Acephen

34. Alvedon

35. Anaflon

36. Apamide

37. Dymadon

38. Febridol

39. Febrilix

40. Febrolin

41. Finimal

42. Homoolan

43. Lestemp

44. Paracet

45. Tabalgin

46. Tralgon

47. Tussapap

48. Valadol

49. Valgesic

50. Vermidon

51. Alpiny

52. Amadil

53. Anhiba

54. Calpol

55. Dirox

56. Eneril

57. Fendon

58. Hedex

59. Lyteca

60. Neopap

61. Pacemo

62. Panets

63. Parmol

64. Tapar

65. Tempra

66. Acetamide, N-(4-hydroxyphenyl)-

67. Paracetamolo

68. Dafalgan

69. Dolprone

70. Momentum

71. Ortensan

72. Paldesic

73. Banesin

74. Captin

75. Disprol

76. Enelfa

77. Salzone

78. Exdol

79. P-acetylaminophenol

80. Febro-gesic

81. Nebs

82. Paracetamolum

83. Dolgesic

84. Elixodyne

85. Febrectal

86. Phenaphen

87. Tempanal

88. Abenol

89. Apacet

90. Apadon

91. Cetadol

92. Fensum

93. Janupap

94. Minoset

95. Napafen

96. Neodol

97. Nobedon

98. Pacemol

99. Panodil

100. Parapan

101. Pedric

102. Phendon

103. Rounox

104. Suppap

105. Korum

106. Pinex

107. Temlo

108. 4-(acetylamino)phenol

109. Ben-u-ron

110. Dial-a-gesic

111. Anacin-3

112. Calmanticold

113. Codoliprane

114. Demogripal

115. Dolegrippin

116. Doloreduct

117. Dristancito

118. Duracetamol

119. Eu-med

120. Grippostad

121. Gynospasmine

122. Medocodene

123. Paedialgon

124. Paracetanol

125. Parakapton

126. Pediapirin

127. Phenipirin

128. Phogoglandin

129. Predualito

130. Sanicopyrine

131. Scentalgyl

132. Sunetheton

133. Tachiprina

134. Termalgine

135. Treuphadol

136. Abrolet

137. Acertol

138. Acetamol

139. Acetofen

140. Afebrin

141. Afebryl

142. Aferadol

143. Algesidal

144. Algomol

145. Alpinyl

146. Analter

147. Antidol

148. Apitrelal

149. Atralidon

150. Babikan

151. Bacetamol

152. Cadafen

153. Calapol

154. Causalon

155. Cefalex

156. Codabrol

157. Codalgin

158. Codapane

159. Codicet

160. Codisal

161. Cofamol

162. Cosutone

163. Cuponol

164. Curadon

165. Custodial

166. Darocet

167. Daygrip

168. Deminofen

169. Democyl

170. Desfebre

171. Dimindol

172. Dolefin

173. Dolofugin

174. Dolorfug

175. Dolorstop

176. Dolotec

177. Dorocoff

178. Dularin

179. Durapan

180. Ecosetol

181. Excipain

182. Fanalgic

183. Farmadol

184. Febranine

185. Febrectol

186. Febricet

187. Febrinol

188. Fepanil

189. Finiweh

190. Fluparmol

191. Geluprane

192. Ildamol

193. Inalgex

194. Infadrops

195. Kataprin

196. Labamol

197. Lekadol

198. Lemgrip

199. Lupocet

200. Magnidol

201. Malidens

202. Maxadol

203. Mexalen

204. Minafen

205. Miralgin

206. Nealgyl

207. Neodolito

208. Neotrend

209. Neuridon

210. Nodolex

211. Ofirmev

212. Oralgan

213. Oxycocet

214. Pacimol

215. Panacete

216. Panadeine

217. Panadiene

218. Panaleve

219. Panamax

220. Panasorbe

221. Panofen

222. Pantalgin

223. Paracemol

224. Paracenol

225. Paracetol

226. Paracin

227. Paracod

228. Paracodol

229. Parador

230. Paradrops

231. Paralen

232. Paralief

233. Paralink

234. Paralyoc

235. Paramol

236. Paramolan

237. Paranox

238. Parasedol

239. Parasin

240. Paraspen

241. Parcetol

242. Parogal

243. Pediatrix

244. Perfalgan

245. Piramin

246. Pirinasol

247. Polmofen

248. Predimol

249. Prontina

250. Puernol

251. Pulmofen

252. Pyrigesic

253. Pyromed

254. Remedol

255. Rivalgyl

256. Rubophen

257. Rupemol

258. Sanicet

259. Schmerzex

260. Sedalito

261. Semolacin

262. Seskamol

263. Setakop

264. Setamol

265. Sifenol

266. Sinaspril

267. Sinedol

268. Stanback

269. Stopain

270. Supofen

271. Tazamol

272. Termacet

273. Termalgin

274. Termofren

275. Titralgan

276. Tricoton

277. Upsanol

278. Utragin

279. Veralgina

280. Viruflu

281. Vivimed

282. Zatinol

283. Abrol

284. Algina

285. Anapap

286. Andox

287. Asetam

288. Asomal

289. Aspac

290. Asplin

291. Benmyo

292. Curpol

293. Dhamol

294. Dolcor

295. Dolko

296. Dresan

297. Dypap

298. Febrex

299. Febrin

300. Lemsip

301. Malgis

302. Oltyl

303. Paceco

304. Pacet

305. Paedol

306. Painex

307. Pamol

308. Panex

309. Parake

310. Paroma

311. Plicet

312. Prodol

313. Reliv

314. Scanol

315. Setol

316. Sinmol

317. Tiffy

318. Tylex

319. Tylol

320. Tymol

321. Verpol

322. Volpan

323. Zolben

324. Neocitran

325. Nilnocen

326. Nina

327. Rubiemol

328. Vips

329. Supadol Mono

330. Treupel Mon

331. Bickie-mol

332. Fortalidon P

333. Gattaphen T

334. Gripin Bebe

335. Influbene N

336. Lonarid Mono

337. Lyteca Syrup

338. Panadeine Co

339. Dymadon Co

340. Toximer P

341. Treupel N

342. Accu-tap

343. 4-acetaminophenol

344. Helon N

345. Malex N

346. Spalt N

347. Tylex Cd

348. N-acetyl-4-aminophenol

349. Sk-apap

350. Paracetamole

351. Conacetol

352. Darvocet

353. Empracet

354. Panasorb

355. A-per

356. Apamid

357. Parelan

358. Prompt

359. Vicodin

360. Fevor

361. Freka-cetamol

362. Codisal Forte

363. Croix Blanche

364. Dolorol Forte

365. Dymadon Forte

366. Junior Disprol

367. Kinder Finimal

368. Liquigesic Co

369. Mono Praecimed

370. Percocet-demi

371. Perdolan Mono

372. Rockamol Plus

373. Viclor Richet

374. Actifed Plus

375. Kratofin Simplex

376. Neo-fepramol

377. Paracetamol Al

378. Paracetamol Bc

379. Paracetamol Pb

380. Acetanilide, 4'-hydroxy-

381. Claradol Codeine

382. Geralgine-p

383. Melabon Infantil

384. Migraleve Yellow

385. Paracetamol Saar

386. Pyregesic-c

387. Anti-algos

388. Para-suppo

389. Pasolind N

390. Supramol-m

391. No-febril

392. Panado-co

393. Para-tabs

394. Paracetamol Hexal

395. Paracetamol Raffo

396. Paracetamol Rosch

397. Paracetamol Stada

398. Dol-stop

399. Anadin Dla Dzieci

400. P-hydroxyphenolacetamide

401. Percocet-5

402. Cod-acamol Forte

403. Contra-schmerz P

404. Hy-phen

405. Medinol Paediatric

406. Paracetamol Basics

407. Panado-co Caplets

408. Paracetamol Von Ct

409. Pe-tam

410. Paracetamol Fecofar

411. Paracetamol Harkley

412. Paracetamol Heumann

413. Paracetamol Nycomed

414. Codral Pain Relief

415. Paracetamol Hanseler

416. Paracetamol Winthrop

417. 4-hydroxyacetanilide

418. Phenaphen W/codeine

419. Spalt Fur Die Nacht

420. A.f. Anacin

421. Capital With Codeine

422. Paracetamol Genericon

423. Anexsia

424. Demilets

425. Efferalgan

426. Endecon

427. Intensin

428. Naldegesic

429. Propacet

430. Resfenol

431. Theraflu

432. Wygesic

433. Paracetamol Ratiopharm

434. Coricidin Sinus

435. Paracetamol Italfarmaco

436. Sudafed Sinus

437. Coricidin D

438. Paracetamol Dc

439. Quiet World

440. Paracetamol Antipanin P

441. St Joseph Aspirin-free

442. New Cortal For Children

443. Infants' Feverall

444. St. Joseph Fever Reducer

445. Midol Teen Formula

446. Paracetamol Dr. Schmidgall

447. Acetamide, N-(p-hydroxyphenyl)-

448. P-hydroxy-acetanilid

449. Aspirin-free Anacin

450. Children's Tylenol Chewable

451. Nci-c55801

452. Pcm Paracetamol Lichtenstein

453. Tylenol Allergy Sinus

454. P-(acetylamino)phenol

455. Rhinex D-lay Tablets

456. Acetaminophene

457. Midol Regular Strength

458. Paracetamol Smithkline Beecham

459. Scherzatabletten Rezeptur 534

460. Percogesic With Codeine

461. 4-hydroxyanilid Kyseliny Octove

462. Bayer Select Head Cold

463. Bayer Select Allergy-sinus

464. Bayer Select Headache Pain

465. Dristan Cold No Drowsiness

466. Prestwick_13

467. St Joseph Aspirin-free For Children

468. 4-acetylaminophenol

469. Children's Acetaminophen Elixir Drops

470. Mfcd00002328

471. Children's Acetaminophen Oral Solution

472. Midol Pm Night Time Formula

473. Triaminic Sore Throat Formula

474. N-(4-hydroxyphenyl)ethanamide

475. Bayer Select Sinus Pain Relief

476. Phenol, P-acetamido-

477. Sine-off Sinus Medicine Caplets

478. Chebi:46195

479. Roxicet 5/500

480. Tocris-1706

481. Nsc-3991

482. N-acetyl-para-aminophenol

483. 4-(n-acetylamino)phenol

484. Acetaminophen (4-hydroxyacetanilide)

485. Bayer Select Menstrual Multi-symptom

486. Acetaco

487. N-acetyl-4-hydroxyaniline

488. St. Joseph Cold Tablets For Children

489. Chembl112

490. Nsc-109028

491. N-(4-hydroxyphenyl)acetamide (tylenol)

492. N-(4-hydroxyphenyl)-acetamide

493. 362o9itl9d

494. Aminofen

495. Dtxsid2020006

496. Atasol

497. Duaneo

498. Duorol

499. Component Of Dialog

500. Component Of Dilone

501. Fever All

502. Paracetamol (inn)

503. Component Of Endecon

504. Component Of Percocet

505. Component Of Phenaphen

506. Tyl

507. Component Of Percogesic

508. Dsstox_cid_6

509. Ncgc00016361-07

510. Acetominophen

511. Actamin

512. Cas-103-90-2

513. Pasolind

514. Redutemp

515. Robigesic

516. Valorin

517. Aceta Elixir

518. Paracetamol [inn]

519. Dafalgan Codeine

520. Jin Gang

521. Wln: Qr Dmv1

522. Dsstox_rid_75318

523. Dsstox_gsid_20006

524. Component Of Hycomine Compound

525. Acetavance

526. Paracetamolo [italian]

527. Calonal

528. Flexsure

529. Acenol (pharmaceutical)

530. N-(4-hydroxyphenyl)acetanilide

531. Drixoral Sinus

532. Aceta Tablets

533. Paracetamol [inn:ban]

534. Valorin Extra

535. Ccris 3

536. Snaplets-fr

537. Oraphen-pd

538. Phenaphen Caplets

539. Paracetamolum [inn-latin]

540. Tylenol (caplet)

541. Tylenol (geltab)

542. Tylenol 8-hour

543. Smr000112065

544. Tavist Allergy/sinus/headache

545. Dapa X-s

546. Drixoral Cold & Flu

547. Hsdb 3001

548. Sr-01000597517

549. Einecs 203-157-5

550. 222 Af

551. Acetaminophen [usp:jan]

552. Paracetamol (acetaminophen)

553. Nsc 109028

554. Acetominophene

555. Unii-362o9itl9d

556. 4-hydroxyanilid Kyseliny Octove [czech]

557. Children's Acetaminophen Elixir Solution

558. Claratal

559. Daphalgan

560. Resprin

561. Apacet Capsules

562. Atasol Caplets

563. Atasol Tablets

564. Tempra Caplets

565. Tylenol Caplets

566. Tylenol Elixir

567. Tylenol Gelcaps

568. Tylenol Tablets

569. Actamin Extra

570. Actamin Super

571. Aminofen Max

572. Anexsia 10/660

573. Apacet Elixir

574. Atasol Drops

575. Exdol Strong

576. P-acetoaminophen

577. Tempra Drops

578. Tempra Syrup

579. Tylenol Drops

580. Alpha-per

581. Citramon P

582. Excedrin Caplets

583. Dial-alpha-gesic

584. Apo-acetaminophen

585. 4-acetominophenol

586. Genebs X-tra

587. Paracetamol;tylenol

588. 4-acetamido Phenol

589. 4-acetamido-phenol

590. Tempra D.s

591. Apap, Paracetamol

592. P-hydroxyacetoanilide

593. Tylenol (tn)

594. Supac (salt/mix)

595. Tylox (salt/mix)

596. Zydone (salt/mix)

597. Atasol Forte Caplets

598. Atasol Forte Tablets

599. Atasol Oral Solution

600. Para-acetylaminophenol

601. Anexsia (salt/mix)

602. Endecon (salt/mix)

603. Sinubid (salt/mix)

604. Talacen (salt/mix)

605. Vicodin (salt/mix)

606. Wygesic (salt/mix)

607. Acetaminophen Uniserts

608. Datril Extra-strength

609. Tylenol Infants Drops

610. Demilets (salt/mix)

611. Empracet (salt/mix)

612. Intensin (salt/mix)

613. Propacet (salt/mix)

614. Suppap-120

615. Suppap-325

616. Suppap-650

617. Panadol Extra Strength

618. Theraflu (salt/mix)

619. Coricidin (salt/mix)

620. Liquiprin (salt/mix)

621. Hy-phen (salt/mix)

622. Iv-apap

623. Phenol Derivative, 11

624. Spectrum_000016

625. Tempra Chewable Tablets

626. Naldegesic (salt/mix)

627. Actimol Chewable Tablets

628. Feverall Junior Strength

629. Darvocet-n (salt/mix)

630. Anacin-3 Extra Strength

631. Liquiprin Infants" Drops

632. N-acetyl Para Aminophenol

633. Prestwick0_000868

634. Prestwick1_000868

635. Prestwick2_000868

636. Prestwick3_000868

637. Spectrum2_000085

638. Spectrum3_000283

639. Spectrum4_000140

640. Spectrum5_000736

641. Coricidin D (salt/mix)

642. Quiet World (salt/mix)

643. Genapap Children's Elixir

644. Tylenol Children's Elixir

645. 4-acetamidophenol, 98%

646. Actifed Plus (salt/mix)

647. Acetaminophen [mi]

648. Paracetamol [iarc]

649. Epitope Id:117710

650. Genapap Children's Tablets

651. Sudafed Sinus (salt/mix)

652. Acetaminophen [jan]

653. Ec 203-157-5

654. Actimol Infants' Suspension

655. Drixoral Sinus (salt/mix)

656. Liquiprin Children's Elixir

657. Schembl3480

658. Acetaminophen (jp17/usp)

659. Acetaminophen [hsdb]

660. Acetaminophen [inci]

661. Coricidin Sinus (salt/mix)

662. N-(4-hydroxyfenyl)ethanamid

663. Paracetamol [mart.]

664. Acetaminophen [vandf]

665. Bspbio_000915

666. Bspbio_001786

667. Dds-06a

668. Kbiogr_000560

669. Kbioss_000356

670. Paracetamol [who-dd]

671. Paracetamol [who-ip]

672. 4-13-00-01091 (beilstein Handbook Reference)

673. Actimol Children's Suspension

674. Apacet Extra Strength Caplets

675. Apacet Extra Strength Tablets

676. Aspirin-free Excedrin Caplets

677. Genebs Extra Strength Caplets

678. Mls001146925

679. Mls001331684

680. Mls002154041

681. Bidd:gt0005

682. Divk1c_000660

683. Spectrum1500101

684. Genapap Extra Strength Caplets

685. Genapap Extra Strength Tablets

686. Spbio_000010

687. Spbio_002836

688. Tapanol Extra Strength Caplets

689. Tapanol Extra Strength Tablets

690. Tylenol Extra Strength Caplets

691. Tylenol Extra Strength Gelcaps

692. Tylenol Extra Strength Tablets

693. Acetaminophen [usp-rs]

694. Actimol Junior Strength Caplets

695. Apacet Regular Strength Tablets

696. Bpbio1_001007

697. Excedrin Extra Strength Caplets

698. Genebs Regular Strength Tablets

699. Gtpl5239

700. Panadol Junior Strength Caplets

701. Sgcut00014

702. Tylenol Junior Strength Caplets

703. Midol Teen Formula (salt/mix)

704. Genapap Regular Strength Tablets

705. Panadol Maximum Strength Caplets

706. Panadol Maximum Strength Tablets

707. Schembl19474893

708. Tylenol Regular Strength Caplets

709. Tylenol Regular Strength Tablets

710. Aspirin-free Anacin (salt/mix)

711. Bdbm26197

712. Hms502a22

713. Kbio1_000660

714. Kbio2_000356

715. Kbio2_002924

716. Kbio2_005492

717. Kbio3_001286

718. Nsc3991

719. Tylenol Arthritis Extended Relief

720. Acetaminophen, Analytical Standard

721. Ninds_000660

722. Tylenol Infants" Suspension Drops

723. Bcpp000441

724. Drixoral Cold & Flu (salt/mix)

725. Hms1570n17

726. Hms1920a03

727. Hms2091g03

728. Hms2097n17

729. Hms2269g20

730. Hms3268a10

731. Hms3412d16

732. Hms3676d16

733. Hms3714n17

734. Paracetamol [ep Monograph]

735. Pharmakon1600-01500101

736. Tylenol Allergy Sinus (salt/mix)

737. Acetaminophen [orange Book]

738. Midol Regular Strength (salt/mix)

739. Act06727

740. Allay Component Acetaminophen

741. Amy39958

742. Bcp23431

743. Bucet Component Acetaminophen

744. Esgic Component Acetaminophen

745. Norco Component Acetaminophen

746. Nsc 3991

747. Str00901

748. To_000023

749. Triad Component Acetaminophen

750. Tylenol Children's Chewable Tablets

751. Tylox Component Acetaminophen

752. Acetaminophen [usp Impurity]

753. Acetaminophen, Bioxtra, >=99.0%

754. Bayer Select Head Cold (salt/mix)

755. Robitussin Night Relief (salt/mix)

756. Tox21_110397

757. Tox21_201930

758. Tox21_300100

759. Ac8790

760. Acetaminophen [usp Monograph]

761. Bancap Component Acetaminophen

762. Bbl005229

763. Ccg-38901

764. Codrix Component Acetaminophen

765. Femcet Component Acetaminophen

766. Lortab Component Acetaminophen

767. Norcet Component Acetaminophen

768. Nsc109028

769. Nsc755853

770. Oxycet Component Acetaminophen

771. Paracetamolum [who-ip Latin]

772. Stl140694

773. Tencon Component Acetaminophen

774. Trezix Component Acetaminophen

775. Tylenol Children's Suspension Liquid

776. Zinc13550868

777. Zydone Component Acetaminophen

778. Anexsia Component Acetaminophen

779. Anoquan Component Acetaminophen

780. Butapap Component Acetaminophen

781. Roxicet Component Acetaminophen

782. Roxilox Component Acetaminophen

783. Sedapap Component Acetaminophen

784. Talacen Component Acetaminophen

785. Tycolet Component Acetaminophen

786. Vicodin Component Acetaminophen

787. Wygesic Component Acetaminophen

788. Akos000121004

789. Darvocet Component Acetaminophen

790. Excedrin Component Acetaminophen

791. Feverall Sprinkle Caps Junior Strength

792. Fioricet Component Acetaminophen

793. Hy-phen Component Acetaminophen

794. Ornex Severe Cold Formula (salt/mix)

795. Percocet Component Acetaminophen

796. Tox21_110397_1

797. Triaprin Component Acetaminophen

798. Ultracet Component Acetaminophen

799. Xartemis Component Acetaminophen

800. Acetaminophen Component Of Allay

801. Acetaminophen Component Of Bucet

802. Acetaminophen Component Of Esgic

803. Acetaminophen Component Of Norco

804. Acetaminophen Component Of Triad

805. Acetaminophen Component Of Tylox

806. Bayer Select Allergy-sinus (salt/mix)

807. Bcp9000225

808. Co-gesic Component Acetaminophen

809. Db00316

810. Dhc Plus Component Acetaminophen

811. Nsc-755853

812. Paracetamol 100 Microg/ml In Methanol

813. Acetaminophen Component Of Bancap

814. Acetaminophen Component Of Codrix

815. Acetaminophen Component Of Femcet

816. Acetaminophen Component Of Lortab

817. Acetaminophen Component Of Norcet

818. Acetaminophen Component Of Oxycet

819. Acetaminophen Component Of Tencon

820. Acetaminophen Component Of Zydone

821. Bancap Hc Component Acetaminophen

822. Idi1_000660

823. Lorcet-hd Component Acetaminophen

824. Phrenilin Component Acetaminophen

825. Sine-aid, Maximum Strength (salt/mix)

826. Sudafed Severe Cold Formula (salt/mix)

827. Acetaminophen Component Of Anexsia

828. Acetaminophen Component Of Anoquan

829. Acetaminophen Component Of Butapap

830. Acetaminophen Component Of Roxicet

831. Acetaminophen Component Of Roxilox

832. Acetaminophen Component Of Sedapap

833. Acetaminophen Component Of Talacen

834. Acetaminophen Component Of Tycolet

835. Acetaminophen Component Of Vicodin

836. Acetaminophen Component Of Wygesic

837. Ncgc00016361-01

838. Ncgc00016361-02

839. Ncgc00016361-03

840. Ncgc00016361-04

841. Ncgc00016361-05

842. Ncgc00016361-06

843. Ncgc00016361-08

844. Ncgc00016361-09

845. Ncgc00016361-10

846. Ncgc00016361-12

847. Ncgc00016361-13

848. Ncgc00016361-20

849. Ncgc00025267-01

850. Ncgc00025267-02

851. Ncgc00025267-03

852. Ncgc00025267-04

853. Ncgc00025267-05

854. Ncgc00253912-01

855. Ncgc00259479-01

856. Tylenol Junior Strength Chewable Tablets

857. Ac-23969

858. Acetaminophen Component Of Darvocet

859. Acetaminophen Component Of Excedrin

860. Acetaminophen Component Of Fioricet

861. Acetaminophen Component Of Hy-phen

862. Acetaminophen Component Of Percocet

863. Acetaminophen Component Of Triaprin

864. Acetaminophen Component Of Ultracet

865. Acetaminophen Component Of Xartemis

866. Hy-66005

867. Midol Pm Night Time Formula (salt/mix)

868. Sy001162

869. Triaminic Sore Throat Formula (salt/mix)

870. Acetaminophen Component Of Co-gesic

871. Acetaminophen Component Of Dhc Plus

872. Acetaminophen Component Of Phrenilin

873. Bcp0726000305

874. Duradyne Dhc Component Acetaminophen

875. Sbi-0051269.p003

876. Acetaminophen Component Of Bancap Hc

877. Acetaminophen Component Of Lorcet-hd

878. Bayer Select Sinus Pain Relief (salt/mix)

879. Drixoral Plus Component Acetaminophen

880. Ab00051905

881. Aspirin Free Anacin Maximum Strength Caplets

882. Aspirin Free Anacin Maximum Strength Tablets

883. Dolene Ap-65 Component Acetaminophen

884. Ft-0658035

885. Ft-0661041

886. Ft-0661042

887. H0190

888. Medigesic Plus Component Acetaminophen

889. Sine-off Sinus Medicine Caplets (salt/mix)

890. Synalgos-dc-a Component Acetaminophen

891. Acetaminophen Component Of Duradyne Dhc

892. N-(4-hydroxyphenyl)-acetamide-[13c2,15n]

893. Acetaminophen Component Of Dolene Ap-65

894. Acetaminophen Component Of Drixoral Plus

895. Acetaminophen Component Of Synalgos-dc-a

896. C06804

897. D00217

898. Q57055

899. Ab00051905-09

900. Ab00051905_10

901. Acetaminophen Component Of Medigesic Plus

902. Aspirin Free Anacin Maximum Strength Gel Caplets

903. Bayer Select Menstrual Multi-symptom (salt/mix)

904. Contac Cough & Sore Throat Formula (salt/mix)

905. L024125

906. St. Joseph Cold Tablets For Children (salt/mix)

907. Tylenol Extra Strength Adult Liquid Pain Reliever

908. J-001064

909. J-514275

910. Paracetamol (acetaminophen) 1.0 Mg/ml In Methanol

911. Sr-01000597517-1

912. Sr-01000597517-2

913. Sr-01000597517-4

914. Acetaminophenol 4-acetamino Phenol Paracetamol Somedon

915. Brd-k41524689-001-08-6

916. F3096-1731

917. F48b493f-b1fd-410c-aa0a-f40ec71a0689

918. Bayer Select Maximum Strength Headache Pain Relief Formula

919. Paracetamol, British Pharmacopoeia (bp) Reference Standard

920. Paracetamol, European Pharmacopoeia (ep) Reference Standard

921. Acetaminophen Solution, Drug Standard, 1.0 Mg/ml In Methanol

922. Acetaminophen, United States Pharmacopeia (usp) Reference Standard

923. Acetaminophen, Meets Usp Testing Specifications, 98.0-102.0%, Powder

924. Acetaminophen Solution, 1.0 Mg/ml In Methanol, Ampule Of 1 Ml, Certified Reference Material

925. Acetaminophen, Pharmaceutical Secondary Standard; Certified Reference Material

926. Paracetamol For Equipment Qualification, Europepharmacopoeia (ep) Reference Standard

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 151.16 g/mol
Molecular Formula C8H9NO2
XLogP30.5
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count2
Rotatable Bond Count1
Exact Mass151.063328530 g/mol
Monoisotopic Mass151.063328530 g/mol
Topological Polar Surface Area49.3 Ų
Heavy Atom Count11
Formal Charge0
Complexity139
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 20  
Drug NameAcephen
PubMed HealthAcetaminophen
Drug ClassesAcetaminophen Combination, Analgesic, Antipyretic
Active IngredientAcetaminophen
Dosage FormSuppository
RouteRectal
Strength650mg; 120mg; 325mg
Market StatusOver the Counter
CompanyG And W Labs

2 of 20  
Drug NameAcetaminophen
PubMed HealthHydrocodone/Acetaminophen (By mouth)
Drug ClassesAnalgesic, Opioid/Acetaminophen Combination
Drug LabelAcetaminophen and codeine phosphate is supplied in tablet form for oral administration.Acetaminophen, 4'-hydroxyacetanilide, a slightly bitter, white, odorless, crystalline powder, is a non-opiate, non-salicylate analgesic and antipyretic. It has the
Active IngredientAcetaminophen
Dosage FormTablet, extended release; Suppository
RouteRectal; Oral
Strength650mg; 120mg; 325mg
Market StatusOver the Counter
CompanyOhm Labs; Perrigo; Perrigo New York; Ranbaxy Labs; Taro Pharms North

3 of 20  
Drug NameButapap
PubMed HealthAcetaminophen
Drug ClassesAcetaminophen Combination, Analgesic, Antipyretic
Active Ingredientbutalbital; Acetaminophen
Dosage FormTablet
RouteOral
Strength50mg; 325mg
Market StatusPrescription
CompanyMikart

4 of 20  
Drug NameInfants' feverall
PubMed HealthAcetaminophen and Codeine
Drug ClassesAnalgesic, Codeine, Opioid/Acetaminophen Combination
Active IngredientAcetaminophen
Dosage FormSuppository
RouteRectal
Strength80mg
Market StatusOver the Counter
CompanyTaro Pharms North

5 of 20  
Drug NameNeopap
Active IngredientAcetaminophen
Dosage FormSuppository
RouteRectal
Strength120mg
Market StatusOver the Counter
CompanyPolymedica

6 of 20  
Drug NameNorco
Drug LabelAcetaminophen is a non-salicylate antipyretic and non-opioid analgesic agent. Its chemical name is N-acetyl-p-aminophenol. Acetaminophen has a molecular weight of 151.16. Its structural formula is: OFIRMEV injection is a sterile, clear, colorless, no...
Active Ingredienthydrocodone bitartrate; Acetaminophen
Dosage FormTablet
RouteOral
Strength7.5mg; 5mg; 10mg; 325mg
Market StatusPrescription
CompanyActavis Labs Fl; Watson Labs

7 of 20  
Drug NameOfirmev
Active IngredientAcetaminophen
Dosage FormSolution
RouteIv (infusion)
Strength1000mg/100ml (10mg/ml)
Market StatusPrescription
CompanyCadence Pharms

8 of 20  
Drug NameOxycet
Active Ingredientoxycodone hydrochloride; Acetaminophen
Dosage FormTablet
RouteOral
Strength5mg; 325mg
Market StatusPrescription
CompanyMallinckrodt

9 of 20  
Drug NamePercocet
Active Ingredientoxycodone hydrochloride; Acetaminophen
Dosage FormTablet
RouteOral
Strength2.5mg; 7.5mg; 5mg; 10mg; 325mg
Market StatusPrescription
CompanyVintage Pharms

10 of 20  
Drug NameTylenol
Active IngredientAcetaminophen
Dosage FormTablet, extended release
RouteOral
Strength650mg
Market StatusOver the Counter
CompanyMcneil Cons

11 of 20  
Drug NameAcephen
PubMed HealthAcetaminophen
Drug ClassesAcetaminophen Combination, Analgesic, Antipyretic
Active IngredientAcetaminophen
Dosage FormSuppository
RouteRectal
Strength650mg; 120mg; 325mg
Market StatusOver the Counter
CompanyG And W Labs

12 of 20  
Drug NameAcetaminophen
PubMed HealthHydrocodone/Acetaminophen (By mouth)
Drug ClassesAnalgesic, Opioid/Acetaminophen Combination
Drug LabelAcetaminophen and codeine phosphate is supplied in tablet form for oral administration.Acetaminophen, 4'-hydroxyacetanilide, a slightly bitter, white, odorless, crystalline powder, is a non-opiate, non-salicylate analgesic and antipyretic. It has the
Active IngredientAcetaminophen
Dosage FormTablet, extended release; Suppository
RouteRectal; Oral
Strength650mg; 120mg; 325mg
Market StatusOver the Counter
CompanyOhm Labs; Perrigo; Perrigo New York; Ranbaxy Labs; Taro Pharms North

13 of 20  
Drug NameButapap
PubMed HealthAcetaminophen
Drug ClassesAcetaminophen Combination, Analgesic, Antipyretic
Active Ingredientbutalbital; Acetaminophen
Dosage FormTablet
RouteOral
Strength50mg; 325mg
Market StatusPrescription
CompanyMikart

14 of 20  
Drug NameInfants' feverall
PubMed HealthAcetaminophen and Codeine
Drug ClassesAnalgesic, Codeine, Opioid/Acetaminophen Combination
Active IngredientAcetaminophen
Dosage FormSuppository
RouteRectal
Strength80mg
Market StatusOver the Counter
CompanyTaro Pharms North

15 of 20  
Drug NameNeopap
Active IngredientAcetaminophen
Dosage FormSuppository
RouteRectal
Strength120mg
Market StatusOver the Counter
CompanyPolymedica

16 of 20  
Drug NameNorco
Drug LabelAcetaminophen is a non-salicylate antipyretic and non-opioid analgesic agent. Its chemical name is N-acetyl-p-aminophenol. Acetaminophen has a molecular weight of 151.16. Its structural formula is: OFIRMEV injection is a sterile, clear, colorless, no...
Active Ingredienthydrocodone bitartrate; Acetaminophen
Dosage FormTablet
RouteOral
Strength7.5mg; 5mg; 10mg; 325mg
Market StatusPrescription
CompanyActavis Labs Fl; Watson Labs

17 of 20  
Drug NameOfirmev
Active IngredientAcetaminophen
Dosage FormSolution
RouteIv (infusion)
Strength1000mg/100ml (10mg/ml)
Market StatusPrescription
CompanyCadence Pharms

18 of 20  
Drug NameOxycet
Active Ingredientoxycodone hydrochloride; Acetaminophen
Dosage FormTablet
RouteOral
Strength5mg; 325mg
Market StatusPrescription
CompanyMallinckrodt

19 of 20  
Drug NamePercocet
Active Ingredientoxycodone hydrochloride; Acetaminophen
Dosage FormTablet
RouteOral
Strength2.5mg; 7.5mg; 5mg; 10mg; 325mg
Market StatusPrescription
CompanyVintage Pharms

20 of 20  
Drug NameTylenol
Active IngredientAcetaminophen
Dosage FormTablet, extended release
RouteOral
Strength650mg
Market StatusOver the Counter
CompanyMcneil Cons

4.2 Therapeutic Uses

Analgesics, Non-Narcotic; Antipyretics

National Library of Medicine's Medical Subject Headings. Acetaminophen. Online file (MeSH, 2014). Available from, as of January 30, 2014: https://www.nlm.nih.gov/mesh/2014/mesh_browser/MBrowser.html


Ofirmev (acetaminophen) injection is indicated for the management of mild to moderate pain the management of moderate to severe pain with adjunctive opioid analgesics the reduction of fever. /Included in US product label/

US Natl Inst Health; DailyMed. Current Medication Information for OFIRMEV (acetaminophen) injection, solution (October 2013). Available from, as of March 6, 2014: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=c5177abd-9465-40d8-861d-3904496d82b7


Acetaminophen is used to provide temporary analgesia in the treatment of mild to moderate pain. Acetaminophen also is used in fixed combination with other agents (e.g., chlorpheniramine, dextromethorphan, diphenhydramine, doxylamine, guaifenesin, phenylephrine, pseudoephedrine) for short-term relief of minor aches and pain, headache, and/or other symptoms (e.g., rhinorrhea, sneezing, lacrimation, itching eyes, oronasopharyngeal itching, nasal congestion, cough) associated with seasonal allergic rhinitis (e.g., hay fever), other upper respiratory allergies, or the common cold.

American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013, p. 2206


Acetaminophen has been used in the treatment of pain in various combinations with aspirin, caffeine, opiates, and/or other agents. Acetaminophen ... in combination with oral doses of an opiate (e.g., codeine, oxycodone) produces greater analgesic effect than that produced by either acetaminophen or higher doses of the opiate alone.

American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013, p. 2206


For more Therapeutic Uses (Complete) data for ACETAMINOPHEN (11 total), please visit the HSDB record page.


4.3 Drug Warning

The U.S. Food and Drug Administration (FDA) is informing the public that acetaminophen has been associated with a risk of rare but serious skin reactions. These skin reactions, known as Stevens-Johnson Syndrome (SJS), toxic epidermal necrolysis (TEN), and acute generalized exanthematous pustulosis (AGEP), can be fatal. Acetaminophen is a common active ingredient to treat pain and reduce fever; it is included in many prescription and over-the-counter (OTC) products. Reddening of the skin, rash, blisters, and detachment of the upper surface of the skin can occur with the use of drug products that contain acetaminophen. These reactions can occur with first-time use of acetaminophen or at any time while it is being taken. ... Anyone who develops a skin rash or reaction while using acetaminophen or any other pain reliever/fever reducer should stop the drug and seek medical attention right away. Anyone who has experienced a serious skin reaction with acetaminophen should not take the drug again and should contact their health care professional to discuss alternative pain relievers/fever reducers. Health care professionals should be aware of this rare risk and consider acetaminophen, along with other drugs already known to have such an association, when assessing patients with potentially drug-induced skin reactions.

US FDA; FDA Drug Safety Communication: FDA Warns of Rare but Serious Skin Reactions with the Pain Reliever/Fever Reducer Acetaminophen (8/1/2013). Available from, as of March 6, 2014: https://www.fda.gov/drugs/drugsafety/ucm363041.htm


FDA is recommending health care professionals discontinue prescribing and dispensing prescription combination drug products that contain more than 325 milligrams (mg) of acetaminophen1 per tablet, capsule, or other dosage unit. There are no available data to show that taking more than 325 mg of acetaminophen per dosage unit provides additional benefit that outweighs the added risks for liver injury. Further, limiting the amount of acetaminophen per dosage unit will reduce the risk of severe liver injury from inadvertent acetaminophen overdose, which can lead to liver failure, liver transplant, and death.

US FDA; FDA Drug Safety and Availability: FDA recommends health care professionals discontinue prescribing and dispensing prescription combination drug products with more than 325 mg of acetaminophen to protect consumers (1/14/2014). Available from, as of March 9, 2014: https://www.fda.gov/Drugs/DrugSafety/ucm381644.htm


/BOXED WARNING/ WARNING: RISK OF MEDICATION ERRORS AND HEPATOTOXICITY. Take care when prescribing, preparing, and administering Ofirmev Injection to avoid dosing errors which could result in accidental overdose and death. In particular, be careful to ensure that: the dose in milligrams (mg) and milliliters (mL) is not confused; the dosing is based on weight for patients under 50 kg; infusion pumps are properly programmed; and the total daily dose of acetaminophen from all sources does not exceed maximum daily limits. Ofirmev contains acetaminophen. Acetaminophen has been associated with cases of acute liver failure, at times resulting in liver transplant and death. Most of the cases of liver injury are associated with the use of acetaminophen at doses that exceed the maximum daily limits, and often involve more than one acetaminophen-containing product.

US Natl Inst Health; DailyMed. Current Medication Information for OFIRMEV (acetaminophen) injection, solution (October 2013). Available from, as of March 6, 2014: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=c5177abd-9465-40d8-861d-3904496d82b7


Use caution when administering acetaminophen in patients with the following conditions: hepatic impairment or active hepatic disease, alcoholism, chronic malnutrition, severe hypovolemia (e.g., due to dehydration or blood loss), or severe renal impairment (creatinine clearance = 30 mL/min).

US Natl Inst Health; DailyMed. Current Medication Information for OFIRMEV (acetaminophen) injection, solution (October 2013). Available from, as of March 6, 2014: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=c5177abd-9465-40d8-861d-3904496d82b7


For more Drug Warnings (Complete) data for ACETAMINOPHEN (23 total), please visit the HSDB record page.


4.4 Minimum/Potential Fatal Human Dose

In adults, hepatic toxicity rarely has occurred with acute overdoses of less than 10 g, although hepatotoxicity has been reported in fasting patients ingesting 4-10 g of acetaminophen. Fatalities are rare with less than 15 g.

American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013, p. 2210


4.5 Drug Indication

In general, acetaminophen is used for the treatment of mild to moderate pain and reduction of fever. It is available over the counter in various forms, the most common being oral forms. Acetaminophen _injection_ is indicated for the management of mild to moderate pain, the management of moderate to severe pain with adjunctive opioid analgesics, and the reduction of fever. Because of its low risk of causing allergic reactions, this drug can be administered in patients who are intolerant to salicylates and those with allergic tendencies, including bronchial asthmatics. Specific dosing guidelines should be followed when administering acetaminophen to children.


FDA Label


Moderate pain and fever


5 Pharmacology and Biochemistry
5.1 Pharmacology

Animal and clinical studies have determined that acetaminophen has both antipyretic and analgesic effects. This drug has been shown to lack anti-inflammatory effects. As opposed to the _salicylate_ drug class, acetaminophen does not disrupt tubular secretion of uric acid and does not affect acid-base balance if taken at the recommended doses. Acetaminophen does not disrupt hemostasis and does not have inhibitory activities against platelet aggregation. Allergic reactions are rare occurrences following acetaminophen use.


5.2 MeSH Pharmacological Classification

Analgesics, Non-Narcotic

A subclass of analgesic agents that typically do not bind to OPIOID RECEPTORS and are not addictive. Many non-narcotic analgesics are offered as NONPRESCRIPTION DRUGS. (See all compounds classified as Analgesics, Non-Narcotic.)


Antipyretics

Drugs that are used to reduce body temperature in fever. (See all compounds classified as Antipyretics.)


5.3 FDA Pharmacological Classification
5.3.1 Pharmacological Classes
Central Nervous System Stimulant [EPC]; Central Nervous System Stimulation [PE]; Cyclooxygenase Inhibitors [MoA]; Decreased Platelet Aggregation [PE]; Decreased Prostaglandin Production [PE]; Histamine Receptor Antagonists [MoA]; Histamine-1 Receptor Antagonist [EPC]; Methylxanthine [EPC]; Nonsteroidal Anti-inflammatory Drug [EPC]; Platelet Aggregation Inhibitor [EPC]; Sigma-1 Agonist [EPC]; Sigma-1 Receptor Agonists [MoA]; Uncompetitive N-methyl-D-aspartate Receptor Antagonist [EPC]; Uncompetitive NMDA Receptor Antagonists [MoA]; Xanthines [CS]; Anti-Inflammatory Agents, Non-Steroidal [CS]; Antihistamine [EPC]; Histamine H1 Receptor Antagonists [MoA]
5.4 ATC Code

N02BE01

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355


N - Nervous system

N02 - Analgesics

N02B - Other analgesics and antipyretics

N02BE - Anilides

N02BE01 - Paracetamol


5.5 Absorption, Distribution and Excretion

Absorption

Acetaminophen has 88% oral bioavailability and reaches its highest plasma concentration 90 minutes after ingestion. Peak blood levels of free acetaminophen are not reached until 3 hours after rectal administration of the suppository form of acetaminophen and the peak blood concentration is approximately 50% of the observed concentration after the ingestion of an equivalent oral dose (10-20 mcg/mL). The percentage of a systemically absorbed rectal dose of acetaminophen is inconsistent, demonstrated by major differences in the bioavailability of acetaminophen after a dose administered rectally. Higher rectal doses or an increased frequency of administration may be used to attain blood concentrations of acetaminophen similar to those attained after oral acetaminophen administration.


Route of Elimination

Acetaminophen metabolites are mainly excreted in the urine. Less than 5% is excreted in the urine as free (unconjugated) acetaminophen and at least 90% of the administered dose is excreted within 24 hours.


Volume of Distribution

Volume of distribution is about 0.9L/kg. 10 to 20% of the drug is bound to red blood cells. Acetaminophen appears to be widely distributed throughout most body tissues except in fat.


Clearance

Adults: 0.27 L/h/kg following a 15 mg/kg intravenous (IV) dose. Children: 0.34 L/h/kg following a 15 mg/kg intravenous (IV dose).


Acetaminophen is rapidly and almost completely absorbed from the GI tract following oral administration. In healthy men, steady-state oral bioavailability of 1.3-g doses of extended-release tablets of acetaminophen administered every 8 hours for a total of 7 doses was equal to 1-g doses of conventional tablets of acetaminophen given every 6 hours for a total of 7 doses. Food may delay slightly absorption of extended-release tablets of acetaminophen. Following oral administration of immediate- or extended-release acetaminophen preparations, peak plasma concentrations are attained within 10-60 or 60-120 minutes, respectively. Following oral administration of a single 500-mg conventional tablet or a single 650-mg extended-release tablet, average plasma acetaminophen concentrations of 2.1 or 1.8 ug/mL, respectively, occur at 6 or 8 hours, respectively. In addition, dissolution of the extended-release tablets may depend slightly on the gastric or intestinal pH. Dissolution appears to be slightly faster in the alkaline pH of the intestines compared with the acidic pH of the stomach; however, this is of no clinical importance. Following administration of conventional preparations of acetaminophen, only small amounts of the drug are detectable in plasma after 8 hours. The extended-release tablets of acetaminophen release the drug for up to 8 hours, but in vitro data indicate that at least 95% of the dose is released within 5 hours.

American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013, p. 2212


Following rectal administration of acetaminophen, there is considerable variation in peak plasma concentrations attained, and time to reach peak plasma concentrations is substantially longer than after oral administration.

American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013, p. 2212


In 12 nursing mothers (nursing 2-22 months) given a single oral dose of 650 mg, peak levels of acetaminophen occurred at 1-2 hours in the range of 10-15 ug/mL. Assuming 90 mL of milk were ingested at 3-, 6-, and 9-hour intervals after ingestion, the amount of drug available to the infant was estimated to range from 0.04% to 0.23% of the maternal dose.

Briggs, G.G., Freeman, R.K., Yaffee, S.J.; Drugs in Pregancy and Lactation Nineth Edition. Wolters Kluwer/Lippincott Williams & Wilkins, Philadelphia, PA. 2011, p. 11


Acetaminophen is rapidly and uniformly distributed into most body tissues. About 25% of acetaminophen in blood is bound to plasma proteins.

American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013, p. 2212


For more Absorption, Distribution and Excretion (Complete) data for ACETAMINOPHEN (11 total), please visit the HSDB record page.


5.6 Metabolism/Metabolites

Acetaminophen is the major metabolite of _phenacetin_ and _acetanilid_. Acetaminophen is mainly metabolized in the liver by first-order kinetics and its metabolism of comprised of 3 pathways: conjugation with glucuronide, conjugation with sulfate, and oxidation through the cytochrome P450 enzyme pathway, mainly CYP2E1, to produce a reactive metabolite (N-acetyl-p-benzoquinone imine or NAPQI). At normal therapeutic doses, NAPQI undergoes fast conjugation with glutathione and is subsequently metabolized to produce both cysteine and mercapturic acid conjugates. High doses of acetaminophen (overdoses) can lead to hepatic necrosis due to the depletion of glutathione and of binding of high levels of reactive metabolite (NAPQI) to important parts of liver cells. The abovementioned damage to the liver can be prevented by the early administration of sulfhydryl compounds, for example, methionine and N-acetylcysteine.


About 80-85% of the acetaminophen in the body undergoes conjugation principally with glucuronic acid and to a lesser extent with sulfuric acid. Acetaminophen also is metabolized by microsomal enzyme systems in the liver.

American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013, p. 2212


In vitro and animal data indicate that small quantities of acetaminophen are metabolized by a cytochrome P-450 microsomal enzyme to a reactive intermediate metabolite (N-acetyl-p-benzoquinoneimine, N-acetylimidoquinone, NAPQI) which is further metabolized via conjugation with glutathione and ultimately excreted in urine as a mercapturic acid. It has been suggested that this intermediate metabolite is responsible for acetaminophen-induced liver necrosis and that high doses of acetaminophen may deplete glutathione so that inactivation of this toxic metabolite is decreased. At high doses, the capacity of metabolic pathways for conjugation with glucuronic acid and sulfuric acid may be exceeded, resulting in increased metabolism of acetaminophen by alternative pathways. In addition, it also has been suggested that in fasting individuals conjugation of high doses of acetaminophen with glucuronic acid may be reduced, secondary to decreased hepatic carbohydrate reserves and microsomal oxidation may be increased, resulting in increased risk of hepatotoxicity.

American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013, p. 2212


Yields 4-acetamidocatechol in rat; yields s-(5-acetamido-2-hydroxyphenyl)-l-cysteine probably in man. Yields p-acetamidophenyl-beta-d-glucuronide in rabbit; yields p-acetamidophenyl-beta-d-glucuronide in rat, in guinea pig, & in ferret; yields p-acetamidophenyl-beta-d-glucuronide in man & in dog; yields p-acetamidophenyl sulfate in rabbit, guinea pig, & ferret; yields p-acetamidophenyl sulfate in rat & in man; yields p-methoxyacetanilide in guinea pig; yields quinol probably in rat. /From table/

Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic Compounds. New York: Wiley, 1976., p. A-10


Children have less capacity for glucuronidation of the drug than do adults. A small proportion of acetaminophen undgoes n-hydroxylation to form n-acetyl-benzoquinoneimine, a highly reactive intermediate. This metabolite normally reacts with sulfhydryl groups in glutathione. However, after large doses of acetaminophen the metabolite is formed in amounts sufficient to deplete hepatic glutathione; under these circumstances reaction with sulfhydryl groups in hepatic proteins is increased and hepatic necrosis can result.

Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 704


For more Metabolism/Metabolites (Complete) data for ACETAMINOPHEN (7 total), please visit the HSDB record page.


Acetaminophen has known human metabolites that include (2S,3S,4S,5R)-6-(4-Acetamidophenoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid, 3-Hydroxyacetaminophen, Acetaminophen sulfate, and N-Acetyl-p-benzoquinone.

Acetaminophen is a known human metabolite of O-isopropyl acetaminophen, acetanilide, p-Methoxyacetanilide, and phenacetin.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560


5.7 Biological Half-Life

The half-life for adults is 2.5 h after an intravenous dose of 15 mg/kg. After an overdose, the half-life can range from 4 to 8 hours depending on the severity of injury to the liver, as it heavily metabolizes acetaminophen.


The elimination half life is 1-3 hours after a therapeutic dose but may be greater than 12 hours after an overdose.

OLSON, K.R. (Ed). Poisoning and Drug Overdose, Sixth Edition. McGraw-Hill, New York, NY 2012, p. 69


5.8 Mechanism of Action

According to its FDA labeling, acetaminophen's exact mechanism of action has not been fully established - despite this, it is often categorized alongside NSAIDs (nonsteroidal anti-inflammatory drugs) due to its ability to inhibit the cyclooxygenase (COX) pathways. It is thought to exert central actions which ultimately lead to the alleviation of pain symptoms. One theory is that acetaminophen increases the pain threshold by inhibiting two isoforms of cyclooxygenase, COX-1 and COX-2, which are involved in prostaglandin (PG) synthesis. Prostaglandins are responsible for eliciting pain sensations. Acetaminophen does not inhibit cyclooxygenase in peripheral tissues and, therefore, has no peripheral anti-inflammatory effects. Though acetylsalicylic acid (aspirin) is an irreversible inhibitor of COX and directly blocks the active site of this enzyme, studies have shown that acetaminophen (paracetamol) blocks COX indirectly. Studies also suggest that acetaminophen selectively blocks a variant type of the COX enzyme that is unique from the known variants COX-1 and COX-2. This enzyme has been referred to as _COX-3_. The antipyretic actions of acetaminophen are likely attributed to direct action on heat-regulating centers in the brain, resulting in peripheral vasodilation, sweating, and loss of body heat. The exact mechanism of action of this drug is not fully understood at this time, but future research may contribute to deeper knowledge.


Acetaminophen produces analgesia and antipyresis by a mechanism similar to that of salicylates. Unlike salicylates, however, acetaminophen does not have uricosuric activity. There is some evidence that acetaminophen has weak anti-inflammatory activity in some nonrheumatoid conditions (e.g., in patients who have had oral surgery). ... Acetaminophen lowers body temperature in patients with fever but rarely lowers normal body temperature. The drug acts on the hypothalamus to produce antipyresis; heat dissipation is increased as a result of vasodilation and increased peripheral blood flow.

American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013, p. 2211


The effects of acetaminophen on cyclooxygenase activity have not been fully determined. Acetaminophen is a weak, reversible, isoform-nonspecific cyclooxygenase inhibitor at dosages of 1 g daily. The inhibitory effect of acetaminophen on cyclooxygenase-1 is limited, and the drug does not inhibit platelet function. Therapeutic doses of acetaminophen appear to have little effect on cardiovascular and respiratory systems; however, toxic doses may cause circulatory failure and rapid, shallow breathing.

American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013, p. 2211


Acetaminophen (N-acetyl-p-aminophenol (APAP)) is the most common antipyretic/analgesic medicine worldwide. If APAP is overdosed, its metabolite, N-acetyl-p-benzo-quinoneimine (NAPQI), causes liver damage. However, epidemiological evidence has associated previous use of therapeutic APAP doses with the risk of chronic obstructive pulmonary disease (COPD) and asthma. The transient receptor potential ankyrin-1 (TRPA1) channel is expressed by peptidergic primary sensory neurons. Because NAPQI, like other TRPA1 activators, is an electrophilic molecule, /the researchers/ hypothesized that APAP, via NAPQI, stimulates TRPA1, thus causing airway neurogenic inflammation. NAPQI selectively excites human recombinant and native (neuroblastoma cells) TRPA1. TRPA1 activation by NAPQI releases proinflammatory neuropeptides (substance P and calcitonin gene-related peptide) from sensory nerve terminals in rodent airways, thereby causing neurogenic edema and neutrophilia. Single or repeated administration of therapeutic (15-60 mg/kg) APAP doses to mice produces detectable levels of NAPQI in the lung, and increases neutrophil numbers, myeloperoxidase activity, and cytokine and chemokine levels in the airways or skin. Inflammatory responses evoked by NAPQI and APAP are abated by TRPA1 antagonism or are absent in TRPA1-deficient mice. This novel pathway, distinguished from the tissue-damaging effect of NAPQI, may contribute to the risk of COPD and asthma associated with therapeutic APAP use.

PMID:20720158 Nassini R et al; FASEB J 24 (12): 4904-16 (2010)


Acetaminophen is at present one of the most commonly used analgesics and antipyretics. Recent evidence has suggested that oxidative stress is involved in the mechanism of acetaminophen intoxication. Paraoxonase-1 (PON1) plays an important role as an endogenous free-radical scavenging molecule. The aim of this study was to evaluate the influence of serum PON1 activity and oxidative stress in patients with acetaminophen intoxication. A total of 20 patients with acetaminophen intoxication and 25 healthy controls were enrolled. Serum total antioxidant capacity (TAC), lipid hydroperoxide (LOOH) levels, and paraoxonase and arylesterase activities were measured spectrophotometrically. The serum TAC levels and the paraoxonase and arylesterase activities were significantly lower in patients with acetaminophen intoxication compared with controls (all, p < 0.001), while the serum LOOH levels were significantly higher (p < 0.001). Results suggest that decreased PON1 activity seems to be associated with increased oxidative stress in patients with acetaminophen intoxication. Measuring serum PON1 activity may be useful in assessing the development of toxicity risk in acetaminophen toxicity. It would be useful to recommend vitamins with antioxidant effects such as vitamins C and E along with medical treatments.

PMID:24501102 Karadas S et al; Hum Exp Toxicol 33 (11): 1134-40 (2014)


For more Mechanism of Action (Complete) data for ACETAMINOPHEN (9 total), please visit the HSDB record page.


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  • SUPPOSITORY;RECTAL - 120MG
  • SUPPOSITORY;RECTAL - 325MG
  • SUPPOSITORY;RECTAL - 650MG
  • SUPPOSITORY;RECTAL - 80MG
  • TABLET, EXTENDED RELEASE;ORAL - 325MG;7.5MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**
  • TABLET;ORAL - 250MG;250MG;65MG
  • TABLET;ORAL - 325MG;37.5MG
  • SOLUTION;INTRAVENOUS - 1GM/100ML (10MG/ML)
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  • TABLET;ORAL - 300MG;30MG
  • TABLET;ORAL - 300MG;60MG
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  • TABLET;ORAL - 325MG;50MG;40MG
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