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Chemistry

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Also known as: 69-53-4, Aminobenzylpenicillin, Ampicillin acid, Amcill, Polycillin, Principen
Molecular Formula
C16H19N3O4S
Molecular Weight
349.4  g/mol
InChI Key
AVKUERGKIZMTKX-NJBDSQKTSA-N
FDA UNII
7C782967RD

Ampicillin
Semi-synthetic derivative of penicillin that functions as an orally active broad-spectrum antibiotic.
Ampicillin is a Penicillin-class Antibacterial.
1 2D Structure

Ampicillin

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(2S,5R,6R)-6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
2.1.2 InChI
InChI=1S/C16H19N3O4S/c1-16(2)11(15(22)23)19-13(21)10(14(19)24-16)18-12(20)9(17)8-6-4-3-5-7-8/h3-7,9-11,14H,17H2,1-2H3,(H,18,20)(H,22,23)/t9-,10-,11+,14-/m1/s1
2.1.3 InChI Key
AVKUERGKIZMTKX-NJBDSQKTSA-N
2.1.4 Canonical SMILES
CC1(C(N2C(S1)C(C2=O)NC(=O)C(C3=CC=CC=C3)N)C(=O)O)C
2.1.5 Isomeric SMILES
CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](C3=CC=CC=C3)N)C(=O)O)C
2.2 Other Identifiers
2.2.1 UNII
7C782967RD
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Amcill

2. Aminobenzyl Penicillin

3. Aminobenzylpenicillin

4. Ampicillin Sodium

5. Ampicillin Trihydrate

6. Antibiotic Ks R1

7. Antibiotic Ks-r1

8. Ks-r1, Antibiotic

9. Omnipen

10. Penicillin, Aminobenzyl

11. Pentrexyl

12. Polycillin

13. Sodium, Ampicillin

14. Trihydrate, Ampicillin

15. Ukapen

2.3.2 Depositor-Supplied Synonyms

1. 69-53-4

2. Aminobenzylpenicillin

3. Ampicillin Acid

4. Amcill

5. Polycillin

6. Principen

7. Tokiocillin

8. Ampicillin Anhydrous

9. Ampicilline

10. Semicillin

11. Ultrabion

12. Anhydrous Ampicillin

13. Omnipen

14. Ampicillinum

15. Pentrexyl

16. Synpenin

17. Novo-ampicillin

18. D-ampicillin

19. Penbritin

20. D-(-)-ampicillin

21. Adobacillin

22. Amblosin

23. Ampichel

24. Ampicilina

25. Ampifarm

26. Ampipenin

27. Ampiscel

28. Amplacilina

29. Amplipenyl

30. Amplisom

31. Amplital

32. Bonapicillin

33. Britacil

34. Campicillin

35. Copharcilin

36. Delcillin

37. Divercillin

38. Doktacillin

39. Duphacillin

40. Grampenil

41. Guicitrina

42. Lifeampil

43. Norobrittin

44. Orbicilina

45. Penbristol

46. Penbrock

47. Penicline

48. Pentrexl

49. Princillin

50. Racenacillin

51. Rosampline

52. Roscillin

53. Servicillin

54. Sumipanto

55. Texcillin

56. Totalciclina

57. Trifacilina

58. Ultrabron

59. Viccillin

60. Acillin

61. Amfipen

62. Ampicil

63. Ampikel

64. Ampimed

65. Ampisyn

66. Ampivax

67. Ampivet

68. Amplin

69. Binotal

70. Morepen

71. Nuvapen

72. Penimic

73. Pensyn

74. Pentrex

75. Ponecil

76. Tolomol

77. Totapen

78. Vampen

79. Cimex

80. Supen

81. Ampicillin Anhydrate

82. Totacillin

83. Pfizerpen A

84. Amipenix S

85. Ampi-bol

86. Sk-ampicillin

87. Amfipen V

88. Pen Ampil

89. Qidamp

90. Ampi-tab

91. D-cillin

92. Olin Kid

93. Ro-ampen

94. Ampi-co

95. Austrapen

96. Pen A

97. Ampicillina [dcit]

98. Bayer 5427

99. Abpc

100. Ampicillin, Anhydrous

101. Ampicilina [inn-spanish]

102. Ampicilline [inn-french]

103. Ampicillinum [inn-latin]

104. Ampicin

105. D-(-)-alpha-aminopenicillin

106. Deripen

107. Wypicil

108. Alpen

109. Ay-6108

110. Ampicillin A

111. D-(-)-alpha-aminobenzylpenicillin

112. Polycillin-n

113. Totacillin-n

114. Penbritin-s

115. Omnipen-n

116. Brl 1341

117. P-50

118. Penbritin Syrup

119. Semicillin R

120. Nsc-528986

121. D-(-)-6-(alpha-aminophenylacetamido)penicillanic Acid

122. Brl-1341

123. Ks-r1

124. Penbritin Paediatric

125. Ampicillin (anhydrous)

126. Redicilin

127. Ab-pc

128. 6-(d(-)-alpha-aminophenylacetamido)penicillanic Acid

129. Guicitrine

130. Ampen

131. Nsc 528986

132. Ab-pc Sol

133. C16h19n3o4s

134. Chebi:28971

135. Ampicillin Hydrate

136. Alpha-aminobenzylpenicillin

137. 6-(d-(2-amino-2-phenylacetamido))-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid

138. Mls000028405

139. (2s,5r,6r)-6-[[(2r)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

140. (2s,5r,6r)-6-{[(2r)-2-amino-2-phenylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

141. Ampicillina

142. Hi 63

143. Ukapen

144. Pfizerpen-a

145. Wy-5103

146. Ampi

147. Poly-cillin

148. 7c782967rd

149. (2s,5r,6r)-6-((r)-2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid

150. P 50

151. Sq 17382

152. Wy 5103

153. Penicillin, (aminophenylmethyl)-

154. Smr000058352

155. Ampicillin Base

156. Mfcd00005175

157. Dsstox_cid_2602

158. Ay 6108

159. Dsstox_rid_76654

160. Dsstox_gsid_22602

161. Polyflex (veterinary)

162. Ampicillanyl

163. Ampicillin [usan:ban:inn:jan]

164. Cas-69-53-4

165. (2s,5r,6r)-6-[(r)-2-amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

166. (2s,5r,6r)-6-{[(2r)-2-amino-2-phenylethanoyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

167. Omnipen (tn)

168. Totacillin (sodium)

169. Ba 7305

170. Hsdb 3009

171. Ampicillin (usp/inn)

172. Einecs 200-709-7

173. Vidopen

174. Vidocillin

175. Marcillin

176. Pentritin

177. Nsc528986

178. D-(-)-.alpha.-aminobenzylpenicillin

179. Unii-7c782967rd

180. Ampicillin,(s)

181. Ncgc00018160-02

182. (2s,5r,6r)-6-((r)-2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

183. (2s,5r,6r)-6-[[(2r)-2-amino-2-phenyl-acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

184. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 6-((aminophenylacetyl)amino)-3,3-dimethyl-7-oxo-, (2s-(2alpha,5alpha,6beta(s*)))-

185. Ampicillin [usan:usp:inn:ban:jan]

186. Spectrum_000050

187. 1h8s

188. Ay 6108

189. Ampicillin [mi]

190. Ampicillin [inn]

191. D-a-aminobenzylpenicillin

192. Opera_id_1630

193. Prestwick0_000114

194. Prestwick1_000114

195. Prestwick2_000114

196. Prestwick3_000114

197. Spectrum2_000769

198. Spectrum3_000301

199. Spectrum4_000149

200. Spectrum5_000814

201. Ampicillin [hsdb]

202. Ampicillin [iarc]

203. Ampicillin [usan]

204. Ampicillin [vandf]

205. Chembl174

206. Epitope Id:115008

207. Epitope Id:116057

208. Ec 200-709-7

209. Ampicillin [mart.]

210. Schembl3526

211. Ampicillin [usp-rs]

212. Ampicillin [who-dd]

213. Ampicillin [who-ip]

214. Bspbio_000128

215. Bspbio_001862

216. Kbiogr_000598

217. Kbioss_000430

218. Anhydrous Ampicillin (jp17)

219. Mls001074168

220. Bidd:gt0184

221. Divk1c_000466

222. Spbio_000818

223. Spbio_002067

224. Ampicillin, Analytical Standard

225. D-(-)-a-aminobenzylpenicillin

226. Bpbio1_000142

227. Dtxsid4022602

228. Chebi:53713

229. Gtpl10896

230. Kbio1_000466

231. Kbio2_000430

232. Kbio2_002998

233. Kbio2_005566

234. Kbio3_001362

235. Ampicillin [ep Monograph]

236. Ninds_000466

237. Ampicillin [usp Monograph]

238. Anhydrous Ampicillin [jan]

239. Hms2090i11

240. Hms2233h23

241. Ampicillin Acid; Principen; Amcill

242. Ampicillinum [who-ip Latin]

243. Hy-b0522

244. Zinc3830218

245. Tox21_113049

246. Tox21_301416

247. Bdbm50350465

248. Ampicillin Anhydrous [who-ip]

249. Akos015888156

250. Tox21_113049_1

251. Ac-8805

252. Db00415

253. 6beta-[(2r)-2-amino-2-phenylacetamido]-2,2-dimethylpenam-3alpha-carboxylic Acid

254. Idi1_000466

255. Smp1_000211

256. Ampicillin Anhydrous [green Book]

257. Ncgc00023282-05

258. Ncgc00023282-06

259. Ncgc00023282-21

260. Ncgc00178944-03

261. Ncgc00248937-01

262. Ncgc00255127-01

263. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 6-(2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-, D-(-)-

264. Ba166034

265. Sbi-0051283.p003

266. 6-(a-aminophenylacetamido)penicillanic Acid

267. Sultamicillin Impurity C [ep Impurity]

268. C06574

269. D00204

270. 6-[d(-)-a-aminophenylacetamido]penicillanic Acid

271. A936108

272. Ampicillin Anhydrous, Pharmaceutical Grade

273. Q244150

274. 6-d(-)-alpha-aminophenylacetamido-penicillanic Acid

275. Piperacillin Sodium Impurity A [ep Impurity]

276. Brd-k68432770-001-08-0

277. Ampicillin, Anhydrous, 96.0-100.5% (anhydrous Basis)

278. Ampicillin, United States Pharmacopeia (usp) Reference Standard

279. Anhydrous Ampicillin, British Pharmacopoeia (bp) Reference Standard

280. Ampicillin, Anhydrous, European Pharmacopoeia (ep) Reference Standard

281. (2s,5r,6r)-6-(((r,e)-2-amino-1-hydroxy-2-phenylethylidene)amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

282. (2s,5r,6r)-6-[(r)-2-amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid

283. (2s,5r,6r)-6-{[(2r)-2-amino-2-phenylethanoyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic

284. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 6-(((2r)-aminophenylacetyl)amino)-3,3-dimethyl-7-oxo-, (2s,5r,6r)-

285. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 6-((aminophenylacetyl)amino)-3,3-dimethyl-7-oxo-, (2s-(2.alpha.,5.alpha.,6.beta.(s*)))-

286. 4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid,6-[[(2r)-aminophenylacetyl]amino]-3,3-dimethyl-7-oxo-, Trihydrate,(2s,5r,6r)-

287. 6-[(aminophenylacetyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid, 9ci

288. Ampicillin; D(-)-alpha-aminobenzylpenicillin; 6-[d(-)-alpha-aminophenyllacetamido]penicillanic Acid

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 349.4 g/mol
Molecular Formula C16H19N3O4S
XLogP3-1.1
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count6
Rotatable Bond Count4
Exact Mass349.10962727 g/mol
Monoisotopic Mass349.10962727 g/mol
Topological Polar Surface Area138 Ų
Heavy Atom Count24
Formal Charge0
Complexity562
Isotope Atom Count0
Defined Atom Stereocenter Count4
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 2  
Drug NameAmpicillin sodium
Drug LabelAmpicillin for Injection, USP the monosodium salt of [2S-[2,5,6(S*)]]-6- [(aminophenylacetyl)amino]-3,3-dimethyl-7-oxo-4thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, is a synthetic penicillin for intramuscular or intravenous use. The pha...
Active IngredientAmpicillin sodium
Dosage FormInjectable
RouteInjection
Strengtheq 2gm base/vial; eq 125mg base/vial; eq 500mg base/vial; eq 10gm base/vial; eq 250mg base/vial; eq 1gm base/vial
Market StatusPrescription
CompanyIstituto Bio Ita Spa; Antibiotice; Hanford Gc; Acs Dobfar Spa; Aurobindo Pharma; Strides Arcolab; Sandoz; Agila Speclts

2 of 2  
Drug NameAmpicillin sodium
Drug LabelAmpicillin for Injection, USP the monosodium salt of [2S-[2,5,6(S*)]]-6- [(aminophenylacetyl)amino]-3,3-dimethyl-7-oxo-4thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, is a synthetic penicillin for intramuscular or intravenous use. The pha...
Active IngredientAmpicillin sodium
Dosage FormInjectable
RouteInjection
Strengtheq 2gm base/vial; eq 125mg base/vial; eq 500mg base/vial; eq 10gm base/vial; eq 250mg base/vial; eq 1gm base/vial
Market StatusPrescription
CompanyIstituto Bio Ita Spa; Antibiotice; Hanford Gc; Acs Dobfar Spa; Aurobindo Pharma; Strides Arcolab; Sandoz; Agila Speclts

4.2 Therapeutic Uses

Penicillins

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)


FOR MILD TO MODERATELY SEVERE DISEASE, ORAL...ADULTS...1-4 G/DAY, DIVIDED INTO EQUAL PORTIONS...EVERY 6 HR. FOR SEVERE INFECTIONS...BEST TO ADMIN... PARENTERALLY...6-12 G/DAY. ...MENINGITIS REQUIRES...300-400 MG/KG/DAY PARENTERALLY (IN EQUALLY DIVIDED PORTIONS...EVERY 4 HR) FOR CHILDREN, & 12 G OR MORE/DAY FOR ADULTS.

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 1079


DOSE VARIES WITH TYPE & SEVERITY OF INFECTION...RENAL FUNCTION &...AGE. FOR CHILDREN.../NOT/ ON BASIS OF BODY WT OR SURFACE AREA; BECAUSE DRUG...EXCRETED MAINLY BY KIDNEY ...RENAL FUNCTION TO GREAT EXTENT DETERMINES DOSE. VERY YOUNG BABIES...REQUIRE SMALL DOSES ...CHILDREN 3-4 YR.../DOSE/ ALMOST AS LARGE AS...ADULTS.

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 1079


Ampicillin /is/ indicated in the treatment of acute otitis media caused by susceptible organisms. /Included in US product labeling/

USP Convention. USPDI - Drug Information for the Health Care Professional. 15 th ed. Volume 1. Rockville, MD: United States Pharmacopeial Convention, Inc., 1995. (Plus updates.), p. 2149


For more Therapeutic Uses (Complete) data for AMPICILLIN (18 total), please visit the HSDB record page.


4.3 Drug Warning

IN 1 INSTANCE, FATAL PSEUDOMEMBRANOUS COLITIS OCCURRED FOLLOWING 5 DAYS OF ORAL AMPICILLIN THERAPY IN DOSAGE OF 2 G DAILY. VERY RARELY, AMPICILLIN HAS PRODUCED INTERSTITIAL NEPHRITIS; 1 CASE OF INTERSTITIAL NEPHRITIS REPORTEDLY PROGRESSED TO ACUTE RENAL FAILURE. ...CRYSTALLURIA HAS BEEN REPORTED...

American Hospital Formulary Service. Volumes I and II. Washington, DC: American Society of Hospital Pharmacists, to 1984., p. 8:12:16


PERIODIC ASSESSMENT OF RENAL, HEPATIC & HEMATOPOIETIC FUNCTION SHOULD BE CONDUCTED DURING PROLONGED THERAPY, ESP IN PREMATURE, NEWBORN & OTHER INFANTS.

American Hospital Formulary Service. Volumes I and II. Washington, DC: American Society of Hospital Pharmacists, to 1984., p. 8:12:16


ABSORPTION EFFICIENCY & RATE OF ELIMINATION OF AMPICILLIN...DECR IN PT WITH SHIGELLOSIS. POOR ABSORPTION...GENERALLY OBSERVED IN YOUNGER PATIENTS WITH MARKED DIARRHEA. ... DELAYED EXCRETION. MARKED RETENTION...IN PLASMA...NOTED IN PT WITH RENAL FAILURE.

The Chemical Society. Foreign Compound Metabolism in Mammals Volume 3. London: The Chemical Society, 1975., p. 169


NATIONAL REGISTRY OF POSSIBLE DRUG INDUCED OCULAR SIDE EFFECTS ESTABLISHED IN 1975 BY FDA IN ORDER TO MAKE PHYSICIANS AWARE THAT SOME DRUGS SUCH AS AMPICILLIN MAY CAUSE SIDE EFFECTS TO EYE IS DISCUSSED.

HECHT A; DRUG EFFECTS ON EYE; FDA CONSUM (12): 14 (1978)


For more Drug Warnings (Complete) data for AMPICILLIN (16 total), please visit the HSDB record page.


4.4 Drug Indication

For treatment of infection (Respiratory, GI, UTI and meningitis) due to E. coli, P. mirabilis, enterococci, Shigella, S. typhosa and other Salmonella, nonpenicillinase-producing N. gononhoeae, H. influenzae, staphylococci, streptococci including streptoc


5 Pharmacology and Biochemistry
5.1 Pharmacology

Ampicillin is a penicillin beta-lactam antibiotic used in the treatment of bacterial infections caused by susceptible, usually gram-positive, organisms. The name "penicillin" can either refer to several variants of penicillin available, or to the group of antibiotics derived from the penicillins. Ampicillin has in vitro activity against gram-positive and gram-negative aerobic and anaerobic bacteria. The bactericidal activity of Ampicillin results from the inhibition of cell wall synthesis and is mediated through Ampicillin binding to penicillin binding proteins (PBPs). Ampicillin is stable against hydrolysis by a variety of beta-lactamases, including penicillinases, and cephalosporinases and extended spectrum beta-lactamases.


5.2 MeSH Pharmacological Classification

Anti-Bacterial Agents

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
AMPICILLIN
5.3.2 FDA UNII
7C782967RD
5.3.3 Pharmacological Classes
Penicillins [CS]; Penicillin-class Antibacterial [EPC]
5.4 ATC Code

J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01C - Beta-lactam antibacterials, penicillins

J01CA - Penicillins with extended spectrum

J01CA01 - Ampicillin


S - Sensory organs

S01 - Ophthalmologicals

S01A - Antiinfectives

S01AA - Antibiotics

S01AA19 - Ampicillin


5.5 Absorption, Distribution and Excretion

Route of Elimination

Ampicillin is excreted largely unchanged in the urine.


INTAKE OF FOOD PRIOR TO INGESTION OF AMPICILLIN RESULTS IN LESS COMPLETE ABSORPTION. ... /IT/ APPEARS IN BILE, UNDERGOES ENTEROHEPATIC CIRCULATION & IS EXCRETED IN...FECES. BILIARY CONCN...DEPENDENT ON INTEGRITY OF GALLBLADDER & ITS DUCTS.

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 1079


Ampicillin is distributed to liver, bile, muscle, kidney, crop, and fat following absorption from the GI or injection site. Ampicillin has been used therapeutically and prophylactically for avian salmonellosis with promising results. ... Ampicillin is excreted in bile.

Booth, N.H., L.E. McDonald (eds.). Veterinary Pharmacology and Therapeutics. 5th ed. Ames, Iowa: Iowa State University Press, 1982., p. 735


Anhydrous ampicillin and ampicillin trihydrate are generally stable in the presence of acidic gastric secretions, and 30-55% of an oral dose of the drugs is absorbed from the GI tract in fasting adults. Although peak serum concn may occur as soon as 1 hr after administration, the maximum serum concn is usually attained in approx 2 hr.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 95. Bethesda, MD: American Society of Hospital Pharmacists, Inc., 1995 (Plus Supplements 1995)., p. 298


Two hr after oral administration of 250 mg of ampicillin in fasting individuals, average peak serum concn of 1.8-2.9 ug/ml are attained. A 500-mg oral dose results in average peak serum concn of 3-6 ug/ml. Concn of the antibiotic in serum are less than 1 ug/ml 6 hr after a 500-mg oral dose.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 95. Bethesda, MD: American Society of Hospital Pharmacists, Inc., 1995 (Plus Supplements 1995)., p. 298


For more Absorption, Distribution and Excretion (Complete) data for AMPICILLIN (16 total), please visit the HSDB record page.


5.6 Metabolism/Metabolites

AMPICILLIN IS DEGRADED BY PENICILLINASE...

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1144


YIELDS ALPHA-AMINOBENZYLPENICILLOIC ACID IN BACILLUS, IN PENICILLIUM, AND L-PHENYLGLYCINE IN ESCHERICHIA. /FROM TABLE/

Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic Compounds. New York: Wiley, 1976., p. A-34


Healthy subjects metabolize about 20% of a given dose (250-500 mg) of ampicillin. Within 12 hr, 7% of the total dose is excreted as metabolites in urine ... Ampicillin is metabolized to 5R,6R-penicilloic acid and 5S,6R-penicilloic acid ... and to piperazine-2,5-dione after oral intake ... Other, unidentified metabolites have been reported ... .

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V50 160


5.7 Biological Half-Life

The half-life of all aminopenicillins is approximately 60-90 minutes.

Booth, N.H., L.E. McDonald (eds.). Veterinary Pharmacology and Therapeutics. 5th ed. Ames, Iowa: Iowa State University Press, 1982., p. 735


Following ip injection ... the serum half-life /of ampicillin/ was estimated to be 27 min ... .

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V50 157 (1990)


... /ampicillin's/ plasma half-time is usually 1-2 hr ... but is longer in elderly people ... In patients with renal failure, the half-time was as long as 20 hr ... .

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V50 160 (1990)


5.8 Mechanism of Action

By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, Ampicillin inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that Ampicillin interferes with an autolysin inhibitor.


SINCE PENICILLIN HAS NO EFFECT ON EXISTING CELL WALLS, BACTERIA MUST BE MULTIPLYING FOR BACTERICIDAL ACTION OF PENICILLIN TO BE MANIFEST. /PENICILLINS/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1135


The penicillins and their metabolites are potent immunogens because of their ability to combine with proteins and act as haptens for acute antibody-mediated reactions. The most frequent (about 95 percent) or "major" determinant of penicillin allergy is the penicilloyl determinant produced by opening the beta-lactam ring of the penicillin. This allows linkage of the penicillin to protein at the amide group. "Minor" determinants (less frequent) are the other metabolites formed, including native penicillin and penicilloic acids. /Penicillins/

Haddad, L.M., Clinical Management of Poisoning and Drug Overdose. 2nd ed. Philadelphia, PA: W.B. Saunders Co., 1990., p. 953


Bactericidal; inhibit bacterial cell wall synthesis. Action is dependent on the ability of penicillins to reach and bind penicillin binding proteins located on the inner membrane of the bacterial cell wall. Penicillin binding proteins (which include transpeptidases, carboxypeptidases, and endopeptidases) are enzymes that are involved in the terminal stages of assembling the bacterial cell wall and in reshaping the cell wall during growth and division. Penicillins bind to, and inactivate, penicillin binding proteins, resulting in the weakening of the bacterial cell wall and lysis. /Penicillins/

USP Convention. USPDI - Drug Information for the Health Care Professional. 15 th ed. Volume 1. Rockville, MD: United States Pharmacopeial Convention, Inc., 1995. (Plus updates.), p. 2150


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05-Jan-2021
31-Aug-2024
KGS
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Average Price (USD/KGS)

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Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

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(USD/KGS)
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