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Chemistry

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Also known as: 990-73-8, Leptanal, Phentanyl citrate, Actiq, Fentanyl dihydrogen citrate, Abstral
Molecular Formula
C28H36N2O8
Molecular Weight
528.6  g/mol
InChI Key
IVLVTNPOHDFFCJ-UHFFFAOYSA-N
FDA UNII
MUN5LYG46H

Fentanyl Citrate
A potent narcotic analgesic, abuse of which leads to habituation or addiction. It is primarily a mu-opioid agonist. Fentanyl is also used as an adjunct to general anesthetics, and as an anesthetic for induction and maintenance. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1078)
1 2D Structure

Fentanyl Citrate

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-hydroxypropane-1,2,3-tricarboxylic acid;N-phenyl-N-[1-(2-phenylethyl)piperidin-4-yl]propanamide
2.1.2 InChI
InChI=1S/C22H28N2O.C6H8O7/c1-2-22(25)24(20-11-7-4-8-12-20)21-14-17-23(18-15-21)16-13-19-9-5-3-6-10-19;7-3(8)1-6(13,5(11)12)2-4(9)10/h3-12,21H,2,13-18H2,1H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)
2.1.3 InChI Key
IVLVTNPOHDFFCJ-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCC(=O)N(C1CCN(CC1)CCC2=CC=CC=C2)C3=CC=CC=C3.C(C(=O)O)C(CC(=O)O)(C(=O)O)O
2.2 Other Identifiers
2.2.1 UNII
MUN5LYG46H
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Duragesic

2. Durogesic

3. Fentanest

4. Fentanyl

5. Fentora

6. Phentanyl

7. R 4263

8. R-4263

9. R4263

10. Sublimaze

11. Transmucosal Oral Fentanyl Citrate

2.3.2 Depositor-Supplied Synonyms

1. 990-73-8

2. Leptanal

3. Phentanyl Citrate

4. Actiq

5. Fentanyl Dihydrogen Citrate

6. Abstral

7. Fentanyl Citrate Salt

8. Lazanda

9. Onsolis

10. Mcn-jr-4263-49

11. Instanyl

12. Fentanyl Buccal

13. Fentanyl Citrate Cii

14. Mun5lyg46h

15. Oralet

16. N-(1-phenethyl-4-piperidyl)propionanilide Citrate

17. N-(1-phenethyl-4-piperidyl)propionanilide Citrate (1:1)

18. N-(1-phenethyl-4-piperidyl)propionanilide Dihydrogen Citrate

19. Chebi:31602

20. Fentaz

21. N-(1-phenethyl-4-piperidinyl)propionanilide Dihydrogen Citrate

22. R-4263

23. Kw-2246

24. Propanamide, N-phenyl-n-(1-(2-phenylethyl)-4-piperidinyl)-, 2-hydroxy-1,2,3-propanetricarboxylate (1:1)

25. N-(1-phenethylpiperidin-4-yl)-n-phenylpropionamide Citrate

26. Rapinyl

27. 2-hydroxypropane-1,2,3-tricarboxylic Acid;n-phenyl-n-[1-(2-phenylethyl)piperidin-4-yl]propanamide

28. Mcn-jr 4263

29. Sublimaze Preservative Free

30. Einecs 213-588-0

31. Unii-mun5lyg46h

32. Fentanyl Citrate Preservative Free

33. R 5240

34. Fentanyl Monocitrate

35. Abstral (tn)

36. Fentora (tn)

37. Lazanda (tn)

38. Oralet (tn)

39. Fentanyl Citrate [usan:usp:ban:jan]

40. Propionanilide, N-(1-phenethyl-4-piperidyl)-, Citrate (1:1)

41. Chembl688

42. Schembl40733

43. Fentanyl Citrate [mi]

44. Fentanyl Citrate [jan]

45. Fentanyl Citrate (jp17/usp)

46. Fentanyl Citrate [usan]

47. Fentanyl Citrate [vandf]

48. Dtxsid80243933

49. Fentanyl Citrate [mart.]

50. Fentanyl Citrate [who-dd]

51. Fentanyl Citrate [ema Epar]

52. Fentanyl Citrate [green Book]

53. Akos024457504

54. Fentanyl Citrate [orange Book]

55. Fentanyl Citrate Cii [usp-rs]

56. Fentanyl Citrate [ep Monograph]

57. Fentanyl Citrate [usp Monograph]

58. Innovar Component Fentanyl Citrate

59. B5403

60. Fentanyl Citrate Component Of Innovar

61. D01399

62. 990f738

63. Q27104201

64. N-phenyl-n-[1-(2-phenylethyl)-4-piperidyl]propanamide Citrate

65. Fentanyl Citrate, European Pharmacopoeia (ep) Reference Standard

66. N-phenyl-n-[1-(2-phenylethyl)-4-piperidinyl]propanamide Citrate

67. Fentanyl Citrate, United States Pharmacopeia (usp) Reference Standard

68. Fentanyl Citrate Salt Solution, Drug Standard, 100 Mug/ml In Methanol: Tert-butanol (3:2)

69. N-(1-phenethylpiperidin-4-yl)-n-phenylpropionamide 2-hydroxypropane-1,2,3-tricarboxylate

70. N-phenyl-n-[1-(2-phenylethyl)piperidin-4-yl]propanamide 2-hydroxypropane-1,2,3-tricarboxylate

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 528.6 g/mol
Molecular Formula C28H36N2O8
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count9
Rotatable Bond Count11
Exact Mass528.24716611 g/mol
Monoisotopic Mass528.24716611 g/mol
Topological Polar Surface Area156 Ų
Heavy Atom Count38
Formal Charge0
Complexity618
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Drug Information
1 of 8  
Drug NameAbstral
PubMed HealthFentanyl
Drug ClassesAnalgesic, Anesthetic Adjunct
Drug LabelABSTRAL (fentanyl) sublingual tablet is a solid formulation of fentanyl citrate, a potent opioid analgesic intended for oral sublingual administration. ABSTRAL is formulated as a white tablet available in six strengths, distinguishable by the shape o...
Active IngredientFentanyl citrate
Dosage FormTablet
RouteSublingual
Strengtheq 0.1mg base; eq 0.8mg base; eq 0.3mg base; eq 0.6mg base; eq 0.4mg base; eq 0.2mg base
Market StatusPrescription
CompanyGalena Biopharma

2 of 8  
Drug NameFentanyl citrate
Drug LabelOral transmucosal fentanyl citrate is a solid formulation of fentanyl citrate, a potent opioid analgesic, intended for oral transmucosal administration. Oral transmucosal fentanyl citrate is formulated as a white to off-white solid drug matrix on a h...
Active IngredientFentanyl citrate
Dosage FormInjectable; Troche/lozenge
RouteTransmucosal; Injection
Strengtheq 0.05mg base/ml; eq 0.8mg base; eq 1.6mg base; eq 0.6mg base; eq 1.2mg base; eq 0.4mg base; eq 0.2mg base
Market StatusPrescription
CompanyHospira; Mallinckrodt; Par Pharm

3 of 8  
Drug NameFentanyl citrate preservative free
Active IngredientFentanyl citrate
Dosage FormInjectable
RouteInjection
Strengtheq 0.05mg base/ml
Market StatusPrescription
CompanyHospira; Hikma Maple

4 of 8  
Drug NameSublimaze preservative free
Active IngredientFentanyl citrate
Dosage FormInjectable
RouteInjection
Strengtheq 0.05mg base/ml
Market StatusPrescription
CompanyAkorn

5 of 8  
Drug NameAbstral
PubMed HealthFentanyl
Drug ClassesAnalgesic, Anesthetic Adjunct
Drug LabelABSTRAL (fentanyl) sublingual tablet is a solid formulation of fentanyl citrate, a potent opioid analgesic intended for oral sublingual administration. ABSTRAL is formulated as a white tablet available in six strengths, distinguishable by the shape o...
Active IngredientFentanyl citrate
Dosage FormTablet
RouteSublingual
Strengtheq 0.1mg base; eq 0.8mg base; eq 0.3mg base; eq 0.6mg base; eq 0.4mg base; eq 0.2mg base
Market StatusPrescription
CompanyGalena Biopharma

6 of 8  
Drug NameFentanyl citrate
Drug LabelOral transmucosal fentanyl citrate is a solid formulation of fentanyl citrate, a potent opioid analgesic, intended for oral transmucosal administration. Oral transmucosal fentanyl citrate is formulated as a white to off-white solid drug matrix on a h...
Active IngredientFentanyl citrate
Dosage FormInjectable; Troche/lozenge
RouteTransmucosal; Injection
Strengtheq 0.05mg base/ml; eq 0.8mg base; eq 1.6mg base; eq 0.6mg base; eq 1.2mg base; eq 0.4mg base; eq 0.2mg base
Market StatusPrescription
CompanyHospira; Mallinckrodt; Par Pharm

7 of 8  
Drug NameFentanyl citrate preservative free
Active IngredientFentanyl citrate
Dosage FormInjectable
RouteInjection
Strengtheq 0.05mg base/ml
Market StatusPrescription
CompanyHospira; Hikma Maple

8 of 8  
Drug NameSublimaze preservative free
Active IngredientFentanyl citrate
Dosage FormInjectable
RouteInjection
Strengtheq 0.05mg base/ml
Market StatusPrescription
CompanyAkorn

4.2 Drug Indication

Instanyl is indicated for the management of breakthrough pain in adults already receiving maintenance opioid therapy for chronic cancer pain. Breakthrough pain is a transitory exacerbation of pain that occurs on a background of otherwise controlled persistent pain.

Patients receiving maintenance opioid therapy are those who are taking at least 60 mg of oral morphine daily, at least 25 micrograms of transdermal fentanyl per hour, at least 30 mg oxycodone daily, at least 8 mg of oral hydromorphone daily or an equianalgesic dose of another opioid for a week or longer.


Treatment of acute pain, Prevention of acute pain


Acute pain


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Analgesics, Opioid

Compounds with activity like OPIATE ALKALOIDS, acting at OPIOID RECEPTORS. Properties include induction of ANALGESIA or NARCOSIS. (See all compounds classified as Analgesics, Opioid.)


Anesthetics, Intravenous

Ultrashort-acting anesthetics that are used for induction. Loss of consciousness is rapid and induction is pleasant, but there is no muscle relaxation and reflexes frequently are not reduced adequately. Repeated administration results in accumulation and prolongs the recovery time. Since these agents have little if any analgesic activity, they are seldom used alone except in brief minor procedures. (From AMA Drug Evaluations Annual, 1994, p174) (See all compounds classified as Anesthetics, Intravenous.)


Narcotics

Agents that induce NARCOSIS. Narcotics include agents that cause somnolence or induced sleep (STUPOR); natural or synthetic derivatives of OPIUM or MORPHINE o