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Also known as: 159989-64-7, Viracept, Ag-1343, Viracept (tn), Nelfinavir (inn), Ho3ogh5d7i

Molecular Formula

C₃₂H₄₅N₃O₄S

Molecular Weight

567.8 g/mol

InChI Key

QAGYKUNXZHXKMR-HKWSIXNMSA-N

FDA UNII

HO3OGH5D7I

A potent HIV protease inhibitor. It is used in combination with other antiviral drugs in the treatment of HIV in both adults and children.

Nelfinavir is a Protease Inhibitor. The mechanism of action of nelfinavir is as a HIV Protease Inhibitor, and Cytochrome P450 3A Inhibitor.

1 2D Structure

Nelfinavir

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(3S,4aS,8aS)-N-tert-butyl-2-[(2R,3R)-2-hydroxy-3-[(3-hydroxy-2-methylbenzoyl)amino]-4-phenylsulfanylbutyl]-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinoline-3-carboxamide

2.1.2 InChI

InChI=1S/C32H45N3O4S/c1-21-25(15-10-16-28(21)36)30(38)33-26(20-40-24-13-6-5-7-14-24)29(37)19-35-18-23-12-9-8-11-22(23)17-27(35)31(39)34-32(2,3)4/h5-7,10,13-16,22-23,26-27,29,36-37H,8-9,11-12,17-20H2,1-4H3,(H,33,38)(H,34,39)/t22-,23+,26-,27-,29+/m0/s1

2.1.3 InChI Key

QAGYKUNXZHXKMR-HKWSIXNMSA-N

2.1.4 Canonical SMILES

CC1=C(C=CC=C1O)C(=O)NC(CSC2=CC=CC=C2)C(CN3CC4CCCCC4CC3C(=O)NC(C)(C)C)O

2.1.5 Isomeric SMILES

CC1=C(C=CC=C1O)C(=O)N[C@@H](CSC2=CC=CC=C2)[C@@H](CN3C[C@H]4CCCC[C@H]4C[C@H]3C(=O)NC(C)(C)C)O

2.2 Other Identifiers

2.2.1 UNII

HO3OGH5D7I

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Ag 1343

2. Ag-1343

3. Ag1343

4. Mesylate, Nelfinavir

5. Monomethane Sulfonate, Nelfinavir

6. Nelfinavir Mesylate

7. Nelfinavir Monomethane Sulfonate

8. Sulfonate, Nelfinavir Monomethane

9. Viracept

2.3.2 Depositor-Supplied Synonyms

1. 159989-64-7

2. Viracept

3. Ag-1343

4. Viracept (tn)

5. Nelfinavir (inn)

6. Ho3ogh5d7i

7. (3s,4as,8as)-n-tert-butyl-2-[(2r,3r)-2-hydroxy-3-[(3-hydroxy-2-methylbenzoyl)amino]-4-phenylsulfanylbutyl]-3,4,4a,5,6,7,8,8a-octahydro-1h-isoquinoline-3-carboxamide

8. Nsc-747167

9. Chebi:7496

10. 1un

11. 2-[2-hydroxy-3-(3-hydroxy-2-methyl-benzoylamino)-4-phenyl Sulfanyl-butyl]-decahydro-isoquinoline-3-carboxylic Acid Tert-butylamide

12. Nlf

13. Nelfinavir [inn]

14. Nelfinavir [inn:ban]

15. Nfv

16. (3s,4as,8as)-n-(tert-butyl)-2-((2r,3r)-2-hydroxy-3-(3-hydroxy-2-methylbenzamido)-4-(phenylthio)butyl)decahydroisoquinoline-3-carboxamide

17. Chembl1205

18. (3s,4as,8as)-n-tert-butyl-2-[(2r,3r)-2-hydroxy-3-[(3-hydroxy-2-methyl-benzoyl)amino]-4-phenylsulfanyl-butyl]-3,4,4a,5,6,7,8,8a-octahydro-1h-isoquinoline-3-carboxamide

19. (3s,4as,8as)-n-tert-butyl-2-[(2r,3r)-2-hydroxy-3-[(3-hydroxy-2-methylphenyl)formamido]-4-(phenylsulfanyl)butyl]-decahydroisoquinoline-3-carboxamide

20. 3-isoquinolinecarboxamide, N-(1,1-dimethylethyl)decahydro-2-((2r,3r)-2-hydroxy-3-((3-hydroxy-2-methylbenzoyl)amino)-4-(phenylthio)butyl)-, (3s,4as,8as)-

21. Smr000596515

22. Nsc722664

23. Ncgc00090782-03

24. Nelfinavir Mesylate Ag1343

25. Unii-ho3ogh5d7i

26. Met-sdf-1.beta. & Nelfinavir

27. 1ohr

28. 3-isoquinolinecarboxamide, N-(1,1-dimethylethyl)decahydro-2-[(2r,3r)-2-hydroxy-3-[(3-hydroxy-2-methylbenzoyl)amino]-4-(phenylthio)butyl]-, (3s,4as,8as)-

29. (3s-(2(2s*,3s*),3alpha,4abeta,8abeta))-n-(1,1-dimethylethyl)decahydro-2-(2-hydroxy-3-((3-hydroxy-2-methylbenzoyl)amino)-4-(phenylthio)butyl)-3-isoquinolinecarboxamide

30. Nelfinavir [mi]

31. Nelfinavir [vandf]

32. Chembl584

33. Nelfinavir [who-dd]

34. Bidd:pxr0143

35. Schembl38218

36. Mls001195634

37. Mls001304729

38. N-(1,1-dimethylethyl)decahydro-2-(2-hydroxy-3-((3-hydroxy-2-methylbenzoyl)amino)-4-(phenylthio)butyl)-3-isoquinolinecarboxamide (3s-(2(2s*,3s*),3alpha,4abeta,8abeta))-

39. Bidd:gt0395

40. Nelfinavir [ema Epar]

41. Dtxsid5035080

42. Gtpl11090

43. Hms2232i04

44. Met-stromal Cell-derived Factor-1.beta. (human) & Nelfinavir

45. Zinc3833846

46. Bdbm50061306

47. Mfcd01938163

48. Nsc747167

49. Akos000280862

50. Am84529

51. Cs-0677

52. Db00220

53. Nsc 747167

54. Mrf-0000208

55. Ncgc00090782-04

56. Ncgc00090782-05

57. Ncgc00090782-17

58. 3-isoquinolinecarboxamide, N-(1,1-dimethylethyl)decahydro-2-(2-hydroxy-3-((3-hydroxy-2-methylbenzoyl)amino)-4-(phenylthio)butyl)-, (3s-(2-(2s*,3s*),3-alpha,4a-beta,8a-beta))-

59. Ac-20032

60. As-75258

61. Hy-15287

62. 89n647

63. C07257

64. C73027

65. D08259

66. Ab00698259-15

67. A810095

68. A810096

69. Q423366

70. (3s, 4as, 8as)-2-[(2r, 3r)-2-hydroxy-3-(3-hydroxy-2-methyl-benzoylamino)-4-phenylthiobutyl]decahydroisoquinoline-3-carboxylic Acid T-butylamide

71. (3s, 4as, 8as)-2-[(2r, 3r)-2-hydroxy-3-(3-hydroxy-2-methylbenzoylamino)-4-phenylthiobutyl]decahydroisoquinoline-3-carboxylic Acid T-butylamide

72. (3s,4abeta,8abeta)-n-tert-butyl-2-[(2r,3r)-2-hydroxy-3-(2-methyl-3-hydroxybenzoylamino)-4-(phenylthio)butyl]decahydroisoquinoline-3alpha-carboxamide

73. (3s,4as,8as)-2-[(2r,3r)-2-hydroxy-3-(3-hydroxy-2-methyl-benzoylamino)-4-phenylsulfanyl-butyl]-decahydro-isoquinoline-3-carboxylic Acid Tert-butylamide; Compound With Methanesulfonic Acid

74. (3s,4as,8as)-2-[(2r,3r)-2-hydroxy-3-(3-hydroxy-2-methylbenzoylamino)-4-phenylthiobutyl]decahydroisoquinoline-3-carboxylic Acid T-butylamide

75. (3s,4as,8as)-n-tert-butyl-2-[(2r,3r)-2-hydroxy-3-[(3-hydroxy-2-methylbenzoyl)amino]-4-(phenylsulfanyl)butyl]decahydroisoquinoline-3-carboxamide

76. (3s,4as,8as)-n-tert-butyl-2-[(2r,3r)-2-hydroxy-3-[[(3-hydroxy-2-methylphenyl)-oxomethyl]amino]-4-(phenylthio)butyl]-3,4,4a,5,6,7,8,8a-octahydro-1h-isoquinoline-3-carboxamide

77. (3s,4as,8as)-n-tert-butyl-2-[(2r,3r)-2-hydroxy-3-{[(3-hydroxy-2-methylphenyl)carbonyl]amino}-4-(phenylsulfanyl)butyl]decahydroisoquinoline-3-carboxamide

78. (3s,4as,8as)-n-tert-butyl-2-[(2r,3r)-3-[(2-methyl-3-oxidanyl-phenyl)carbonylamino]-2-oxidanyl-4-phenylsulfanyl-butyl]-3,4,4a,5,6,7,8,8a-octahydro-1h-isoquinoline-3-carboxamide

79. 3-isoquinolinecarboxamide, N-(1,1-dimethylethyl)decahydro-2- [(2r,3r)-2-hydroxy-3-[(3-hydroxy-2-methylbenzoyl)amino]-4-(phenylthio)butyl]-, (3s,4as,8as)-

80. 3-isoquinolinecarboxamide,1-dimethyl Ethyl)decahydro-2-[(2r,3r)-2-hydroxy-3-[(3-hydroxy-2-methylbenzoyl)amino]-4-(phenylthio)butyl]-, (3s,4as,8as)-

81. 3-isoquinolinecarboxamide,1-dimethylethyl)decahydro-2-[2-hydroxy-3-[(3-hydroxy-2-methylbenzoyl)amino]-4-(phenylthio)butyl]-, [3s-[2(2s*,3s*),3.alpha.,4a.beta.,8a.beta.]]-

82. N-(tert-butyl)-2-(2-hydroxy-3-(3-hydroxy-2-methylbenzamido)-4-(phenylthio)butyl)decahydroisoquinoline-3-carboxamide

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₃₂H₄₅N₃O₄S
Molecular Weight	567.8 g/mol
XLogP3	5.7
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	10
Exact Mass	567.31307810 g/mol
Monoisotopic Mass	567.31307810 g/mol
Topological Polar Surface Area	127 Å²
Heavy Atom Count	40
Formal Charge	0
Complexity	830
Isotope Atom Count	0
Defined Atom Stereocenter Count	5
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Viracept
PubMed Health	Nelfinavir (By mouth)
Drug Classes	Antiretroviral Agent
Drug Label	VIRACEPT (nelfinavir mesylate) is an inhibitor of the human immunodeficiency virus (HIV) protease.VIRACEPT Tablets are available for oral administration as a light blue, capsule-shaped tablet with a clear film coating in 250 mg strength (as nelfi...
Active Ingredient	Nelfinavir mesylate
Dosage Form	Tablet
Route	Oral
Strength	eq 625mg base; eq 250mg base
Market Status	Prescription
Company	Agouron

2 of 2
Drug Name	Viracept
PubMed Health	Nelfinavir (By mouth)
Drug Classes	Antiretroviral Agent
Drug Label	VIRACEPT (nelfinavir mesylate) is an inhibitor of the human immunodeficiency virus (HIV) protease.VIRACEPT Tablets are available for oral administration as a light blue, capsule-shaped tablet with a clear film coating in 250 mg strength (as nelfi...
Active Ingredient	Nelfinavir mesylate
Dosage Form	Tablet
Route	Oral
Strength	eq 625mg base; eq 250mg base
Market Status	Prescription
Company	Agouron

4.2 Drug Indication

Used in combination with other antiviral drugs in the treatment of HIV in both adults and children.

FDA Label

Viracept is indicated in antiretroviral combination treatment of human-immunodeficiency-virus (HIV-1)-infected adults, adolescents and children of three years of age and older.

In protease-inhibitor (PI)-experienced patients, the choice of nelfinavir should be based on individual viral resistance testing and treatment history.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Nelfinavir is a protease inhibitor with activity against Human Immunodeficiency Virus Type 1 (HIV-1). Protease inhibitors block the part of HIV called protease. HIV-1 protease is an enzyme required for the proteolytic cleavage of the viral polyprotein precursors into the individual functional proteins found in infectious HIV-1. Nelfinavir binds to the protease active site and inhibits the activity of the enzyme. This inhibition prevents cleavage of the viral polyproteins resulting in the formation of immature non-infectious viral particles. Protease inhibitors are almost always used in combination with at least two other anti-HIV drugs.

5.2 MeSH Pharmacological Classification

HIV Protease Inhibitors

Inhibitors of HIV PROTEASE, an enzyme required for production of proteins needed for viral assembly. (See all compounds classified as HIV Protease Inhibitors.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

NELFINAVIR

5.3.2 FDA UNII

HO3OGH5D7I

5.3.3 Pharmacological Classes

Mechanisms of Action [MoA] - Cytochrome P450 3A Inhibitors

5.4 ATC Code

J05AE04

J - Antiinfectives for systemic use

J05 - Antivirals for systemic use

J05A - Direct acting antivirals

J05AE - Protease inhibitors

J05AE04 - Nelfinavir

5.5 Absorption, Distribution and Excretion

Absorption

Well absorbed following oral administration.

Route of Elimination

The terminal half-life in plasma was typically 3.5 to 5 hours. The majority (87%) of an oral 750 mg dose containing 14C-nelfinavir was recovered in the feces; fecal radioactivity consisted of numerous oxidative metabolites (78%) and unchanged nelfinavir (22%). Only 12% of the dose was recovered in urine, of which unchanged nelfinavir was the major component.

Volume of Distribution

2 to 7 L/kg

5.6 Metabolism/Metabolites

Primarily hepatic via cytochrome P450 (CYP450) enzymes. CYP3A and CYP2C19 appear to be the predominant enzymes that metabolize nelfinavir in humans. One major and several minor metabolites are found in plasma; the major oxidative metabolite has in vitro antiviral activity comparable to that of the parent drug.

Nelfinavir has known human metabolites that include 3,4-Dihydroxynelfinavir and Nelfinavir hydroxyl-t- butylamide.

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

5.7 Biological Half-Life

3.5 - 5 hours

5.8 Mechanism of Action

Nelfinavir inhibits the HIV viral proteinase enzyme which prevents cleavage of the gag-pol polyprotein, resulting in noninfectious, immature viral particles.

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