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Also known as: 149845-06-7, Invirase, Fortovase, Saquinavir mesilate, Saquinavir, mesylate, Ro 31-8959/003
Molecular Formula
C39H54N6O8S
Molecular Weight
766.9  g/mol
InChI Key
IRHXGOXEBNJUSN-YOXDLBRISA-N
FDA UNII
UHB9Z3841A

Saquinavir Mesylate
An HIV protease inhibitor which acts as an analog of an HIV protease cleavage site. It is a highly specific inhibitor of HIV-1 and HIV-2 proteases, and also inhibits CYTOCHROME P-450 CYP3A.
1 2D Structure

Saquinavir Mesylate

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(2S)-N-[(2S,3R)-4-[(3S,4aS,8aS)-3-(tert-butylcarbamoyl)-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinolin-2-yl]-3-hydroxy-1-phenylbutan-2-yl]-2-(quinoline-2-carbonylamino)butanediamide;methanesulfonic acid
2.1.2 InChI
InChI=1S/C38H50N6O5.CH4O3S/c1-38(2,3)43-37(49)32-20-26-14-7-8-15-27(26)22-44(32)23-33(45)30(19-24-11-5-4-6-12-24)41-36(48)31(21-34(39)46)42-35(47)29-18-17-25-13-9-10-16-28(25)40-29;1-5(2,3)4/h4-6,9-13,16-18,26-27,30-33,45H,7-8,14-15,19-23H2,1-3H3,(H2,39,46)(H,41,48)(H,42,47)(H,43,49);1H3,(H,2,3,4)/t26-,27+,30-,31-,32-,33+;/m0./s1
2.1.3 InChI Key
IRHXGOXEBNJUSN-YOXDLBRISA-N
2.1.4 Canonical SMILES
CC(C)(C)NC(=O)C1CC2CCCCC2CN1CC(C(CC3=CC=CC=C3)NC(=O)C(CC(=O)N)NC(=O)C4=NC5=CC=CC=C5C=C4)O.CS(=O)(=O)O
2.1.5 Isomeric SMILES
CC(C)(C)NC(=O)[C@@H]1C[C@@H]2CCCC[C@@H]2CN1C[C@H]([C@H](CC3=CC=CC=C3)NC(=O)[C@H](CC(=O)N)NC(=O)C4=NC5=CC=CC=C5C=C4)O.CS(=O)(=O)O
2.2 Other Identifiers
2.2.1 UNII
UHB9Z3841A
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Invirase

2. Monomethanesulfonate, Saquinavir

3. Ro 31 8959

4. Ro 31-8959

5. Ro 318959

6. Saquinavir

7. Saquinavir Monomethanesulfonate

8. Saquinivir

2.3.2 Depositor-Supplied Synonyms

1. 149845-06-7

2. Invirase

3. Fortovase

4. Saquinavir Mesilate

5. Saquinavir, Mesylate

6. Ro 31-8959/003

7. Saquinavir Methanesulfonate Salt

8. Uhb9z3841a

9. Butanediamide, N1-[(1s,2r)-3-[(3s,4as,8as)-3-[[(1,1-dimethylethyl)amino]carbonyl]octahydro-2(1h)-isoquinolinyl]-2-hydroxy-1-(phenylmethyl)propyl]-2-[(2-quinolinylcarbonyl)amino]-, (2s)-, Methanesulfonate (1:1)

10. Chebi:32121

11. (2s)-n-[(2s,3r)-4-[(3s,4as,8as)-3-(tert-butylcarbamoyl)-3,4,4a,5,6,7,8,8a-octahydro-1h-isoquinolin-2-yl]-3-hydroxy-1-phenylbutan-2-yl]-2-(quinoline-2-carbonylamino)butanediamide;methanesulfonic Acid

12. (s)-n1-((2s,3r)-4-((3s,4as,8as)-3-(tert-butylcarbamoyl)octahydroisoquinolin-2(1h)-yl)-3-hydroxy-1-phenylbutan-2-yl)-2-(quinoline-2-carboxamido)succinamide Methanesulfonate

13. Ncgc00091469-01

14. Ro-318959003

15. Dsstox_cid_3835

16. Ro-31-8959/003

17. Saquinavir Mesilate (jan)

18. Dsstox_rid_77202

19. Dsstox_gsid_23835

20. Saquinavir Mesilate [jan]

21. Saquinavir Mesylate [usan]

22. Saquinavir Monomethanesulfonate Salt

23. Unii-uhb9z3841a

24. Saquinavir Mesylate [usan:usp]

25. Invirase (tn)

26. N1-{(1s,2r)-1-benzyl-3-[(3s,4as,8as)-3-[(tert-butylamino)carbonyl]octahydroisoquinolin-2(1h)-yl]-2-hydroxypropyl}-n2-(quinolin-2-ylcarbonyl)-l-aspartamide Methanesulfonate (salt)

27. Cas-149845-06-7

28. Saquinavir Mesylate (aids Initiative)

29. Sqv

30. Saquinavir Mesylate (usp)

31. Saquinavir Mesylate- Bio-x

32. Schembl42352

33. (s)-n-((alphas)-alpha-((1r)-2-((3s,4as,8as)-3-(tert-butylcarbamoyl)octahydro-2(1h)-isoquinolyl)-1-hydroxyethyl)phenethyl)-2-quinaldamidosuccinamide Monomethanesulfonate (salt)

34. Mls001401395

35. Chembl282042

36. Dtxsid9023835

37. Hms1571o10

38. Hms2051d04

39. Hms2098o10

40. Hms2231c15

41. Hms3715o10

42. Saquinavir Mesylate [vandf]

43. Saquinavir Mesilate [mart.]

44. Tox21_111137

45. Tox21_202533

46. Saquinavir Mesilate [who-dd]

47. Saquinavir Mesilate [who-ip]

48. Saquinavir Mesylate [usp-rs]

49. Akos015962362

50. Ac-1333

51. Ccg-100992

52. Ks-1110

53. Nc00242

54. Ncgc00260082-01

55. Saquinavir Mesylate [orange Book]

56. (2s)-n1[(1s,2r)-3-[(3s,4as,8as)-3-[[(1,1-dimethylethyl)amino]carbonyl]octahydro-2-(1h)-isoquinolinyl]-2-hydroxy-1-(phenylmethyl)propyl]-2-[(2-quinolinylcarbonyl)amino]butanediamide Mesylate

57. Bs164392

58. Butanediamide, N(sup 1)-(3-(3-(((1,1-dimethylethyl)amino)carbonyl)octahydro-2(1h)-isoquinolinyl)-2-hydroxy-1-(phenylmethyl)propyl)-2-((2-quinolinylcarbonyl)amino)-, (3s-(2(1r*(r*),2s*),3alpha,4abeta,8abeta))-, Monomethanesulfonate (salt)

59. Butanediamide, N1-((1s,2r)-3-((3s,4as,8as)-3-(((1,1-dimethylethyl)amino)carbonyl)octahydro-2(1h)-isoquinolinyl)-2-hydroxy-1-(phenylmethyl)propyl)-2-((2-quinolinylcarbonyl)amino)-, (2s)-, Monomethanesulfonate (salt)

60. R-56

61. Saquinavir Mesilate [ep Monograph]

62. Saquinavir Mesylate [usp Impurity]

63. Smr000469290

64. Saquinavir Mesylate [usp Monograph]

65. Saquinavir Methanesulfonate Salt [mi]

66. Ro-31-8959-003

67. Saquinavir Mesylate, >=98% (hplc), Powder

68. D01160

69. 845s067

70. Sr-01000763454

71. J-008634

72. Sr-01000763454-4

73. Q27114794

74. Saquinavir Mesilate, European Pharmacopoeia (ep) Reference Standard

75. Saquinavir Mesylate, United States Pharmacopeia (usp) Reference Standard

76. Saquinavir For System Suitability, European Pharmacopoeia (ep) Reference Standard

77. (2s)-n1-[(1s,2r)-3-[(3s,4as,8as)-3-[[(1,1-dimethylethyl)amino]carbonyl]octahydro-2(1h)-isoquinolinyl]-2-hydroxy-1-(phenylmethyl)propyl]-2-[(2-quinolinylcarbonyl)amino]butanediamide Methanesulfonate

78. (s)-n-((.alpha.s)-.alpha.-((1r)-2-((3s,4as,8as)-3-(tert-butylcarbamoyl)octahydro-2(1h)-isoquinolyl)-1-hydroxyethyl)phenethyl)-2-quinaldamidosuccinamide Monomethanesulfonate

79. (s)-n-((.alpha.s)-.alpha.-((1r)-2-((3s,4as,8as)-3-(tert-butylcarbamoyl)octahydro-2(1h)-isoquinolyl)-1-hydroxyethyl)phenethyl)-2-quinaldamidosuccinamide Monomethanesulphonate

80. Butanediamide, N(sup 1)-(3-(3-(((1,1-dimethylethyl)amino)carbonyl)octahydro-2(1h)-isoquinolinyl)-2-hydroxy-1-(phenylmethyl)propyl)-2-((2-quinolinylcarbonyl)amino)-, (3s-(2(1r*(r*),2s*),3.alpha.,4a.beta.,8a.beta.))-, Monomethanesulfonate

81. Butanediamide, N(sup 1)-(3-(3-(((1,1-dimethylethyl)amino)carbonyl)octahydro-2(1h)-isoquinolinyl)-2-hydroxy-1-(phenylmethyl)propyl)-2-((2-quinolinylcarbonyl)amino)-, (3s-(2(1r*(r*),2s*),3.alpha.,4a.beta.,8a.beta.))-, Monomethanesulphonate

82. N-t-butyl-decahydro-2-[2(r)-hydroxy-4-phenyl-3(s)-[[n-(2-quinolylcarbonyl)-l-asparaginyl]amino]butyl]-(4as,8as)-isoquinoline-3(s)-carboxamide Methanesulphonate

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 766.9 g/mol
Molecular Formula C39H54N6O8S
Hydrogen Bond Donor Count6
Hydrogen Bond Acceptor Count10
Rotatable Bond Count13
Exact Mass766.37238388 g/mol
Monoisotopic Mass766.37238388 g/mol
Topological Polar Surface Area230 Ų
Heavy Atom Count54
Formal Charge0
Complexity1230
Isotope Atom Count0
Defined Atom Stereocenter Count6
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 2  
Drug NameInvirase
PubMed HealthSaquinavir (By mouth)
Drug ClassesAntiretroviral Agent
Drug LabelINVIRASE brand of saquinavir mesylate is an inhibitor of the human immunodeficiency virus (HIV) protease. INVIRASE is available as light brown and green, opaque hard gelatin capsules for oral administration in a 200-mg strength (as saquinavir free ba...
Active IngredientSaquinavir mesylate
Dosage FormTablet; Capsule
RouteOral
Strengtheq 500mg base; eq 200mg base
Market StatusPrescription
CompanyHoffman La Roche; Hoffmann La Roche

2 of 2  
Drug NameInvirase
PubMed HealthSaquinavir (By mouth)
Drug ClassesAntiretroviral Agent
Drug LabelINVIRASE brand of saquinavir mesylate is an inhibitor of the human immunodeficiency virus (HIV) protease. INVIRASE is available as light brown and green, opaque hard gelatin capsules for oral administration in a 200-mg strength (as saquinavir free ba...
Active IngredientSaquinavir mesylate
Dosage FormTablet; Capsule
RouteOral
Strengtheq 500mg base; eq 200mg base
Market StatusPrescription
CompanyHoffman La Roche; Hoffmann La Roche

4.2 Drug Indication

Invirase is indicated for the treatment of HIV-1-infected adult patients. Invirase should only be given in combination with ritonavir and other antiretroviral medicinal products.


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Cytochrome P-450 CYP3A Inhibitors

Drugs and compounds which inhibit or antagonize the biosynthesis or actions of CYTOCHROME P-450 CYP3A. (See all compounds classified as Cytochrome P-450 CYP3A Inhibitors.)


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.)


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
HIV Protease Inhibitors [MoA]; Protease Inhibitor [EPC]; Cytochrome P450 3A Inhibitors [MoA]
5.3 ATC Code

J05AE01


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