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    Chemistry

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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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