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    Fosamprenavir

    ACTIVE PHARMA INGREDIENTS

    INTERMEDIATES

    FINISHED DOSAGE FORMULATIONS

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    2D Structure
    Also known as: 226700-81-8, Fosamprenavir calcium salt, Lexiva, Telzir, Fosamprenavir (calcium salt), Fosamprenavir calcium [usan]
    Molecular Formula
    C25H34CaN3O9PS
    Molecular Weight
    623.7  g/mol
    InChI Key
    PMDQGYMGQKTCSX-HQROKSDRSA-L
    FDA UNII
    ID1GU2627N
    Fosamprenavir Calcium is the calcium salt form of fosamprenavir, prodrug of amprenavir, and a human immunodeficiency virus (HIV) protease inhibitor with antiviral property. Fosamprenavir is converted to amprenavir by cellular phosphatases in the epithelial cells of the intestine. Then amprenavir binds to the active site of HIV-1 protease, thereby preventing the proteolytic cleavage of viral Gag-Pol polypeptide into individual functional proteins, thereby leading to the formation of immature non-infectious viral particles.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    calcium;[(2R,3S)-1-[(4-aminophenyl)sulfonyl-(2-methylpropyl)amino]-3-[[(3S)-oxolan-3-yl]oxycarbonylamino]-4-phenylbutan-2-yl] phosphate
    2.1.2 InChI
    InChI=1S/C25H36N3O9PS.Ca/c1-18(2)15-28(39(33,34)22-10-8-20(26)9-11-22)16-24(37-38(30,31)32)23(14-19-6-4-3-5-7-19)27-25(29)36-21-12-13-35-17-21;/h3-11,18,21,23-24H,12-17,26H2,1-2H3,(H,27,29)(H2,30,31,32);/q;+2/p-2/t21-,23-,24+;/m0./s1
    2.1.3 InChI Key
    PMDQGYMGQKTCSX-HQROKSDRSA-L
    2.1.4 Canonical SMILES
    CC(C)CN(CC(C(CC1=CC=CC=C1)NC(=O)OC2CCOC2)OP(=O)([O-])[O-])S(=O)(=O)C3=CC=C(C=C3)N.[Ca+2]
    2.1.5 Isomeric SMILES
    CC(C)CN(C[C@H]([C@H](CC1=CC=CC=C1)NC(=O)O[C@H]2CCOC2)OP(=O)([O-])[O-])S(=O)(=O)C3=CC=C(C=C3)N.[Ca+2]
    2.2 Other Identifiers
    2.2.1 UNII
    ID1GU2627N
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. (3-(((4-aminophenyl)sulfonyl)(2-methylpropyl)amino)-1-(phenylmethyl)-2-(phosphonooxy)propyl)carbamic Acid C-(tetrahydro-3-furanyl) Ester

    2. Fos-amprenavir

    3. Fosamprenavir

    4. Fosamprenavir Sodium

    5. Gw 433908

    6. Gw 433908a

    7. Gw 433908g

    8. Gw 908

    9. Gw-433908

    10. Gw-433908a

    11. Gw-433908g

    12. Gw-908

    13. Gw433908

    14. Gw433908g

    15. Lexiva

    16. Telzir

    17. Vx 175

    18. Vx-175

    2.3.2 Depositor-Supplied Synonyms

    1. 226700-81-8

    2. Fosamprenavir Calcium Salt

    3. Lexiva

    4. Telzir

    5. Fosamprenavir (calcium Salt)

    6. Fosamprenavir Calcium [usan]

    7. Gw433908g

    8. Gw 433908g

    9. Gw-433908g

    10. Id1gu2627n

    11. Lexiva (tn)

    12. Calcium;[(2r,3s)-1-[(4-aminophenyl)sulfonyl-(2-methylpropyl)amino]-3-[[(3s)-oxolan-3-yl]oxycarbonylamino]-4-phenylbutan-2-yl] Phosphate

    13. Carbamic Acid, ((1s,2r)-3-(((4-aminophenyl)sulfonyl)(2-methylpropyl)amino)-1-(phenylmethyl)-2-(phosphonooxy)propyl)-, C-((3s)-tetrahydro-3-furanyl) Ester, Calcium Salt (1:1)

    14. Fosamprenavir Calcium (usan)

    15. Amprenavir Phosphate Calcium

    16. Calcium (2r,3s)-1-(4-amino-n-isobutylphenylsulfonamido)-4-phenyl-3-(((((s)-tetrahydrofuran-3-yl)oxy)carbonyl)amino)butan-2-yl Phosphate

    17. Unii-id1gu2627n

    18. Telzir (tn)

    19. Ncgc00168771-01

    20. Dsstox_cid_26777

    21. Dsstox_rid_81896

    22. Dsstox_gsid_46777

    23. ((3s)oxolan-3-yloxy)-n-((1s,2r)-3-(((4-aminophenyl)sulfonyl)(2-methylpropyl)amino)-1-benzyl-2-(phosphonooxy)propyl)carboxamide Calcium Salt

    24. Mls006012033

    25. Schembl1649283

    26. Chembl1200734

    27. Dtxsid0046777

    28. Amy6787

    29. Tox21_112632

    30. Fosamprenavir Calcium [mart.]

    31. Akos015950832

    32. Fosamprenavir Calcium [who-dd]

    33. Cs-1411

    34. Fosamprenavir Calcium Salt [mi]

    35. Fosamprenavir Calcium [ema Epar]

    36. Fosamprenavir Calcium, >=98% (hplc)

    37. (3s)-tetrahydro-3-furyl ((alphas)-alpha-((1r)-1-hydroxy-2-(n(sup 1)-isobutylsulfanilamido)ethyl)phenethyl)carbamate, Calcium Phosphate (ester) (1:1)

    38. As-82030

    39. Carbamic Acid, ((1s,2r)-3-(((4-aminophenyl)sulfonyl)(2-methylpropyl)amino)-1-(phenylmethyl)-2-(phosphonooxy)propyl)-, C-((3s)-tetrahydro-3-furanyl) Ester, Calcium Salt

    40. Hy-17431

    41. Smr004703563

    42. Fosamprenavir Calcium [orange Book]

    43. Cas-226700-81-8

    44. C74170

    45. D03835

    46. Q27280661

    47. (3s)-tetrahydro-3-furyl ((.alpha.s)-.alpha.-((1r)-1-hydroxy-2-(n(sup 1)-isobutylsulfanilamido)ethyl)phenethyl)carbamate, Calcium Phosphate (ester) (1:1)

    48. (3s)-tetrahydro-3-furyl ((.alpha.s)-.alpha.-((1r)-1-hydroxy-2-(n1-isobutylsulfanilamido)ethyl)phenethyl)carbamate, Calcium Phosphate (ester) (1:1)

    49. Calcium(2r,3s)-1-(4-amino-n-isobutylphenylsulfonamido)-4-phenyl-3-(((((s)-tetrahydrofuran-3-yl)oxy)carbonyl)amino)butan-2-ylphosphate

    2.4 Create Date
    2005-08-08
    3 Chemical and Physical Properties
    Molecular Weight 623.7 g/mol
    Molecular Formula C25H34CaN3O9PS
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count11
    Rotatable Bond Count13
    Exact Mass623.1379287 g/mol
    Monoisotopic Mass623.1379287 g/mol
    Topological Polar Surface Area192 Ų
    Heavy Atom Count40
    Formal Charge0
    Complexity901
    Isotope Atom Count0
    Defined Atom Stereocenter Count3
    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 NameLexiva
    PubMed HealthFosamprenavir (By mouth)
    Drug ClassesAntiretroviral Agent
    Drug LabelLEXIVA (fosamprenavir calcium) is a prodrug of amprenavir, an inhibitor of HIV protease. The chemical name of fosamprenavir calcium is (3S)-tetrahydrofuran-3-yl (1S,2R)-3-[[(4-aminophenyl) sulfonyl](isobutyl)amino]-1-benzyl-2-(phosphonooxy) propylcar...
    Active IngredientFosamprenavir calcium
    Dosage FormTablet; Suspension
    RouteOral
    Strengtheq 700mg base; eq 50mg base/ml
    Market StatusPrescription
    CompanyViiv Hlthcare

    2 of 2  
    Drug NameLexiva
    PubMed HealthFosamprenavir (By mouth)
    Drug ClassesAntiretroviral Agent
    Drug LabelLEXIVA (fosamprenavir calcium) is a prodrug of amprenavir, an inhibitor of HIV protease. The chemical name of fosamprenavir calcium is (3S)-tetrahydrofuran-3-yl (1S,2R)-3-[[(4-aminophenyl) sulfonyl](isobutyl)amino]-1-benzyl-2-(phosphonooxy) propylcar...
    Active IngredientFosamprenavir calcium
    Dosage FormTablet; Suspension
    RouteOral
    Strengtheq 700mg base; eq 50mg base/ml
    Market StatusPrescription
    CompanyViiv Hlthcare

    4.2 Drug Indication

    Telzir in combination with low-dose ritonavir is indicated for the treatment of human-immunodeficiency-virus-type-1-infected adults, adolescents and children of six years and above in combination with other antiretroviral medicinal products.

    In moderately antiretroviral-experienced adults, Telzir in combination with low-dose ritonavir has not been shown to be as effective as lopinavir / ritonavir. No comparative studies have been undertaken in children or adolescents.

    In heavily pretreated patients, the use of Telzir in combination with low-dose ritonavir has not been sufficiently studied.

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

    5 Pharmacology and Biochemistry
    5.1 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.)

    Anti-HIV Agents

    Agents used to treat AIDS and/or stop the spread of the HIV infection. These do not include drugs used to treat symptoms or opportunistic infections associated with AIDS. (See all compounds classified as Anti-HIV Agents.)

    5.2 FDA Pharmacological Classification
    5.2.1 Pharmacological Classes
    Cytochrome P450 3A4 Inhibitors [MoA]; HIV Protease Inhibitors [MoA]; P-Glycoprotein Inducers [MoA]; Protease Inhibitor [EPC]; Cytochrome P450 3A4 Inducers [MoA]
    5.3 ATC Code

    J05AE07