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Fosamprenavir

Fosamprenavir

Synopsis, Chemistry

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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

Fosamprenavir

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 Formula	C₂₅H₃₄CaN₃O₉PS
Molecular Weight	623.7 g/mol
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	11
Rotatable Bond Count	13
Exact Mass	623.1379287 g/mol
Monoisotopic Mass	623.1379287 g/mol
Topological Polar Surface Area	192 Å²
Heavy Atom Count	40
Formal Charge	0
Complexity	901
Isotope Atom Count	0
Defined Atom Stereocenter Count	3
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Lexiva
PubMed Health	Fosamprenavir (By mouth)
Drug Classes	Antiretroviral Agent
Drug Label	LEXIVA (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 Ingredient	Fosamprenavir calcium
Dosage Form	Tablet; Suspension
Route	Oral
Strength	eq 700mg base; eq 50mg base/ml
Market Status	Prescription
Company	Viiv Hlthcare

2 of 2
Drug Name	Lexiva
PubMed Health	Fosamprenavir (By mouth)
Drug Classes	Antiretroviral Agent
Drug Label	LEXIVA (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 Ingredient	Fosamprenavir calcium
Dosage Form	Tablet; Suspension
Route	Oral
Strength	eq 700mg base; eq 50mg base/ml
Market Status	Prescription
Company	Viiv 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

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