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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
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 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


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ABOUT THIS PAGE

FOSAMPRENAVIR CALCIUM Manufacturers

A FOSAMPRENAVIR CALCIUM manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of FOSAMPRENAVIR CALCIUM, including repackagers and relabelers. The FDA regulates FOSAMPRENAVIR CALCIUM manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. FOSAMPRENAVIR CALCIUM API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

click here to find a list of FOSAMPRENAVIR CALCIUM manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

FOSAMPRENAVIR CALCIUM Suppliers

A FOSAMPRENAVIR CALCIUM supplier is an individual or a company that provides FOSAMPRENAVIR CALCIUM active pharmaceutical ingredient (API) or FOSAMPRENAVIR CALCIUM finished formulations upon request. The FOSAMPRENAVIR CALCIUM suppliers may include FOSAMPRENAVIR CALCIUM API manufacturers, exporters, distributors and traders.

click here to find a list of FOSAMPRENAVIR CALCIUM suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

FOSAMPRENAVIR CALCIUM USDMF

A FOSAMPRENAVIR CALCIUM DMF (Drug Master File) is a document detailing the whole manufacturing process of FOSAMPRENAVIR CALCIUM active pharmaceutical ingredient (API) in detail. Different forms of FOSAMPRENAVIR CALCIUM DMFs exist exist since differing nations have different regulations, such as FOSAMPRENAVIR CALCIUM USDMF, ASMF (EDMF), JDMF, CDMF, etc.

A FOSAMPRENAVIR CALCIUM DMF submitted to regulatory agencies in the US is known as a USDMF. FOSAMPRENAVIR CALCIUM USDMF includes data on FOSAMPRENAVIR CALCIUM's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The FOSAMPRENAVIR CALCIUM USDMF is kept confidential to protect the manufacturer’s intellectual property.

click here to find a list of FOSAMPRENAVIR CALCIUM suppliers with USDMF on PharmaCompass.

FOSAMPRENAVIR CALCIUM WC

A FOSAMPRENAVIR CALCIUM written confirmation (FOSAMPRENAVIR CALCIUM WC) is an official document issued by a regulatory agency to a FOSAMPRENAVIR CALCIUM manufacturer, verifying that the manufacturing facility of a FOSAMPRENAVIR CALCIUM active pharmaceutical ingredient (API) adheres to the Good Manufacturing Practices (GMP) regulations of the importing country. When exporting FOSAMPRENAVIR CALCIUM APIs or FOSAMPRENAVIR CALCIUM finished pharmaceutical products to another nation, regulatory agencies frequently require a FOSAMPRENAVIR CALCIUM WC (written confirmation) as part of the regulatory process.

click here to find a list of FOSAMPRENAVIR CALCIUM suppliers with Written Confirmation (WC) on PharmaCompass.

FOSAMPRENAVIR CALCIUM NDC

National Drug Code is a comprehensive database maintained by the FDA that contains information on all drugs marketed in the US. This directory includes information about finished drug products, unfinished drug products, and compounded drug products, including those containing FOSAMPRENAVIR CALCIUM as an active pharmaceutical ingredient (API).

Finished drug products

The FDA updates the NDC directory daily. The NDC numbers for FOSAMPRENAVIR CALCIUM API and other APIs are published in this directory by the FDA.

Unfinished drugs

The NDC unfinished drugs database includes product listing information submitted for all unfinished drugs, such as active pharmaceutical ingredients (APIs), drugs intended for further processing and bulk drug substances for compounding.

Pharmaceutical companies that manufacture FOSAMPRENAVIR CALCIUM as an active pharmaceutical ingredient (API) must furnish the FDA with an updated record of all drugs that they produce, prepare, propagate, compound, or process for commercial distribution in the US at their facilities.

Compounded drug products

The NDC directory also contains data on finished compounded human drug products that contain FOSAMPRENAVIR CALCIUM and are produced by outsourcing facilities. While these outsourcing facilities are not mandated to assign a FOSAMPRENAVIR CALCIUM NDC to their finished compounded human drug products, they may choose to do so.

click here to find a list of FOSAMPRENAVIR CALCIUM suppliers with NDC on PharmaCompass.

FOSAMPRENAVIR CALCIUM GMP

FOSAMPRENAVIR CALCIUM Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of FOSAMPRENAVIR CALCIUM GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right FOSAMPRENAVIR CALCIUM GMP manufacturer or FOSAMPRENAVIR CALCIUM GMP API supplier for your needs.

FOSAMPRENAVIR CALCIUM CoA

A FOSAMPRENAVIR CALCIUM CoA (Certificate of Analysis) is a formal document that attests to FOSAMPRENAVIR CALCIUM's compliance with FOSAMPRENAVIR CALCIUM specifications and serves as a tool for batch-level quality control.

FOSAMPRENAVIR CALCIUM CoA mostly includes findings from lab analyses of a specific batch. For each FOSAMPRENAVIR CALCIUM CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

FOSAMPRENAVIR CALCIUM may be tested according to a variety of international standards, such as European Pharmacopoeia (FOSAMPRENAVIR CALCIUM EP), FOSAMPRENAVIR CALCIUM JP (Japanese Pharmacopeia) and the US Pharmacopoeia (FOSAMPRENAVIR CALCIUM USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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