Fosamprenavir (Calcium Salt)

Modify Date: 2025-08-21 17:44:02

Fosamprenavir (Calcium Salt) Structure
Fosamprenavir (Calcium Salt) structure
Common Name Fosamprenavir (Calcium Salt)
CAS Number 226700-81-8 Molecular Weight 623.669
Density N/A Boiling Point N/A
Molecular Formula C25H34CaN3O9PS Melting Point 282-284ºC
MSDS N/A Flash Point N/A

 Use of Fosamprenavir (Calcium Salt)


GW433908 is a phosphate ester prodrug of the antiretroviral protease inhibitor amprenavir, with improved solubility over the parent molecule and a potential for reduced pill burden on current dosing regimens; GW433908G is the calcium salt of the prodrug.IC50 Value:Target: HIV Proteasein vitro: There were no significant changes in buprenorphine or PI plasma levels and no significant changes in medication adverse effects or opioid withdrawal. Increased concentrations of the inactive metabolite buprenorphine-3-glucuronide suggested that darunavir-ritonavir and fosamprenavir-ritonavir induced glucuronidation of buprenorphine[1].in vivo: Fosamprenavir-ritonavir administered with methadone did not alter plasma amprenavir pharmacokinetics compared with historical control data; nor did it alter the unbound R-methadone at 2 and 6 hours after methadone dosing. Pharmacodynamic indexes remained essentially unchanged after adding fosamprenavir-ritonavir to methadone [2]. After a high-fat meal compared with fasting, (1) the bioavailability of GW433908G suspension was decreased by 20% and Cmax by 41%, and (2) for GW433908G tablets, there was no influence on AUC(12% lower Cmax). After a low-fat meal compared with fasting, (1) there was bioequivalence for GW433908G tablets, but (2) bioavailability was decreased by 23% for amprenavir capsules (Cmax was also lower, by 46%) [3].Clinical trial: Study of an Investigational Regimen Including FDA Approved HIV Drugs In HIV-Infected Pediatric Subjects. Phase 2

 Names

Name Fosamprenavir calcium
Synonym More Synonyms

 Fosamprenavir (Calcium Salt) Biological Activity

Description GW433908 is a phosphate ester prodrug of the antiretroviral protease inhibitor amprenavir, with improved solubility over the parent molecule and a potential for reduced pill burden on current dosing regimens; GW433908G is the calcium salt of the prodrug.IC50 Value:Target: HIV Proteasein vitro: There were no significant changes in buprenorphine or PI plasma levels and no significant changes in medication adverse effects or opioid withdrawal. Increased concentrations of the inactive metabolite buprenorphine-3-glucuronide suggested that darunavir-ritonavir and fosamprenavir-ritonavir induced glucuronidation of buprenorphine[1].in vivo: Fosamprenavir-ritonavir administered with methadone did not alter plasma amprenavir pharmacokinetics compared with historical control data; nor did it alter the unbound R-methadone at 2 and 6 hours after methadone dosing. Pharmacodynamic indexes remained essentially unchanged after adding fosamprenavir-ritonavir to methadone [2]. After a high-fat meal compared with fasting, (1) the bioavailability of GW433908G suspension was decreased by 20% and Cmax by 41%, and (2) for GW433908G tablets, there was no influence on AUC(12% lower Cmax). After a low-fat meal compared with fasting, (1) there was bioequivalence for GW433908G tablets, but (2) bioavailability was decreased by 23% for amprenavir capsules (Cmax was also lower, by 46%) [3].Clinical trial: Study of an Investigational Regimen Including FDA Approved HIV Drugs In HIV-Infected Pediatric Subjects. Phase 2
Related Catalog
References

[1]. Gruber VA, Rainey PM, Moody DE, Interactions between buprenorphine and the protease inhibitors darunavir-ritonavir and fosamprenavir-ritonavir. Clin Infect Dis. 2012 Feb 1;54(3):414-23.

[2]. Cao YJ, Smith PF, Wire MB, Pharmacokinetics and pharmacodynamics of methadone enantiomers after coadministration with fosamprenavir-ritonavir in opioid-dependent subjects. Pharmacotherapy. 2008 Jul;28(7):863-74.

[3]. Falcoz C, Jenkins JM, Bye C, Pharmacokinetics of GW433908, a prodrug of amprenavir, in healthy male volunteers. J Clin Pharmacol. 2002 Aug;42(8):887-98.

 Chemical & Physical Properties

Melting Point 282-284ºC
Molecular Formula C25H34CaN3O9PS
Molecular Weight 623.669
Exact Mass 623.137939
PSA 201.57000
LogP 5.44910
Storage condition 2-8℃

 Synonyms

Telzir
Lexiva
calcium (1R,2S)-1-({[(4-aminophenyl)sulfonyl](2-methylpropyl)amino}methyl)-3-phenyl-2-({[(3S)-tetrahydrofuran-3-yloxy]carbonyl}amino)propyl phosphate
Carbamic acid, N-[(1S,2R)-3-[[(4-aminophenyl)sulfonyl](2-methylpropyl)amino]-1-(phenylmethyl)-2-(phosphonooxy)propyl]-, (3S)-tetrahydro-3-furanyl ester, calcium salt (1:1)
calcium [(3s)-oxolan-3-yl] n-[(2s,3r)-4-[(4-aminophenyl)sulfonyl-(2-methylpropyl)amino]-1-phenyl-3-phosphonatooxy-butan-2-yl]carbamate
carbamic acid, [(1S,2R)-3-[[(4-aminophenyl)sulfonyl](2-methylpropyl)amino]-1-(phenylmethyl)-2-(phosphonooxy)propyl]-, (3S)-tetrahydro-3-furanyl ester, calcium salt (1:1)
Calcium-(1R,2S)-1-({[(4-aminophenyl)sulfonyl](2-methylpropyl)amino}methyl)-3-phenyl-2-({[(3S)-tetrahydrofuran-3-yloxy]carbonyl}amino)propylphosphat
Calcium (2R,3S)-1-{[(4-aminophenyl)sulfonyl](isobutyl)amino}-4-phenyl-3-({[(3S)-tetrahydro-3-furanyloxy]carbonyl}amino)-2-butanyl phosphate
[(2R,3S)-1-[(4-aminophenyl)sulfonyl-(2-methylpropyl)amino]-3-[[(3S)-oxolan-3-yl]oxycarbonylamino]-4-phenyl-butan-2-yl]oxyphosphonic acid
Fosamprenavir Calcium Salt
phosphate de (1R,2S)-1-({[(4-aminophényl)sulfonyl](2-méthylpropyl)amino}méthyl)-3-phényl-2-({[(3S)-tétrahydrofuran-3-yloxy]carbonyl}amino)propyle de calcium
Fosamprenavir (Calcium Salt)
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