Amprenavir , ≥97% , 161814-49-9

Synonym(s):
N-[(1S,2R)-3-[[(4-Aminophenyl)sulfonyl](2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid (3S)-tetrahydro-3-furanyl ester;VX-478

CAS NO.：161814-49-9

Empirical Formula: C25H35N3O6S

Molecular Weight: 505.63

MDL number: MFCD00934214

EINECS: 827-179-5

PRODUCT Properties

• Melting point: 72-74°C
• Density: 1.30±0.1 g/cm3(Predicted)
• storage temp.: -20°C
• solubility: DMSO: soluble20mg/mL, clear
• form: powder
• pka: 11.54±0.46(Predicted)
• color: white to beige
• optical activity: [α]/D +8 to +12°, c = 0.5 in methanol
• BCS Class: 2
• InChIKey: YMARZQAQMVYCKC-OEMFJLHTSA-N

Description and Uses

Amprenavir was launched as Agenerase in the US for the treatment of AIDS patients in combination with approved agent antiretroviral nucleoside analogs. It is the fifth non-peptidic inhibitor of HIV-1 protease to be marketed in this indication after the last approved Neflinavir. Amprenavir, designed via a structure-based process, is the smallest molecule in the 《navir》 class and exhibits a reduced peptidic character. An improved process for preparation comprising four steps from a (1S, 2R)-2-hydroxy-3-aminopropylcarbamate has been developed. Amprenavir is a potent inhibitor of HIV-1 aspartyl protease (Ki = 0.6nM), an enzyme required by the virus to cleave pro-form polyproteins to structural proteins during the last stage in the replication process. The compound displays good oral bioavailability in humans and penetrates the CNS, which is an important advantage in long-term treatment. Its plasma half-life is approximately 10h. Treatment with Amprenavir in combination with nucleoside analog reverse transcriptase inhibitors considerably decreases viral load and restores CD4+ T-cell counts in patients with HIV infection.

Protease inhibitor, anti-HIV agent

Safety

• Symbol(GHS): GHS07
• Signal word: Warning
• Hazard statements: H302-H315-H319-H332-H335
• Precautionary statements: P261-P280-P305+P351+P338
• RIDADR: 3077
• WGK Germany: 3
• HS Code: 29350090