CAS 161814-49-9|Amprenavir

Introduction：Basic information about CAS 161814-49-9|Amprenavir, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Amprenavir BiologicalActivity
3. Chemical & Physical Properties
4. Safety Information
5. Customs
6. Articles41
7. Synonyms

Common Name	Amprenavir
CAS Number	161814-49-9	Molecular Weight	505.627
Density	1.3±0.1 g/cm3	Boiling Point	722.5±70.0 °C at 760 mmHg
Molecular Formula	C₂₅H₃₅N₃O₆S	Melting Point	72-74ºC
MSDS	ChineseUSA	Flash Point	390.8±35.7 °C

Names

Name	amprenavir
Synonym	More Synonyms

Amprenavir BiologicalActivity

Description	Amprenavir (Agenerase) is a HIV protease inhibitor(Ki=0.6 nM) used to treat HIV infection.IC50 Value: 0.6 nM (Ki); Against wild-type clinical HIV isolates:14.6 +/- 12.5 ng/mL (mean +/- SD) [1].Target: HIV proteasein vitro: Amprenavir has an enzyme inhibition constant (Ki = 0.6 nM) that falls within the Ki range of the other protease inhibitors. Amprenavir's in vitro 50% inhibitory concentration (IC50) against wild-type clinical HIV isolates is 14.6 +/- 12.5 ng/mL (mean +/- SD) [1]. Amprenavir had direct inhibitory effects on invasion of Huh-7 hepatocarcinoma cell lines, inhibiting MMP proteolytic activation [2].in vivo: Amprenavir was able to promote regression of hepatocarcinoma growth in vivo by anti-angiogenetic and overall anti-tumor activities, independently by PI3K/AKT related pathways that at today is one of the more suggestive hypothesis to explain the anti-tumor effects of the different protease inhibitors [2]. Amprenavir efficiently activated PXR and induced PXR target gene expression in vitro and in vivo. Short-term exposure to amprenavirsignificantly increased plasma total cholesterol and atherogenic low-density lipoprotein cholesterol levels in wild-type mice, but not in PXR-deficient mice [3]. Amprenavir has been approved for adults and children; the recommended capsule doses are 1200 mg twice daily for adults and 20 mg/kg twice daily or 15 mg/kg 3 times daily for children < 13 years of age or adolescents < 50 kg [1].Clinical trial: A Study to Compare Three Doses of T-20 When Given in Combination With Abacavir, Amprenavir, Ritonavir, and Efavirenz to HIV-Infected Adults. Phase 2
Related Catalog	Signaling Pathways >>Metabolic Enzyme/Protease >>HIV ProteaseSignaling Pathways >>Anti-infection >>HIVResearch Areas >>Infection
References	[1]. Sadler BM, Stein DS. Clinical pharmacology and pharmacokinetics of amprenavir. Ann Pharmacother. 2002 Jan;36(1):102-18. [2]. Esposito V, Verdina A, Manente L, Amprenavir inhibits the migration in human hepatocarcinoma cell and the growth of xenografts. J Cell Physiol. 2013 Mar;228(3):640-5. [3]. Helsley RN, Sui Y, Ai N, Pregnane X Receptor Mediates Dyslipidemia Induced by the HIV Protease Inhibitor Amprenavir in Mice. Mol Pharmacol. 2013 Jun;83(6):1190-9.

Description

Amprenavir (Agenerase) is a HIV protease inhibitor(Ki=0.6 nM) used to treat HIV infection.IC50 Value: 0.6 nM (Ki); Against wild-type clinical HIV isolates:14.6 +/- 12.5 ng/mL (mean +/- SD) [1].Target: HIV proteasein vitro: Amprenavir has an enzyme inhibition constant (Ki = 0.6 nM) that falls within the Ki range of the other protease inhibitors. Amprenavir's in vitro 50% inhibitory concentration (IC50) against wild-type clinical HIV isolates is 14.6 +/- 12.5 ng/mL (mean +/- SD) [1]. Amprenavir had direct inhibitory effects on invasion of Huh-7 hepatocarcinoma cell lines, inhibiting MMP proteolytic activation [2].in vivo: Amprenavir was able to promote regression of hepatocarcinoma growth in vivo by anti-angiogenetic and overall anti-tumor activities, independently by PI3K/AKT related pathways that at today is one of the more suggestive hypothesis to explain the anti-tumor effects of the different protease inhibitors [2]. Amprenavir efficiently activated PXR and induced PXR target gene expression in vitro and in vivo. Short-term exposure to amprenavirsignificantly increased plasma total cholesterol and atherogenic low-density lipoprotein cholesterol levels in wild-type mice, but not in PXR-deficient mice [3]. Amprenavir has been approved for adults and children; the recommended capsule doses are 1200 mg twice daily for adults and 20 mg/kg twice daily or 15 mg/kg 3 times daily for children < 13 years of age or adolescents < 50 kg [1].Clinical trial: A Study to Compare Three Doses of T-20 When Given in Combination With Abacavir, Amprenavir, Ritonavir, and Efavirenz to HIV-Infected Adults. Phase 2

Related Catalog

Signaling Pathways >>Metabolic Enzyme/Protease >>HIV ProteaseSignaling Pathways >>Anti-infection >>HIVResearch Areas >>Infection

References

[1]. Sadler BM, Stein DS. Clinical pharmacology and pharmacokinetics of amprenavir. Ann Pharmacother. 2002 Jan;36(1):102-18.

[2]. Esposito V, Verdina A, Manente L, Amprenavir inhibits the migration in human hepatocarcinoma cell and the growth of xenografts. J Cell Physiol. 2013 Mar;228(3):640-5.

[3]. Helsley RN, Sui Y, Ai N, Pregnane X Receptor Mediates Dyslipidemia Induced by the HIV Protease Inhibitor Amprenavir in Mice. Mol Pharmacol. 2013 Jun;83(6):1190-9.

Chemical & Physical Properties

Density	1.3±0.1 g/cm3
Boiling Point	722.5±70.0 °C at 760 mmHg
Melting Point	72-74ºC
Molecular Formula	C₂₅H₃₅N₃O₆S
Molecular Weight	505.627
Flash Point	390.8±35.7 °C
Exact Mass	505.224670
PSA	139.57000
LogP	4.68
Vapour Pressure	0.0±2.5 mmHg at 25°C
Index of Refraction	1.602
InChIKey	YMARZQAQMVYCKC-OEMFJLHTSA-N
SMILES	CC(C)CN(CC(O)C(Cc1ccccc1)NC(=O)OC1CCOC1)S(=O)(=O)c1ccc(N)cc1
Storage condition	-20°C Freezer
Water Solubility	DMSO: soluble20mg/mL, clear

Safety Information

RIDADR	3077
HS Code	2935009090

Customs

HS Code	2935009090
Summary	2935009090 other sulphonamides VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:35.0%

Articles41

A comparison of in vitro ADME properties and pharmacokinetics of azithromycin and selected 15-membered ring macrolides in rodents.

Eur. J. Drug Metab. Pharmacokinet. 39(4) , 263-76, (2014)

The purpose of this study was to evaluate the impact of structural modifications on the 15-membered macrolactone ring and/or substituents on the in vitro ADME properties and in vivo pharmacokinetic (P...

Parallel ultra high pressure liquid chromatography-mass spectrometry for the quantification of HIV protease inhibitors using dried spot sample collection format.

J. Chromatogr. B. Analyt. Technol. Biomed. Life Sci. 965 , 244-53, (2014)

An assay was developed and validated for the quantification of eight protease inhibitors (indinavir (IDV), ritonavir (RTV), lopinavir (LPV), saquinavir (SQV), amprenavir (APV), nelfinavir (NFV), ataza...

HZ08 reverse P-glycoprotein mediated multidrug resistance in vitro and in vivo.

PLoS ONE 10(2) , e0116886, (2015)

Multidrug efflux transporter P-glycoprotein (P-gp) is highly expressed on membrane of tumor cells and is implicated in resistance to tumor chemotherapy. HZ08 is synthesized and studied in order to fin...

Synonyms

Vertex

Benzenesulfonamide, 4-amino-N-[(2R,3S)-2-hydroxy-3-[[(1E)-hydroxy[[(3S)-tetrahydro-3-furanyl]oxy]methylene]amino]-4-phenylbutyl]-N-(2-methylpropyl)-

VX-478

(3S)-tetrahydro-3-furyl N-[(1S,2R)-3-(4-amino-N-isobutylbenzenesulfonamido)-1-benzyl-2-hydroxypropyl]carbamate

(3S)-Tetrahydro-3-furanyl hydrogen [(2S,3R)-4-{[(4-aminophenyl)sulfonyl](isobutyl)amino}-3-hydroxy-1-phenyl-2-butanyl]carbonimidate

(3S)-Tetrahydro-3-furanyl [(2S,3R)-4-{[(4-aminophenyl)sulfonyl](isobutyl)amino}-3-hydroxy-1-phenyl-2-butanyl]carbamate

[(1S,2R)]-[3-[[(4-Aminophenyl)sulfonyl](2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic Acid (3S)-tetrahydro-3-furanyl Ester

Amprenavir (agenerase)

(3S)-tetrahydrofuran-3-yl [(2S,3R)-4-{[(4-aminophenyl)sulfonyl](2-methylpropyl)amino}-3-hydroxy-1-phenylbutan-2-yl]carbamate

Prozei

carbamic acid, [(1S,2R)-3-[[(4-aminophenyl)sulfonyl](2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]-, (3S)-tetrahydro-3-furanyl ester

[(3S)-oxolan-3-yl] N-[(2S,3R)-4-[(4-aminophenyl)sulfonyl-(2-methylpropyl)amino]-3-hydroxy-1-phenylbutan-2-yl]carbamate

141W94

(3S)-Tetrahydrofuran-3-yl [(2S,3R)-4-{[(4-aminophenyl)sulfonyl](isobutyl)amino}-3-hydroxy-1-phenylbutan-2-yl]carbamate

4-Amino-N-((2syn,3S)-2-hydroxy-4-phenyl-3-((S)-tetrahydrofuran-3-yloxycarbonylamino)-butyl)-N-isobutylbenzene Sulfonamide

Vertex VX478

Carbamic acid, N-[(1S,2R)-3-[[(4-aminophenyl)sulfonyl](2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]-, (3S)-tetrahydro-3-furanyl ester

Amprenavir

Agenerase

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