Amprenavir
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MedKoo CAT#: 371890

CAS#: 161814-49-9

Description: Amprenavir (original brand name Agenerase, GlaxoSmithKline) is a protease inhibitor used to treat HIV infection. The mechanism of action of amprenavir is as a HIV Protease Inhibitor and Cytochrome P450 3A4 Inhibitor. It was approved by the Food and Drug Administration on April 15, 1999, for twice-a-day dosing instead of needing to be taken every eight hours.


Chemical Structure

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Amprenavir
CAS# 161814-49-9

Theoretical Analysis

MedKoo Cat#: 371890
Name: Amprenavir
CAS#: 161814-49-9
Chemical Formula: C25H35N3O6S
Exact Mass: 505.22466
Molecular Weight: 505.63
Elemental Analysis: C, 59.39; H, 6.98; N, 8.31; O, 18.99; S, 6.34

Price and Availability

Size Price Availability Quantity
5.0mg USD 180.0 2 Weeks
25.0mg USD 430.0 2 Weeks
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Synonym: VX-478; VX 478; VX478; Amprenavir; Agenerase; Prozei.

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

InChi Key: YMARZQAQMVYCKC-UHFFFAOYSA-N

InChi Code: InChI=1S/C25H35N3O6S/c1-18(2)15-28(35(31,32)22-10-8-20(26)9-11-22)16-24(29)23(14-19-6-4-3-5-7-19)27-25(30)34-21-12-13-33-17-21/h3-11,18,21,23-24,29H,12-17,26H2,1-2H3,(H,27,30)

SMILES Code: CC(C)CN(CC(C(CC1=CC=CC=C1)NC(=O)OC2CCOC2)O)S(=O)(=O)C3=CC=C(C=C3)N

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 505.63 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Chen J, Wang X, Zhu T, Zhang Q, Zhang JZ. A Comparative Insight into Amprenavir Resistance of Mutations V32I, G48V, I50V, I54V, and I84V in HIV-1 Protease Based on Thermodynamic Integration and MM-PBSA Methods. J Chem Inf Model. 2015 Sep 28;55(9):1903-13. doi: 10.1021/acs.jcim.5b00173. Epub 2015 Sep 4. PubMed PMID: 26317593.

2: Dumond JB, Rigdon J, Mollan K, Tierney C, Kashuba AD, Aweeka F, Collier AC. Brief Report: Significant Decreases in Both Total and Unbound Lopinavir and Amprenavir Exposures During Coadministration: ACTG Protocol A5143/A5147s Results. J Acquir Immune Defic Syndr. 2015 Dec 15;70(5):510-4. doi: 10.1097/QAI.0000000000000777. PubMed PMID: 26230332; PubMed Central PMCID: PMC4648657.

3: Yu Y, Wang J, Shao Q, Shi J, Zhu W. Effects of drug-resistant mutations on the dynamic properties of HIV-1 protease and inhibition by Amprenavir and Darunavir. Sci Rep. 2015 May 27;5:10517. doi: 10.1038/srep10517. PubMed PMID: 26012849; PubMed Central PMCID: PMC4444956.

4: Nakamura MU, Araujo Júnior E, Simões JM, Oliveria RM, Kulay LJ. Effect of six antiretroviral drugs (delavirdine, stavudine, lamivudine, nelfinavir, amprenavir and lopinavir/ritonavir in association) on albino pregnant rats (Rattus norvegicus Albinus, Rodentia, Mammalia): biological assay. Ceska Gynekol. 2014 Summer;79(4):295-304. PubMed PMID: 25398151.

5: Chen J, Liang Z, Wang W, Yi C, Zhang S, Zhang Q. Revealing origin of decrease in potency of darunavir and amprenavir against HIV-2 relative to HIV-1 protease by molecular dynamics simulations. Sci Rep. 2014 Nov 3;4:6872. doi: 10.1038/srep06872. PubMed PMID: 25362963; PubMed Central PMCID: PMC4217091.

6: Barbour AM, Gibiansky L, Wire MB. Population pharmacokinetic modeling and simulation of amprenavir following fosamprenavir/ritonavir administration for dose optimization in HIV infected pediatric patients. J Clin Pharmacol. 2014 Feb;54(2):206-14. doi: 10.1002/jcph.205. Epub 2013 Nov 5. PubMed PMID: 25272370.

7: Leonis G, Steinbrecher T, Papadopoulos MG. A contribution to the drug resistance mechanism of darunavir, amprenavir, indinavir, and saquinavir complexes with HIV-1 protease due to flap mutation I50V: a systematic MM-PBSA and thermodynamic integration study. J Chem Inf Model. 2013 Aug 26;53(8):2141-53. doi: 10.1021/ci4002102. Epub 2013 Jul 24. PubMed PMID: 23834142.

8: Dufek MB, Bridges AS, Thakker DR. Intestinal first-pass metabolism by cytochrome p450 and not p-glycoprotein is the major barrier to amprenavir absorption. Drug Metab Dispos. 2013 Sep;41(9):1695-702. doi: 10.1124/dmd.113.052191. Epub 2013 Jul 2. PubMed PMID: 23821186.

9: Weber IT, Waltman MJ, Mustyakimov M, Blakeley MP, Keen DA, Ghosh AK, Langan P, Kovalevsky AY. Joint X-ray/neutron crystallographic study of HIV-1 protease with clinical inhibitor amprenavir: insights for drug design. J Med Chem. 2013 Jul 11;56(13):5631-5. doi: 10.1021/jm400684f. Epub 2013 Jun 28. PubMed PMID: 23772563; PubMed Central PMCID: PMC3815997.

10: Helsley RN, Sui Y, Ai N, Park SH, Welsh WJ, Zhou C. Pregnane X receptor mediates dyslipidemia induced by the HIV protease inhibitor amprenavir in mice. Mol Pharmacol. 2013 Jun;83(6):1190-9. doi: 10.1124/mol.113.085753. Epub 2013 Mar 21. PubMed PMID: 23519392; PubMed Central PMCID: PMC3657097.