Amprenavir | protease inhibitor | CAS#161814-49-9

MedKoo Cat#: 371890 | Name: Amprenavir

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

Amprenavir

CAS#161814-49-9

Theoretical Analysis

MedKoo Cat#: 371890

Name: Amprenavir

CAS#: 161814-49-9

Chemical Formula: C25H35N3O6S

Exact Mass: 505.2247

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
5mg	USD 180.00
25mg	USD 430.00

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Related CAS #

No Data

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

More Info

Instruction

View handling instruction

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.

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

1: Adkins JC, Faulds D. Amprenavir. Drugs. 1998 Jun;55(6):837-42; discussion 843-4. doi: 10.2165/00003495-199855060-00015. PMID: 9617598. 2: Noble S, Goa KL. Amprenavir: a review of its clinical potential in patients with HIV infection. Drugs. 2000 Dec;60(6):1383-410. doi: 10.2165/00003495-200060060-00012. PMID: 11152018. 3: Arvieux C, Tribut O. Amprenavir or fosamprenavir plus ritonavir in HIV infection: pharmacology, efficacy and tolerability profile. Drugs. 2005;65(5):633-59. doi: 10.2165/00003495-200565050-00005. PMID: 15748098. 4: Fung HB, Kirschenbaum HL, Hameed R. Amprenavir: a new human immunodeficiency virus type 1 protease inhibitor. Clin Ther. 2000 May;22(5):549-72. doi: 10.1016/S0149-2918(00)80044-2. PMID: 10868554. 5: Gatell JM. From amprenavir to GW433908. J HIV Ther. 2001 Nov;6(4):95-9. PMID: 11740410. 6: Sadler BM, Stein DS. Clinical pharmacology and pharmacokinetics of amprenavir. Ann Pharmacother. 2002 Jan;36(1):102-18. doi: 10.1345/aph.10423. PMID: 11816239. 7: Gatell J. Coming therapies: amprenavir. Int J Clin Pract Suppl. 1999 Jun;103:42-4. PMID: 10622044. 8: Wire MB, Shelton MJ, Studenberg S. Fosamprenavir : clinical pharmacokinetics and drug interactions of the amprenavir prodrug. Clin Pharmacokinet. 2006;45(2):137-68. doi: 10.2165/00003088-200645020-00002. PMID: 16485915. 9: Amprenavir approved. STEP Perspect. 1999 Summer;99(2):8. PMID: 11366753. 10: Ishizawa M, Komatsu H. [Pharmacological study and clinical effect of HIV protease inhibitor amprenavir]. Nihon Yakurigaku Zasshi. 2001 Jan;117(1):59-64. Japanese. doi: 10.1254/fpj.117.59. PMID: 11233298. 11: LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet]. Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases; 2012–. Fosamprenavir. 2017 Sep 1. PMID: 31643343. 12: Simmons P. Amprenavir (Agenerase). Res Initiat Treat Action. 1999 Jul 1;5(3):7-10. PMID: 11366726. 13: Kodoth S, Bakshi S, Scimeca P, Black K, Pahwa S. Possible linkage of amprenavir with intracranial bleeding in an HIV-infected hemophiliac. AIDS Patient Care STDS. 2001 Jul;15(7):347-52. doi: 10.1089/108729101750301898. PMID: 11483161. 14: Amprenavir approved. AIDS Patient Care STDS. 1999 Jul;13(7):438. PMID: 10870601. 15: Amprenavir (Agenerase). Res Initiat Treat Action. 2000 Mar;6(1):32-3. PMID: 11708186. 16: Croteau D, Letendre S, Best BM, Rossi SS, Ellis RJ, Clifford DB, Collier AC, Gelman BB, Marra CM, McArthur J, McCutchan JA, Morgello S, Simpson DM, Way L, Capparelli E, Grant I; CHARTER Group. Therapeutic amprenavir concentrations in cerebrospinal fluid. Antimicrob Agents Chemother. 2012 Apr;56(4):1985-9. doi: 10.1128/AAC.05098-11. Epub 2012 Jan 30. PMID: 22290964; PMCID: PMC3318381. 17: Paulsen D, Elston R, Snowden W, Tisdale M, Ross L. Differentiation of genotypic resistance profiles for amprenavir and lopinavir, a valuable aid for choice of therapy in protease inhibitor-experienced HIV-1-infected subjects. J Antimicrob Chemother. 2003 Sep;52(3):319-23. doi: 10.1093/jac/dkg392. Epub 2003 Aug 13. PMID: 12917233. 18: Esposito V, Verdina A, Manente L, Spugnini EP, Viglietti R, Parrella R, Pagliano P, Parrella G, Galati R, De Luca A, Baldi A, Montesarchio V, Chirianni A. Amprenavir inhibits the migration in human hepatocarcinoma cell and the growth of xenografts. J Cell Physiol. 2013 Mar;228(3):640-5. doi: 10.1002/jcp.24173. PMID: 22886568. 19: Tran JQ, Petersen C, Garrett M, Hee B, Kerr BM. Pharmacokinetic interaction between amprenavir and delavirdine: evidence of induced clearance by amprenavir. Clin Pharmacol Ther. 2002 Dec;72(6):615-26. doi: 10.1067/mcp.2002.128868. PMID: 12496743. 20: Halder UC. Predicted antiviral drugs Darunavir, Amprenavir, Rimantadine and Saquinavir can potentially bind to neutralize SARS-CoV-2 conserved proteins. J Biol Res (Thessalon). 2021 Aug 4;28(1):18. doi: 10.1186/s40709-021-00149-2. PMID: 34344455; PMCID: PMC8331326.