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MedKoo Cat#: 464908 | Name: GS-8374

Description:

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

GS-8374 is a potent and selective inhibitor of HIV-1 protease, effectively inhibiting protease mutants with amino acid insertions, also inhibiting major aspartyl peptidase 1 (May1), a secreted Cryptococcus neoformans protease.

Chemical Structure

GS-8374
GS-8374
CAS#unknown

Theoretical Analysis

MedKoo Cat#: 464908

Name: GS-8374

CAS#: unknown

Chemical Formula: C33H49N2O12PS

Exact Mass: 728.2744

Molecular Weight: 728.79

Elemental Analysis: C, 54.39; H, 6.78; N, 3.84; O, 26.34; P, 4.25; S, 4.40

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
Bulk Inquiry
Related CAS #
No Data
Synonym
GS-8374; GS8374; GS 8374;
IUPAC/Chemical Name
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl ((2S,3R)-1-(4-((diethoxyphosphoryl)methoxy)phenyl)-3-hydroxy-4-((N-isobutyl-4-methoxyphenyl)sulfonamido)butan-2-yl)carbamate
InChi Key
FCLYPCIMVVLLRN-FXSYQQGGSA-N
InChi Code
InChI=1S/C33H49N2O12PS/c1-6-45-48(38,46-7-2)22-44-26-10-8-24(9-11-26)18-29(34-33(37)47-31-21-43-32-28(31)16-17-42-32)30(36)20-35(19-23(3)4)49(39,40)27-14-12-25(41-5)13-15-27/h8-15,23,28-32,36H,6-7,16-22H2,1-5H3,(H,34,37)/t28-,29-,30+,31-,32+/m0/s1
SMILES Code
CCOP(COC1=CC=C(C[C@H](NC(O[C@H]2CO[C@@H]3[C@H]2CCO3)=O)[C@H](O)CN(S(C4=CC=C(OC)C=C4)(=O)=O)CC(C)C)C=C1)(OCC)=O
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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

Preparing Stock Solutions

The following data is based on the product molecular weight 728.79 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
1: Grantz Šašková K, Kozíšek M, Stray K, de Jong D, Rezáová P, Brynda J, van Maarseveen NM, Nijhuis M, Cihlár T, Konvalinka J. GS-8374, a prototype phosphonate-containing inhibitor of HIV-1 protease, effectively inhibits protease mutants with amino acid insertions. J Virol. 2014 Mar;88(6):3586-90. doi: 10.1128/JVI.02688-13. Epub 2013 Dec 26. PMID: 24371077; PMCID: PMC3957959. 2: Stray KM, Callebaut C, Glass B, Tsai L, Xu L, Müller B, Kräusslich HG, Cihlar T. Mutations in multiple domains of Gag drive the emergence of in vitro resistance to the phosphonate-containing HIV-1 protease inhibitor GS-8374. J Virol. 2013 Jan;87(1):454-63. doi: 10.1128/JVI.01211-12. Epub 2012 Oct 24. PMID: 23097440; PMCID: PMC3536386. 3: Callebaut C, Stray K, Tsai L, Williams M, Yang ZY, Cannizzaro C, Leavitt SA, Liu X, Wang K, Murray BP, Mulato A, Hatada M, Priskich T, Parkin N, Swaminathan S, Lee W, He GX, Xu L, Cihlar T. In vitro characterization of GS-8374, a novel phosphonate-containing inhibitor of HIV-1 protease with a favorable resistance profile. Antimicrob Agents Chemother. 2011 Apr;55(4):1366-76. doi: 10.1128/AAC.01183-10. Epub 2011 Jan 18. PMID: 21245449; PMCID: PMC3067135. 4: Hruz PW, Yan Q, Tsai L, Koster J, Xu L, Cihlar T, Callebaut C. GS-8374, a novel HIV protease inhibitor, does not alter glucose homeostasis in cultured adipocytes or in a healthy-rodent model system. Antimicrob Agents Chemother. 2011 Apr;55(4):1377-82. doi: 10.1128/AAC.01184-10. Epub 2011 Jan 18. PMID: 21245443; PMCID: PMC3067185. 5: Gulnik SV, Eissenstat M. Approaches to the design of HIV protease inhibitors with improved resistance profiles. Curr Opin HIV AIDS. 2008 Nov;3(6):633-41. doi: 10.1097/COH.0b013e328313911d. PMID: 19373035.