GS-6620

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

MedKoo CAT#: 528427

CAS#: 1350735-70-4

Description: GS-6620 is a HCV nonstructural protein 5B (NS5B) inhibitor potentially for the treatment of HCV infection. GS-6620 showed limited activities against other viruses, maintaining only some of its activity against the closely related bovine viral diarrhea virus. The active 5'-triphosphate metabolite of GS-6620 is a chain terminator of viral RNA synthesis and a competitive inhibitor of NS5B-catalyzed ATP incorporation, with Ki/Km values of 0.23 and 0.18 for HCV NS5B genotypes 1b and 2a, respectively. With its unique dual substitutions of 1'-CN and 2'-C-Me on the ribose ring, the active triphosphate metabolite was found to have enhanced selectivity for the HCV NS5B polymerase over host RNA polymerases. GS-6620 demonstrated a high barrier to resistance in vitro.

Chemical Structure

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GS-6620
CAS# 1350735-70-4
Instruction

Theoretical Analysis

MedKoo Cat#: 528427
Name: GS-6620
CAS#: 1350735-70-4
Chemical Formula: C29H37N6O9P
Exact Mass: 644.24
Molecular Weight: 644.622
Elemental Analysis: C, 54.03; H, 5.79; N, 13.04; O, 22.34; P, 4.80

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: GS-6620; GS 6620; GS6620

IUPAC/Chemical Name: (2R,3R,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-4-hydroxy-2-((((((S)-1-isopropoxy-1-oxopropan-2-yl)amino)(phenoxy)phosphoryl)oxy)methyl)-4-methyltetrahydrofuran-3-yl isobutyrate

InChi Key: YAAQYJCOIFNMKX-CVANIGNKSA-N

InChi Code: InChI=1S/C29H37N6O9P/c1-17(2)26(36)42-24-22(43-29(15-30,28(24,6)38)23-13-12-21-25(31)32-16-33-35(21)23)14-40-45(39,44-20-10-8-7-9-11-20)34-19(5)27(37)41-18(3)4/h7-13,16-19,22,24,38H,14H2,1-6H3,(H,34,39)(H2,31,32,33)/t19-,22+,24+,28+,29-,45?/m0/s1

SMILES Code: C[C@H](NP(OC[C@@H]1[C@@H](OC(C(C)C)=O)[C@@](C)(O)[C@](C#N)(C2=CC=C3N2N=CN=C3N)O1)(OC4=CC=CC=C4)=O)C(OC(C)C)=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: Soluble in DMSO

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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 644.62 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Yang H, Yang C, Wang Y, Rhodes G, Robinson M, Cheng G, Qi X, Mo H, Tian Y, Pakdaman R, Sheng XC, Kim CU, Delaney WE 4th. Preclinical characterization of the novel HCV NS3 protease inhibitor GS-9256. Antivir Ther. 2017 Jan 20. doi: 10.3851/IMP3132. [Epub ahead of print] PubMed PMID: 28106531.

2: De Clercq E. C-Nucleosides To Be Revisited. J Med Chem. 2016 Mar 24;59(6):2301-11. doi: 10.1021/acs.jmedchem.5b01157. Review. PubMed PMID: 26513594.

3: Mish MR, Cho A, Kirschberg T, Xu J, Zonte CS, Fenaux M, Park Y, Babusis D, Feng JY, Ray AS, Kim CU. Preparation and biological evaluation of 1'-cyano-2'-C-methyl pyrimidine nucleosides as HCV NS5B polymerase inhibitors. Bioorg Med Chem Lett. 2014 Jul 15;24(14):3092-5. doi: 10.1016/j.bmcl.2014.05.015. PubMed PMID: 24907145.

4: Gentile I, Coppola N, Buonomo AR, Zappulo E, Borgia G. Investigational nucleoside and nucleotide polymerase inhibitors and their use in treating hepatitis C virus. Expert Opin Investig Drugs. 2014 Sep;23(9):1211-23. doi: 10.1517/13543784.2014.921680. Review. PubMed PMID: 24848437.

5: Feng JY, Cheng G, Perry J, Barauskas O, Xu Y, Fenaux M, Eng S, Tirunagari N, Peng B, Yu M, Tian Y, Lee YJ, Stepan G, Lagpacan LL, Jin D, Hung M, Ku KS, Han B, Kitrinos K, Perron M, Birkus G, Wong KA, Zhong W, Kim CU, Carey A, Cho A, Ray AS. Inhibition of hepatitis C virus replication by GS-6620, a potent C-nucleoside monophosphate prodrug. Antimicrob Agents Chemother. 2014;58(4):1930-42. doi: 10.1128/AAC.02351-13. PubMed PMID: 24419349; PubMed Central PMCID: PMC4023746.

6: Murakami E, Wang T, Babusis D, Lepist EI, Sauer D, Park Y, Vela JE, Shih R, Birkus G, Stefanidis D, Kim CU, Cho A, Ray AS. Metabolism and pharmacokinetics of the anti-hepatitis C virus nucleotide prodrug GS-6620. Antimicrob Agents Chemother. 2014;58(4):1943-51. doi: 10.1128/AAC.02350-13. PubMed PMID: 24419340; PubMed Central PMCID: PMC4023801.

7: Yang H, Robinson M, Corsa AC, Peng B, Cheng G, Tian Y, Wang Y, Pakdaman R, Shen M, Qi X, Mo H, Tay C, Krawczyk S, Sheng XC, Kim CU, Yang C, Delaney WE 4th. Preclinical characterization of the novel hepatitis C virus NS3 protease inhibitor GS-9451. Antimicrob Agents Chemother. 2014;58(2):647-53. doi: 10.1128/AAC.00487-13. PubMed PMID: 23939899; PubMed Central PMCID: PMC3910871.

8: Cho A, Zhang L, Xu J, Lee R, Butler T, Metobo S, Aktoudianakis V, Lew W, Ye H, Clarke M, Doerffler E, Byun D, Wang T, Babusis D, Carey AC, German P, Sauer D, Zhong W, Rossi S, Fenaux M, McHutchison JG, Perry J, Feng J, Ray AS, Kim CU. Discovery of the first C-nucleoside HCV polymerase inhibitor (GS-6620) with demonstrated antiviral response in HCV infected patients. J Med Chem. 2014 Mar 13;57(5):1812-25. doi: 10.1021/jm400201a. PubMed PMID: 23547794.