Vedroprevir

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

MedKoo CAT#: 326685

CAS#: 1098189-15-1

Description: Vedroprevir, also known as GS9451, is a selective hepatitis C virus (HCV) NS3 protease inhibitor in development for the treatment of genotype 1 (GT1) HCV infection. GS-9451 was less active in GT2a replicon cells (EC50 = 316 nM). GS-9451 retained wild-type activity against multiple classes of NS5B and NS5A inhibitor resistance mutations. GS-9451 showed good oral bioavailability in all three species tested.


Chemical Structure

img
Vedroprevir
CAS# 1098189-15-1

Theoretical Analysis

MedKoo Cat#: 326685
Name: Vedroprevir
CAS#: 1098189-15-1
Chemical Formula: C45H60ClN7O9S
Exact Mass: 909.39
Molecular Weight: 910.525
Elemental Analysis: C, 59.36; H, 6.64; Cl, 3.89; N, 10.77; O, 15.81; S, 3.52

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.

Request quote for custom synthesis

Synonym: GS9451; GS-9451; GS 9451; Vedroprevir

IUPAC/Chemical Name: (1R,2R)-1-((2S,4R)-1-((2S)-2-(((((1R,5S)-bicyclo[3.1.0]hexan-3-yl)oxy)carbonyl)amino)-3,3-dimethylbutanoyl)-4-((8-chloro-2-(2-(isopropylamino)thiazol-4-yl)-7-(2-morpholinoethoxy)quinolin-4-yl)oxy)pyrrolidine-2-carboxamido)-2-ethylcyclopropane-1-carboxylic acid

InChi Key: OTXAMWFYPMNDME-OPUYQWCOSA-N

InChi Code: InChI=1S/C45H60ClN7O9S/c1-7-27-21-45(27,41(56)57)51-39(54)33-19-29(22-53(33)40(55)38(44(4,5)6)50-43(58)62-28-17-25-16-26(25)18-28)61-35-20-31(32-23-63-42(49-32)47-24(2)3)48-37-30(35)8-9-34(36(37)46)60-15-12-52-10-13-59-14-11-52/h8-9,20,23-29,33,38H,7,10-19,21-22H2,1-6H3,(H,47,49)(H,50,58)(H,51,54)(H,56,57)/t25-,26+,27-,28?,29-,33+,38-,45-/m1/s1

SMILES Code: O=C([C@]1(NC([C@H]2N(C([C@@H](NC(OC3C[C@@]4([H])C[C@@]4([H])C3)=O)C(C)(C)C)=O)C[C@H](OC5=CC(C6=CSC(NC(C)C)=N6)=NC7=C(Cl)C(OCCN8CCOCC8)=CC=C57)C2)=O)[C@H](CC)C1)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, 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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 910.53 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:

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

1: Meissner EG, Kohli A, Virtaneva K, Sturdevant D, Martens C, Porcella SF, McHutchison JG, Masur H, Kottilil S. Achieving sustained virologic response after interferon-free hepatitis C virus treatment correlates with hepatic interferon gene expression changes independent of cirrhosis. J Viral Hepat. 2016 Feb 3. doi: 10.1111/jvh.12510. [Epub ahead of print] PubMed PMID: 26840694.

2: Petersen T, Townsend K, Gordon LA, Sidharthan S, Silk R, Nelson A, Gross C, Calderón M, Proschan M, Osinusi A, Polis MA, Masur H, Kottilil S, Kohli A. High adherence to all-oral directly acting antiviral HCV therapy among an inner-city patient population in a phase 2a study. Hepatol Int. 2016 Mar;10(2):310-9. doi: 10.1007/s12072-015-9680-7. Epub 2015 Nov 26. PubMed PMID: 26612014; PubMed Central PMCID: PMC4778154.

3: Kohli A, Kattakuzhy S, Sidharthan S, Nelson A, McLaughlin M, Seamon C, Wilson E, Meissner EG, Sims Z, Silk R, Gross C, Akoth E, Tang L, Price A, Jolley TA, Emmanuel B, Proschan M, Teferi G, Chavez J, Abbott S, Osinusi A, Mo H, Polis MA, Masur H, Kottilil S. Four-Week Direct-Acting Antiviral Regimens in Noncirrhotic Patients With Hepatitis C Virus Genotype 1 Infection: An Open-Label, Nonrandomized Trial. Ann Intern Med. 2015 Dec 15;163(12):899-907. doi: 10.7326/M15-0642. Epub 2015 Nov 24. PubMed PMID: 26595450.

4: Wilson EM, Kattakuzhy S, Sidharthan S, Sims Z, Tang L, McLaughlin M, Price A, Nelson A, Silk R, Gross C, Akoth E, Mo H, Subramanian GM, Pang PS, McHutchison JG, Osinusi A, Masur H, Kohli A, Kottilil S. Successful Retreatment of Chronic HCV Genotype-1 Infection With Ledipasvir and Sofosbuvir After Initial Short Course Therapy With Direct-Acting Antiviral Regimens. Clin Infect Dis. 2016 Feb 1;62(3):280-8. doi: 10.1093/cid/civ874. Epub 2015 Oct 31. PubMed PMID: 26521268; PubMed Central PMCID: PMC4706633.

5: Kattakuzhy S, Wilson E, Sidharthan S, Sims Z, McLaughlin M, Price A, Silk R, Gross C, Akoth E, McManus M, Emmanuel B, Shrivastava S, Tang L, Nelson A, Teferi G, Chavez J, Lam B, Mo H, Osinusi A, Polis MA, Masur H, Kohli A, Kottilil S. Moderate Sustained Virologic Response Rates With 6-Week Combination Directly Acting Anti-Hepatitis C Virus Therapy in Patients With Advanced Liver Disease. Clin Infect Dis. 2016 Feb 15;62(4):440-7. doi: 10.1093/cid/civ897. Epub 2015 Oct 26. PubMed PMID: 26503379; PubMed Central PMCID: PMC4725378.

6: Sidharthan S, Kohli A, Sims Z, Nelson A, Osinusi A, Masur H, Kottilil S. Utility of hepatitis C viral load monitoring on direct-acting antiviral therapy. Clin Infect Dis. 2015 Jun 15;60(12):1743-51. doi: 10.1093/cid/civ170. Epub 2015 Mar 2. PubMed PMID: 25733369; PubMed Central PMCID: PMC4834854.

7: Kohli A, Osinusi A, Sims Z, Nelson A, Meissner EG, Barrett LL, Bon D, Marti MM, Silk R, Kotb C, Gross C, Jolley TA, Sidharthan S, Petersen T, Townsend K, Egerson D, Kapoor R, Spurlin E, Sneller M, Proschan M, Herrmann E, Kwan R, Teferi G, Talwani R, Diaz G, Kleiner DE, Wood BJ, Chavez J, Abbott S, Symonds WT, Subramanian GM, Pang PS, McHutchison J, Polis MA, Fauci AS, Masur H, Kottilil S. Virological response after 6 week triple-drug regimens for hepatitis C: a proof-of-concept phase 2A cohort study. Lancet. 2015 Mar 21;385(9973):1107-13. doi: 10.1016/S0140-6736(14)61228-9. Epub 2015 Jan 13. PubMed PMID: 25591505; PubMed Central PMCID: PMC4427052.

8: Foster GR. Shorter treatments for hepatitis C: another step forward? Lancet. 2015 Mar 21;385(9973):1054-5. doi: 10.1016/S0140-6736(14)61600-7. Epub 2015 Jan 13. PubMed PMID: 25591504.

9: Dvory-Sobol H, Voitenleitner C, Mabery E, Skurnac T, Lawitz EJ, McHutchison J, Svarovskaia ES, Delaney W, Miller MD, Mo H. Clinical and in vitro resistance to GS-9669, a thumb site II nonnucleoside inhibitor of the hepatitis C virus NS5B polymerase. Antimicrob Agents Chemother. 2014 Nov;58(11):6599-606. doi: 10.1128/AAC.02815-14. Epub 2014 Aug 25. PubMed PMID: 25155588; PubMed Central PMCID: PMC4249356.

10: Barauskas O, Corsa AC, Wang R, Hluhanich S, Jin D, Hung M, Yang H, Delaney WE 4th, Schultz BE. Binding kinetics, potency, and selectivity of the hepatitis C virus NS3 protease inhibitors GS-9256 and vedroprevir. Biochim Biophys Acta. 2014 Dec;1840(12):3292-8. doi: 10.1016/j.bbagen.2014.08.002. Epub 2014 Aug 17. PubMed PMID: 25139683.

11: De Clercq E. Current race in the development of DAAs (direct-acting antivirals) against HCV. Biochem Pharmacol. 2014 Jun 15;89(4):441-52. doi: 10.1016/j.bcp.2014.04.005. Epub 2014 Apr 13. PubMed PMID: 24735613.

12: Wyles DL, Rodriguez-Torres M, Lawitz E, Shiffman ML, Pol S, Herring RW, Massetto B, Kanwar B, Trenkle JD, Pang PS, Zhu Y, Mo H, Brainard DM, Subramanian GM, McHutchison JG, Habersetzer F, Sulkowski MS. All-oral combination of ledipasvir, vedroprevir, tegobuvir, and ribavirin in treatment-naïve patients with genotype 1 HCV infection. Hepatology. 2014 Jul;60(1):56-64. doi: 10.1002/hep.27053. Epub 2014 May 28. PubMed PMID: 24501005.

13: 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. Epub 2013 Aug 12. PubMed PMID: 23939899; PubMed Central PMCID: PMC3910871.

14: Martel-Laferrière V, Dieterich DT. Update on combinations of DAAs with and without pegylated-interferon and ribavirin: triple and quadruple therapy more than doubles SVR. Clin Liver Dis. 2013 Feb;17(1):93-103. doi: 10.1016/j.cld.2012.09.001. Review. PubMed PMID: 23177285.

15: Lawitz EJ, Hill JM, Marbury T, Demicco MP, Delaney W, Yang J, Moorehead L, Mathias A, Mo H, McHutchison JG, Rodriguez-Torres M, Gordon SC. A Phase I, randomized, placebo-controlled, 3-day, ascending-dose study of GS-9451, an NS3/4A protease inhibitor, in genotype 1 hepatitis C patients. Antivir Ther. 2013;18(3):311-9. doi: 10.3851/IMP2415. Epub 2012 Oct 9. PubMed PMID: 23047118.

16: Dvory-Sobol H, Wong KA, Ku KS, Bae A, Lawitz EJ, Pang PS, Harris J, Miller MD, Mo H. Characterization of resistance to the protease inhibitor GS-9451 in hepatitis C virus-infected patients. Antimicrob Agents Chemother. 2012 Oct;56(10):5289-95. doi: 10.1128/AAC.00780-12. Epub 2012 Aug 6. PubMed PMID: 22869562; PubMed Central PMCID: PMC3457362.

17: Svarovskaia ES, Martin R, McHutchison JG, Miller MD, Mo H. Abundant drug-resistant NS3 mutants detected by deep sequencing in hepatitis C virus-infected patients undergoing NS3 protease inhibitor monotherapy. J Clin Microbiol. 2012 Oct;50(10):3267-74. doi: 10.1128/JCM.00838-12. Epub 2012 Jul 25. PubMed PMID: 22837328; PubMed Central PMCID: PMC3457457.

18: Sheng XC, Appleby T, Butler T, Cai R, Chen X, Cho A, Clarke MO, Cottell J, Delaney WE 4th, Doerffler E, Link J, Ji M, Pakdaman R, Pyun HJ, Wu Q, Xu J, Kim CU. Discovery of GS-9451: an acid inhibitor of the hepatitis C virus NS3/4A protease. Bioorg Med Chem Lett. 2012 Apr 1;22(7):2629-34. doi: 10.1016/j.bmcl.2012.01.017. Epub 2012 Feb 1. PubMed PMID: 22366653.