Voxilaprevir
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MedKoo CAT#: 562012

CAS#: 1535212-07-7

Description: Voxilaprevir is a pan-genotypic hepatitis C virus (HCV) non-structural 3/4A (NS3/4A) serine protease inhibitor. It inhibits replication of wild-type HCV genotypes 1a, 1b, 2a, 2b, 3a, 4a, 5a, and 6a (EC50s = 1.9-6.6 nM in replicon assays). Voxilaprevir also inhibits replication of mutant HCV genotypes containing NS3 resistance-associated substitutions (EC50s = 3.1, 2.7, and 4 nM for HCV genotypes 1a Q80K, 1a R155K, and 1b D168E, respectively). Formulations containing Voxilaprevir have been used in the treatment of chronic HCV infection.


Chemical Structure

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Voxilaprevir
CAS# 1535212-07-7

Theoretical Analysis

MedKoo Cat#: 562012
Name: Voxilaprevir
CAS#: 1535212-07-7
Chemical Formula: C40H52F4N6O9S
Exact Mass: 868.3453
Molecular Weight: 868.94
Elemental Analysis: C, 55.29; H, 6.03; F, 8.75; N, 9.67; O, 16.57; S, 3.69

Price and Availability

Size Price Availability Quantity
1.0mg USD 280.0 2 Weeks
5.0mg USD 740.0 2 Weeks
10.0mg USD 1240.0 2 Weeks
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Synonym: Voxilaprevir; GS-9857; GS 9857; GS9857; Vosevi;

IUPAC/Chemical Name: (33R,34S,35S,91R,92R,5S)-5-(tert-butyl)-N-((1R,2R)-2-(difluoromethyl)-1-(((1-methylcyclopropyl)sulfonyl)carbamoyl)cyclopropyl)-34-ethyl-14,14-difluoro-17-methoxy-4,7-dioxo-2,8-dioxa-6-aza-1(2,3)-quinoxalina-3(3,1)-pyrrolidina-9(1,2)-cyclopropanacyclotetradecaphane-35-carboxamide

InChi Key: MZBLZLWXUBZHSL-FZNJKFJKSA-N

InChi Code: InChI=1S/C40H52F4N6O9S/c1-7-22-27-19-50(28(22)32(51)48-39(18-23(39)31(41)42)35(53)49-60(55,56)38(5)14-15-38)34(52)30(37(2,3)4)47-36(54)59-26-16-20(26)10-8-9-13-40(43,44)29-33(58-27)46-25-17-21(57-6)11-12-24(25)45-29/h11-12,17,20,22-23,26-28,30-31H,7-10,13-16,18-19H2,1-6H3,(H,47,54)(H,48,51)(H,49,53)/t20-,22-,23+,26-,27+,28+,30-,39-/m1/s1

SMILES Code: COC(C=C1)=CC2=C1N=C(C(O[C@@H](C3)[C@@H](CC)[C@@H](C(N[C@]4(C(NS(=O)(C5(C)CC5)=O)=O)C[C@H]4C(F)F)=O)N3C6=O)=N2)C(F)(F)CCCC[C@H]7[C@@H](C7)OC(N[C@H]6C(C)(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

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 30.0 34.52
DMSO 30.0 34.52
Ethanol 1.0 1.15

Preparing Stock Solutions

The following data is based on the product molecular weight 868.94 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: Santander Ballestín S, Gómez Martín D, Lorente Pérez S, Luesma Bartolomé MJ. Hepatitis C: A Pharmacological Therapeutic Update. J Clin Med. 2021 Apr 8;10(8):1568. doi: 10.3390/jcm10081568. PMID: 33917830; PMCID: PMC8068207.

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3: Sarrazin C. Treatment failure with DAA therapy: Importance of resistance. J Hepatol. 2021 Mar 12:S0168-8278(21)00169-0. doi: 10.1016/j.jhep.2021.03.004. Epub ahead of print. PMID: 33716089.

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5: Boff da Costa R, Boff Costa M, Longo L, Miotto DE, Hirata Dellavia G, Trucollo Michalczuk M, Reis Álvares-da-Silva M. Direct antiviral agents for hepatitis C and drug interaction risk: A retrospective cohort study with real and simulated data on medication interaction, prevalence of comorbidities and comedications. PLoS One. 2021 Feb 12;16(2):e0245767. doi: 10.1371/journal.pone.0245767. PMID: 33577593; PMCID: PMC7880426.

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8: Higley C, Hsu CC, Smith C, Nadella S, Lalos AT. Safety and efficacy of sofosbuvir/velpatasvir/voxilaprevir in post-liver transplant patients with previous direct-acting antiviral failure: Six case reports. World J Hepatol. 2020 Dec 27;12(12):1341-1348. doi: 10.4254/wjh.v12.i12.1341. PMID: 33442459; PMCID: PMC7772723.

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11: Hsu PY, Wei YJ, Lee JJ, Niu SW, Huang JC, Hsu CT, Jang TY, Yeh ML, Huang CI, Liang PC, Lin YH, Hsieh MY, Hsieh MH, Chen SC, Dai CY, Lin ZY, Chen SC, Huang JF, Chang JM, Hwang SJ, Chuang WL, Huang CF, Chiu YW, Yu ML. Comedications and potential drug-drug interactions with direct-acting antivirals in hepatitis C patients on hemodialysis. Clin Mol Hepatol. 2021 Jan;27(1):186-196. doi: 10.3350/cmh.2020.0180. Epub 2020 Dec 3. PMID: 33317251; PMCID: PMC7820195.

12: Dietz J, Di Maio VC, de Salazar A, Merino D, Vermehren J, Paolucci S, Kremer AE, Lara M, Pardo MR, Zoller H, Degasperi E, Peiffer KH, Sighinolfi L, Téllez F, Graf C, Ghisetti V, Schreiber J, Fernández-Fuertes E, Boglione L, Muñoz-Medina L, Stauber R, Gennari W, Figueruela B, Santos J, Lampertico P, Zeuzem S, Ceccherini-Silberstein F, García F, Sarrazin C; HCV Virology Italian Resistance Network (VIRONET-C) collaborators; Spanish GEHEP-004 Collaborators; Members of the German HCV resistance study group. Failure on voxilaprevir, velpatasvir, sofosbuvir and efficacy of rescue therapy. J Hepatol. 2021 Apr;74(4):801-810. doi: 10.1016/j.jhep.2020.11.017. Epub 2020 Nov 19. PMID: 33220331.

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15: Zhuang L, Li J, Zhang Y, Ji S, Li Y, Zhao Y, Li B, Li W, Quan M, Duan Y, Zhao H, Cheng D, Wang X, Ou W, Xing H. Real-World Effectiveness of Direct-Acting Antiviral Regimens against Hepatitis C Virus (HCV) Genotype 3 Infection: A Systematic Review and Meta-Analysis. Ann Hepatol. 2020 Oct 12;23:100268. doi: 10.1016/j.aohep.2020.09.012. Epub ahead of print. PMID: 33059055.

16: Vermehren J, Serfert Y, Cornberg M, Stoehr A, Klinker H, Simon KG, Teuber G, Deterding K, Schulze Zur Wiesch J, Jung MC, Manns MP, Zeuzem S, Wedemeyer H, Sarrazin C. Sofosbuvir, velpatasvir, and voxilaprevir for patients with failure of previous direct-acting antiviral therapy for chronic hepatitis C: Results from the German Hepatitis C-Registry (DHC-R). Z Gastroenterol. 2020 Sep;58(9):841-846. English. doi: 10.1055/a-1217-7669. Epub 2020 Sep 18. PMID: 32947629.

17: Papaluca T, Roberts SK, Strasser SI, Stuart KA, Farrell G, MacQuillan G, Dore GJ, Wade AJ, George J, Hazeldine S, O'Beirne J, Wigg A, Fisher L, McGarity B, Sawhney R, Sinclair M, Thomas J, Valiozis I, Weltman M, Wilson M, Woodward A, Ahlenstiel G, Haque M, Levy M, Prewett E, Sievert W, Sood S, Tse E, Valaydon Z, Bowden S, Douglas M, New K, O'Keefe J, Hellard M, Doyle J, Stoove M, Thompson AJ. Efficacy and safety of sofosbuvir/velpatasvir/voxilaprevir for HCV NS5A-inhibitor experienced patients with difficult to cure characteristics. Clin Infect Dis. 2020 Sep 5:ciaa1318. doi: 10.1093/cid/ciaa1318. Epub ahead of print. PMID: 32887983.

18: Bellesini M, Bianchin M, Corradi C, Donadini MP, Raschi E, Squizzato A. Drug-Drug Interactions between Direct Oral Anticoagulants and Hepatitis C Direct-Acting Antiviral Agents: Looking for Evidence Through a Systematic Review. Clin Drug Investig. 2020 Nov;40(11):1001-1008. doi: 10.1007/s40261-020-00962-y. PMID: 32809123; PMCID: PMC7595962.

19: Ruiz-Boy S, Rodriguez-Reyes M, Sotoca-Momblona JM. Effectiveness of sofosbuvir/velpatasvir/voxilaprevir in patients with chronic hepatitis C virus infection and virologic failure to direct-acting antivirals. Med Clin (Barc). 2020 Aug 14:S0025-7753(20)30507-8. English, Spanish. doi: 10.1016/j.medcli.2020.05.054. Epub ahead of print. PMID: 32807510.

20: de Salazar A, Dietz J, di Maio VC, Vermehren J, Paolucci S, Müllhaupt B, Coppola N, Cabezas J, Stauber RE, Puoti M, Arenas Ruiz Tapiador JI, Graf C, Aragri M, Jimenez M, Callegaro A, Pascasio Acevedo JM, Macias Rodriguez MA, Rosales Zabal JM, Micheli V, Garcia Del Toro M, Téllez F, García F, Sarrazin C, Ceccherini-Silberstein F; GEHEP-004 cohort, the European HCV Resistance Study Group and the HCV Virology Italian Resistance Network (VIRONET C). Prevalence of resistance-associated substitutions and retreatment of patients failing a glecaprevir/pibrentasvir regimen. J Antimicrob Chemother. 2020 Nov 1;75(11):3349-3358. doi: 10.1093/jac/dkaa304. PMID: 32772078.