Lomibuvir | VX-222 | CAS#1026785-55-6 | 1026785-59-0 | NS5B polymerase inhibitor

MedKoo Cat#: 319718 | Name: Lomibuvir

Description:

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

Lomibuvir, also known as VX-222, VCH-222 and VX22, is an nonnucleoside NS5B polymerase inhibitor. VX-222 inhibits the 1b/Con1 HCV subgenomic replicon, with 50% effective concentrations (EC(50)s) 5 nM. VX-222 binds to the HCV polymerase with dissociation constants of 17 nM. In phase 1 and 2 clinical studies, VX-222 demonstrated effective antiviral efficacy, with substantial reductions in plasma HCV RNA in patients chronically infected with genotype 1 HCV.

Chemical Structure

Lomibuvir

CAS#1026785-55-6 (or 1026785-59-0)

Theoretical Analysis

MedKoo Cat#: 319718

Name: Lomibuvir

CAS#: 1026785-55-6 (or 1026785-59-0)

Chemical Formula: C25H35NO4S

Exact Mass: 445.2287

Molecular Weight: 445.62

Elemental Analysis: C, 67.38; H, 7.92; N, 3.14; O, 14.36; S, 7.19

Price and Availability

Size	Price	Availability
500mg	USD 2,950.00	2 Weeks
1g	USD 4,350.00	2 Weeks
2g	USD 8,250.00	2 Weeks

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Related CAS #

No Data

Synonym

VX-222; VX222; VX 222; VCH-222; VCH222; VCH 222; VX-22; VX22; VX 22; Lomibuvir

IUPAC/Chemical Name

5-(3,3-dimethylbut-1-yn-1-yl)-3-((1r,4R)-N-((1r,4R)-4-hydroxycyclohexyl)-4-methylcyclohexane-1-carboxamido)thiophene-2-carboxylic acid

InChi Key

WPMJNLCLKAKMLA-VVPTUSLJSA-N

InChi Code

InChI=1S/C25H35NO4S/c1-16-5-7-17(8-6-16)23(28)26(18-9-11-19(27)12-10-18)21-15-20(13-14-25(2,3)4)31-22(21)24(29)30/h15-19,27H,5-12H2,1-4H3,(H,29,30)/t16-,17-,18-,19-

SMILES Code

O=C(C1=C(N([C@H]2CC[C@H](O)CC2)C([C@H]3CC[C@H](C)CC3)=O)C=C(C#CC(C)(C)C)S1)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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Lomibuvir (VX-222), a selective, non-nucleoside polymerase inhibitor, targets thumb pocket 2 of the HCV NS5B polymerase (RdRp) with a Kd of 17 nM.

In vitro activity:

TBD

In vivo activity:

TBD

	Solvent	mg/mL	mM
Solubility
	DMSO	100.0	224.41

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 445.62 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.

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:

TBD

In vitro protocol:

TBD

In vivo protocol:

TBD

1: Gentile I, Buonomo AR, Zappulo E, Borgia G. Discontinued drugs in 2012 - 2013: hepatitis C virus infection. Expert Opin Investig Drugs. 2015 Feb;24(2):239-51. doi: 10.1517/13543784.2015.982274. Epub 2014 Nov 11. PubMed PMID: 25384989. 2: Eltahla AA, Tay E, Douglas MW, White PA. Cross-genotypic examination of hepatitis C virus polymerase inhibitors reveals a novel mechanism of action for thumb binders. Antimicrob Agents Chemother. 2014 Dec;58(12):7215-24. doi: 10.1128/AAC.03699-14. Epub 2014 Sep 22. PubMed PMID: 25246395; PubMed Central PMCID: PMC4249545. 3: 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. 4: Jiang M, Zhang EZ, Ardzinski A, Tigges A, Davis A, Sullivan JC, Nelson M, Spanks J, Dorrian J, Nicolas O, Bartels DJ, Rao BG, Rijnbrand R, Kieffer TL. Genotypic and phenotypic analyses of hepatitis C virus variants observed in clinical studies of VX-222, a nonnucleoside NS5B polymerase inhibitor. Antimicrob Agents Chemother. 2014 Sep;58(9):5456-65. doi: 10.1128/AAC.03052-14. Epub 2014 Jun 30. PubMed PMID: 24982088; PubMed Central PMCID: PMC4135882. 5: Di Bisceglie AM, Sulkowski M, Gane E, Jacobson IM, Nelson D, DeSouza C, Alves K, George S, Kieffer T, Zhang EZ, Kauffman R, Asmal M, Koziel MJ. VX-222, a non-nucleoside NS5B polymerase inhibitor, in telaprevir-based regimens for genotype 1 hepatitis C virus infection. Eur J Gastroenterol Hepatol. 2014 Jul;26(7):761-73. doi: 10.1097/MEG.0000000000000084. PubMed PMID: 24901821. 6: Xue W, Jiao P, Liu H, Yao X. Molecular modeling and residue interaction network studies on the mechanism of binding and resistance of the HCV NS5B polymerase mutants to VX-222 and ANA598. Antiviral Res. 2014 Apr;104:40-51. doi: 10.1016/j.antiviral.2014.01.006. Epub 2014 Jan 23. PubMed PMID: 24462692. 7: Fenaux M, Eng S, Leavitt SA, Lee YJ, Mabery EM, Tian Y, Byun D, Canales E, Clarke MO, Doerffler E, Lazerwith SE, Lew W, Liu Q, Mertzman M, Morganelli P, Xu L, Ye H, Zhang J, Matles M, Murray BP, Mwangi J, Zhang J, Hashash A, Krawczyk SH, Bidgood AM, Appleby TC, Watkins WJ. Preclinical characterization of GS-9669, a thumb site II inhibitor of the hepatitis C virus NS5B polymerase. Antimicrob Agents Chemother. 2013 Feb;57(2):804-10. doi: 10.1128/AAC.02052-12. Epub 2012 Nov 26. PubMed PMID: 23183437; PubMed Central PMCID: PMC3553741. 8: Yi G, Deval J, Fan B, Cai H, Soulard C, Ranjith-Kumar CT, Smith DB, Blatt L, Beigelman L, Kao CC. Biochemical study of the comparative inhibition of hepatitis C virus RNA polymerase by VX-222 and filibuvir. Antimicrob Agents Chemother. 2012 Feb;56(2):830-7. doi: 10.1128/AAC.05438-11. Epub 2011 Dec 5. PubMed PMID: 22143520; PubMed Central PMCID: PMC3264230.