Lomibuvir

• CAT Number: I007687
• CAS Number: 1026785-55-6 (or 1026785-59-0)
• Molecular Formula: C25H35NO4S
• Molecular Weight: 445.618
• Purity: ≥95%
• Synonyms: VX-222; VX222; VX 222; VCH-222; VCH222; VCH 222; VX-22; VX22; VX 22; Lomibuvir;5-(3,3-dimethylbut-1-yn-1-yl)-3-((1r,4R)-N-((1r,4R)-4-hydroxycyclohexyl)-4-methylcyclohexane-1-carboxamido)thiophene-2-carboxylic acid
• Target: NS5B polymerase inhibitor
• Solubility: Soluble in DMSO, not in water
• Storage: 0 - 4°C for short term , or -20°C for long term.
• IUPAC Name: 5-(3,3-dimethylbut-1-ynyl)-3-[(4-hydroxycyclohexyl)-(4-methylcyclohexanecarbonyl)amino]thiophene-2-carboxylic acid
• InChI: 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)
• InChIKey: WPMJNLCLKAKMLA-UHFFFAOYSA-N
• SMILES: CC1CCC(CC1)C(=O)N(C2CCC(CC2)O)C3=C(SC(=C3)C#CC(C)(C)C)C(=O)O

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.

Reference

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.