WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 205941
CAS#: 244133-31-1
Description: VRT-043198, the active metabolite of VX-765 (Belnacasan), is a Caspase inhibitor. VRT-043198 exhibits 100- to 10,000-fold selectivity against other caspase-3 and -6 to -9. VRT-043198 inhibited the release of interleukin (IL)-1beta and IL-18, but it had little effect on the release of several other cytokines, including IL-1alpha, tumor necrosis factor-alpha, IL-6 and IL-8.
MedKoo Cat#: 205941
Name: VRT-043198
CAS#: 244133-31-1
Chemical Formula: C22H29ClN4O6
Exact Mass: 480.17756
Molecular Weight: 480.94
Elemental Analysis: C, 54.94; H, 6.08; Cl, 7.37; N, 11.65; O, 19.96
Synonym: VRT043198, VRT-043198, VRT 043198; mitabolite of VX-765 (Belnacasan);
IUPAC/Chemical Name: 1. (2S)-1-((S)-2-(4-amino-3-chlorobenzamido)-3,3-dimethylbutanoyl)-N-((3S)-2-hydroxy-5-oxotetrahydrofuran-3-yl)pyrrolidine-2-carboxamide (ring-close) 2. (S)-3-((S)-1-((S)-2-(4-amino-3-chlorobenzamido)-3,3-dimethylbutanoyl)pyrrolidine-2-carboxamido)-4-oxobutanoic acid (ring open)
InChi Key: GGAMPJOZFRKVQR-CIWGKMQQSA-N; SOZONDBMOYWSRW-QANKJYHBSA-N.
InChi Code: InChI=1S/C22H29ClN4O6/c1-22(2,3)17(26-18(29)11-6-7-13(24)12(23)9-11)20(31)27-8-4-5-15(27)19(30)25-14-10-16(28)33-21(14)32/h6-7,9,14-15,17,21,32H,4-5,8,10,24H2,1-3H3,(H,25,30)(H,26,29)/t14-,15-,17+,21?/m0/s1; InChI=1S/C22H29ClN4O6/c1-22(2,3)18(26-19(31)12-6-7-15(24)14(23)9-12)21(33)27-8-4-5-16(27)20(32)25-13(11-28)10-17(29)30/h6-7,9,11,13,16,18H,4-5,8,10,24H2,1-3H3,(H,25,32)(H,26,31)(H,29,30)/t13-,16-,18+/m0/s1
SMILES Code: 1. O=C([C@H]1N(C([C@H](C(C)(C)C)NC(C2=CC=C(N)C(Cl)=C2)=O)=O)CCC1)N[C@@H](C3)C(O)OC3=O (ring-close) 2. O=C([C@H]1N(C([C@@H](NC(C2=CC=C(N)C(Cl)=C2)=O)C(C)(C)C)=O)CCC1)N[C@@H](CC(O)=O)C=O (ring-open)
1: Adriaenssens Y, Jiménez Fernández D, Vande Walle L, Elvas F, Joossens J, Lambeir A, Augustyns K, Lamkanfi M, Van der Veken P. Carboxylate isosteres for caspase inhibitors: the acylsulfonamide case revisited. Org Biomol Chem. 2017 Sep 13;15(35):7456-7473. doi: 10.1039/c7ob01403a. PubMed PMID: 28837200.
2: Wannamaker W, Davies R, Namchuk M, Pollard J, Ford P, Ku G, Decker C, Charifson P, Weber P, Germann UA, Kuida K, Randle JC. (S)-1-((S)-2-{[1-(4-amino-3-chloro-phenyl)-methanoyl]-amino}-3,3-dimethyl-butanoy l)-pyrrolidine-2-carboxylic acid ((2R,3S)-2-ethoxy-5-oxo-tetrahydro-furan-3-yl)-amide (VX-765), an orally available selective interleukin (IL)-converting enzyme/caspase-1 inhibitor, exhibits potent anti-inflammatory activities by inhibiting the release of IL-1beta and IL-18. J Pharmacol Exp Ther. 2007 May;321(2):509-16. Epub 2007 Feb 8. PubMed PMID: 17289835.
