| Description |
Labelled Telaprevir. VX-950 is a potent, selective, peptidomimetic inhibitor of the hepatitis C virus (HCV) NS3-4A serine protease, and it demonstrated excellent antiviral activity both in genotype 1b HCV replicon cells (50% inhibitory concentration [IC50] = 354 nM) and in human fetal hepatocytes infected with genotype 1a HCV-positive patient sera (IC50 = 280 nM). VX-950 forms a covalent but reversible complex with the genotype 1a HCV NS3-4A protease in a slow-on, slow-off process with a steady-state inhibition constant (K(i)*) of 7 nM. Dissociation of the covalent enzyme-inhibitor complex of VX-950 and genotype 1a HCV protease has a half-life of almost an hour. A >4-log10 reduction in the HCV RNA levels was observed after a 2-week incubation of replicon cells with VX-950, with no rebound of viral RNA observed after withdrawal of the inhibitor. In several animal species, VX-950 exhibits a favorable pharmacokinetic profile with high exposure in the liver. In a recently developed HCV protease mouse model, VX-950 showed excellent inhibition of HCV NS3-4A protease activity in the liver. |
| Synonyms |
(1S,3aR,6aS)-(2S)-2-Cyclohexyl-N-(2-pyrazinylcarbonyl)glycyl-3-methyl-L-valyl-N-[(1S)-1-[2-[(cyclopropyl-d4)amino]-2-oxoacetyl]butyl]octahydrocyclopenta[c]pyrrole-1-carboxamide; LY 570310-d4; MP 424-d4; VRT 111950-d4; VX 950-d4 |
| IUPAC Name |
(3S,3aS,6aR)-2-[(2S)-2-[[(2S)-2-cyclohexyl-2-(pyrazine-2-carbonylamino)acetyl]amino]-3,3-dimethylbutanoyl]-N-[(3S)-1,2-dioxo-1-[(2,2,3,3-tetradeuteriocyclopropyl)amino]hexan-3-yl]-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrole-3-carboxamide |
| Related CAS |
402957-28-2 (unlabelled)
|
| Canonical SMILES |
O=C(N[C@@H](C1CCCCC1)C(N[C@@H](C(C)(C)C)C(N2[C@H](C(N[C@H](C(C(NC3C([2H])([2H])C3([2H])[2H])=O)=O)CCC)=O)[C@](CCC4)([H])[C@]4([H])C2)=O)=O)C5=NC=CN=C5 |
| InChI |
InChI=1S/C36H53N7O6/c1-5-10-25(29(44)34(48)39-23-15-16-23)40-33(47)28-24-14-9-13-22(24)20-43(28)35(49)30(36(2,3)4)42-32(46)27(21-11-7-6-8-12-21)41-31(45)26-19-37-17-18-38-26/h17-19,21-25,27-28,30H,5-16,20H2,1-4H3,(H,39,48)(H,40,47)(H,41,45)(H,42,46)/t22-,24-,25-,27-,28-,30+/m0/s1/i15D2,16D2 |
| InChI Key |
BBAWEDCPNXPBQM-WSZQYWDLSA-N |
| Melting Point |
116-123°C |
| Purity |
>98% |
| Solubility |
Soluble in Chloroform, Methanol (Slightly) |
| Appearance |
Pale Yellow to Light Yellow Waxy Solid |
| Storage |
Store at-20°C Freezer, Under Inert Atmosphere |
| Quality Standard |
- |
![Telaprevir-[d4]](https://resource.bocsci.com/structure/telaprevir-%5Bd4%5D.gif)
