Vaniprevir

Vaniprevir (MK-7009) is a macrocyclic hepatitis C virus (HCV) NS3/4A protease inhibitor, developed by Merck & Co., which is currently in clinical testing.[1]

Vaniprevir
Names
IUPAC name
(1R,21S,24S)-21-tert-Butyl-N-((1R,2R)-1-{[(cyclopropylsulfonyl)amino]carbonyl}-2-ethylcyclopropyl)-16,16-dimethyl-3,19,22-trioxo-2,18-dioxa-4,20,23-triazatetracyclo[21.2.1.14,7.06,11]-heptacosa-6,8,10-triene-24-carboxamide
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.207.830
EC Number
  • 682-506-7
KEGG
PubChem CID
UNII
InChI
  • InChI=1S/C38H55N5O9S/c1-7-25-18-38(25,33(46)41-53(49,50)27-14-15-27)40-31(44)29-17-26-20-43(29)32(45)30(36(2,3)4)39-34(47)51-22-37(5,6)16-9-8-11-23-12-10-13-24-19-42(21-28(23)24)35(48)52-26/h10,12-13,25-27,29-30H,7-9,11,14-22H2,1-6H3,(H,39,47)(H,40,44)(H,41,46)/t25-,26-,29+,30-,38-/m1/s1
    Key: KUQWGLQLLVFLSM-ONAXAZCASA-N
SMILES
  • CC(C)(C)[C@H]1NC(=O)OCC(C)(C)CCCCc2cccc3CN(Cc23)C(=O)O[C@H]4C[C@@H](N(C4)C1=O)C(=O)N[C@@]5(C[C@H]5C=C)C(=O)NS(=O)(=O)C6CC6
Properties
Chemical formula
C38H55N5O9S
Molar mass 757.94 g·mol−1
Appearance White powder
Hazards
GHS labelling:
Pictograms
Signal word
Warning
Hazard statements
H373
Precautionary statements
P260, P314, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

In Japan, it was approved for treating hepatitis C in 2014 under the brand name Vanihep.[2][3]

References

  1. McCauley JA, McIntyre CJ, Rudd MT, Nguyen KT, Romano JJ, Butcher JW, Gilbert KF, Bush KJ, Holloway MK, Swestock J, Wan BL, Carroll SS, DiMuzio JM, Graham DJ, Ludmerer SW, Mao SS, Stahlhut MW, Fandozzi CM, Trainor N, Olsen DB, Vacca JP, Liverton NJ (March 2010). "Discovery of vaniprevir (MK-7009), a macrocyclic hepatitis C virus NS3/4a protease inhibitor". J. Med. Chem. 53 (6): 2443–63. doi:10.1021/jm9015526. PMID 20163176.
  2. "First recommendation for HCV drug vaniprevir, in Japan". datamonitorhealthcare.com. September 25, 2014.
  3. "New Drugs Approved" (PDF). Pharmaceuticals and Medical Devices Agency. {{cite journal}}: Cite journal requires |journal= (help)
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