Grazoprevir

from Wikipedia, the free encyclopedia
Structural formula
Grazoprevir structural formula
General
Surname Grazoprevir
other names
  • (1 R , 18 R , 20 R , 24 S , 27 S ) - N - {(1 R , 2 S ) -1 - [(Cyclopropylsulfonyl) carbamoyl] -2-vinylcyclopropyl} -7-methoxy-24- (2nd -methyl-2-propanyl) -22,25-dioxo-2,21-dioxa-4,11,23,26-tetraazapentacyclo [24.2.1.0 3.12 .0 5.10 .0 18.20 ] nonacosa-3 , 5,7,9,11-pentaen-27-carboxamide ( IUPAC )
  • MK-5172
Molecular formula C 38 H 50 N 6 O 9 S
External identifiers / databases
CAS number 1350514-68-9
PubChem 44603531
ChemSpider 28506694
DrugBank DB11575
Wikidata Q19786991
Drug information
ATC code

J05 AX68

properties
Molar mass 766.90 g mol −1
Physical state

firmly

safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS hazard labeling
no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Grazoprevir (synonym MK-5172 ) is an antiviral drug from the quinoxaline group that is used to treat infections with the hepatitis C virus .

properties

Grazoprevir is a second generation inhibitor and inhibits the viral protease consisting of the heterodimer NS3 / NS4A . It is effective against most HCV subtypes that are resistant to first generation HCV protease inhibitors .

Interactions

Grazoprevir is removed from the bloodstream by the proteins SLCO1B1 and SLCO1B3 . Drugs that inhibit these proteins increase the concentration of grazeprovir in the blood plasma , such as rifampicin , ciclosporin , the HIV drugs atazanavir , darunavir , lopinavir , saquinavir , tipranavir , cobicistat . It is broken down in the liver by cytochrome P450 3A4 . Drugs that induce CYP3A4 lower the concentration of grazoprevir, such as efavirenz , carbamazepine or St. John's wort , whereas CYP3A4 inhibitors increase the concentration.

Trade names

Grazoprevir is sold in combination with Elbasvir under the trade name Zepatier by MSD Sharp & Dohme .

Individual evidence

  1. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  2. ↑ S. Harper, JA McCauley, MT Rudd, M. Ferrara, M. DiFilippo, B. Crescenzi, U. Koch, A. Petrocchi, MK Holloway, JW Butcher, JJ Romano, KJ ​​Bush, KF Gilbert, CJ McIntyre, KT Nguyen, E. Nizi, SS Carroll, SW Ludmerer, C. Burlein, JM DiMuzio, DJ Graham, CM McHale, MW Stahlhut, DB Olsen, E. Monteagudo, S. Cianetti, C. Giuliano, V. Pucci, N. Trainor , CM Fandozzi, M. Rowley, PJ Coleman, JP Vacca, V. Summa, NJ Liverton: Discovery of MK-5172, a Macrocyclic Hepatitis C Virus NS3 / 4a Protease Inhibitor. In: ACS medicinal chemistry letters. Volume 3, number 4, April 2012, pp. 332-336, doi: 10.1021 / ml300017p , PMID 24900473 , PMC 4025840 (free full text).
  3. ↑ I. Gentile, AR Buonomo, F. Borgia, E. Zappulo, G. Castaldo, G. Borgia: MK-5172: a second-generation protease inhibitor for the treatment of hepatitis C virus infection. In: Expert opinion on investigational drugs. Volume 23, number 5, May 2014, pp. 719-728, doi: 10.1517 / 13543784.2014.902049 , PMID 24666106 .