Elbasvir

Elbasvir
Clinical data
Trade namesZepatier (combination with grazoprevir)
Other namesMK-8742
License data
Routes of
administration
Oral
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Protein binding>99.9%
MetabolismCYP3A4
Elimination half-life24 hours
Excretion>90% via faeces, <1% via urine
Identifiers
  • Dimethyl N,N’-([(6S)-6H-indolo[1,2-c] [1,3]benzoxazine-3,10-diyl]bis{1H-imidazole-5,2-diyl-(2S)-pyrrolidine-2,1-diyl[(2S)-1-oxo-3-methylbutane-1,2-diyl]})biscarbamate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
CompTox Dashboard (EPA)
ECHA InfoCard100.234.242 Edit this at Wikidata
Chemical and physical data
FormulaC49H55N9O7
Molar mass882.035 g·mol−1
3D model (JSmol)
  • CC(C)[C@@H](C(=O)N1CCC[C@H]1c2[nH]cc(n2)c3ccc4c(c3)cc-5n4[C@@H](Oc6c5ccc(c6)c7c[nH]c(n7)[C@@H]8CCCN8C(=O)[C@H](C(C)C)NC(=O)OC)c9ccccc9)NC(=O)OC
  • InChI=1S/C49H55N9O7/c1-27(2)41(54-48(61)63-5)45(59)56-20-10-14-37(56)43-50-25-34(52-43)30-17-19-36-32(22-30)23-39-33-18-16-31(24-40(33)65-47(58(36)39)29-12-8-7-9-13-29)35-26-51-44(53-35)38-15-11-21-57(38)46(60)42(28(3)4)55-49(62)64-6/h7-9,12-13,16-19,22-28,37-38,41-42,47H,10-11,14-15,20-21H2,1-6H3,(H,50,52)(H,51,53)(H,54,61)(H,55,62)/t37-,38-,41-,42-,47-/m0/s1
  • Key:BVAZQCUMNICBAQ-PZHYSIFUSA-N

Elbasvir is a drug approved by the FDA in January 2016[1] for the treatment of hepatitis C. It was developed by Merck and completed Phase III trials, used in combination with the NS3/4A protease inhibitor grazoprevir under the trade name Zepatier, either with or without ribavirin.[2]

Elbasvir is a highly potent and selective NS5A inhibitor of the hepatitis C virus NS5A replication complex.[3] It has only been investigated as a combination product with other complementary hepatitis C antiviral drugs such as grazoprevir and MK-3682, and it is unclear whether elbasvir would show robust antiviral activity if it was administered by itself. Nevertheless, combination products of this type represent the most successful approach yet developed for actually curing hepatitis C, rather than merely slowing the progression of the disease.[4]

  1. ^ FDA approves Zepatier for treatment of chronic hepatitis C genotypes 1 and 4. January 28, 2016
  2. ^ Lawitz E, Gane E, Pearlman B, Tam E, Ghesquiere W, Guyader D, et al. (March 2015). "Efficacy and safety of 12 weeks versus 18 weeks of treatment with grazoprevir (MK-5172) and elbasvir (MK-8742) with or without ribavirin for hepatitis C virus genotype 1 infection in previously untreated patients with cirrhosis and patients with previous null response with or without cirrhosis (C-WORTHY): a randomised, open-label phase 2 trial". Lancet. 385 (9973): 1075–86. doi:10.1016/S0140-6736(14)61795-5. PMID 25467591.
  3. ^ Coburn CA, Meinke PT, Chang W, Fandozzi CM, Graham DJ, Hu B, et al. (December 2013). "Discovery of MK-8742: an HCV NS5A inhibitor with broad genotype activity". ChemMedChem. 8 (12): 1930–40. doi:10.1002/cmdc.201300343. PMID 24127258. S2CID 10543092.
  4. ^ Gentile I, Buonomo AR, Zappulo E, Borgia G (July 2014). "Interferon-free therapies for chronic hepatitis C: toward a hepatitis C virus-free world?". Expert Review of Anti-Infective Therapy. 12 (7): 763–73. doi:10.1586/14787210.2014.929497. PMID 24918116. S2CID 207199323.