Structure via PubChem · Public domain (PubChem)
grazoprevir
Sign in to saveAlso known as grazoprevir anhydrous, MK-5172
Grazoprevir is a drug approved for the treatment of hepatitis C. It was developed by Merck and completed Phase III trials, used in combination with the NS5A replication complex inhibitor elbasvir under the trade name Zepatier, either with or without ribavirin.
Chemical data
- Formula
- C38H50N6O9S
- Molecular weight
- 766.9 g/mol
- IUPAC name
- (1R,18R,20R,24S,27S)-24-tert-butyl-N-[(1R,2S)-1-(cyclopropylsulfonylcarbamoyl)-2-ethenylcyclopropyl]-7-methoxy-22,25-dioxo-2,21-dioxa-4,11,23,26-tetrazapentacyclo[24.2.1.03,12.05,10.018,20]nonacosa-3,5(10),6,8,11-pentaene-27-carboxamide
- SMILES
- CC(C)(C)[C@H]1C(=O)N2C[C@@H](C[C@H]2C(=O)N[C@@]3(C[C@H]3C=C)C(=O)NS(=O)(=O)C4CC4)OC5=NC6=C(C=CC(=C6)OC)N=C5CCCCC[C@@H]7C[C@H]7OC(=O)N1
- InChIKey
- OBMNJSNZOWALQB-NCQNOWPTSA-N
- XLogP
- 4.7
- Polar surface area
- 204 Ų
- H-bond donors
- 3
- H-bond acceptors
- 11
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 2016
- Admin. routes
- oral
- Indications
- chronic hepatitis C virus infection, hepatitis C virus infection
via ChEMBL · EBI
Research
464 papers- Grazoprevir.2006
- Elbasvir/grazoprevir.Australian prescriber · 2017
- Grazoprevir/elbasvir combination therapy for HCV infection.Therapeutic advances in gastroenterology · 2017
- Elbasvir and grazoprevir for the treatment of hepatitis C.Expert review of anti-infective therapy · 2021
- Elbasvir/Grazoprevir: A Review in Chronic HCV Genotypes 1 and 4.Drugs · 2017
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 766.336
- Has use
- medication
Show 6 more facts
- canonical SMILES
- CC(C)(C)C1C(=O)N2CC(CC2C(=O)NC3(CC3C=C)C(=O)NS(=O)(=O)C4CC4)OC5=NC6=C(C=CC(=C6)OC)N=C5CCCCCC7CC7OC(=O)N1
- chemical formula
- C₃₈H₅₀N₆O₉S
- Commons category
- Grazoprevir
- isomeric SMILES
- COC1=CC2=NC3=C(CCCCC[C@@H]4C[C@H]4OC(=O)N[C@H](C(=O)N5C[C@@H](C[C@H]5C(=O)N[C@@]6(C[C@H]6C=C)C(=O)NS(=O)(=O)C7CC7)O3)C(C)(C)C)N=C2C=C1
- medical condition treated
- hepatitis C
- route of administration
- oral administration
via Wikidata · CC0
~4 min read
Encyclopedic overview
6 sectionsContents
- Side effects
- Interactions
- Pharmacology
- Mechanism of action
- Pharmacokinetics
- References
{{Drugbox | IUPAC_name = (1R,18R,20R,24S,27S)-N-{(1R,2S)-1-[(Cyclopropylsulfonyl)carbamoyl]-2-vinylcyclopropyl}-7-methoxy-24-(2-methyl-2-propanyl)-22,25-dioxo-2,21-dioxa-4,11,23,26-tetraazapentacyclo[24.2.1.03,12.05,10.0 18,20]nonacosa-3,5,7,9,11-pentaene-27-carboxamide | image = Grazoprevir.svg | image_class = skin-invert-image
| tradename = Zepatier (combination with elbasvir) | Drugs.com = | MedlinePlus = | pregnancy_AU = | pregnancy_US = | pregnancy_category = | licence_EU = yes | legal_AU = | legal_CA = | legal_UK = | legal_US = Rx-only | legal_status = | routes_of_administration = Oral
Excerpted from Wikipedia’s “grazoprevir” article, available under the CC BY-SA 4.0 licence.