Glecaprevir

Glecaprevir (INN,[1]) is a hepatitis C virus (HCV) nonstructural (NS) protein 3/4A protease inhibitor that was identified jointly by AbbVie and Enanta Pharmaceuticals. It is being developed as a treatment of chronic hepatitis C infection in co-formulation with an HCV NS5A inhibitor pibrentasvir. Together they demonstrated potent antiviral activity against major HCV genotypes and high barriers to resistance in vitro.[2]

Glecaprevir

Clinical data
Trade names	Mavyret (combination with pibrentasvir)
Other names	ABT-493
Routes of administration	By mouth
ATC code	None
Pharmacokinetic data
Protein binding	97.5%
Metabolism	CYP3A
Elimination half-life	6 hours
Excretion	Faeces (92.1%), urine (0.7%)
Identifiers
IUPAC name (3aR,7S,10S,12R,21E,24aR)-7-tert-Butyl-N-{(1R,2R)-2-(difluoromethyl)-1-[(1-methylcyclopropane-1-sulfonyl)carbamoyl]cyclopropyl}-20,20-difluoro-5,8-dioxo-2,3,3a,5,6,7,8,11,12,20,23,24a-dodecahydro-1H,10H-9,12-methanocyclopenta[18,19][1,10,17,3,6]trioxadiazacyclonon adecino[11,12-b]quinoxaline-10-carboxamide
CAS Number	1365970-03-1
PubChem CID	66828839
DrugBank	DB13879
ChemSpider	35013015
UNII	K6BUU8J72P
KEGG	D10814
Chemical and physical data
Formula	C38H46F4N6O9S
Molar mass	838.87 g·mol^−1
3D model (JSmol)	Interactive image
SMILES CC1(CC1)S(=O)(=O)NC(=O)[C@]2(C[C@H]2C(F)F)NC(=O)[C@@H]3C[C@@H]4CN3C(=O)[C@@H](NC(=O)O[C@@H]5CCC[C@H]5OC/C=C/C(C6=NC7=CC=CC=C7N=C6O4)(F)F)C(C)(C)C
InChI InChI=1S/C38H46F4N6O9S/c1-35(2,3)28-32(50)48-19-20(17-24(48)30(49)46-37(18-21(37)29(39)40)33(51)47-58(53,54)36(4)14-15-36)56-31-27(43-22-9-5-6-10-23(22)44-31)38(41,42)13-8-16-55-25-11-7-12-26(25)57-34(52)45-28/h5-6,8-10,13,20-21,24-26,28-29H,7,11-12,14-19H2,1-4H3,(H,45,52)(H,46,49)(H,47,51)/b13-8+/t20-,21+,24+,25-,26-,28-,37-/m1/s1 Key:MLSQGNCUYAMAHD-ITNVBOSISA-N

On 19 December 2016, AbbVie submitted a new drug application to the U.S. Food and Drug Administration for the glecaprevir/pibrentasvir (trade name Mavyret) regimen for the treatment of all major genotypes (1–6) of chronic hepatitis C. On 3 August 2017 the FDA approved the combination for hepatitis C treatment.[3] In Europe, it was approved on 17 August 2017 for the same indication, under the trade name Maviret.[4]

See also

• Protease inhibitor (pharmacology)

References

1. "International Nonproprietary Names for Pharmaceutical Substances (INN). Recommended International Nonproprietary Names: List 76" (PDF). World Health Organization. p. 503. Retrieved 25 February 2017.
2. Lawitz EJ, O'Riordan WD, Asatryan A, Freilich BL, Box TD, Overcash JS, et al. (December 2015). "Potent Antiviral Activities of the Direct-Acting Antivirals ABT-493 and ABT-530 with Three-Day Monotherapy for Hepatitis C Virus Genotype 1 Infection". Antimicrobial Agents and Chemotherapy. 60 (3): 1546–55. doi:10.1128/AAC.02264-15. PMC 4775945. PMID 26711747.
3. "AbbVie Submits New Drug Application to U.S. FDA for its Investigational Regimen of Glecaprevir/Pibrentasvir (G/P) for the Treatment of All Major Genotypes of Chronic Hepatitis C." AbbVie Inc. North Chicago, Illinois, U.S.A. December 19, 2016. Retrieved 25 February 2017.
4. "Maviret: EPAR – Summary for the public" (PDF). European Medicines Agency. 2017-08-17.