Glecaprevir

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;
CompTox Dashboard (EPA)	DTXSID901027945 ;
Chemical and physical data
Formula	C38H46F4N6O9S
Molar mass	838.87 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(C)(C)[C@@H]1NC(=O)O[C@@H]2CCC[C@H]2OC/C=C/C(F)(F)c2nc3ccccc3nc2O[C@@H]2C[C@@H](C(=O)N[C@]3(C(=O)NS(=O)(=O)C4(C)CC4)C[C@H]3C(F)F)N(C2)C1=O;
	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;

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.^[2] 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.^[3]

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.^[4] In Europe, it was approved on 17 August 2017 for the same indication, under the trade name Maviret.^[5]

References

^ "International Nonproprietary Names for Pharmaceutical Substances (INN). Recommended International Nonproprietary Names: List 76" (PDF). World Health Organization. p. 503. Retrieved 25 February 2017.
^ Notman, Nina (August 14, 2023). "ACS names its 2023 Heroes of Chemistry". Chemical & Engineering News. Vol. 101, no. 26. Archived from the original on 2024-03-16. Retrieved 2024-04-04.
^ 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.
^ "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. Archived from the original on 20 August 2017. Retrieved 25 February 2017.
^ "Maviret: EPAR – Summary for the public" (PDF). European Medicines Agency. 2017-08-17. Archived from the original (PDF) on 2017-10-19. Retrieved 2017-10-20.

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[INN-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] Notman, Nina (August 14, 2023). "ACS names its 2023 Heroes of Chemistry". Chemical & Engineering News. Vol. 101, no. 26. Archived from the original on 2024-03-16. Retrieved 2024-04-04.

[3] 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.

[4] "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. Archived from the original on 20 August 2017. Retrieved 25 February 2017.

[5] "Maviret: EPAR – Summary for the public" (PDF). European Medicines Agency. 2017-08-17. Archived from the original (PDF) on 2017-10-19. Retrieved 2017-10-20.

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See also

References