glecaprevir

{{short description|Chemical compound}}

{{Drugbox

| 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

| image = Glecaprevir.svg

| image_class = skin-invert-image

| width =

| tradename = Mavyret (combination with pibrentasvir)

| Drugs.com =

| licence_US =

| pregnancy_AU =

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| legal_AU =

| legal_CA =

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| routes_of_administration = By mouth

| bioavailability =

| protein_bound = 97.5%

| metabolism = CYP3A

| elimination_half-life = 6 hours

| excretion = Faeces (92.1%), urine (0.7%)

| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 1365970-03-1

| ATC_prefix = None

| ATC_suffix =

| PubChem = 66828839

| DrugBank = DB13879

| ChemSpiderID = 35013015

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = K6BUU8J72P

| KEGG = D10814

| ChEMBL =

| NIAID_ChemDB =

| PDB_ligand =

| synonyms = ABT-493

| chemical_formula =

| C = 38 | H = 46 | F = 4 | N=6 | O=9 | S=1

| molecular_weight =

| 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

| StdInChI = 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

| StdInChIKey = MLSQGNCUYAMAHD-ITNVBOSISA-N

}}

Glecaprevir (INN,{{cite web | title = International Nonproprietary Names for Pharmaceutical Substances (INN). Recommended International Nonproprietary Names: List 76 | url =https://www.who.int/medicines/publications/druginformation/innlists/RL76.pdf | publisher = World Health Organization | access-date = 25 February 2017 | page = 503}}) is a hepatitis C virus (HCV) nonstructural (NS) protein 3/4A protease inhibitor that was identified jointly by AbbVie and Enanta Pharmaceuticals.{{Cite news |url=https://cen.acs.org/articles/92/i38/Madeleine-Jacobs-Named-President-CEO.html |title=ACS names its 2023 Heroes of Chemistry |date=August 14, 2023 |volume=101 |issue=26 |work=Chemical & Engineering News |last=Notman |first=Nina |access-date=2024-04-04 |archive-url=

https://web.archive.org/web/20240316194612/https://cen.acs.org/acs-news/ACS-names-2023-Heroes-Chemistry/101/web/2023/07 |archive-date=2024-03-16}} 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.{{cite journal | vauthors = Lawitz EJ, O'Riordan WD, Asatryan A, Freilich BL, Box TD, Overcash JS, Lovell S, Ng TI, Liu W, Campbell A, Lin CW, Yao B, Kort J | display-authors = 6 | title = Potent Antiviral Activities of the Direct-Acting Antivirals ABT-493 and ABT-530 with Three-Day Monotherapy for Hepatitis C Virus Genotype 1 Infection | journal = Antimicrobial Agents and Chemotherapy | volume = 60 | issue = 3 | pages = 1546–55 | date = December 2015 | pmid = 26711747 | pmc = 4775945 | doi = 10.1128/AAC.02264-15 }}

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.{{cite news | title = 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. | url = https://news.abbvie.com/news/abbvie-submits-new-drug-application-to-us-fda-for-its-investigational-regimen-glecaprevirpibrentasvir-gp-for-treatment-all-major-genotypes-chronic-hepatitis-c.htm | access-date = 25 February 2017 | publisher = AbbVie Inc. North Chicago, Illinois, U.S.A. | date = December 19, 2016 | language = en | archive-date = 20 August 2017 | archive-url = https://web.archive.org/web/20170820203045/https://news.abbvie.com/news/abbvie-submits-new-drug-application-to-us-fda-for-its-investigational-regimen-glecaprevirpibrentasvir-gp-for-treatment-all-major-genotypes-chronic-hepatitis-c.htm | url-status = dead }} In Europe, it was approved on 17 August 2017 for the same indication, under the trade name Maviret.{{cite web|url=http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Summary_for_the_public/human/004430/WC500233680.pdf|title=Maviret: EPAR – Summary for the public|publisher=European Medicines Agency|date=2017-08-17|access-date=2017-10-20|archive-date=2017-10-19|archive-url=https://web.archive.org/web/20171019163924/http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Summary_for_the_public/human/004430/WC500233680.pdf|url-status=dead}}