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glecaprevir   Click here for help

GtoPdb Ligand ID: 11267

Synonyms: ABT-493 | ABT493 | Maviret® | Mavyret® (glecaprevir + pibrentasvir)
Approved drug PDB Ligand
glecaprevir is an approved drug (EMA & FDA (2017))
Compound class: Synthetic organic
Comment: Glecaprevir is an orally available anti-hepatitis C virus (HCV) drug. It is a direct-acting inhibitor of the HCV NS3/4A protease, and thereby targets viral RNA replication.

glecaprevir is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 14
Hydrogen bond donors 3
Rotatable bonds 9
Topological polar surface area 203.6
Molecular weight 838.3
XLogP 4.64
No. Lipinski's rules broken 1

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES O=C1O[C@@H]2CCC[C@H]2OC/C=C/C(F)(F)c2c(O[C@H]3CN(C(=O)[C@@H](N1)C(C)(C)C)[C@@H](C3)C(=O)N[C@@]1(C[C@H]1C(F)F)C(=O)NS(=O)(=O)C1(C)CC1)nc1c(n2)cccc1
Isomeric SMILES O=C1O[C@@H]2CCC[C@H]2OC/C=C/C(F)(F)c2c(O[C@H]3CN(C(=O)[C@@H](N1)C(C)(C)C)[C@@H](C3)C(=O)N[C@@]1(C[C@H]1C(F)F)C(=O)NS(=O)(=O)C1(C)CC1)nc1c(n2)cccc1
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
InChI Key MLSQGNCUYAMAHD-ITNVBOSISA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes. EU EMA (2017)  |  US FDA (2017)
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
International Nonproprietary Names Click here for help
INN number INN
10261 glecaprevir
Synonyms Click here for help
ABT-493 | ABT493 | Maviret® | Mavyret® (glecaprevir + pibrentasvir)
Database Links Click here for help
CAS Registry No. 1365970-03-1 (source: WHO INN record)
ChEMBL Ligand CHEMBL3545363
DrugBank Ligand DB13879
DrugCentral Ligand 5243
GtoPdb PubChem SID 434321702
PubChem CID 66828839
RCSB PDB Ligand O31
Search Google for chemical match using the InChIKey MLSQGNCUYAMAHD-ITNVBOSISA-N
Search Google for chemicals with the same backbone MLSQGNCUYAMAHD
Search PubMed clinical trials glecaprevir
Search PubMed titles glecaprevir
Search PubMed titles/abstracts glecaprevir
UniChem Compound Search for chemical match using the InChIKey MLSQGNCUYAMAHD-ITNVBOSISA-N
UniChem Connectivity Search for chemical match using the InChIKey MLSQGNCUYAMAHD-ITNVBOSISA-N

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MedChemExpress
Glecaprevir (links to external site)
Cat. No. HY-17634