cabotegravir   Click here for help

GtoPdb Ligand ID: 11386

Synonyms: Apretude® | CAB | Cabenuva® (cabotegravir + rilpivirine) | GSK-1265744 | GSK1265744 | GSK744 | Vocabria®
Approved drug
cabotegravir is an approved drug (EMA (2020), FDA (2021))
Compound class: Synthetic organic
Comment: Cabotegravir (GSK1265744, CAB) is a long-acting HIV integrase inhibitor. It is structurally related to dolutegravir.
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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Click here for structure editor
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 5
Hydrogen bond donors 2
Rotatable bonds 4
Topological polar surface area 100.87
Molecular weight 405.11
XLogP 3.72
No. Lipinski's rules broken 0

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 Fc1ccc(c(c1)F)CNC(=O)c1cn2C[C@H]3OC[C@@H](N3C(=O)c2c(c1=O)O)C
Isomeric SMILES Fc1ccc(c(c1)F)CNC(=O)c1cn2C[C@H]3OC[C@@H](N3C(=O)c2c(c1=O)O)C
InChI InChI=1S/C19H17F2N3O5/c1-9-8-29-14-7-23-6-12(16(25)17(26)15(23)19(28)24(9)14)18(27)22-5-10-2-3-11(20)4-13(10)21/h2-4,6,9,14,26H,5,7-8H2,1H3,(H,22,27)/t9-,14+/m0/s1
InChI Key WCWSTNLSLKSJPK-LKFCYVNXSA-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 (EMA (2020), FDA (2021))
International Nonproprietary Names Click here for help
INN number INN
9903 cabotegravir
Synonyms Click here for help
Apretude® | CAB | Cabenuva® (cabotegravir + rilpivirine) | GSK-1265744 | GSK1265744 | GSK744 | Vocabria®
Database Links Click here for help
BindingDB Ligand 50492496
CAS Registry No. 1051375-10-0 (source: WHO INN record)
ChEMBL Ligand CHEMBL2403238
DrugBank Ligand DB11751
GtoPdb PubChem SID 440816755
PubChem CID 54713659
Search Google for chemical match using the InChIKey WCWSTNLSLKSJPK-LKFCYVNXSA-N
Search Google for chemicals with the same backbone WCWSTNLSLKSJPK
Search PubMed clinical trials cabotegravir
Search PubMed titles cabotegravir
Search PubMed titles/abstracts cabotegravir
UniChem Compound Search for chemical match using the InChIKey WCWSTNLSLKSJPK-LKFCYVNXSA-N
UniChem Connectivity Search for chemical match using the InChIKey WCWSTNLSLKSJPK-LKFCYVNXSA-N