Cabotegravir sodiumProduct ingredient for Cabotegravir

Name
Cabotegravir sodium
Drug Entry
Cabotegravir

Cabotegravir, or GSK1265744, is an HIV-1 integrase inhibitor that is prescribed with the non-nucleoside reverse transcriptase inhibitor, rilpivirine.4,5,6 Early research into cabotegravir showed it had lower oral bioavailability than dolutegravir.4 The devlopment of cabotegravir was later developed to create a long acting monthly intramuscular injection.4,6

Cabotegravir was granted FDA approval on 21 January 2021.7

Accession Number
DBSALT002064
Structure
Thumb
Synonyms
Cabotegravir sodium
External IDs
GSK-1265744B / GSK1265744B / S 265744B / S-265744B
UNII
3L12PT535M
CAS Number
1051375-13-3
Weight
Average: 427.34
Monoisotopic: 427.09557123
Chemical Formula
C19H16F2N3NaO5
InChI Key
AEZBWGMXBKPGFP-KIUAEZIZSA-M
InChI
InChI=1S/C19H17F2N3O5.Na/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);/q;+1/p-1/t9-,14+;/m0./s1
IUPAC Name
sodium (3R,6S)-12-{[(2,4-difluorophenyl)methyl]carbamoyl}-6-methyl-8,11-dioxo-4-oxa-1,7-diazatricyclo[7.4.0.0^{3,7}]trideca-9,12-dien-10-olate
SMILES
[Na+].[H][C@@]12CN3C=C(C(=O)NCC4=CC=C(F)C=C4F)C(=O)C([O-])=C3C(=O)N1[C@@H](C)CO2
ChemSpider
32702138
ChEMBL
CHEMBL3137330
Wikipedia
Cabotegravir
Predicted Properties
PropertyValueSource
logP1.04ChemAxon
pKa (Strongest Acidic)10.04ChemAxon
pKa (Strongest Basic)-0.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area102.01 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity108.45 m3·mol-1ChemAxon
Polarizability37.45 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon