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.4,6,7 Early research into cabotegravir showed it had lower oral bioavailability than dolutegravir,4 which resulted in the development of long acting monthly intramuscular injection formulation for cabotegravir.4,7

Cabotegravir was granted FDA approval on 21 January 2021 in combination with rilpivirine to treat HIV-1 infection in virologically suppressed individuals.8 While previously administered once monthly only, this combination product was granted FDA approval for dosing every two months on February 01, 2022 11 and without the need for an oral lead-in period prior.7

Accession Number
DBSALT002064
Structure
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