U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C19H16F2N3O5.Na
Molecular Weight 427.3347
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CABOTEGRAVIR SODIUM

SMILES

C[C@@]1([H])CO[C@]2([H])Cn3cc(c(=O)c(c3C(=O)N12)[O-])C(=NCc4ccc(cc4F)F)O.[Na+]

InChI

InChIKey=AEZBWGMXBKPGFP-KIUAEZIZSA-M
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

HIDE SMILES / InChI

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C19H16F2N3O5
Molecular Weight 404.345
Charge -1
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment:: https://www.ncbi.nlm.nih.gov/pubmed/27799824

Cabotegravir is an investigational drug that is being studied for the treatment and prevention of HIV infection. Cabotegravir belongs to a class (group) of HIV drugs called integrase inhibitors. Integrase inhibitors block an HIV enzyme called integrase. (An enzyme is a protein that starts or increases the speed of a chemical reaction.) By blocking integrase, integrase inhibitors prevent HIV from multiplying and can reduce the amount of HIV in the body. Cabotegravir does not require boosting with an additional drug. Two forms of cabotegravir are being studied: tablets that are taken by mouth (known as oral cabotegravir or oral CAB) and a long-acting injectable form that is injected into the muscle (known as cabotegravir LA or CAB LA; LA stands for "long-acting"). (A long-acting drug formulation works over a long period of time. Using this type of drug might mean that the drug could be taken less often, making a treatment or prevention regimen simpler to take.) Cabotegravir is in Phase-III clinical trials for HIV infections.

Originator

Curator's Comment:: # Shionogi - GlaxoSmithKline (JV)

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.200000000000000011 nM [IC50]
0.810000000000000053 µM [IC50]
0.409999999999999976 µM [IC50]
Conditions
PubMed

PubMed

TitleDatePubMed
Profile of cabotegravir and its potential in the treatment and prevention of HIV-1 infection: evidence to date.
2016
Effect of Cabotegravir on Cardiac Repolarization in Healthy Subjects.
2016 Nov
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment:: Long-acting cabotegravir is readily absorbed following intramuscular and subcutaneous administration https://www.ncbi.nlm.nih.gov/pubmed/26049948
10, 30, or 60 mg once daily
Route of Administration: Oral
Cabotegravir (GSK1265744) inhibited HIV replication with low or subnanomolar efficacy, it inhibited the HIV-1 integrase catalyzed strand transfer reaction with an IC50 of 3.0 nM in vitro. The antiviral EC50 against HIV-1 Ba-L was 0.22 nM, and that against NL432 was 0.34 nM in PBMCs, 0.57 nM using CellTiter-Glo and 1.3 nM using
Substance Class Chemical
Created
by admin
on Sat Jun 26 16:34:11 UTC 2021
Edited
by admin
on Sat Jun 26 16:34:11 UTC 2021
Record UNII
3L12PT535M
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CABOTEGRAVIR SODIUM
USAN   WHO-DD  
USAN  
Official Name English
GSK1265744B
Code English
VOCABRIA
Brand Name English
SODIUM (3S,11AR)-8-(((2,4-DIFLUOROPHENYL)METHYL)CARBAMOYL)-3-METHYL-5,7-DIOXO-2,3,5,7,11,11A-HEXAHYDROOXAZOLO(3,2-A)PYRIDO(1,2-D)PYRAZIN-6-OLATE
Systematic Name English
GSK-1265744B
Code English
CABOTEGRAVIR SODIUM [WHO-DD]
Common Name English
CABOTEGRAVIR SODIUM [JAN]
Common Name English
CABOTEGRAVIR SODIUM [USAN]
Common Name English
S-265744B
Code English
OXAZOLO(3,2-A)PYRIDO(1,2-D)PYRAZINE-8-CARBOXAMIDE, N-((2,4-DIFLUOROPHENYL)METHYL)-2,3,5,7,11,11A-HEXAHYDRO-6-HYDROXY-3-METHYL-5,7-DIOXO-, SODIUM SALT (1:1), (3S,11AR)-
Systematic Name English
Code System Code Type Description
NCI_THESAURUS
C166681
Created by admin on Sat Jun 26 16:34:11 UTC 2021 , Edited by admin on Sat Jun 26 16:34:11 UTC 2021
PRIMARY
DRUG BANK
DBSALT002064
Created by admin on Sat Jun 26 16:34:11 UTC 2021 , Edited by admin on Sat Jun 26 16:34:11 UTC 2021
PRIMARY
ChEMBL
CHEMBL2403238
Created by admin on Sat Jun 26 16:34:11 UTC 2021 , Edited by admin on Sat Jun 26 16:34:11 UTC 2021
PRIMARY
PUBCHEM
46215800
Created by admin on Sat Jun 26 16:34:11 UTC 2021 , Edited by admin on Sat Jun 26 16:34:11 UTC 2021
PRIMARY
FDA UNII
3L12PT535M
Created by admin on Sat Jun 26 16:34:11 UTC 2021 , Edited by admin on Sat Jun 26 16:34:11 UTC 2021
PRIMARY
CAS
1051375-13-3
Created by admin on Sat Jun 26 16:34:11 UTC 2021 , Edited by admin on Sat Jun 26 16:34:11 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY