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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H17F2N3O5
Molecular Weight 405.3529
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CABOTEGRAVIR

SMILES

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

InChI

InChIKey=WCWSTNLSLKSJPK-LKFCYVNXSA-N
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

HIDE SMILES / InChI

Molecular Formula C19H17F2N3O5
Molecular Weight 405.3529
Charge 0
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
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 01:03:54 UTC 2021
Edited
by admin
on Sat Jun 26 01:03:54 UTC 2021
Record UNII
HMH0132Z1Q
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CABOTEGRAVIR
INN   USAN   WHO-DD  
USAN   INN  
Official Name English
GSK1265744A
Code English
GSK1265744
Code English
GSK744
Code English
CABOTEGRAVIR [WHO-DD]
Common Name English
(3S,11AR)-N-((2,4-DIFLUOROPHENYL)METHYL)-6-HYDROXY-3-METHYL-5,7-DIOXO-2,3,5,7,11,11A-HEXAHYDROOXAZOLO(3,2-A)PYRIDO(1,2-D)PYRAZINE-8-CARBOXAMIDE
Systematic Name English
GSK-1265744A
Code English
CABOTEGRAVIR [JAN]
Common Name English
CABOTEGRAVIR [INN]
Common Name English
GSK-1265744
Common Name English
CABOTEGRAVIR [USAN]
Common Name English
CABENUVA COMPONENT CABOTEGRAVIR
Brand Name English
CABOTEGRAVIR COMPONENT OF CABENUVA
Brand Name 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-, (3S,11AR)-
Systematic Name English
S-265744
Code English
Code System Code Type Description
INN
9903
Created by admin on Sat Jun 26 01:03:55 UTC 2021 , Edited by admin on Sat Jun 26 01:03:55 UTC 2021
PRIMARY
EPA CompTox
1051375-10-0
Created by admin on Sat Jun 26 01:03:55 UTC 2021 , Edited by admin on Sat Jun 26 01:03:55 UTC 2021
PRIMARY
FDA UNII
HMH0132Z1Q
Created by admin on Sat Jun 26 01:03:55 UTC 2021 , Edited by admin on Sat Jun 26 01:03:55 UTC 2021
PRIMARY
DRUG BANK
DB11751
Created by admin on Sat Jun 26 01:03:54 UTC 2021 , Edited by admin on Sat Jun 26 01:03:54 UTC 2021
PRIMARY
CAS
1264720-72-0
Created by admin on Sat Jun 26 01:03:54 UTC 2021 , Edited by admin on Sat Jun 26 01:03:54 UTC 2021
NO STRUCTURE GIVEN
NCI_THESAURUS
C169820
Created by admin on Sat Jun 26 01:03:55 UTC 2021 , Edited by admin on Sat Jun 26 01:03:55 UTC 2021
PRIMARY
ChEMBL
CHEMBL2403238
Created by admin on Sat Jun 26 01:03:54 UTC 2021 , Edited by admin on Sat Jun 26 01:03:54 UTC 2021
PRIMARY
CAS
1051375-10-0
Created by admin on Sat Jun 26 01:03:54 UTC 2021 , Edited by admin on Sat Jun 26 01:03:54 UTC 2021
PRIMARY
PUBCHEM
54713659
Created by admin on Sat Jun 26 01:03:55 UTC 2021 , Edited by admin on Sat Jun 26 01:03:55 UTC 2021
PRIMARY
WIKIPEDIA
GSK 1265744
Created by admin on Sat Jun 26 01:03:55 UTC 2021 , Edited by admin on Sat Jun 26 01:03:55 UTC 2021
PRIMARY
EVMPD
SUB179611
Created by admin on Sat Jun 26 01:03:54 UTC 2021 , Edited by admin on Sat Jun 26 01:03:54 UTC 2021
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
TRANSPORTER -> SUBSTRATE
Cabotegravir is a substrate of P-gp and BCRP in vitro; however, because of its high permeability, no alteration in cabotegravir absorption is expected with coadministration of P-gp or BCRP inhibitors.
METABOLIC ENZYME -> SUBSTRATE
TRANSPORTER -> SUBSTRATE
Cabotegravir is a substrate of P-gp and BCRP in vitro; however, because of its high permeability, no alteration in cabotegravir absorption is expected with coadministration of P-gp or BCRP inhibitors.
TRANSPORTER -> INHIBITOR
IN VITRO
IC50
TRANSPORTER -> INHIBITOR
IN VITRO
IC50
BINDER->LIGAND
METABOLIC ENZYME -> SUBSTRATE
MINOR
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Blood-to-plasma ratio PHARMACOKINETIC ORAL ADMINISTRATION
PHARMACOKINETIC
Tmax PHARMACOKINETIC ORAL ADMINISTRATION
PHARMACOKINETIC