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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H17F2N3O5
Molecular Weight 405.3522
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CABOTEGRAVIR

SMILES

[H][C@@]12CN3C=C(C(=O)NCC4=CC=C(F)C=C4F)C(=O)C(O)=C3C(=O)N1[C@@H](C)CO2

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

Description
Curator's Comment: Description was created based on several sources, including 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
0.2 nM [IC50]
0.81 µM [IC50]
0.41 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
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 MTT in MT-4 cells, and 0.5 nM in the PHIV assay, which uses a pseudotyped self-inactivating virus.
Name Type Language
CABOTEGRAVIR
INN   USAN   WHO-DD  
USAN   INN  
Official Name English
GSK1265744A
Code English
GSK1265744
Code English
GSK744
Code English
Apretude
Brand 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
Code English
CABOTEGRAVIR [USAN]
Common Name English
Cabotegravir [WHO-DD]
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
CABOTEGRAVIR [ORANGE BOOK]
Common Name English
S-265744
Code English
Code System Code Type Description
SMS_ID
100000165751
Created by admin on Thu Jul 06 08:54:48 UTC 2023 , Edited by admin on Thu Jul 06 08:54:48 UTC 2023
PRIMARY
INN
9903
Created by admin on Thu Jul 06 08:54:48 UTC 2023 , Edited by admin on Thu Jul 06 08:54:48 UTC 2023
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USAN
AB-84
Created by admin on Thu Jul 06 08:54:48 UTC 2023 , Edited by admin on Thu Jul 06 08:54:48 UTC 2023
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FDA UNII
HMH0132Z1Q
Created by admin on Thu Jul 06 08:54:48 UTC 2023 , Edited by admin on Thu Jul 06 08:54:48 UTC 2023
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CHEBI
172944
Created by admin on Thu Jul 06 08:54:48 UTC 2023 , Edited by admin on Thu Jul 06 08:54:48 UTC 2023
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DRUG BANK
DB11751
Created by admin on Thu Jul 06 08:54:48 UTC 2023 , Edited by admin on Thu Jul 06 08:54:48 UTC 2023
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CAS
1264720-72-0
Created by admin on Thu Jul 06 08:54:48 UTC 2023 , Edited by admin on Thu Jul 06 08:54:48 UTC 2023
NO STRUCTURE GIVEN
NCI_THESAURUS
C169820
Created by admin on Thu Jul 06 08:54:48 UTC 2023 , Edited by admin on Thu Jul 06 08:54:48 UTC 2023
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ChEMBL
CHEMBL2403238
Created by admin on Thu Jul 06 08:54:48 UTC 2023 , Edited by admin on Thu Jul 06 08:54:48 UTC 2023
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CAS
1051375-10-0
Created by admin on Thu Jul 06 08:54:48 UTC 2023 , Edited by admin on Thu Jul 06 08:54:48 UTC 2023
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RXCUI
2475077
Created by admin on Thu Jul 06 08:54:48 UTC 2023 , Edited by admin on Thu Jul 06 08:54:48 UTC 2023
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DAILYMED
HMH0132Z1Q
Created by admin on Thu Jul 06 08:54:48 UTC 2023 , Edited by admin on Thu Jul 06 08:54:48 UTC 2023
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PUBCHEM
54713659
Created by admin on Thu Jul 06 08:54:48 UTC 2023 , Edited by admin on Thu Jul 06 08:54:48 UTC 2023
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WIKIPEDIA
GSK 1265744
Created by admin on Thu Jul 06 08:54:48 UTC 2023 , Edited by admin on Thu Jul 06 08:54:48 UTC 2023
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EPA CompTox
DTXSID50146982
Created by admin on Thu Jul 06 08:54:48 UTC 2023 , Edited by admin on Thu Jul 06 08:54:48 UTC 2023
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EVMPD
SUB179611
Created by admin on Thu Jul 06 08:54:48 UTC 2023 , Edited by admin on Thu Jul 06 08:54:48 UTC 2023
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