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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H16F2N3O5.Na
Molecular Weight 427.334
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CABOTEGRAVIR SODIUM

SMILES

[Na+].C[C@H]1CO[C@@H]2CN3C=C(C(=O)NCC4=CC=C(F)C=C4F)C(=O)C([O-])=C3C(=O)N12

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 C19H16F2N3O5
Molecular Weight 404.3442
Charge -1
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula Na
Molecular Weight 22.98976928
Charge 1
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
0.2 nM [IC50]
0.81 µM [IC50]
0.41 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
3.61 μg/mL
30 mg single, oral
CABOTEGRAVIR plasma
Homo sapiens
3.39 μg/mL
30 mg single, oral
CABOTEGRAVIR plasma
Homo sapiens
3.4 μg/mL
30 mg single, oral
CABOTEGRAVIR plasma
Homo sapiens
3.44 μg/mL
30 mg single, oral
CABOTEGRAVIR plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
146 μg × h/mL
30 mg single, oral
CABOTEGRAVIR plasma
Homo sapiens
59.7 μg × h/mL
30 mg single, oral
CABOTEGRAVIR plasma
Homo sapiens
144 μg × h/mL
30 mg single, oral
CABOTEGRAVIR plasma
Homo sapiens
146 μg × h/mL
30 mg single, oral
CABOTEGRAVIR plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
38.5 h
30 mg single, oral
CABOTEGRAVIR plasma
Homo sapiens
16.4 h
30 mg single, oral
CABOTEGRAVIR plasma
Homo sapiens
40.8 h
30 mg single, oral
CABOTEGRAVIR plasma
Homo sapiens
39.6 h
30 mg single, oral
CABOTEGRAVIR plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
0.12%
30 mg single, oral
CABOTEGRAVIR plasma
Homo sapiens
0.17%
30 mg single, oral
CABOTEGRAVIR plasma
Homo sapiens

Doses

AEs

Drug as perpetrator​

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
10, 30, or 60 mg once daily
Route of Administration: Oral
In Vitro Use Guide
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.
Substance Class Chemical
Record UNII
3L12PT535M
Record Status Validated (UNII)
Record Version