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Cabotegravir (GSK-1265744) sodium is a orally active and long-acting HIV integrase strand transfer inhibitor and organic anion transporter 1/3 ( OAT1 / OAT3 ) inhibitor with IC 50 values of 2.5 nM, 0.41 μM and 0.81 μM for HIV ADA , OAT3 and OAT1, respectively. Cabotegravir sodium is primarily metabolized by uridine diphosphate glucuronosyltransferase (UGT) 1A1, with low potential to interact with other antiretroviral agents (ARVs). Cabotegravir sodium can be used to research AIDS
In Vitro
Cabotegravir (GSK-1265744) inhibits the HIV-1 integrase catalyzed strand transfer reaction with an IC 50 of 3.0 nM in vitro. The antiviral EC 50 against HIV-1 Ba-L is 0.22 nM and that against NL432 is 0.34 nM in PBMCs, 0.57 nM using CellTiter-Glo and 1.3 nM using MTT in MT-4, and 0.5 nM in the PHIV assay, which uses a pseudotyped self-inactivating virus. MCE has not independently confirmed the accuracy of these methods. They are for reference only. Cell Viability AssayCell Line: MT-4 cells Concentration: 0-32 nM Incubation Time: 4 or 5 days Result: Showed antiviral activity with an EC 50 of 1.3 nM.
In Vivo
The half-life of Cabotegravir is up to 54 days in mice . Cabotegravir (25 or 50 mg/kg; i.v.; single dose or twice) protects Macaques against intravenous challenge with SIVmac251. MCE has not independently confirmed the accuracy of these methods. They are for reference only.
Form:Solid
IC50& Target:IC 50 : 2.5 nM (HIV ADA ), IC 50 : 0.41 μM (OAT3), 0.81 μM (OAT1)
| Canonical Smiles | CC1COC2N1C(=O)C3=C(C(=O)C(=CN3C2)C(=O)NCC4=C(C=C(C=C4)F)F)[O-].[Na+] |
|---|---|
| IUPAC Name | sodium;(3R,6S)-12-[(2,4-difluorophenyl)methylcarbamoyl]-6-methyl-8,11-dioxo-4-oxa-1,7-diazatricyclo[7.4.0.03,7]trideca-9,12-dien-10-olate |
| 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 |
| Isomeric SMILES | C[C@H]1CO[C@H]2N1C(=O)C3=C(C(=O)C(=CN3C2)C(=O)NCC4=C(C=C(C=C4)F)F)[O-].[Na+] |
| Alternate CAS | 1051375-13-3 |
| PubChem CID | 46215800 |
| MeSH Entry Terms | (3S,11aR)-N-((2,6-difluoropyridin-3-yl)methyl)-6-hydroxy-3-methyl-5,7-dioxo-2,3,5,7,11,11a-hexahydro(1,3)oxazolo(3,2-a)pyrido(1,2-d)pyrazine-8-carboxamide;Apretude;cabotegravir;cabotegravir extended-release injectable suspension;cabotegravir sodium;GSK-12 |
| Molecular Weight | 427.33 |
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View spec sheet →Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Organoheterocyclic compounds |
| Class | Pyridines and derivatives |
| Subclass | Pyridinecarboxylic acids and derivatives |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Pyridinecarboxylic acids and derivatives |
| Alternative Parents | 2-heteroaryl carboxamides Fluorobenzenes Pyridinolates Aryl fluorides Oxazolidines Vinylogous acids Tertiary carboxylic acid amides Vinylogous amides Heteroaromatic compounds Tertiary amines Secondary carboxylic acid amides Amino acids and derivatives Cyclic ketones Lactams Oxacyclic compounds Azacyclic compounds Organic metal halides Organic sodium salts Organofluorides Organic oxides Organic zwitterions Hydrocarbon derivatives |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Pyridine carboxylic acid or derivatives - 2-heteroaryl carboxamide - Pyridinolate - Fluorobenzene - Halobenzene - Aryl fluoride - Aryl halide - Monocyclic benzene moiety - Benzenoid - Oxazolidine - Heteroaromatic compound - Tertiary carboxylic acid amide - Vinylogous acid - Vinylogous amide - Carboxamide group - Lactam - Amino acid or derivatives - Secondary carboxylic acid amide - Tertiary amine - Cyclic ketone - Oxacycle - Organic metal halide - Azacycle - Carboxylic acid derivative - Organic alkali metal salt - Organic salt - Organofluoride - Organohalogen compound - Organonitrogen compound - Hydrocarbon derivative - Organic oxide - Organooxygen compound - Amine - Organic nitrogen compound - Organic sodium salt - Organic zwitterion - Organic oxygen compound - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as pyridinecarboxylic acids and derivatives. These are compounds containing a pyridine ring bearing a carboxylic acid group or a derivative thereof. |
| External Descriptors | Not available |
| Solubility | DMSO : 6.9 mg/mL (16.15 mM; ultrasonic and warming and heat to 60°C) |
|---|---|
| Molecular Weight | 427.300 g/mol |
| XLogP3 | |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 8 |
| Rotatable Bond Count | 3 |
| Exact Mass | 427.096 Da |
| Monoisotopic Mass | 427.096 Da |
| Topological Polar Surface Area | 102.000 Ų |
| Heavy Atom Count | 30 |
| Formal Charge | 0 |
| Complexity | 820.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 2 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 0 |
| Covalently-Bonded Unit Count | 2 |