Dolutegravir
(3S,7R)-N-[(2,4-difluorophenyl)methyl]-11-hydroxy-7-methyl-9,12-dioxo-4-oxa-1,8-diazatricyclo[8.4.0.03,8]tetradeca-10,13-diene-13-carboxamide
Molecular Identity
Dolutegravir
(3S,7R)-N-[(2,4-difluorophenyl)methyl]-11-hydroxy-7-methyl-9,12-dioxo-4-oxa-1,8-diazatricyclo[8.4.0.03,8]tetradeca-10,13-diene-13-carboxamide
PubChem CID: 54726191
Dolutegravir is a monocarboxylic acid amide obtained by formal condensation of the carboxy group of (4R,12aS)-7-hydroxy-4-methyl-6,8-dioxo-3,4,6,8,12,12a-hexahydro-2H-pyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazine-9-carboxylic acid with the amino group of 2,4-difluorobenzylamine. Used (as its sodium salt) for treatment of HIV-1. It has a role as a HIV-1 integrase inhibitor. It is a secondary carboxamide, an organic heterotricyclic compound, a monocarboxylic acid amide and a difluorobenzene. It is a conjugate acid of a dolutegravir(1-).
2D Structure
Properties
C20H19F2N3O5
Molecular Formula
419.40
Molecular Weight
g/mol
419.1293
Exact Mass
Da
2.4
XLogP
Drug-like (Lipinski: < 5)
99.2
TPSA
Good oral absorption (< 140 A²)
2
H-Bond Donors
8
H-Bond Acceptors
829
Complexity
SMILES
Canonical SMILES
SMILES: Synonyms(20)
Dolutegravir1051375-16-6GSK1349572S/GSK1349572GSK 1349572GSK-1349572S-349572(4R,12aS)-N-[(2,4-Difluorophenyl)methyl]-3,4,6,8,12,12a-hexahydro-7-hydroxy-4-methyl-6,8-dioxo-2H-pyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazine-9-carboxamideDKO1W9H7M1CHEBI:76010DTXSID909093562H-Pyrido(1',2':4,5)pyrazino(2,1-b)(1,3)oxazine-9-carboxamide, N-((2,4-difluorophenyl)methyl)-3,4,6,8,12,12a-hexahydro-7-hydroxy-4-methyl-6,8-dioxo-, (4R,12aS)-dolutegravirum(4R,12aS)-N-((2,4-difluorophenyl)methyl)-3,4,6,8,12,12a-hexahydro-7-hydroxy-4-methyl-6,8-dioxo-2H-Pyrido(1',2':4,5)pyrazino(2,1-b)(1,3)oxazine-9-carboxamide(4R,12aS)-N-((2,4-difluorophenyl)methyl)-7-hydroxy-4-methyl-6,8-dioxo-3,4,12,12a-tetrahydro-2H-pyrido(5,6)pyrazino(2,6-b)(1,3)oxazine-9-carboxamide
Data from PubChem (NCBI)
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