dolutegravir   Click here for help

GtoPdb Ligand ID: 7365

Synonyms: GSK 1349572 | GSK-1349572 | GSK1349572 | S-349572 | Tivicay®
Approved drug PDB Ligand
dolutegravir is an approved drug (FDA (2013), EMA (2014))
Compound class: Synthetic organic
Comment: Dolutegravir is an HIV viral integrase inhibitor class drug.

dolutegravir is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 6
Hydrogen bond donors 2
Rotatable bonds 4
Topological polar surface area 100.87
Molecular weight 419.13
XLogP 4.07
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES Fc1ccc(c(c1)F)CNC(=O)c1cn2CC3OCCC(N3C(=O)c2c(c1=O)O)C
Isomeric SMILES Fc1ccc(c(c1)F)CNC(=O)c1cn2C[C@@H]3OCC[C@H](N3C(=O)c2c(c1=O)O)C
InChI InChI=1S/C20H19F2N3O5/c1-10-4-5-30-15-9-24-8-13(17(26)18(27)16(24)20(29)25(10)15)19(28)23-7-11-2-3-12(21)6-14(11)22/h2-3,6,8,10,15,27H,4-5,7,9H2,1H3,(H,23,28)/t10-,15+/m1/s1
InChI Key RHWKPHLQXYSBKR-BMIGLBTASA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2013), EMA (2014))
Approved drug? Yes. FDA (2013)  |  EMA (2014)
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
(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
International Nonproprietary Names Click here for help
INN number INN
9261 dolutegravir
Synonyms Click here for help
GSK 1349572 | GSK-1349572 | GSK1349572 | S-349572 | Tivicay®
Database Links Click here for help
CAS Registry No. 1051375-16-6 (source: Scifinder)
ChEMBL Ligand CHEMBL1229211
DrugBank Ligand DB08930
DrugCentral Ligand 4805
GtoPdb PubChem SID 178103937
PubChem CID 54726191
RCSB PDB Ligand DLU
Search Google for chemical match using the InChIKey RHWKPHLQXYSBKR-BMIGLBTASA-N
Search Google for chemicals with the same backbone RHWKPHLQXYSBKR
Search PubMed clinical trials dolutegravir
Search PubMed titles dolutegravir
Search PubMed titles/abstracts dolutegravir
UniChem Compound Search for chemical match using the InChIKey RHWKPHLQXYSBKR-BMIGLBTASA-N
UniChem Connectivity Search for chemical match using the InChIKey RHWKPHLQXYSBKR-BMIGLBTASA-N
Wikipedia Dolutegravir

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MedChemExpress
Dolutegravir (links to external site)
Cat. No. HY-13238