abacavir   Click here for help

GtoPdb Ligand ID: 11152

Abbreviated name: ABC
Synonyms: 1592U89 | Ziagen®
Approved drug PDB Ligand
abacavir is an approved drug (FDA (1998), EMA (1999))
Compound class: Synthetic organic
Comment: Abacavir is a nucleoside analogue reverse transcriptase inhibitor (NRTI) class antiretroviral drug.
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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 3
Rotatable bonds 4
Topological polar surface area 101.88
Molecular weight 286.15
XLogP 1.05
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 OC[C@@H]1C=C[C@@H](C1)n1cnc2c1nc(N)nc2NC1CC1
Isomeric SMILES OC[C@@H]1C=C[C@@H](C1)n1cnc2c1nc(N)nc2NC1CC1
InChI InChI=1S/C14H18N6O/c15-14-18-12(17-9-2-3-9)11-13(19-14)20(7-16-11)10-4-1-8(5-10)6-21/h1,4,7-10,21H,2-3,5-6H2,(H3,15,17,18,19)/t8-,10+/m1/s1
InChI Key MCGSCOLBFJQGHM-SCZZXKLOSA-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 (1998)  |  EMA (1999)
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
[(1S,4R)-4-[2-amino-6-(cyclopropylamino)purin-9-yl]-1-cyclopent-2-enyl]methanol
International Nonproprietary Names Click here for help
INN number INN
7544 abacavir
Synonyms Click here for help
1592U89 | Ziagen®
Database Links Click here for help
CAS Registry No. 136470-78-5 (source: Scifinder)
ChEBI CHEBI:421707
ChEMBL Ligand CHEMBL1380
DrugCentral Ligand 34
GtoPdb PubChem SID 434122212
PubChem CID 441300
RCSB PDB Ligand 1KX
Search Google for chemical match using the InChIKey MCGSCOLBFJQGHM-SCZZXKLOSA-N
Search Google for chemicals with the same backbone MCGSCOLBFJQGHM
Search PubMed clinical trials abacavir
Search PubMed titles abacavir
Search PubMed titles/abstracts abacavir
UniChem Compound Search for chemical match using the InChIKey MCGSCOLBFJQGHM-SCZZXKLOSA-N
UniChem Connectivity Search for chemical match using the InChIKey MCGSCOLBFJQGHM-SCZZXKLOSA-N
Wikipedia Abacavir

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MedChemExpress
Abacavir (links to external site)
Cat. No. HY-17423