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.
Click here for help
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: abacavir

2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
SMILES / InChI / InChIKey
Click here for help
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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1998), EMA (1999))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
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
Search UniChem for chemical match using the InChIKey MCGSCOLBFJQGHM-SCZZXKLOSA-N
Search UniChem for chemicals with the same backbone MCGSCOLBFJQGHM
Wikipedia Abacavir