abacavir   

GtoPdb Ligand ID: 11152

Abbreviated name: ABC
Synonyms: 1592U89 | Ziagen®
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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Physico-chemical Properties
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
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
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
[(1S,4R)-4-[2-amino-6-(cyclopropylamino)purin-9-yl]-1-cyclopent-2-enyl]methanol
International Nonproprietary Names
INN number INN
7544 abacavir
Synonyms
1592U89 | Ziagen®
Database Links
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
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Wikipedia Abacavir