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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View more information in the IUPHAR Pharmacology Education Project: abacavir

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 CDK toolkit. 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
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.

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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
No information available.
Summary of Clinical Use Click here for help
Abacavir is used in the treatment of HIV-1 infection in combination with other antiretroviral agents.
External links Click here for help
For extended ADME data see the following:

Electronic Medicines Compendium (eMC)
Drugs.com
European Medicines Agency (EMA)