CHEBI:421707 - abacavir

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ChEBI Name abacavir
ChEBI ID CHEBI:421707
Definition A 2,6-diaminopurine that is (1S)-cyclopent-2-en-1-ylmethanol in which the pro-R hydrogen at the 4-position is substituted by a 2-amino-6-(cyclopropylamino)-9H-purin-9-yl group. A nucleoside analogue reverse transcriptase inhibitor (NRTI) with antiretroviral activity against HIV, it is used (particularly as the sulfate) with other antiretrovirals in combination therapy of HIV infection.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:441792, CHEBI:2360, CHEBI:193608, CHEBI:520984, CHEBI:525912
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Formula C14H18N6O
Net Charge 0
Average Mass 286.33230
Monoisotopic Mass 286.154
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
InChIKey MCGSCOLBFJQGHM-SCZZXKLOSA-N
SMILES Nc1nc(NC2CC2)c2ncn([C@@H]3C[C@H](CO)C=C3)c2n1
Roles Classification
Biological Role(s): drug allergen
Any drug which causes the onset of an allergic reaction.
HIV-1 reverse transcriptase inhibitor
An entity which inhibits the activity of HIV-1 reverse transcriptase.
antiviral drug
A substance used in the prophylaxis or therapy of virus diseases.
Application(s): drug allergen
Any drug which causes the onset of an allergic reaction.
antiviral drug
A substance used in the prophylaxis or therapy of virus diseases.
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ChEBI Ontology
Outgoing abacavir (CHEBI:421707) has role antiviral drug (CHEBI:36044)
abacavir (CHEBI:421707) has role drug allergen (CHEBI:88188)
abacavir (CHEBI:421707) has role HIV-1 reverse transcriptase inhibitor (CHEBI:53756)
abacavir (CHEBI:421707) is a 2,6-diaminopurines (CHEBI:38001)
Incoming abacavir 5'-carboxylic acid (CHEBI:64192) has functional parent abacavir (CHEBI:421707)
abacavir 5'-glucuronide (CHEBI:64189) has functional parent abacavir (CHEBI:421707)
abacavir monophosphate (CHEBI:64112) has functional parent abacavir (CHEBI:421707)
abacavir sulfate (CHEBI:2361) has functional parent abacavir (CHEBI:421707)
IUPAC Name
{(1S,4R)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]cyclopent-2-en-1-yl}methanol
INN Source
abacavir ChemIDplus
Synonyms Sources
Abacavir KEGG COMPOUND
ABC ChEBI
{(1S-cis)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]cyclopent-2-en-1-yl}methanol ChEBI
Manual Xrefs Databases
34 DrugCentral
Abacavir Wikipedia
C07624 KEGG COMPOUND
D07057 KEGG DRUG
DB01048 DrugBank
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Registry Numbers Types Sources
136470-78-5 CAS Registry Number ChemIDplus
7493116 Beilstein Registry Number Beilstein
7493116 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
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Last Modified
30 April 2018