CHEBI:64356 - pregabalin

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ChEBI Name pregabalin
ChEBI ID CHEBI:64356
Definition A γ-amino acid that is γ-aminobutyric acid (GABA) carrying an isobutyl substitutent at the β-position (the S-enantiomer). Binds with high affinity to the α2-δ site (an auxiliary subunit of voltage-gated calcium channels) in central nervous system tissues.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Anonymous
Supplier Information
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Formula C8H17NO2
Net Charge 0
Average Mass 159.22610
InChI InChI=1S/C8H17NO2/c1-6(2)3-7(5-9)4-8(10)11/h6-7H,3-5,9H2,1-2H3,(H,10,11)/t7-/m0/s1
InChIKey AYXYPKUFHZROOJ-ZETCQYMHSA-N
SMILES CC(C)C[C@H](CN)CC(O)=O
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): calcium channel blocker
One of a class of drugs that acts by selective inhibition of calcium influx through cell membranes or on the release and binding of calcium in intracellular pools.
Application(s): anticonvulsant
A drug used to prevent seizures or reduce their severity.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing pregabalin (CHEBI:64356) has functional parent γ-aminobutyric acid (CHEBI:16865)
pregabalin (CHEBI:64356) has role anticonvulsant (CHEBI:35623)
pregabalin (CHEBI:64356) has role calcium channel blocker (CHEBI:38215)
pregabalin (CHEBI:64356) is a γ-amino acid (CHEBI:33707)
IUPAC Name
(3S)-3-(aminomethyl)-5-methylhexanoic acid
INN Source
pregabalin KEGG DRUG
Synonyms Sources
(S)-3-Isobutyl GABA ChemIDplus
3-Isobutyl GABA ChemIDplus
Brand Name Source
Lyrica KEGG DRUG
Database Links Databases
D02716 KEGG DRUG
DB00230 DrugBank
EP1178034 Patent
EP2418194 Patent
Pregabalin Wikipedia
US2008311635 Patent
US6359169 Patent
View more database links
Registry Numbers Types Sources
148553-50-8 CAS Registry Number ChemIDplus
148553-50-8 CAS Registry Number KEGG DRUG
8404778 Reaxys Registry Number Reaxys
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Last Modified
10 April 2012