pregabalin (CHEBI:64356)

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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

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Formula

C8H17NO2

Net Charge

Average Mass

159.22610

Monoisotopic Mass

159.12593

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 base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound ) 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.

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

Brand Name	Source
Lyrica	KEGG DRUG

Last Modified

22 February 2017