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CHEBI:64356 - pregabalin

ChEBI IDCHEBI:64356
ChEBI Namepregabalin
Stars
DefinitionA 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.
Last Modified22 February 2017
DownloadsMolfile
FormulaC8H17NO2
Net Charge0
Average Mass159.229
Monoisotopic Mass159.12593
SMILESCC(C)C[C@H](CN)CC(=O)O
InChIInChI=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
InChIKeyAYXYPKUFHZROOJ-ZETCQYMHSA-N
Wikipedia
Roles Classification
Chemical Roles:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Role:
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:
anticonvulsant  A drug used to prevent seizures or reduce their severity.
ChEBI Ontology
Outgoing Relation(s)
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
pregabalinKEGG DRUG
Synonyms  Source
3-Isobutyl GABAChemIDplus
(S)-3-Isobutyl GABAChemIDplus
Brand Name  Source
LyricaKEGG DRUG
Manual XrefsDatabases
2255DrugCentral
D02716KEGG DRUG
DB00230DrugBank
EP1178034Patent
EP2418194Patent
PregabalinWikipedia
US2008311635Patent
US6359169Patent
Registry NumbersSources
Reaxys:8404778Reaxys
CAS:148553-50-8ChemIDplus
CAS:148553-50-8KEGG DRUG
Citations