CHEBI:42797 - gabapentin

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ChEBI Name gabapentin
ChEBI ID CHEBI:42797
Definition A γ-amino acid that is cyclohexane substituted at position 1 by aminomethyl and carboxymethyl groups. Used for treatment of neuropathic pain and restless legs syndrome.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:5237
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Formula C9H17NO2
Net Charge 0
Average Mass 171.23680
Monoisotopic Mass 171.126
InChI InChI=1S/C9H17NO2/c10-7-9(6-8(11)12)4-2-1-3-5-9/h1-7,10H2,(H,11,12)
InChIKey UGJMXCAKCUNAIE-UHFFFAOYSA-N
SMILES NCC1(CCCCC1)CC(O)=O
Roles Classification
Chemical Role(s): environmental contaminant
Any minor or unwanted substance introduced into the environment that can have undesired effects.
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.
xenobiotic
A xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means.
Application(s): anticonvulsant
A drug used to prevent seizures or reduce their severity.
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ChEBI Ontology
Outgoing gabapentin (CHEBI:42797) has functional parent γ-aminobutyric acid (CHEBI:16865)
gabapentin (CHEBI:42797) has role anticonvulsant (CHEBI:35623)
gabapentin (CHEBI:42797) has role calcium channel blocker (CHEBI:38215)
gabapentin (CHEBI:42797) has role environmental contaminant (CHEBI:78298)
gabapentin (CHEBI:42797) has role xenobiotic (CHEBI:35703)
gabapentin (CHEBI:42797) is a γ-amino acid (CHEBI:33707)
Incoming gabapentin enacarbil (CHEBI:68840) has functional parent gabapentin (CHEBI:42797)
IUPAC Name
[1-(aminomethyl)cyclohexyl]acetic acid
INNs Sources
gabapentin KEGG DRUG
gabapentina WHO MedNet
gabapentine DrugBank
gabapentinum DrugBank
Synonym Source
1-(Aminomethyl)cyclohexaneacetic acid ChemIDplus
Brand Name Source
Neurontin DrugBank
Manual Xrefs Databases
1264 DrugCentral
2975 VSDB
D00332 KEGG DRUG
DB00996 DrugBank
EP1140793 Patent
Gabapentin Wikipedia
GBN PDBeChem
HMDB0005015 HMDB
LSM-5716 LINCS
US2008103334 Patent
US2008269326 Patent
US2009043126 Patent
US2009292138 Patent
US2012046272 Patent
WO2005037784 Patent
WO2008060572 Patent
WO2010023694 Patent
View more database links
Registry Numbers Types Sources
2359739 Beilstein Registry Number ChemIDplus
2359739 Reaxys Registry Number Reaxys
60142-96-3 CAS Registry Number ChemIDplus
60142-96-3 CAS Registry Number KEGG DRUG
Citations Waiting for Citations Types Sources
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Last Modified
22 February 2017