CHEBI:68840 - gabapentin enacarbil

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ChEBI Name gabapentin enacarbil
ChEBI ID CHEBI:68840
Definition A carbamate ester that is the N-[1-(isobutyryloxy)ethoxy]carbonyl derivative of [1-(aminomethyl)cyclohexyl]acetic acid. The prodrug for gabapentin, used for treatment of neuropathic pain and restless legs syndrome.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C16H27NO6
Net Charge 0
Average Mass 329.38870
InChI InChI=1S/C16H27NO6/c1-11(2)14(20)22-12(3)23-15(21)17-10-16(9-13(18)19)7-5-4-6-8-16/h11-12H,4-10H2,1-3H3,(H,17,21)(H,18,19)
InChIKey TZDUHAJSIBHXDL-UHFFFAOYSA-N
SMILES CC(C)C(=O)OC(C)OC(=O)NCC1(CCCCC1)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): prodrug
A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
anticonvulsant
A drug used to prevent seizures or reduce their severity.
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ChEBI Ontology
Outgoing gabapentin enacarbil (CHEBI:68840) has functional parent γ-aminobutyric acid (CHEBI:16865)
gabapentin enacarbil (CHEBI:68840) has functional parent gabapentin (CHEBI:42797)
gabapentin enacarbil (CHEBI:68840) has role anticonvulsant (CHEBI:35623)
gabapentin enacarbil (CHEBI:68840) has role calcium channel blocker (CHEBI:38215)
gabapentin enacarbil (CHEBI:68840) has role prodrug (CHEBI:50266)
gabapentin enacarbil (CHEBI:68840) is a acetal (CHEBI:59769)
gabapentin enacarbil (CHEBI:68840) is a carbamate ester (CHEBI:23003)
gabapentin enacarbil (CHEBI:68840) is a carboxylic ester (CHEBI:33308)
gabapentin enacarbil (CHEBI:68840) is a monocarboxylic acid (CHEBI:25384)
IUPAC Name
{1-[({[1-(isobutyryloxy)ethoxy]carbonyl}amino)methyl]cyclohexyl}acetic acid
INNs Sources
gabapentin enacarbil KEGG DRUG
gabapentina enacarbilo WHO MedNet
gabapentine enacarbil WHO MedNet
gabapentinum enacarbilum WHO MedNet
Synonyms Sources
XP 13512 ChemIDplus
XP-13512 ChemIDplus
XP13512 ChemIDplus
Brand Name Source
Horizant KEGG DRUG
Database Links Databases
Gabapentin_enacarbil Wikipedia
US2006229361 Patent
US2007049626 Patent
WO2005037784 Patent
WO2005066122 Patent
WO2006050514 Patent
WO2008073257 Patent
WO2010063002 Patent
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Registry Numbers Types Sources
10188772 Reaxys Registry Number Reaxys
478296-72-9 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
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Last Modified
14 November 2012