gabapentin enacarbil (CHEBI:68840)

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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.

Supplier Information	ChemicalBook:CB01011737

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Wikipedia	License

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Formula

C16H27NO6

Net Charge

Average Mass

329.38870

Monoisotopic Mass

329.18384

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.

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

Brand Name	Source
Horizant	KEGG DRUG

Citations

Last Modified

22 February 2017