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CHEBI:68840 - gabapentin enacarbil

Default Structure
ChEBI IDCHEBI:68840
ChEBI Namegabapentin enacarbil
Stars
DefinitionA 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.
Last Modified22 February 2017
SubmitterSteve
DownloadsMolfile
FormulaC16H27NO6
Net Charge0
Average Mass329.393
Monoisotopic Mass329.18384
SMILESCC(OC(=O)NCC1(CC(=O)O)CCCCC1)OC(=O)C(C)C
InChIInChI=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)
InChIKeyTZDUHAJSIBHXDL-UHFFFAOYSA-N
Wikipedia
Roles Classification
Chemical Role:
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.
Applications:
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 Relation(s)
gabapentin enacarbil (CHEBI:68840) has functional parent gabapentin (CHEBI:42797)
gabapentin enacarbil (CHEBI:68840) has functional parent γ-aminobutyric acid (CHEBI:16865)
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  Source
gabapentina enacarbiloWHO MedNet
gabapentine enacarbilWHO MedNet
gabapentin enacarbilKEGG DRUG
gabapentinum enacarbilumWHO MedNet
Synonyms  Source
XP 13512ChemIDplus
XP-13512ChemIDplus
XP13512ChemIDplus
Brand Name  Source
HorizantKEGG DRUG
Manual XrefsDatabases
4177DrugCentral
Gabapentin_enacarbilWikipedia
US2006229361Patent
US2007049626Patent
WO2005037784Patent
WO2005066122Patent
WO2006050514Patent
WO2008073257Patent
WO2010063002Patent
Registry NumbersSources
Reaxys:10188772Reaxys
CAS:478296-72-9ChemIDplus
Citations