GBN

[1-(AMINOMETHYL)CYCLOHEXYL]ACETIC ACID

Created:2005-05-19
Last modified:  2020-06-05

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Chemical Details

Formal Charge0
Atom Count29
Chiral Atom Count0
Bond Count29
Aromatic Bond Count0
2D diagram of GBN
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Chemical Component Summary

Name[1-(AMINOMETHYL)CYCLOHEXYL]ACETIC ACID
SynonymsGABAPENTIN
Systematic Name (OpenEye OEToolkits)2-[1-(aminomethyl)cyclohexyl]ethanoic acid
FormulaC9 H17 N O2
Molecular Weight171.237
TypeNON-POLYMER

Chemical Descriptors

TypeProgramVersionDescriptor
SMILESACDLabs10.04O=C(O)CC1(CN)CCCCC1
SMILESCACTVS3.341NCC1(CCCCC1)CC(O)=O
SMILESOpenEye OEToolkits1.5.0C1CCC(CC1)(CC(=O)O)CN
Canonical SMILESCACTVS3.341 NCC1(CCCCC1)CC(O)=O
Canonical SMILESOpenEye OEToolkits1.5.0 C1CCC(CC1)(CC(=O)O)CN
InChIInChI1.03 InChI=1S/C9H17NO2/c10-7-9(6-8(11)12)4-2-1-3-5-9/h1-7,10H2,(H,11,12)
InChIKeyInChI1.03 UGJMXCAKCUNAIE-UHFFFAOYSA-N

Drug Info: DrugBank

DrugBank IDDB00996 
NameGabapentin
Groups
  • approved
  • investigational
DescriptionGabapentin is a structural analogue of the inhibitory neurotransmitter gamma-aminobutyric acid ([GABA]) that was first approved for use in the United States in 1993.[L8717] It was originally developed as a novel anti-epileptic for the treatment of certain types of seizures[A186277,A186143] - today it is also widely used to treat neuropathic pain.[A14097,A186179] Gabapentin has some stark advantages as compared with other anti-epileptics, such as a relatively benign adverse effect profile, wide therapeutic index, and lack of appreciable metabolism making it unlikely to participate in pharmacokinetic drug interactions.[A186143,A185981,L8717]. It is structurally and functionally related to another GABA derivative, [pregabalin].
Synonyms
  • Gabapentin
  • 1-(Aminomethyl)cyclohexaneacetic acid
  • Gabapentine
  • Gabapentinum
  • Gabapentina
Brand Names
  • Mar-gabapentin
  • Taro-gabapentin
  • Gabarone
  • Ran-gabapentin
  • Gaba 300-EZS
IndicationIn the United States, gabapentin is officially indicated for the treatment of postherpetic neuralgia in adults and for the adjunctive treatment of partial-onset seizures, with or without secondary generalization, in patients 3 years of age and older.[L8717] In Europe, gabapentin is indicated for adjunctive therapy in the treatment of partial-onset seizures, with or without secondary generalization, in patients 6 years of age and older and as monotherapy in patients 12 years of age and older. It is also used in adults for the treatment of various types of peripheral neuropathic pain, such as painful diabetic neuropathy.[L8732]
Categories
  • Acids, Acyclic
  • Acids, Carbocyclic
  • Amines
  • Amino Acids
  • Amino Acids, Peptides, and Proteins
ATC-CodeN02BF01
CAS number60142-96-3

Drug Targets

NameTarget SequencePharmacological ActionActions
Voltage-dependent calcium channel subunit alpha-2/delta-1MAAGCLLALTLTLFQSLLIGPSSEEPFPSAVTIKSWVDKMQEDLVTLAKT...unknowninhibitor
Gamma-aminobutyric acid type B receptor subunit 2MASPRSSGQPGPPPPPPPPPARLLLLLLLPLLLPLAPGAWGWARGAPRPP...unknownantagonist
Gamma-aminobutyric acid type B receptor subunit 1MLLLLLLAPLFLRPPGAGGAQTPNATSEGCQIIHPPWEGGIRYRGLTRDQ...unknownantagonist
Voltage-dependent calcium channel subunit alpha-2/delta-2MAVPARTCGASRPGPARTARPWPGCGPHPGPGTRRPTSGPPRPLWLLLPL...unknowninhibitor
Voltage-dependent N-type calcium channelMVRFGDELGGRYGGPGGGERARGGGAGGAGGPGPGGLQPGQRVLYKQSIA...unknowninhibitor
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL940
PubChem 3446, 6919078
ChEMBL CHEMBL940
ChEBI CHEBI:42797
CCDC/CSD AVAVAV, AWUWIY01, AWUWIY, IKATIY, QIMKIG06, QIMKOM01, FOXNOW, FOXPOY, YUZTET, AVILOH, QIMKIG03, QIMKIG02, QIMKIG, SOCYUF, QIMKIG05, FOXPAK, NUPXAY, AWUWIY02, QIMKIG01, QIMKOM, QIMKOM02, LORQIT, QIMKIG04, AVILUN, QIMKOM03, FOXPEO
COD 4508983, 7212308, 2016527, 2016526, 2011956, 7053757, 2011957, 7053756