Chemical Component Summary

Name(6E)-N-(4-hydroxy-3-methoxybenzyl)-8-methylnon-6-enamide
SynonymsCapsaicin; 8-Methyl-N-vanillyl-trans-6-nonenamide; NGX-4010
Identifiers(E)-N-[(3-methoxy-4-oxidanyl-phenyl)methyl]-8-methyl-non-6-enamide
FormulaC18 H27 N O3
Molecular Weight305.412
TypeNON-POLYMER
Isomeric SMILESCC(C)/C=C/CCCCC(=O)NCc1ccc(c(c1)OC)O
InChIInChI=1S/C18H27NO3/c1-14(2)8-6-4-5-7-9-18(21)19-13-15-10-11-16(20)17(12-15)22-3/h6,8,10-12,14,20H,4-5,7,9,13H2,1-3H3,(H,19,21)/b8-6+
InChIKeyYKPUWZUDDOIDPM-SOFGYWHQSA-N

Chemical Details

Formal Charge0
Atom Count49
Chiral Atom Count0
Bond Count49
Aromatic Bond Count6

Drug Info: DrugBank

DrugBank IDDB06774 
NameCapsaicin
Groups approved
DescriptionCapsaicin is most often used as a topical analgesic and exists in many formulations of cream, liquid, and patch preparations of various strengths; however, it may also be found in some dietary supplements. Capsaicin is a naturally-occurring botanical irritant in chili peppers, synthetically derived for pharmaceutical formulations. The most recent capsaicin FDA approval was Qutenza, an 8% capsaicin patch dermal-delivery system, indicated for neuropathic pain associated with post-herpetic neuralgia.
Synonyms
  • Capsaicina
  • Isodecenoic acid vanillylamide
  • (E)-8-Methyl-N-vanillyl-6-nonenamide
  • trans-8-Methyl-N-vanillyl-6-nonenamide
  • Capsaicin
Brand Names
  • Nufabrx Ankle Sock
  • Capsaicin Regular Cream
  • CVS Capsaicin arthritis pain relief
  • EMU THERAPY Red Hot Pepper Pain Relief Cream
  • Rocksauce Fire
IndicationThe capsaicin 8% patch is indicated in the treatment of neuropathic pain associated with post-herpetic neuralgia. There are multiple topical capsaicin formulations available, including creams and solutions, indicated for temporary analgesia in muscle and join pain as well as neuropathic pain.
Categories
  • Alkaloids
  • Alkenes
  • Amides
  • Analgesics
  • Anesthetics
ATC-Code
  • M02AB01
  • N01BX04
CAS number404-86-4

Drug Targets

NameTarget SequencePharmacological ActionActions
Transient receptor potential cation channel subfamily V member 1MKKWSSTDLGAAADPLQKDTCPDPLDGDPNSRPPPAKPQLSTAKSRTRLF...unknownagonist,regulator
Prohibitin-2MAQNLKDLAGRLPAGPRGMGTALKLLLGAGAVAYGVRESVFTVEGGHRAI...unknown
Cytochrome P450 3A4MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...unknowninhibitor
Prostaglandin G/H synthase 2MLARALLLCAVLALSHTANPCCSHPCQNRGVCMSVGFDQYKCDCTRTGFY...unknowninhibitor
MyeloperoxidaseMGVPFFSSLRCMVDLGPCWAGGLTAEMKLLLALAGLLAILATPQPSEGAA...unknowninhibitor
View More
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 CHEMBL294199
PubChem 1548943
ChEMBL CHEMBL294199
ChEBI CHEBI:94524, CHEBI:3374