Zucapsaicin

Zucapsaicin
Clinical data
Trade names	Civanex
Other names	Civamide; (Z)-Capsaicin; cis-Capsaicin
Routes of; administration	Topical
ATC code	M02AB02 (WHO) ;
Identifiers
	IUPAC name (Z)-N-[(4-Hydroxy-3-methoxyphenyl)methyl]-8-methylnon-6-enamide;
CAS Number	25775-90-0;
PubChem CID	1548942;
DrugBank	DB09120;
ChemSpider	1265956;
UNII	15OX67P384;
KEGG	D06388;
ChEBI	CHEBI:135952;
ChEMBL	ChEMBL313971;
CompTox Dashboard (EPA)	DTXSID101014453 ;
ECHA InfoCard	100.164.527
Chemical and physical data
Formula	C18H27NO3
Molar mass	305.418 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Oc1ccc(cc1OC)CNC(CCCC\C=C/C(C)C)=O;
	InChI InChI=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-; Key:YKPUWZUDDOIDPM-VURMDHGXSA-N;

Zucapsaicin (Civanex) is a medication used to treat osteoarthritis of the knee and other neuropathic pain. Zucapsaicin is a member of phenols and a member of methoxybenzenes.^[1] It is a modulator of transient receptor potential cation channel subfamily V member 1 (TRPV-1), also known as the vanilloid or capsaicin receptor 1 that reduces pain, and improves articular functions.^[2]^{[unreliable medical source?]}^[3] It is the cis-isomer of capsaicin. Civamide, manufactured by Winston Pharmaceuticals, is produced in formulations for oral, nasal, and topical use (patch and cream).^[4]^[5]

Zucapsaicin has been tested for treatment of a variety of conditions associated with ongoing nerve pain. This includes herpes simplex infections; cluster headaches and migraine; and knee osteoarthritis.^[6] It was approved by the Health Canada in 2010 as topical cream marketed under the brand name Zuacta but currently not FDA-approved.^[2] It has a melting point of 71.5–74.5 °C.^[2]

^ "zucapsaicin (CHEBI:135952)". Chemical Entities of Biological Interest (ChEBI). EMBL-EBI. Retrieved 2019-06-25.
^ ^a ^b ^c "Zucapsaicin". DrugBank. Retrieved 2019-06-25.
^ Studer M, McNaughton PA (October 2010). "Modulation of single-channel properties of TRPV1 by phosphorylation". The Journal of Physiology. 588 (Pt 19): 3743–56. doi:10.1113/jphysiol.2010.190611. PMC 2998224. PMID 20693293.
^ "Civamide". Winston Pharmaceuticals. Archived from the original on April 25, 2012. Retrieved November 16, 2011.
^ Sałat K, Jakubowska A, Kulig K (October 2014). "Zucapsaicin for the treatment of neuropathic pain". Expert Opinion on Investigational Drugs. 23 (10): 1433–40. doi:10.1517/13543784.2014.956079. PMID 25171227. S2CID 2969900.
^ Zucapsaicin information from the National Library of Medicine http://druginfo.nlm.nih.gov/drugportal

[1] "zucapsaicin (CHEBI:135952)". Chemical Entities of Biological Interest (ChEBI). EMBL-EBI. Retrieved 2019-06-25.

[:0-2] "Zucapsaicin". DrugBank. Retrieved 2019-06-25.

[:1-3] Studer M, McNaughton PA (October 2010). "Modulation of single-channel properties of TRPV1 by phosphorylation". The Journal of Physiology. 588 (Pt 19): 3743–56. doi:10.1113/jphysiol.2010.190611. PMC 2998224. PMID 20693293.

[4] "Civamide". Winston Pharmaceuticals. Archived from the original on April 25, 2012. Retrieved November 16, 2011.

[:2-5] Sałat K, Jakubowska A, Kulig K (October 2014). "Zucapsaicin for the treatment of neuropathic pain". Expert Opinion on Investigational Drugs. 23 (10): 1433–40. doi:10.1517/13543784.2014.956079. PMID 25171227. S2CID 2969900.

[6] Zucapsaicin information from the National Library of Medicine http://druginfo.nlm.nih.gov/drugportal

[1]

[2]

[3]

[4]

[5]

[6]