WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 326727
Description: Zucapsaicin, also known as cis-Capsaicin, is a medication used to treat osteoarthritis of the knee and other neuropathic pain. It is applied three times daily for a maximum of three months. It reduces pain, and improves articular functions. 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). 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.
MedKoo Cat#: 326727
Chemical Formula: C18H27NO3
Exact Mass: 305.1991
Molecular Weight: 305.418
Elemental Analysis: C, 70.79; H, 8.91; N, 4.59; O, 15.72
Synonym: BRN 4261852; cis-Capsaicin; Civamide; Zucapsaicin, trade name Civanex.
IUPAC/Chemical Name: (Z)-N-(4-hydroxy-3-methoxybenzyl)-8-methylnon-6-enamide
InChi Key: YKPUWZUDDOIDPM-VURMDHGXSA-N
InChi Code: 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-
SMILES Code: CC(C)/C=C\CCCCC(NCC1=CC=C(O)C(OC)=C1)=O
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO, not in water
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
The following data is based on the product molecular weight 305.418 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
|Concentration / Solvent Volume / Mass||1 mg||5 mg||10 mg|
|1 mM||1.15 mL||5.76 mL||11.51 mL|
|5 mM||0.23 mL||1.15 mL||2.3 mL|
|10 mM||0.12 mL||0.58 mL||1.15 mL|
|50 mM||0.02 mL||0.12 mL||0.23 mL|
1: Sałat K, Jakubowska A, Kulig K. Zucapsaicin for the treatment of neuropathic pain. Expert Opin Investig Drugs. 2014 Oct;23(10):1433-40. doi: 10.1517/13543784.2014.956079. Epub 2014 Aug 29. Review. PubMed PMID: 25171227.
2: Schnitzer TJ, Pelletier JP, Haselwood DM, Ellison WT, Ervin JE, Gordon RD, Lisse JR, Archambault WT, Sampson AR, Fezatte HB, Phillips SB, Bernstein JE. Civamide cream 0.075% in patients with osteoarthritis of the knee: a 12-week randomized controlled clinical trial with a longterm extension. J Rheumatol. 2012 Mar;39(3):610-20. doi: 10.3899/jrheum.110192. Epub 2011 Nov 15. PubMed PMID: 22089461.
3: Bayes M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2006 Jul-Aug;28(6):379-412. PubMed PMID: 16894408.
4: Rapoport AM, Bigal ME, Tepper SJ, Sheftell FD. Intranasal medications for the treatment of migraine and cluster headache. CNS Drugs. 2004;18(10):671-85. Review. PubMed PMID: 15270595.
5: Markley HG. Topical agents in the treatment of cluster headache. Curr Pain Headache Rep. 2003 Apr;7(2):139-43. Review. PubMed PMID: 12628056.
6: Saper JR, Klapper J, Mathew NT, Rapoport A, Phillips SB, Bernstein JE. Intranasal civamide for the treatment of episodic cluster headaches. Arch Neurol. 2002 Jun;59(6):990-4. PubMed PMID: 12056936.
7: Diamond S, Freitag F, Phillips SB, Bernstein JE, Saper JR. Intranasal civamide for the acute treatment of migraine headache. Cephalalgia. 2000 Jul;20(6):597-602. PubMed PMID: 11075845.
8: Bourne N, Bernstein DI, Stanberry LR. Civamide (cis-capsaicin) for treatment of primary or recurrent experimental genital herpes. Antimicrob Agents Chemother. 1999 Nov;43(11):2685-8. PubMed PMID: 10543747; PubMed Central PMCID: PMC89543.
9: Arnar DO, Cai JJ, Lee HC, Martins JB. Electrophysiologic effects of civamide (zucapsaicin) on canine cardiac tissue in vivo and in vitro. J Cardiovasc Pharmacol. 1998 Dec;32(6):875-83. PubMed PMID: 9869492.
10: Lu J, Cwik M. Determination of capsaicin and zucapsaicin in human serum by high-performance liquid chromatography with fluorescence detection. J Chromatogr B Biomed Sci Appl. 1997 Nov 7;701(1):135-9. PubMed PMID: 9389349.