ZUCAPSAICIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C18H27NO3
Molecular Weight	305.4119
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC(CNC(=O)CCCC\C=C/C(C)C)=CC=C1O

InChI

InChIKey=YKPUWZUDDOIDPM-VURMDHGXSA-N

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-

HIDE SMILES / InChI

Molecular Formula	C18H27NO3
Molecular Weight	305.4119
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022395lbl.pdf
Curator's Comment: description was created based on several sources, including: https://www.drugs.com/mtm/capsaicin-topical.html http://www.rxlist.com/qutenza-drug.htm http://www.wikidoc.org/index.php/Capsaicin

Capsaicin is a topical analgesic that is FDA approved for the treatment of neuropathic pain associated with postherpetic neuralgia. Capsaicin 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. Capsaicin is an agonist for the transient receptor potential vanilloid I receptor (TRPVI), which is an ion channel-receptor complex expressed on nociceptive nerve fibers in the skin. Common adverse reactions include erythema, rash, pruritus, nausea.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Vanilloid receptor 53 Target ID: CHEMBL4794 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16056236 \| http://www.drugbank.ca/drugs/DB06774	Agonist 2752		1.8 µM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Neuropathic pain associated with postherpetic neuralgia 4 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022395lbl.pdf	Palliative		Approved 8583	QUTENZA Approved Use Qutenza is indicated for the management of neuropathic pain associated with postherpetic neuralgia Launch Date 2009

C_max

Value	Dose	Co-administered	Analyte	Population
1.38 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19494795/	640 μg/cm² single, topical dose: 640 μg/cm² route of administration: Topical experiment type: SINGLE co-administered:		CAPSAICIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
4.36 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19494795/	640 μg/cm² single, topical dose: 640 μg/cm² route of administration: Topical experiment type: SINGLE co-administered:		CAPSAICIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.64 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19494795/	640 μg/cm² single, topical dose: 640 μg/cm² route of administration: Topical experiment type: SINGLE co-administered:		CAPSAICIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
8 % single, topical Recommended Dose: 8 % Route: topical Route: single Dose: 8 % Sources: https://pubmed.ncbi.nlm.nih.gov/20655809	unhealthy, 71.6 +/-10.27 Health Status: unhealthy Age Group: 71.6 +/-10.27 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/20655809	Disc. AE: Neuralgia... AEs leading to discontinuation/dose reduction: Neuralgia (0.9%) Sources: https://pubmed.ncbi.nlm.nih.gov/20655809
8 % 1 times / 3 months multiple, topical Recommended Dose: 8 %, 1 times / 3 months Route: topical Route: multiple Dose: 8 %, 1 times / 3 months Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022395lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022395lbl.pdf	Other AEs: Irritation of eyes, Respiratory tract irritation... Other AEs: Irritation of eyes Respiratory tract irritation Transient blood pressure increase Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022395lbl.pdf

AEs

AE	Significance	Dose	Population
Neuralgia	0.9% Disc. AE	8 % single, topical Recommended Dose: 8 % Route: topical Route: single Dose: 8 % Sources: https://pubmed.ncbi.nlm.nih.gov/20655809	unhealthy, 71.6 +/-10.27 Health Status: unhealthy Age Group: 71.6 +/-10.27 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/20655809
Irritation of eyes		8 % 1 times / 3 months multiple, topical Recommended Dose: 8 %, 1 times / 3 months Route: topical Route: multiple Dose: 8 %, 1 times / 3 months Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022395lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022395lbl.pdf
Respiratory tract irritation		8 % 1 times / 3 months multiple, topical Recommended Dose: 8 %, 1 times / 3 months Route: topical Route: multiple Dose: 8 %, 1 times / 3 months Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022395lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022395lbl.pdf
Transient blood pressure increase		8 % 1 times / 3 months multiple, topical Recommended Dose: 8 %, 1 times / 3 months Route: topical Route: multiple Dose: 8 %, 1 times / 3 months Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022395lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022395lbl.pdf

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
	substrate 1193 inhibitor 2438 inducer 440	inhibitor 2507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP2B6 926 CYP2C19 2057 CYP2E1 1060 CYP3A4/5 296	CYP2C19 1119	CYP1A2 832 CYP2B6 669 CYP2C19 329 CYP2E1 131 CYP3A4/5 133

Drug as perpetrator

Target	Modality	Activity	Metabolite
CYP1A2 2333	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022395s000ClinPharmr.pdf#page=50 Page: 50.0	no	trans-capsaicin 4
CYP2B6 1160	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022395s000ClinPharmr.pdf#page=50 Page: 50.0	no	trans-capsaicin 4
CYP2C19 2141	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022395s000ClinPharmr.pdf#page=50 Page: 50.0	no	trans-capsaicin 4
CYP2C9 2497	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022395s000ClinPharmr.pdf#page=50 Page: 50.0	no	trans-capsaicin 4
CYP2E1 1146	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022395s000ClinPharmr.pdf#page=50 Page: 50.0	no	trans-capsaicin 4
CYP3A4/5 357	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022395s000ClinPharmr.pdf#page=50 Page: 50.0	no	trans-capsaicin 4
CYP3A4/5 357	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022395s000ClinPharmr.pdf#page=50 Page: 50.0	unlikely [IC50 12 uM]	trans-capsaicin 4
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022395s000ClinPharmr.pdf#page=50 Page: 50.0	unlikely [IC50 18 uM]	trans-capsaicin 4
CYP2C9 2497	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022395s000ClinPharmr.pdf#page=50 Page: 50.0	unlikely [IC50 2 uM]	trans-capsaicin 4
CYP1A2 2333	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022395s000ClinPharmr.pdf#page=50 Page: 50.0	unlikely [IC50 2.1 uM]	trans-capsaicin 4
CYP2B6 1160	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022395s000ClinPharmr.pdf#page=50 Page: 50.0	unlikely [IC50 24 uM]	trans-capsaicin 4
CYP2C19 2141	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022395s000ClinPharmr.pdf#page=50 Page: 50.0	unlikely [IC50 3.2 uM]	trans-capsaicin 4
CYP2E1 1146	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022395s000ClinPharmr.pdf#page=50 Page: 50.0	unlikely [IC50 >10 uM]	trans-capsaicin 4

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2C9 1193	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022395s000ClinPharmr.pdf#page=22 Page: 22.0	major
CYP2C19 1119	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022395s000ClinPharmr.pdf#page=22 Page: 22.0	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:3374	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:3374
ChemicalBook	CB32551563	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB32551563
ChemicalBook	CB6112967	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB6112967
eMolecules	479469	https://www.emolecules.com/cgi-bin/more?vid=479469
MolPort	MolPort-001-742-263	https://www.molport.com/shop/molecule-link/MolPort-001-742-263
ZINC	ZINC000001530575	http://zinc15.docking.org/substances/ZINC000001530575

PubMed

Title	Date	PubMed
A comparison of hyperalgesia and neurogenic inflammation induced by melittin and capsaicin in humans.	2003-02-13	12536045
Roles of JNK-1 and p38 in selective induction of apoptosis by capsaicin in ras-transformed human breast epithelial cells.	2003-02-10	12478662
Postdelivery of alfentanil and ketamine has no effect on intradermal capsaicin-induced pain and hyperalgesia.	2002-11-21	12441831
Deficits in visceral pain and referred hyperalgesia in Nav1.8 (SNS/PN3)-null mice.	2002-10-01	12351708
Pain activation of human supraspinal opioid pathways as demonstrated by [11C]-carfentanil and positron emission tomography (PET).	2002-10	12406535
The role of the gastric afferent vagal nerve in ghrelin-induced feeding and growth hormone secretion in rats.	2002-10	12360474
The effect of chronic oral desipramine on capsaicin-induced allodynia and hyperalgesia: a double-blinded, placebo-controlled, crossover study.	2002-10	12351279
High affinity antagonists of the vanilloid receptor.	2002-10	12237342
Phosphorylation of extracellular signal-regulated kinase in primary afferent neurons by noxious stimuli and its involvement in peripheral sensitization.	2002-09-01	12196597
Prostaglandin and protein kinase A-dependent modulation of vanilloid receptor function by metabotropic glutamate receptor 5: potential mechanism for thermal hyperalgesia.	2002-09-01	12196566
Capsaicin regulates vascular endothelial cell growth factor expression by modulation of hypoxia inducing factor-1alpha in human malignant melanoma cells.	2002-09	12242509
Assessment of the reproducibility of intradermal administration of capsaicin as a model for inducing human pain.	2002-09	12237211
Naloxone increases pain induced by topical capsaicin in healthy human volunteers.	2002-09	12237198
Capsaicin-induced muscle pain alters the excitability of the human jaw-stretch reflex.	2002-09	12202650
Opioid-insensitive hypoalgesia to mechanical stimuli at sites ipsilateral and contralateral to experimental muscle pain in human volunteers.	2002-09	12195523
Suppression of phorbol ester-induced NF-kappaB activation by capsaicin in cultured human promyelocytic leukemia cells.	2002-08	12214859
Pharmacological characterisation of the somatostatin analogue TT-232: effects on neurogenic and non-neurogenic inflammation and neuropathic hyperalgesia.	2002-08	12122501
Acupuncture modulation of capsaicin-induced inflammation: effect of intraperitoneal and local administration of naloxone in rats. A blinded controlled study.	2002-06	12165192
5-Hydroxytryptamine(1B/1D) and 5-hydroxytryptamine1F receptors inhibit capsaicin-induced c-fos immunoreactivity within mouse trigeminal nucleus caudalis.	2002-06	12110114
Calcium-calmodulin-dependent protein kinase II contributes to spinal cord central sensitization.	2002-05-15	12019337
The addition of glyceryltrinitrate to capsaicin cream reduces the thermal allodynia associated with the application of capsaicin alone in humans.	2002-04-19	11911994
Regulation of constitutive and induced NF-kappaB activation in malignant melanoma cells by capsaicin modulates interleukin-8 production and cell proliferation.	2002-04	12034025
Ischemia/reperfusion-induced increase in the hepatic level of prostacyclin is mainly mediated by activation of capsaicin-sensitive sensory neurons in rats.	2002-04	12024109
Capsaicin-sensitive nerve fibres induce epithelial cell proliferation, inflammatory cell immigration and transforming growth factor-alpha expression in the rat colonic mucosa in vivo.	2002-04	11989832
Activation of spinal ORL-1 receptors prevents acute cutaneous neurogenic inflammation: role of nociceptin-induced suppression of primary afferent depolarization.	2002-04	11973003
Delayed cardioprotection induced by nitroglycerin is mediated by alpha-calcitonin gene-related peptide.	2002-04	11919648
HSP90 inhibitors alter capsaicin- and ATP-induced currents in rat dorsal root ganglion neurons.	2002-03-25	11930156
Cell death of primary afferent nerve cells in neonatal mice treated with capsaicin.	2002-03	12418083
The orofacial capsaicin test in rats: effects of different capsaicin concentrations and morphine.	2002-03	11932064
The heme oxygenase-1 pathway is involved in calcitonin gene-related peptide-mediated delayed cardioprotection induced by monophosphoryl lipid A in rats.	2002-01-15	11738242
Role of bradykinin in acid-induced mesenteric hyperemia and duodenal villous damage.	2002-01-04	11837250
Concentration-effect relationships for intravenous alfentanil and ketamine infusions in human volunteers: effects on acute thresholds and capsaicin-evoked hyperpathia.	2002-01	11808827
Preliminary efficacy assessment of intrathecal injection of an American formulation of adenosine in humans.	2002-01	11752998
Heat hyperalgesia in humans: assessed by different stimulus temperature profiles.	2002	12160510
Effects of vanilloid receptor agonists and antagonists on gastric antral ulcers in rats.	2001-12-07	11740957
Improvement of preservation with cardioplegic solution by nitroglycerin-induced delayed preconditioning is mediated by calcitonin gene-related peptide.	2001-12	11744139
Transient inhibition of the human motor cortex by capsaicin-induced pain. A study with transcranial magnetic stimulation.	2001-11-13	11698155
Molecular targets for cannabidiol and its synthetic analogues: effect on vanilloid VR1 receptors and on the cellular uptake and enzymatic hydrolysis of anandamide.	2001-10	11606325
Capsaicin as a source for painful stimulation in functional MRI.	2001-10	11599056
Nitric oxide synthase in spinal cord central sensitization following intradermal injection of capsaicin.	2001-10	11576744
Effect of systemic adenosine on pain and secondary hyperalgesia associated with the heat/capsaicin sensitization model in healthy volunteers.	2001-09-19	11561260
Intestinal protection by lafutidine, a histamine H(2)-receptor antagonist, against indomethacin-induced damage in rats--role of endogenous nitric oxide.	2001-09-06	11535926
Cannabinoids attenuate capsaicin-evoked hyperalgesia through spinal and peripheral mechanisms.	2001-09	11514089
Antihyperalgesic effects of the muscarinic receptor ligand vedaclidine in models involving central sensitization in rats.	2001-09	11514081
Comparative effect of Phoneutria nigriventer spider venom and capsaicin on the rat paw oedema.	2001-08-17	11554618
Influence of capsaicin cream in rats with peripheral neuropathy.	2001-08	11516259
Monophosphoryl lipid A-induced delayed preconditioning is mediated by calcitonin gene-related peptide.	2001-05-25	11408036
Hypolocomotor effects in rats of capsaicin and two long chain capsaicin homologues.	2001-05-25	11408034
Involvement of NMDA receptors in the analgesic properties of psychotridine.	2001-05	11417913
Knee joint mobilization reduces secondary mechanical hyperalgesia induced by capsaicin injection into the ankle joint.	2001	11394925

Patents

Sample Use Guides

In Vivo Use Guide

The recommended dose of Qutenza is a single, 60-minute application of up to four patches. Qutenza patch contains 8% capsaicin (640 mcg/cm2).

Route of Administration: Topical

In Vitro Use Guide

In isolated perfused globally ischemic rat hearts, antiischemic efficacy was assessed as a significant extension (36% and 50%) in time to contracture with 30 microM capsaicin and 1 microM diltiazem, respectively.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:11:35 GMT 2025` Edited by `admin` on `Mon Mar 31 18:11:35 GMT 2025`
Record UNII	15OX67P384
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CIS-CAPSAICIN

Preferred Name

English

ZUCAPSAICIN

Official Name

English

(Z)-8-Methyl-N-vanillyl-6-nonenamide

Systematic Name

English

ZUCAPSAICIN [USAN]

Common Name

English

Zucapsaicin [WHO-DD]

Common Name

English

CIVAMIDE

Common Name

English

zucapsaicin [INN]

Common Name

English

6-NONENAMIDE, N-((4-HYDROXY-3-METHOXYPHENYL)METHYL)-8-METHYL-, (Z)-

Systematic Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

272308