VOCACAPSAICIN

Details

Stereochemistry	RACEMIC
Molecular Formula	C26H41N3O4
Molecular Weight	459.6214
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CNCC1CCCCN1C(=O)OC2=CC=C(CNC(=O)CCCC\C=C\C(C)C)C=C2OC

InChI

InChIKey=BXAQOVOOXOHMFY-YRNVUSSQSA-N

InChI=1S/C26H41N3O4/c1-20(2)11-7-5-6-8-13-25(30)28-18-21-14-15-23(24(17-21)32-4)33-26(31)29-16-10-9-12-22(29)19-27-3/h7,11,14-15,17,20,22,27H,5-6,8-10,12-13,16,18-19H2,1-4H3,(H,28,30)/b11-7+

HIDE SMILES / InChI

Molecular Formula	C26H41N3O4
Molecular Weight	459.6214
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	1
Optical Activity	( + / - )

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
Brain processing of capsaicin-induced secondary hyperalgesia: a functional MRI study.	1999 Aug 11	10449119
Evidence for the involvement of spinal endogenous ATP and P2X receptors in nociceptive responses caused by formalin and capsaicin in mice.	1999 Dec	10602329
Involvement of glutamate in transmission of afferent constrictive inputs from the airways to the nucleus tractus solitarius in ferrets.	2000 Apr 12	10742536
Local inhibitory effects of dynorphin A-(1-17) on capsaicin-induced thermal allodynia in rhesus monkeys.	2000 Aug 18	10940359
Effect of ginsenosides, active components of ginseng, on capsaicin-induced pain-related behavior.	2000 Aug 23	10963761
Importance of endogenous nitric oxide synthase in the rat hypothalamus and amygdala in mediating the response to capsaicin.	2000 Aug 7	10880996
Differential effects of systemically administered ketamine and lidocaine on dynamic and static hyperalgesia induced by intradermal capsaicin in humans.	2000 Feb	10743446
Assessment of mechanisms involved in antinociception caused by sesquiterpene polygodial.	2000 Jan	10604944
Antinociceptive properties of the methanolic extract and two triterpenes isolated from Epidendrum Mosenii stems (Orchidaceae).	2000 Jan 21	10698354
Evidence for activation of the tissue kallikrein-kinin system in nociceptive transmission and inflammatory responses of mice using a specific enzyme inhibitor.	2000 Jul	10882395
ATP in human skin elicits a dose-related pain response which is potentiated under conditions of hyperalgesia.	2000 Jun	10825361
Spatial mapping of the zone of secondary hyperalgesia reveals a gradual decline of pain with distance but sharp borders.	2000 May	10779658
Antinociceptive properties of extracts of new species of plants of the genus Phyllanthus (Euphorbiaceae).	2000 Sep	10967476
Analysis of the native quaternary structure of vanilloid receptor 1.	2001 Jul 27	11358970
Intestinal protection by lafutidine, a histamine H(2)-receptor antagonist, against indomethacin-induced damage in rats--role of endogenous nitric oxide.	2001 Sep-Oct	11535926
Heat hyperalgesia in humans: assessed by different stimulus temperature profiles.	2002	12160510
Suppression of phorbol ester-induced NF-kappaB activation by capsaicin in cultured human promyelocytic leukemia cells.	2002 Aug	12214859
Pharmacological characterisation of the somatostatin analogue TT-232: effects on neurogenic and non-neurogenic inflammation and neuropathic hyperalgesia.	2002 Aug	12122501
Concentration-effect relationships for intravenous alfentanil and ketamine infusions in human volunteers: effects on acute thresholds and capsaicin-evoked hyperpathia.	2002 Jan	11808827
Acupuncture modulation of capsaicin-induced inflammation: effect of intraperitoneal and local administration of naloxone in rats. A blinded controlled study.	2002 Jun	12165192
Pain activation of human supraspinal opioid pathways as demonstrated by [11C]-carfentanil and positron emission tomography (PET).	2002 Oct	12406535
Opioid-insensitive hypoalgesia to mechanical stimuli at sites ipsilateral and contralateral to experimental muscle pain in human volunteers.	2002 Sep	12195523
Prostaglandin and protein kinase A-dependent modulation of vanilloid receptor function by metabotropic glutamate receptor 5: potential mechanism for thermal hyperalgesia.	2002 Sep 1	12196566

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 `Tue Apr 01 22:27:57 GMT 2025` Edited by `admin` on `Tue Apr 01 22:27:57 GMT 2025`
Record UNII	KRJ8H9BOG7
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CA-008

Preferred Name

English

VOCACAPSAICIN

Official Name

English

2-Methoxy-4-{[(6E)-8-methylnon-6-enamido]methyl}phenyl (2RS)-2-[(methylamino)methyl]piperidine-1-carboxylate

Systematic Name

English

VOCACAPSAICIN [USAN]

Common Name

English

vocacapsaicin [INN]

Common Name

English

1-PIPERIDINECARBOXYLIC ACID, 2-((METHYLAMINO)METHYL)-, 2-METHOXY-4-((((6E)-8-METHYL-1-OXO-6-NONEN-1-YL)AMINO)METHYL) PHENYL ESTER

Systematic Name

English

Code System Code Type Description

SMS_ID

300000027512