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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 of VOCACAPSAICIN

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
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
1.8 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
QUTENZA

Approved Use

Qutenza is indicated for the management of neuropathic pain associated with postherpetic neuralgia

Launch Date

2009
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1.38 ng/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
4.36 ng × h/mL
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1.64 h
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

Doses

DosePopulationAdverse events​
8 % single, topical
Recommended
Dose: 8 %
Route: topical
Route: single
Dose: 8 %
Sources:
unhealthy, 71.6 +/-10.27
Health Status: unhealthy
Age Group: 71.6 +/-10.27
Sex: M+F
Sources:
Disc. AE: Neuralgia...
AEs leading to
discontinuation/dose reduction:
Neuralgia (0.9%)
Sources:
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:
unhealthy
Other AEs: Irritation of eyes, Respiratory tract irritation...
Other AEs:
Irritation of eyes
Respiratory tract irritation
Transient blood pressure increase
Sources:
AEs

AEs

AESignificanceDosePopulation
Neuralgia 0.9%
Disc. AE
8 % single, topical
Recommended
Dose: 8 %
Route: topical
Route: single
Dose: 8 %
Sources:
unhealthy, 71.6 +/-10.27
Health Status: unhealthy
Age Group: 71.6 +/-10.27
Sex: M+F
Sources:
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:
unhealthy
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:
unhealthy
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:
unhealthy
Overview

Overview

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
no
no
no
no
no
unlikely [IC50 12 uM]
unlikely [IC50 18 uM]
unlikely [IC50 2 uM]
unlikely [IC50 2.1 uM]
unlikely [IC50 24 uM]
unlikely [IC50 3.2 uM]
unlikely [IC50 >10 uM]
Drug as victim
PubMed

PubMed

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

Sample Use Guides

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
  • Download
Name Type Language
CA-008
Preferred Name English
VOCACAPSAICIN
INN   USAN  
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
Created by admin on Tue Apr 01 22:27:57 GMT 2025 , Edited by admin on Tue Apr 01 22:27:57 GMT 2025
PRIMARY
NCI_THESAURUS
C175877
Created by admin on Tue Apr 01 22:27:57 GMT 2025 , Edited by admin on Tue Apr 01 22:27:57 GMT 2025
PRIMARY
USAN
GH-101
Created by admin on Tue Apr 01 22:27:57 GMT 2025 , Edited by admin on Tue Apr 01 22:27:57 GMT 2025
PRIMARY
CAS
1931116-86-7
Created by admin on Tue Apr 01 22:27:57 GMT 2025 , Edited by admin on Tue Apr 01 22:27:57 GMT 2025
PRIMARY
FDA UNII
KRJ8H9BOG7
Created by admin on Tue Apr 01 22:27:57 GMT 2025 , Edited by admin on Tue Apr 01 22:27:57 GMT 2025
PRIMARY
PUBCHEM
121349852
Created by admin on Tue Apr 01 22:27:57 GMT 2025 , Edited by admin on Tue Apr 01 22:27:57 GMT 2025
PRIMARY
INN
11377
Created by admin on Tue Apr 01 22:27:57 GMT 2025 , Edited by admin on Tue Apr 01 22:27:57 GMT 2025
PRIMARY
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