U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C18H27NO3
Molecular Weight 305.4126
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of CAPSAICIN

SMILES

CC(C)/C(/[H])=C(\[H])/CCCCC(=NCc1ccc(c(c1)OC)O)O

InChI

InChIKey=YKPUWZUDDOIDPM-SOFGYWHQSA-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 305.4126
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

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

1.2583296E12
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: Page: p.975
unhealthy, 71.6 +/-10.27
n = 222
Health Status: unhealthy
Condition: Neuropathic pain associated with postherpetic neuralgia
Age Group: 71.6 +/-10.27
Sex: M+F
Population Size: 222
Sources: Page: p.975
Disc. AE: Neuralgia...
AEs leading to
discontinuation/dose reduction:
Neuralgia (0.9%)
Sources: Page: p.975
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: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Neuropathic pain associated with postherpetic neuralgia
Sources: Page: p.1
Other AEs: Irritation of eyes, Respiratory tract irritation...
Other AEs:
Irritation of eyes
Respiratory tract irritation
Transient blood pressure increase
Sources: Page: p.1
AEs

AEs

AESignificanceDosePopulation
Neuralgia 0.9%
Disc. AE
8 % single, topical
Recommended
Dose: 8 %
Route: topical
Route: single
Dose: 8 %
Sources: Page: p.975
unhealthy, 71.6 +/-10.27
n = 222
Health Status: unhealthy
Condition: Neuropathic pain associated with postherpetic neuralgia
Age Group: 71.6 +/-10.27
Sex: M+F
Population Size: 222
Sources: Page: p.975
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: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Neuropathic pain associated with postherpetic neuralgia
Sources: Page: p.1
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: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Neuropathic pain associated with postherpetic neuralgia
Sources: Page: p.1
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: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Neuropathic pain associated with postherpetic neuralgia
Sources: Page: p.1
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
Antinociceptive profile of hodgkinsine.
2000 Dec
Knee joint mobilization reduces secondary mechanical hyperalgesia induced by capsaicin injection into the ankle joint.
2001
Influence of thermode size for detecting heat pain dysfunction in a capsaicin model of epidermal nerve fiber loss.
2001 Apr
Influence of capsaicin cream in rats with peripheral neuropathy.
2001 Aug
Comparative effect of Phoneutria nigriventer spider venom and capsaicin on the rat paw oedema.
2001 Aug 17
Role of central and peripheral tachykinin NK1 receptors in capsaicin-induced pain and hyperalgesia in mice.
2001 Feb 1
Nerve growth factor regulates VR-1 mRNA levels in cultures of adult dorsal root ganglion neurons.
2001 Jan
Analysis of the native quaternary structure of vanilloid receptor 1.
2001 Jul 27
Antinociceptive effects of delta-opioid agonists in Rhesus monkeys: effects on chemically induced thermal hypersensitivity.
2001 Mar
Involvement of NMDA receptors in the analgesic properties of psychotridine.
2001 May
Monophosphoryl lipid A-induced delayed preconditioning is mediated by calcitonin gene-related peptide.
2001 May 25
Hypolocomotor effects in rats of capsaicin and two long chain capsaicin homologues.
2001 May 25
Transient inhibition of the human motor cortex by capsaicin-induced pain. A study with transcranial magnetic stimulation.
2001 Nov 13
Capsaicin as a source for painful stimulation in functional MRI.
2001 Oct
Nitric oxide synthase in spinal cord central sensitization following intradermal injection of capsaicin.
2001 Oct
Cannabinoids attenuate capsaicin-evoked hyperalgesia through spinal and peripheral mechanisms.
2001 Sep
Antihyperalgesic effects of the muscarinic receptor ligand vedaclidine in models involving central sensitization in rats.
2001 Sep
Effect of systemic adenosine on pain and secondary hyperalgesia associated with the heat/capsaicin sensitization model in healthy volunteers.
2001 Sep-Oct
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
Regulation of constitutive and induced NF-kappaB activation in malignant melanoma cells by capsaicin modulates interleukin-8 production and cell proliferation.
2002 Apr
Ischemia/reperfusion-induced increase in the hepatic level of prostacyclin is mainly mediated by activation of capsaicin-sensitive sensory neurons in rats.
2002 Apr
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 Apr
Activation of spinal ORL-1 receptors prevents acute cutaneous neurogenic inflammation: role of nociceptin-induced suppression of primary afferent depolarization.
2002 Apr
Delayed cardioprotection induced by nitroglycerin is mediated by alpha-calcitonin gene-related peptide.
2002 Apr
The addition of glyceryltrinitrate to capsaicin cream reduces the thermal allodynia associated with the application of capsaicin alone in humans.
2002 Apr 19
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
Role of bradykinin in acid-induced mesenteric hyperemia and duodenal villous damage.
2002 Jan 4
Acupuncture modulation of capsaicin-induced inflammation: effect of intraperitoneal and local administration of naloxone in rats. A blinded controlled study.
2002 Jun
5-Hydroxytryptamine(1B/1D) and 5-hydroxytryptamine1F receptors inhibit capsaicin-induced c-fos immunoreactivity within mouse trigeminal nucleus caudalis.
2002 Jun
Cell death of primary afferent nerve cells in neonatal mice treated with capsaicin.
2002 Mar
The orofacial capsaicin test in rats: effects of different capsaicin concentrations and morphine.
2002 Mar
HSP90 inhibitors alter capsaicin- and ATP-induced currents in rat dorsal root ganglion neurons.
2002 Mar 25
Calcium-calmodulin-dependent protein kinase II contributes to spinal cord central sensitization.
2002 May 15
Postdelivery of alfentanil and ketamine has no effect on intradermal capsaicin-induced pain and hyperalgesia.
2002 Nov-Dec
Pain activation of human supraspinal opioid pathways as demonstrated by [11C]-carfentanil and positron emission tomography (PET).
2002 Oct
The role of the gastric afferent vagal nerve in ghrelin-induced feeding and growth hormone secretion in rats.
2002 Oct
The effect of chronic oral desipramine on capsaicin-induced allodynia and hyperalgesia: a double-blinded, placebo-controlled, crossover study.
2002 Oct
High affinity antagonists of the vanilloid receptor.
2002 Oct
Deficits in visceral pain and referred hyperalgesia in Nav1.8 (SNS/PN3)-null mice.
2002 Oct 1
Capsaicin regulates vascular endothelial cell growth factor expression by modulation of hypoxia inducing factor-1alpha in human malignant melanoma cells.
2002 Sep
Assessment of the reproducibility of intradermal administration of capsaicin as a model for inducing human pain.
2002 Sep
Naloxone increases pain induced by topical capsaicin in healthy human volunteers.
2002 Sep
Capsaicin-induced muscle pain alters the excitability of the human jaw-stretch reflex.
2002 Sep
Opioid-insensitive hypoalgesia to mechanical stimuli at sites ipsilateral and contralateral to experimental muscle pain in human volunteers.
2002 Sep
Phosphorylation of extracellular signal-regulated kinase in primary afferent neurons by noxious stimuli and its involvement in peripheral sensitization.
2002 Sep 1
Prostaglandin and protein kinase A-dependent modulation of vanilloid receptor function by metabotropic glutamate receptor 5: potential mechanism for thermal hyperalgesia.
2002 Sep 1
Roles of JNK-1 and p38 in selective induction of apoptosis by capsaicin in ras-transformed human breast epithelial cells.
2003 Feb 10
A comparison of hyperalgesia and neurogenic inflammation induced by melittin and capsaicin in humans.
2003 Feb 13
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 Fri Jun 25 20:59:41 UTC 2021
Edited
by admin
on Fri Jun 25 20:59:41 UTC 2021
Record UNII
S07O44R1ZM
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CAPSAICIN
DASH   EMA EPAR   HSDB   INCI   INN   JAN   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
INN   INCI  
Official Name English
CAPSAICIN [MART.]
Common Name English
CAPSAICIN [JAN]
Common Name English
OVOCAP
Common Name English
CNTX-4975
Common Name English
CAPSAICIN [EMA EPAR]
Common Name English
AUSANIL
Common Name English
TRANS-CAPSAICIN
Common Name English
(E)-8-METHYL-N-VANILLYL-6-NONENAMIDE
Systematic Name English
CAPSAICIN [INN]
Common Name English
NGX-4010
Code English
RATDEN PE 40
Common Name English
NSC-56353
Code English
CAPSAICIN [ORANGE BOOK]
Common Name English
QUTENZA
Brand Name English
6-NONENAMIDE, (E)-N-((4-HYDROXY-3-METHOXY-PHENYL)METHYL)-8-METHYL
Common Name English
ZOSTRIX
Common Name English
CAPSAICIN (CONSTITUENT OF CAPSICUM) [DSC]
Common Name English
CAPSAICIN [HSDB]
Common Name English
TOGARASHI ORENJI
Common Name English
FEMA NO. 3404
Code English
CAPSAICIN [WHO-DD]
Common Name English
CAPSAICIN [USP MONOGRAPH]
Common Name English
CAPSAICIN [INCI]
Common Name English
N-(4-HYDROXY-3-METHOXYBENZYL)-8-METHYL-6-NONENAMIDE [FHFI]
Common Name English
ALGRX-4975
Code English
MIOTON
Common Name English
CAPSAICIN [USP-RS]
Common Name English
ALGRX 4975
Code English
CAPSAICIN [MI]
Common Name English
NGX-1998
Code English
CAPSAICIN [VANDF]
Common Name English
CAPZASIN-HP
Common Name English
DOLENON
Common Name English
AXSAIN
Common Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 70701
Created by admin on Fri Jun 25 20:59:41 UTC 2021 , Edited by admin on Fri Jun 25 20:59:41 UTC 2021
FDA ORPHAN DRUG 269508
Created by admin on Fri Jun 25 20:59:41 UTC 2021 , Edited by admin on Fri Jun 25 20:59:41 UTC 2021
NCI_THESAURUS C68530
Created by admin on Fri Jun 25 20:59:41 UTC 2021 , Edited by admin on Fri Jun 25 20:59:41 UTC 2021
FDA ORPHAN DRUG 165502
Created by admin on Fri Jun 25 20:59:41 UTC 2021 , Edited by admin on Fri Jun 25 20:59:41 UTC 2021
WHO-VATC QM02AB01
Created by admin on Fri Jun 25 20:59:41 UTC 2021 , Edited by admin on Fri Jun 25 20:59:41 UTC 2021
EMA ASSESSMENT REPORTS QUTENZA (AUTHORIZED: NEURALGIA)
Created by admin on Fri Jun 25 20:59:41 UTC 2021 , Edited by admin on Fri Jun 25 20:59:41 UTC 2021
FDA ORPHAN DRUG 158202
Created by admin on Fri Jun 25 20:59:41 UTC 2021 , Edited by admin on Fri Jun 25 20:59:41 UTC 2021
WHO-ATC N01BX04
Created by admin on Fri Jun 25 20:59:41 UTC 2021 , Edited by admin on Fri Jun 25 20:59:41 UTC 2021
WHO-ATC M02AB01
Created by admin on Fri Jun 25 20:59:41 UTC 2021 , Edited by admin on Fri Jun 25 20:59:41 UTC 2021
FDA ORPHAN DRUG 222506
Created by admin on Fri Jun 25 20:59:41 UTC 2021 , Edited by admin on Fri Jun 25 20:59:41 UTC 2021
DSLD 3807 (Number of products:4)
Created by admin on Fri Jun 25 20:59:41 UTC 2021 , Edited by admin on Fri Jun 25 20:59:41 UTC 2021
NCI_THESAURUS C2198
Created by admin on Fri Jun 25 20:59:41 UTC 2021 , Edited by admin on Fri Jun 25 20:59:41 UTC 2021
EU-Orphan Drug Capsaicin
Created by admin on Fri Jun 25 20:59:41 UTC 2021 , Edited by admin on Fri Jun 25 20:59:41 UTC 2021
WHO-VATC QN01BX04
Created by admin on Fri Jun 25 20:59:41 UTC 2021 , Edited by admin on Fri Jun 25 20:59:41 UTC 2021
FDA ORPHAN DRUG 205705
Created by admin on Fri Jun 25 20:59:41 UTC 2021 , Edited by admin on Fri Jun 25 20:59:41 UTC 2021
Code System Code Type Description
IUPHAR
2486
Created by admin on Fri Jun 25 20:59:41 UTC 2021 , Edited by admin on Fri Jun 25 20:59:41 UTC 2021
PRIMARY
HSDB
954
Created by admin on Fri Jun 25 20:59:41 UTC 2021 , Edited by admin on Fri Jun 25 20:59:41 UTC 2021
PRIMARY
DRUG CENTRAL
3064
Created by admin on Fri Jun 25 20:59:41 UTC 2021 , Edited by admin on Fri Jun 25 20:59:41 UTC 2021
PRIMARY
RXCUI
1992
Created by admin on Fri Jun 25 20:59:41 UTC 2021 , Edited by admin on Fri Jun 25 20:59:41 UTC 2021
PRIMARY RxNorm
EVMPD
SUB13229MIG
Created by admin on Fri Jun 25 20:59:41 UTC 2021 , Edited by admin on Fri Jun 25 20:59:41 UTC 2021
PRIMARY
FDA UNII
S07O44R1ZM
Created by admin on Fri Jun 25 20:59:41 UTC 2021 , Edited by admin on Fri Jun 25 20:59:41 UTC 2021
PRIMARY
USP_CATALOG
1091108
Created by admin on Fri Jun 25 20:59:41 UTC 2021 , Edited by admin on Fri Jun 25 20:59:41 UTC 2021
PRIMARY USP-RS
ECHA (EC/EINECS)
206-969-8
Created by admin on Fri Jun 25 20:59:41 UTC 2021 , Edited by admin on Fri Jun 25 20:59:41 UTC 2021
PRIMARY
WIKIPEDIA
CAPSAICIN
Created by admin on Fri Jun 25 20:59:41 UTC 2021 , Edited by admin on Fri Jun 25 20:59:41 UTC 2021
PRIMARY
CAS
404-86-4
Created by admin on Fri Jun 25 20:59:41 UTC 2021 , Edited by admin on Fri Jun 25 20:59:41 UTC 2021
PRIMARY
MERCK INDEX
M3040
Created by admin on Fri Jun 25 20:59:41 UTC 2021 , Edited by admin on Fri Jun 25 20:59:41 UTC 2021
PRIMARY Merck Index
MESH
D002211
Created by admin on Fri Jun 25 20:59:41 UTC 2021 , Edited by admin on Fri Jun 25 20:59:41 UTC 2021
PRIMARY
INN
10145
Created by admin on Fri Jun 25 20:59:41 UTC 2021 , Edited by admin on Fri Jun 25 20:59:41 UTC 2021
PRIMARY
PUBCHEM
1548943
Created by admin on Fri Jun 25 20:59:41 UTC 2021 , Edited by admin on Fri Jun 25 20:59:41 UTC 2021
PRIMARY
EPA CompTox
404-86-4
Created by admin on Fri Jun 25 20:59:41 UTC 2021 , Edited by admin on Fri Jun 25 20:59:41 UTC 2021
PRIMARY
DRUG BANK
DB06774
Created by admin on Fri Jun 25 20:59:41 UTC 2021 , Edited by admin on Fri Jun 25 20:59:41 UTC 2021
PRIMARY
ChEMBL
CHEMBL294199
Created by admin on Fri Jun 25 20:59:41 UTC 2021 , Edited by admin on Fri Jun 25 20:59:41 UTC 2021
PRIMARY
NCI_THESAURUS
C339
Created by admin on Fri Jun 25 20:59:41 UTC 2021 , Edited by admin on Fri Jun 25 20:59:41 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
48.6% of Capsaicinoid components.
PARENT -> CONSTITUENT ALWAYS PRESENT
48.6% of Capsaicinoid components.
PARENT -> CONSTITUENT ALWAYS PRESENT
48.6% of Capsaicinoid components.
PARENT -> CONSTITUENT ALWAYS PRESENT
48.6% of Capsaicinoid components.
METABOLIC ENZYME -> SUBSTRATE
EXCRETED UNCHANGED
There is no human excretion information available for capsaicin
METABOLIC ENZYME -> SUBSTRATE
WEAK
TARGET -> AGONIST
PARENT -> CONSTITUENT ALWAYS PRESENT
48.6% of Capsaicinoid components.
METABOLIC ENZYME -> SUBSTRATE
WEAK
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
WEAK
Related Record Type Details
PRODRUG -> METABOLITE ACTIVE
HYDROLYSIS INDEPENDENT OF ENZYME
METABOLITE -> PARENT
In incubation medium and skin vanillic acid ranged from 0.11 to 7.97% of the radioactivity in each sample at all concentrations.
SKIN
METABOLITE -> PARENT
MINOR
PLASMA
METABOLITE -> PARENT
In incubation medium and skin vanillylamine ranged from 4.37 to 19.8% of the radioactivity in each sample at all concentrations.
SKIN
Related Record Type Details
ACTIVE MOIETY