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

Details

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

SHOW SMILES / InChI
Structure of CAPSAICIN

SMILES

COC1=C(O)C=CC(CNC(=O)CCCC\C=C\C(C)C)=C1

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

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
Topical EMLA pre-treatment fails to decrease the pain induced by 1% topical capsaicin.
1999 Apr
The effects of intradermal fentanyl and ketamine on capsaicin-induced secondary hyperalgesia and flare reaction.
1999 Dec
Age-related differences in the time course of capsaicin-induced hyperalgesia.
2000 Mar
Peripheral lidocaine but not ketamine inhibits capsaicin-induced hyperalgesia in humans.
2000 Oct
The effect of systemic lidocaine on pain and secondary hyperalgesia associated with the heat/capsaicin sensitization model in healthy volunteers.
2000 Oct
Effect of oral mexiletine on capsaicin-induced allodynia and hyperalgesia: a double-blind, placebo-controlled, crossover study.
2000 Sep-Oct
Knee joint mobilization reduces secondary mechanical hyperalgesia induced by capsaicin injection into the ankle joint.
2001
Improvement of preservation with cardioplegic solution by nitroglycerin-induced delayed preconditioning is mediated by calcitonin gene-related peptide.
2001 Dec
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
Involvement of NMDA receptors in the analgesic properties of psychotridine.
2001 May
Transient inhibition of the human motor cortex by capsaicin-induced pain. A study with transcranial magnetic stimulation.
2001 Nov 13
Molecular targets for cannabidiol and its synthetic analogues: effect on vanilloid VR1 receptors and on the cellular uptake and enzymatic hydrolysis of anandamide.
2001 Oct
Cannabinoids attenuate capsaicin-evoked hyperalgesia through spinal and peripheral mechanisms.
2001 Sep
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
The addition of glyceryltrinitrate to capsaicin cream reduces the thermal allodynia associated with the application of capsaicin alone in humans.
2002 Apr 19
Pharmacological characterisation of the somatostatin analogue TT-232: effects on neurogenic and non-neurogenic inflammation and neuropathic hyperalgesia.
2002 Aug
Preliminary efficacy assessment of intrathecal injection of an American formulation of adenosine in humans.
2002 Jan
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
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
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.
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
Capsaicin [WHO-DD]
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 [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 Wed Jul 05 22:42:42 UTC 2023 , Edited by admin on Wed Jul 05 22:42:42 UTC 2023
FDA ORPHAN DRUG 269508
Created by admin on Wed Jul 05 22:42:42 UTC 2023 , Edited by admin on Wed Jul 05 22:42:42 UTC 2023
NCI_THESAURUS C68530
Created by admin on Wed Jul 05 22:42:42 UTC 2023 , Edited by admin on Wed Jul 05 22:42:42 UTC 2023
FDA ORPHAN DRUG 165502
Created by admin on Wed Jul 05 22:42:42 UTC 2023 , Edited by admin on Wed Jul 05 22:42:42 UTC 2023
WHO-VATC QM02AB01
Created by admin on Wed Jul 05 22:42:42 UTC 2023 , Edited by admin on Wed Jul 05 22:42:42 UTC 2023
EMA ASSESSMENT REPORTS QUTENZA (AUTHORIZED: NEURALGIA)
Created by admin on Wed Jul 05 22:42:42 UTC 2023 , Edited by admin on Wed Jul 05 22:42:42 UTC 2023
FDA ORPHAN DRUG 158202
Created by admin on Wed Jul 05 22:42:42 UTC 2023 , Edited by admin on Wed Jul 05 22:42:42 UTC 2023
WHO-ATC N01BX04
Created by admin on Wed Jul 05 22:42:42 UTC 2023 , Edited by admin on Wed Jul 05 22:42:42 UTC 2023
WHO-ATC M02AB01
Created by admin on Wed Jul 05 22:42:42 UTC 2023 , Edited by admin on Wed Jul 05 22:42:42 UTC 2023
FDA ORPHAN DRUG 222506
Created by admin on Wed Jul 05 22:42:42 UTC 2023 , Edited by admin on Wed Jul 05 22:42:42 UTC 2023
DSLD 3807 (Number of products:4)
Created by admin on Wed Jul 05 22:42:42 UTC 2023 , Edited by admin on Wed Jul 05 22:42:42 UTC 2023
NCI_THESAURUS C2198
Created by admin on Wed Jul 05 22:42:42 UTC 2023 , Edited by admin on Wed Jul 05 22:42:42 UTC 2023
EU-Orphan Drug Capsaicin
Created by admin on Wed Jul 05 22:42:42 UTC 2023 , Edited by admin on Wed Jul 05 22:42:42 UTC 2023
WHO-VATC QN01BX04
Created by admin on Wed Jul 05 22:42:42 UTC 2023 , Edited by admin on Wed Jul 05 22:42:42 UTC 2023
FDA ORPHAN DRUG 205705
Created by admin on Wed Jul 05 22:42:42 UTC 2023 , Edited by admin on Wed Jul 05 22:42:42 UTC 2023
Code System Code Type Description
IUPHAR
2486
Created by admin on Wed Jul 05 22:42:42 UTC 2023 , Edited by admin on Wed Jul 05 22:42:42 UTC 2023
PRIMARY
RS_ITEM_NUM
1091108
Created by admin on Wed Jul 05 22:42:42 UTC 2023 , Edited by admin on Wed Jul 05 22:42:42 UTC 2023
PRIMARY
HSDB
954
Created by admin on Wed Jul 05 22:42:42 UTC 2023 , Edited by admin on Wed Jul 05 22:42:42 UTC 2023
PRIMARY
DRUG CENTRAL
3064
Created by admin on Wed Jul 05 22:42:42 UTC 2023 , Edited by admin on Wed Jul 05 22:42:42 UTC 2023
PRIMARY
RXCUI
1992
Created by admin on Wed Jul 05 22:42:42 UTC 2023 , Edited by admin on Wed Jul 05 22:42:42 UTC 2023
PRIMARY RxNorm
EVMPD
SUB13229MIG
Created by admin on Wed Jul 05 22:42:42 UTC 2023 , Edited by admin on Wed Jul 05 22:42:42 UTC 2023
PRIMARY
CHEBI
3374
Created by admin on Wed Jul 05 22:42:42 UTC 2023 , Edited by admin on Wed Jul 05 22:42:42 UTC 2023
PRIMARY
FDA UNII
S07O44R1ZM
Created by admin on Wed Jul 05 22:42:42 UTC 2023 , Edited by admin on Wed Jul 05 22:42:42 UTC 2023
PRIMARY
ECHA (EC/EINECS)
206-969-8
Created by admin on Wed Jul 05 22:42:42 UTC 2023 , Edited by admin on Wed Jul 05 22:42:42 UTC 2023
PRIMARY
SMS_ID
100000076831
Created by admin on Wed Jul 05 22:42:42 UTC 2023 , Edited by admin on Wed Jul 05 22:42:42 UTC 2023
PRIMARY
WIKIPEDIA
CAPSAICIN
Created by admin on Wed Jul 05 22:42:42 UTC 2023 , Edited by admin on Wed Jul 05 22:42:42 UTC 2023
PRIMARY
CAS
404-86-4
Created by admin on Wed Jul 05 22:42:42 UTC 2023 , Edited by admin on Wed Jul 05 22:42:42 UTC 2023
PRIMARY
MERCK INDEX
M3040
Created by admin on Wed Jul 05 22:42:42 UTC 2023 , Edited by admin on Wed Jul 05 22:42:42 UTC 2023
PRIMARY Merck Index
MESH
D002211
Created by admin on Wed Jul 05 22:42:42 UTC 2023 , Edited by admin on Wed Jul 05 22:42:42 UTC 2023
PRIMARY
INN
10145
Created by admin on Wed Jul 05 22:42:42 UTC 2023 , Edited by admin on Wed Jul 05 22:42:42 UTC 2023
PRIMARY
PUBCHEM
1548943
Created by admin on Wed Jul 05 22:42:42 UTC 2023 , Edited by admin on Wed Jul 05 22:42:42 UTC 2023
PRIMARY
DAILYMED
S07O44R1ZM
Created by admin on Wed Jul 05 22:42:42 UTC 2023 , Edited by admin on Wed Jul 05 22:42:42 UTC 2023
PRIMARY
NSC
56353
Created by admin on Wed Jul 05 22:42:42 UTC 2023 , Edited by admin on Wed Jul 05 22:42:42 UTC 2023
PRIMARY
EPA CompTox
DTXSID9020241
Created by admin on Wed Jul 05 22:42:42 UTC 2023 , Edited by admin on Wed Jul 05 22:42:42 UTC 2023
PRIMARY
DRUG BANK
DB06774
Created by admin on Wed Jul 05 22:42:42 UTC 2023 , Edited by admin on Wed Jul 05 22:42:42 UTC 2023
PRIMARY
ChEMBL
CHEMBL294199
Created by admin on Wed Jul 05 22:42:42 UTC 2023 , Edited by admin on Wed Jul 05 22:42:42 UTC 2023
PRIMARY
NCI_THESAURUS
C339
Created by admin on Wed Jul 05 22:42:42 UTC 2023 , Edited by admin on Wed Jul 05 22:42:42 UTC 2023
PRIMARY