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
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+
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 |
DescriptionCurator'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
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 |
---|---|---|---|
Target ID: CHEMBL4794 |
1.8 µM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Palliative | QUTENZA Approved UseQutenza is indicated for the management of neuropathic pain associated with postherpetic neuralgia Launch Date1.2583296E12 |
Cmax
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 |
T1/2
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: 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 Sources: Page: p.1Respiratory tract irritation Transient blood pressure increase |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022395s000ClinPharmr.pdf#page=22 Page: 22.0 |
major | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022395s000ClinPharmr.pdf#page=22 Page: 22.0 |
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Activation of peripheral kappa opioid receptors inhibits capsaicin-induced thermal nociception in rhesus monkeys. | 1999 Apr |
|
Brain processing of capsaicin-induced secondary hyperalgesia: a functional MRI study. | 1999 Aug 11 |
|
Effect of sympathetic activity on capsaicin-evoked pain, hyperalgesia, and vasodilatation. | 1999 Mar 23 |
|
Capsaicin-sensitive afferent sensory nerves in modulating gastric mucosal defense against noxious agents. | 1999 Nov |
|
Capsaicin inhibits phospholipase C-mediated Ca(2+) increase by blocking thapsigargin-sensitive store-operated Ca(2+) entry in PC12 cells. | 1999 Oct |
|
Protective effect of lafutidine against indomethacin-induced intestinal ulceration in rats: relation to capsaicin-sensitive sensory neurons. | 2000 |
|
Alterations in spinal cord Fos protein expression induced by bladder stimulation following cystitis. | 2000 Apr |
|
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 |
|
Induction of vanilloid receptor channel activity by protein kinase C. | 2000 Dec 21-28 |
|
Cholecystokinin-8 enhances nerve growth factor synthesis and promotes recovery of capsaicin-induced sensory deficit. | 2000 Feb |
|
Evidence for activation of the tissue kallikrein-kinin system in nociceptive transmission and inflammatory responses of mice using a specific enzyme inhibitor. | 2000 Jul |
|
Spatial mapping of the zone of secondary hyperalgesia reveals a gradual decline of pain with distance but sharp borders. | 2000 May |
|
Effect of oral mexiletine on capsaicin-induced allodynia and hyperalgesia: a double-blind, placebo-controlled, crossover study. | 2000 Sep-Oct |
|
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 |
|
Improvement of preservation with cardioplegic solution by nitroglycerin-induced delayed preconditioning is mediated by calcitonin gene-related peptide. | 2001 Dec |
|
Effects of vanilloid receptor agonists and antagonists on gastric antral ulcers in rats. | 2001 Dec 7 |
|
Chronic tobacco smoke exposure increases airway sensitivity to capsaicin in awake guinea pigs. | 2001 Feb |
|
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 |
|
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 |
|
Nitric oxide synthase in spinal cord central sensitization following intradermal injection of capsaicin. | 2001 Oct |
|
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 |
|
Ischemia/reperfusion-induced increase in the hepatic level of prostacyclin is mainly mediated by activation of capsaicin-sensitive sensory neurons in rats. | 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 |
|
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 |
|
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 |
|
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 |
|
Pain activation of human supraspinal opioid pathways as demonstrated by [11C]-carfentanil and positron emission tomography (PET). | 2002 Oct |
|
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 |
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7713171
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
Edited
Wed Jul 05 22:42:42 UTC 2023
by
admin
on
Wed Jul 05 22:42:42 UTC 2023
|
Record UNII |
S07O44R1ZM
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
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 | ||
---|---|---|---|---|---|
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | ||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | ||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 |
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.
|
||
|
DERIVATIVE -> PARENT |
|
||
|
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 | ||
---|---|---|---|---|
|
METABOLITE -> PARENT |
MAJOR
PLASMA
|
||
|
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
|
||
|
METABOLITE -> PARENT |
In human microsomal fraction, 16,17-dehydro-capsaicin was the minor metabolite, but in human S-9 fraction, 16,17-dehydro-capsaicin was the major metabolite.
PLASMA
|
||
|
METABOLITE -> PARENT |
MAJOR
PLASMA
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |