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
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+
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 | ( + / - ) |
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 Date2009 |
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 |
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 Health Status: unhealthy Sources: |
Other AEs: Irritation of eyes, Respiratory tract irritation... Other AEs: Irritation of eyes Sources: Respiratory tract irritation Transient blood pressure increase |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Neuralgia | 0.9% Disc. AE |
8 % single, topical Recommended |
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 Health Status: unhealthy Sources: |
|
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 Health Status: unhealthy Sources: |
|
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 Health Status: unhealthy Sources: |
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 |
---|---|---|
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
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
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admin
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Edited
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Record UNII |
KRJ8H9BOG7
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Record Status |
Validated (UNII)
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Record Version |
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METABOLITE ACTIVE -> PRODRUG |
HYDROLYSIS INDEPENDENT OF ENZYME
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ACTIVE MOIETY |
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