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=CC(CNC(=O)CCCC\C=C\C(C)C)=CC=C1O
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 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 |
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OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
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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 |
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Alterations in spinal cord Fos protein expression induced by bladder stimulation following cystitis. | 2000 Apr |
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Effect of ginsenosides, active components of ginseng, on capsaicin-induced pain-related behavior. | 2000 Aug 23 |
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Differential effects of systemically administered ketamine and lidocaine on dynamic and static hyperalgesia induced by intradermal capsaicin in humans. | 2000 Feb |
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Evidence for activation of the tissue kallikrein-kinin system in nociceptive transmission and inflammatory responses of mice using a specific enzyme inhibitor. | 2000 Jul |
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Activation of the somatosensory cortex during Abeta-fiber mediated hyperalgesia. A MSI study. | 2000 Jul 14 |
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Influence of capsaicin cream in rats with peripheral neuropathy. | 2001 Aug |
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Role of central and peripheral tachykinin NK1 receptors in capsaicin-induced pain and hyperalgesia in mice. | 2001 Feb 1 |
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Nerve growth factor regulates VR-1 mRNA levels in cultures of adult dorsal root ganglion neurons. | 2001 Jan |
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Analysis of the native quaternary structure of vanilloid receptor 1. | 2001 Jul 27 |
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Antihyperalgesic effects of the muscarinic receptor ligand vedaclidine in models involving central sensitization in rats. | 2001 Sep |
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Regulation of constitutive and induced NF-kappaB activation in malignant melanoma cells by capsaicin modulates interleukin-8 production and cell proliferation. | 2002 Apr |
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Ischemia/reperfusion-induced increase in the hepatic level of prostacyclin is mainly mediated by activation of capsaicin-sensitive sensory neurons in rats. | 2002 Apr |
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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 |
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Activation of spinal ORL-1 receptors prevents acute cutaneous neurogenic inflammation: role of nociceptin-induced suppression of primary afferent depolarization. | 2002 Apr |
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The addition of glyceryltrinitrate to capsaicin cream reduces the thermal allodynia associated with the application of capsaicin alone in humans. | 2002 Apr 19 |
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Pharmacological characterisation of the somatostatin analogue TT-232: effects on neurogenic and non-neurogenic inflammation and neuropathic hyperalgesia. | 2002 Aug |
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5-Hydroxytryptamine(1B/1D) and 5-hydroxytryptamine1F receptors inhibit capsaicin-induced c-fos immunoreactivity within mouse trigeminal nucleus caudalis. | 2002 Jun |
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Cell death of primary afferent nerve cells in neonatal mice treated with capsaicin. | 2002 Mar |
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The orofacial capsaicin test in rats: effects of different capsaicin concentrations and morphine. | 2002 Mar |
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HSP90 inhibitors alter capsaicin- and ATP-induced currents in rat dorsal root ganglion neurons. | 2002 Mar 25 |
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Calcium-calmodulin-dependent protein kinase II contributes to spinal cord central sensitization. | 2002 May 15 |
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Postdelivery of alfentanil and ketamine has no effect on intradermal capsaicin-induced pain and hyperalgesia. | 2002 Nov-Dec |
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Pain activation of human supraspinal opioid pathways as demonstrated by [11C]-carfentanil and positron emission tomography (PET). | 2002 Oct |
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The role of the gastric afferent vagal nerve in ghrelin-induced feeding and growth hormone secretion in rats. | 2002 Oct |
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Deficits in visceral pain and referred hyperalgesia in Nav1.8 (SNS/PN3)-null mice. | 2002 Oct 1 |
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Naloxone increases pain induced by topical capsaicin in healthy human volunteers. | 2002 Sep |
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Opioid-insensitive hypoalgesia to mechanical stimuli at sites ipsilateral and contralateral to experimental muscle pain in human volunteers. | 2002 Sep |
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Roles of JNK-1 and p38 in selective induction of apoptosis by capsaicin in ras-transformed human breast epithelial cells. | 2003 Feb 10 |
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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
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
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S07O44R1ZM
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Classification Tree | Code System | Code | ||
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EPA PESTICIDE CODE |
70701
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FDA ORPHAN DRUG |
269508
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NCI_THESAURUS |
C68530
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FDA ORPHAN DRUG |
165502
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WHO-VATC |
QM02AB01
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EMA ASSESSMENT REPORTS |
QUTENZA (AUTHORIZED: NEURALGIA)
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FDA ORPHAN DRUG |
158202
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WHO-ATC |
N01BX04
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M02AB01
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FDA ORPHAN DRUG |
222506
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DSLD |
3807 (Number of products:4)
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NCI_THESAURUS |
C2198
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EU-Orphan Drug |
Capsaicin
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WHO-VATC |
QN01BX04
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FDA ORPHAN DRUG |
205705
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1992
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SUB13229MIG
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3374
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S07O44R1ZM
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206-969-8
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100000076831
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CAPSAICIN
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m3040
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10145
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56353
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DTXSID9020241
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DB06774
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CHEMBL294199
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C339
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Related Record | Type | Details | ||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
48.6% of Capsaicinoid components.
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PARENT -> CONSTITUENT ALWAYS PRESENT |
48.6% of Capsaicinoid components.
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PARENT -> CONSTITUENT ALWAYS PRESENT |
48.6% of Capsaicinoid components.
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PARENT -> CONSTITUENT ALWAYS PRESENT |
48.6% of Capsaicinoid components.
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DERIVATIVE -> PARENT |
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METABOLIC ENZYME -> SUBSTRATE | |||
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EXCRETED UNCHANGED |
There is no human excretion information available for capsaicin
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METABOLIC ENZYME -> SUBSTRATE |
WEAK
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TARGET -> AGONIST | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
48.6% of Capsaicinoid components.
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METABOLIC ENZYME -> SUBSTRATE |
WEAK
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METABOLIC ENZYME -> SUBSTRATE | |||
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METABOLIC ENZYME -> SUBSTRATE |
WEAK
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Related Record | Type | Details | ||
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METABOLITE -> PARENT |
MAJOR
PLASMA
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PRODRUG -> METABOLITE ACTIVE |
HYDROLYSIS INDEPENDENT OF ENZYME
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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
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METABOLITE -> PARENT |
MINOR
PLASMA
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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
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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
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METABOLITE -> PARENT |
MAJOR
PLASMA
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Related Record | Type | Details | ||
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ACTIVE MOIETY |