Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C26H41N3O4.ClH |
| Molecular Weight | 496.082 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 1 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CNCC1CCCCN1C(=O)OC2=CC=C(CNC(=O)CCCC\C=C\C(C)C)C=C2OC
InChI
InChIKey=WOJDHHAJADLOCK-RVDQCCQOSA-N
InChI=1S/C26H41N3O4.ClH/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);1H/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 | ( + / - ) |
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| 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 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
| Target | Modality | Activity | Metabolite | Clinical 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
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| major | ||||
| yes |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Knee joint mobilization reduces secondary mechanical hyperalgesia induced by capsaicin injection into the ankle joint. | 2001 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| The heme oxygenase-1 pathway is involved in calcitonin gene-related peptide-mediated delayed cardioprotection induced by monophosphoryl lipid A in rats. | 2002 Jan 15 |
|
| 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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 14:11:29 GMT 2023
by
admin
on
Sat Dec 16 14:11:29 GMT 2023
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| Record UNII |
0892508P5Q
|
| Record Status |
Validated (UNII)
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| Record Version |
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