Identification
- Summary
Capsaicin is a topical analgesic agent used for the symptomatic relief of neuropathic pain associated with post-herpetic neuralgia, as well as other muscle and joint pain.
- Brand Names
- Capzasin Quick Relief, Capzasin-HP, Castiva Warming, Dendracin Neurodendraxcin, Lidopro, Medi-derm, Medi-derm With Lidocaine, Medrox, Qutenza, Rematex, Xoten-C, Zostrix
- Generic Name
- Capsaicin
- DrugBank Accession Number
- DB06774
- Background
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. The most recent capsaicin FDA approval was Qutenza, an 8% capsaicin patch dermal-delivery system, indicated for neuropathic pain associated with post-herpetic neuralgia.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Capsaicin (DB06774)
- Weight
- Average: 305.4119
Monoisotopic: 305.199093735 - Chemical Formula
- C18H27NO3
- Synonyms
- (E)-8-Methyl-N-vanillyl-6-nonenamide
- Capsaicin
- Capsaicina
- Isodecenoic acid vanillylamide
- trans-8-Methyl-N-vanillyl-6-nonenamide
- External IDs
- ALGRX 4975
- ALGRX-4975
- FEMA NO. 3404
- NGX 4010
- NGX-1998
- NGX-4010
- NSC-56353
Pharmacology
- Indication
The capsaicin 8% patch is indicated in the treatment of neuropathic pain associated with post-herpetic neuralgia. There are multiple topical capsaicin formulations available, including creams and solutions, indicated for temporary analgesia in muscle and join pain as well as neuropathic pain.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Symptomatic treatment of Arthritis ••• ••• Used in combination to treat Back pain lower back Combination Product in combination with: Nimesulide (DB04743) •••••••••••• ••• Symptomatic treatment of Backache ••• ••• Symptomatic treatment of Bruises ••• ••• Used in combination to treat Bursitis Combination Product in combination with: Nimesulide (DB04743) •••••••••••• ••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Capsaicin is a TRPV1 receptor agonist. TRPV1 is a trans-membrane receptor-ion channel complex activated by temperatures higher than 43 degrees Celsius, pH lower than 6, and endogenous lipids. When activated by a combination of these factors, the channel can transiently open and initiate depolarization due to the influx of calcium and sodium ions. Because TRPV1 is commonly expressed in A-delta and mostly C fibers, depolarization results in action potentials which send impulses to the brain and spinal cord. These impulses result in capsaicin effects of warming, tingling, itching, stinging, or burning. Capsaicin also causes more persistent activation of these receptors compared to the environmental agonists, resulting in a loss of response to many sensory stimuli, described as "defunctionalization". Capsaicin is associated with many enzymatic, cytoskeletal, and osmotic changes, as well as disruption of mitochondrial respiration, impairing nociceptor function for extended periods of time.
- Mechanism of action
Capsaicin has been shown to reduce the amount of substance P associated with inflammation - however this is not believed to be its main mechanism in the relief of pain 4. Capsaicin's mechanism of action is attributed to "defunctionalization" of nociceptor fibers by inducing a topical hypersensitivity reaction on the skin. This alteration in pain mechanisms is due to many of the following: temporary loss of membrane potential, inability to transport neurotrophic factors leading to altered phenotype, and reversible retraction of epidermal and dermal nerve fiber terminals.
Target Actions Organism ATransient receptor potential cation channel subfamily V member 1 agonistregulatorHumans UProhibitin-2 Not Available Humans - Absorption
Oral: Following oral administration, capsaicin may be absorbed by a nonactive process from the stomach and whole intestine with an extent of absorption ranging between 50 and 90%, depending on the animal 4. The peak blood concentration can be reached within 1 hour following administration 4. Capsaicin may undergo minor metabolism in the small intestine epithelial cells post-absorption from the stomach into the small intestines. While oral pharmacokinetics information in humans is limited, ingestion of equipotent dose of 26.6 mg of pure capsaicin, capsaicin was detected in the plasma after 10 minutes and the peak plasma concentration of 2.47 ± 0.13 ng/ml was reached at 47.1 ± 2.0 minutes 4.
Systemic: Following intravenous or subcutaneous administration in animals, the concentrations in the brain and spinal cord were approximately 5-fold higher than that in blood and the concentration in the liver was approximately 3-fold higher than that in blood 4.
Topical: Topical capsaicin in humans is rapidly and well absorbed through the skin, however systemic absorption following topical or transdermal administration is unlikely 4. For patients receiving the topical patch containing 179 mg of capsaicin, a population analysis was performed and plasma concentrations of capsaicin were fitted using a one-compartment model with first-order absorption and linear elimination. The mean peak plasma concentration was 1.86 ng/mL but the maximum value observed in any patient was 17.8 ng/mL 4.
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
Capsaicin metabolism after oral administration is unclear, however it is expected to undergo metabolism in the liver with minimal metabolism in the gut lumen. In vitro studies with human hepatic microsomes and S9 fragments indicate that capsaicin is rapidly metabolized, producing three major metabolites, 16-hydroxycapsaicin, 17-hydroxycapsaicin, and 16,17-hydroxycapsaicin, whereas vanillin was a minor metabolite 4. It is proposed that cytochrome P450 (P450) enzymes may play some role in hepatic drug metabolism 4. In vitro studies of capsaicin in human skin suggest slow biotransformation with most capsaicin remaining unchanged.
- Route of elimination
It is proposed that capsaicin mainly undergoes renal excretion, as both the unchanged and glucuronide form. A small fraction of unchanged compound is excreted in the feces and urine. In vivo animal studies demonstrates that less than 10 % of an administered dose was found in faces after 48 h 4.
- Half-life
Following oral ingestion of equipotent dose of 26.6 mg of pure capsaicin, the half life was approximately 24.9 ± 5.0 min 4. Following topical application of 3% solution of capsaicin, the half-life of capsaicin was approximately 24 h 4. The mean population elimination half-life was 1.64 h following application of a topical patch containing 179 mg of capsaicin 4.
- Clearance
Not Available
- Adverse Effects
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Acute oral LD50 and dermal LD50 in mouse are 47.2 mg/kg and >512 mg/kg, respectively MSDS. Capsaicin is shown to be mutagenic for bacteria and yeast MSDS.
Capsaicin can cause serious irritation, conjunctivitis and lacrimation via contact with eyes. It induces a burning sensation and pain in case of contact with eyes and skin. As it is also irritating to the respiratory system, it causes lung irritation and coughing as well as bronchoconstriction. Other respiratory effects include laryngospasm, swelling of the larynx and lungs, chemical pneumonitis,respiratory arrest and central nervous system effects such as convulsions and excitement 5. In case of ingestion, gastrointestinal tract irritation may be observed along with a sensation of warmth or painful burning MSDS. Symptoms of systemic toxicity include disorientation, fear, loss of body motor control including diminished hand-eye coordination, hyperventilation, tachycardia, and pulmonary oedema 5. Careful early decontamination is recommended and medical intervention should be initiated for any life-threatening symptoms. In case of contact, individual must be removed from the source of exposure and the contacted skin and mucous membranes should be thoroughly washed with copious amounts of water 5.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbametapir The serum concentration of Capsaicin can be increased when it is combined with Abametapir. Abatacept The metabolism of Capsaicin can be increased when combined with Abatacept. Abemaciclib The risk or severity of methemoglobinemia can be increased when Abemaciclib is combined with Capsaicin. Abiraterone The serum concentration of Capsaicin can be increased when it is combined with Abiraterone. Acalabrutinib The serum concentration of Acalabrutinib can be increased when it is combined with Capsaicin. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- Zostrix
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Capsaicin Patch 0.025 g/100g Topical PHARMACURE, INC. 2021-02-02 Not applicable US 
Qutenza Kit; Patch 179 mg/179mg Cutaneous Averitas Pharma Inc 2021-03-25 Not applicable US Qutenza Kit; Patch 179 mg/179mg Cutaneous Averitas Pharma Inc 2018-10-30 Not applicable US Qutenza Kit; Patch 179 mg/179mg Cutaneous Averitas Pharma Inc 2018-10-30 Not applicable US Qutenza Patch 179 mg Cutaneous Grunenthal Gmb H 2016-09-08 Not applicable EU 
- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image 2-Count HEAT PATCHES Patch 0.025 g/100g Topical Quality Choice (Chain Drug Marketing Association, Inc.) 2017-06-01 Not applicable US 2-Count HEAT PATCHES Patch 0.25 g/1g Topical Veridian Healthcare 2018-11-21 Not applicable US 2-Count HEAT PATCHES Patch 0.025 g/100g Topical Discount Drug Mart, Inc 2017-06-01 Not applicable US 2-Count HEAT PATCHES Patch 0.025 g/100g Topical Chain Drug Consortium 2017-06-01 Not applicable US A2a Arthritis Cream 0.1 g/100g Topical A2A Integrated Pharmaceuticals, LLC 2020-04-02 Not applicable US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image 1st Medxpatch With Lidocaine 4% Capsaicin (0.025 g/1) + Lidocaine (4 g/1) + Menthol (5 g/1) + Methyl salicylate (20 g/1) Patch Topical 1ST MEDX LLC 2018-03-15 Not applicable US Aflexeryl-MC Capsaicin (0.0375 g/100g) + Levomenthol (5 g/100g) Patch Topical Easy Distributors, Llc 2015-01-14 2016-01-05 US Alegenix Biofrequency Chip Capsaicin (0.0375 g/100g) + Menthol (5 g/100g) Disc Topical Solubiomix 2015-06-01 2016-01-13 US Aleveer Patch Capsaicin (0.0375 g/100g) + Menthol (5 g/100g) Patch Topical Pharmaceutics Corporation 2013-10-01 2015-01-06 US Alivio Capsaicin (2.4 mg/8g) + Menthol (400 mg/8g) Patch Topical Zhejiang Bangli Medical Products Co., Ltd 2015-01-15 2016-08-01 US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image 1st Medxpatch With Lidocaine 4%-rx Capsaicin (0.0375 1/1) + Lidocaine (4 1/1) + Menthol (5 1/1) + Methyl salicylate (20 1/1) Patch Topical Direct Rx 2020-10-14 Not applicable US 1st Medxpatch With Lidocaine 4%-rx Capsaicin (0.0375 g/1) + Lidocaine (4 g/1) + Menthol (5 g/1) + Methyl salicylate (20 g/1) Patch Topical 1ST MEDX LLC 2018-03-15 Not applicable US Adazin Capsaicin (0.035 g/100g) + Benzocaine (2 g/100g) + Lidocaine (2 g/100g) + Methyl salicylate (1 g/100g) Cream Topical Sterling Knight Pharmaceuticals, Llc 2014-12-03 2018-10-01 US AnodyneRx Capsaicin (0.05 g/1) + Lidocaine (2.5 g/1) + Menthol (5 g/1) Patch Topical GenPak Solutions LLC 2015-04-01 2015-04-01 US Anodynz Capsaicin (0.0375 g/100g) + Menthol (5 1/100g) Disc Topical Solubiomix 2015-04-10 2015-04-21 US
Categories
- ATC Codes
- M02AB01 — Capsaicin
- M02AB — Capsaicin and similar agents
- M02A — TOPICAL PRODUCTS FOR JOINT AND MUSCULAR PAIN
- M02 — TOPICAL PRODUCTS FOR JOINT AND MUSCULAR PAIN
- M — MUSCULO-SKELETAL SYSTEM
- Drug Categories
- Alkaloids
- Alkenes
- Amides
- Analgesics
- Anesthetics
- Anesthetics, Local
- Antipruritics
- Basic Lotions and Liniments
- Benzene Derivatives
- Capsaicin and Similar Agents
- Cholinesterase Inhibitors
- Cytochrome P-450 CYP1A2 Inducers
- Cytochrome P-450 CYP1A2 Inducers (strength unknown)
- Cytochrome P-450 CYP1A2 Substrates
- Cytochrome P-450 CYP2E1 Substrates
- Cytochrome P-450 CYP3A Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors (strength unknown)
- Cytochrome P-450 Enzyme Inducers
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Dermatologicals
- Lipids
- Monoamine Oxidase A Inhibitors for interaction with Monoamine Oxidase A substrates
- Peripheral Nervous System Agents
- Phenols
- Polyunsaturated Alkamides
- Sensory System Agents
- Solanaceous Alkaloids
- Topical Products for Joint and Muscular Pain
- TRPV1 Channel Agonists
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as methoxyphenols. These are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Phenols
- Sub Class
- Methoxyphenols
- Direct Parent
- Methoxyphenols
- Alternative Parents
- Phenoxy compounds / Methoxybenzenes / Anisoles / Alkyl aryl ethers / 1-hydroxy-2-unsubstituted benzenoids / N-acyl amines / Secondary carboxylic acid amides / Organopnictogen compounds / Organonitrogen compounds / Organic oxides show 2 more
- Substituents
- 1-hydroxy-2-unsubstituted benzenoid / Alkyl aryl ether / Anisole / Aromatic homomonocyclic compound / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Ether / Fatty acyl / Fatty amide show 14 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- capsaicinoid (CHEBI:3374) / Capsaicinoids and derivatives (C06866)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- S07O44R1ZM
- CAS number
- 404-86-4
- InChI Key
- YKPUWZUDDOIDPM-SOFGYWHQSA-N
- InChI
- 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+
- IUPAC Name
- (6E)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnon-6-enamide
- SMILES
- COC1=C(O)C=CC(CNC(=O)CCCC\C=C\C(C)C)=C1
References
- General References
- Anand P, Bley K: Topical capsaicin for pain management: therapeutic potential and mechanisms of action of the new high-concentration capsaicin 8% patch. Br J Anaesth. 2011 Oct;107(4):490-502. doi: 10.1093/bja/aer260. Epub 2011 Aug 17. [Article]
- Wallace M, Pappagallo M: Qutenza(R): a capsaicin 8% patch for the management of postherpetic neuralgia. Expert Rev Neurother. 2011 Jan;11(1):15-27. doi: 10.1586/ern.10.182. [Article]
- Simpson DM, Estanislao L, Brown SJ, Sampson J: An open-label pilot study of high-concentration capsaicin patch in painful HIV neuropathy. J Pain Symptom Manage. 2008 Mar;35(3):299-306. Epub 2007 Oct 23. [Article]
- O'Neill J, Brock C, Olesen AE, Andresen T, Nilsson M, Dickenson AH: Unravelling the mystery of capsaicin: a tool to understand and treat pain. Pharmacol Rev. 2012 Oct;64(4):939-71. doi: 10.1124/pr.112.006163. [Article]
- Oleoresin Capsicum Toxicology Evaluation and Hazard Review [Link]
- FDA Approved Drug Proucts: QUTENZA® (capsaicin) topical system [Link]
- TITCK Product Information: Thermo Sulidin (Capsaicin and Nimesulide) Topical Gel [Link]
- External Links
- Human Metabolome Database
- HMDB0002227
- KEGG Drug
- D00250
- KEGG Compound
- C06866
- PubChem Compound
- 1548943
- PubChem Substance
- 347827793
- ChemSpider
- 1265957
- BindingDB
- 20461
- 1992
- ChEBI
- 3374
- ChEMBL
- CHEMBL294199
- ZINC
- ZINC000001530575
- PDBe Ligand
- 4DY
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Capsaicin
- PDB Entries
- 2n27 / 7lpa / 7lpb / 7lpd / 7lpe / 7lr0 / 7vek
- FDA label
- Download (532 KB)
- MSDS
- Download (49.8 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Basic Science Acute Exercise / Heat Exposure 1 4 Completed Basic Science Central Sensitisation / Motor Skills Disorders 1 4 Completed Basic Science Healthy Subjects (HS) 1 4 Completed Basic Science Osteoarthritis of the Knee 1 4 Completed Diagnostic Alopecia Areata (AA) 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Patch Topical 0.025 g/100g Patch Topical 0.25 g/1g Cream Topical Patch Topical 0.228 mg/99.13mg Gel Topical 0.05 % Liquid Topical 0.025 % Ointment Topical Lotion Topical Gel Topical 0.06375 g/255g Liquid Topical .15 g/100mL Cream Topical 0.25 mg/1mL Gel Topical 0.00025 g/1g Patch Topical 1.506 mg/1 Plaster Topical 0.25 g/100g Plaster Topical 70 mg/1 Oil Percutaneous; Topical; Transdermal Cream Topical 0.1 g/30mL Cream Topical 0.05925 g/237mL Cream Topical 0.025 mg/1mL Lotion Topical 0.025 % Cream Topical 0.5 mg/1g Oil Topical 1 mg/1mL Cream 0075 % Cream Topical 25 g/1g Liquid Topical 0.15 g/100mL Cream Topical 1 mg/1g Cream Topical 0.075 % Cream Topical 0.025 % Liquid Topical 1.5 mg/1mL Patch Topical 0.702 mg/1 Cream Topical 0.05 % Cream Topical 0.025 g Cream Topical 0.001 g/1g Cream Topical 0.00035 g/1g Cream Topical .025 % Cream Topical .025 g/1g Cream Topical 0.075 g Cream Topical 0.35 mg/1g Patch Topical Cloth Topical 0.09 1/1 Ointment Topical 0.25 g/100mL Patch Topical 249 mg/1 Liquid Topical 0.025 g/100g Patch Transdermal 363 mg Cream Oral 75 mg/1g Liquid Topical 0.15 g/100g Patch Topical 0.025 g/1g Gel Topical 0.1 g/100g Cream; kit; solution / drops Topical; Transdermal Cream; gel; kit; solution Topical Cream Topical 0.27 mg/1g Disc Topical Cream Topical 0.02125 g/85g Patch Topical 0.25 mg/1g Gel Topical 0.025 g/100mL Gel Topical 0.01425 g/57g Liniment Topical Kit Oral; Topical Gel Topical 0.25 mg/1g Liquid Topical 0.25 mg/1mL Cream Topical 0.75 mg/1mL Cream Topical 0.35 mg/1mL Cream Topical 0.17 g/100g Solution Topical Cream Topical 0.1 g/100g Liquid Topical 150 mg/100000mg Liquid Topical Oil Topical Patch Topical 1.2 mg/1000mg Gel Topical .03 mL/5mL Gel Topical 5.8 mL/960mL Cream Topical 0.025 ug/1mL Cream Topical 0.25 mg/1g Cream Topical 0.875 mg/3.5g Cloth Topical 0.036 1/1 Cream Topical 0.0125 g/50g Cream Topical 0.0375 g/50g Cloth Topical 0.13 1/1 Patch Topical 0.6 mg/1 Cream Topical 0.1 g/10g Gel Topical 0.02825 g/113g Cream Topical 0.0265 g/106g Cream Topical .05 g/100g Cream Topical .075 g/100g Cream; kit; solution Topical Cream; kit; tablet, delayed release Oral; Topical Capsule; kit; liquid Oral; Topical Kit Oral Cloth Topical 0.12 g/100g Cloth Topical 0.12 1/1 Cloth Topical 0.2 g/100g Cloth Topical 0.23 1/1 Cloth Topical 0.14 g/100g Cloth Topical 0.16 g/100g Cloth Topical 0.075 1/1 Cloth Topical 0.18 1/1 Cloth Topical 0.23 g/100g Cloth Topical 0.15 g/100g Cloth Topical 0.18 g/100g Cloth Topical 0.19 g/100g Cloth Topical 0.11 g/100g Cream Topical 2.5 mg/1g Gel Topical 0.02125 g/85g Cream Topical 0.0295 g/118mL Stick Topical Spray Topical Patch Topical 0.00025 g/1g Patch Topical 0.00075 g/3g Spray Topical 0.00025 g/1mL Liquid Topical 2.5 mg/1mL Solution Topical 2.5 mg/1mL Cream Topical Patch Topical 0.025 mg/100mg Cream Topical 0.02825 g/113g Gel Topical 0.0295 g/118mL Liquid Topical 0.0015 g/1mL Kit Cutaneous; Topical 640 ug/1cm2 Kit; patch Cutaneous 179 mg/179mg Patch Cutaneous 179 mg Patch Cutaneous 179.000 mg Patch Cutaneous; Topical 179 MG Patch Topical; Transdermal 179 mg Ointment Topical 0.05 g/100g Ointment Topical 0.5 mg/1g Patch Topical Gel Topical Solution Topical 0.25 mg/1mL Lotion Topical 0.025 mL/100mL Patch Topical 0.25 mg/1 Cream Topical 3 g/100g Gel Topical 0.06275 g/251mL Patch Topical 30 mg/1 Solution / drops Topical Spray Topical 0.025 g/100g Cream Topical .025 mg/.001g Kit Topical Gel Topical 156.25 ng/1mL Cream Topical 0.025 g/100g Cream Topical 0.075 g/100g Patch Transdermal Patch Topical 1.75 mg/1 Oil Topical 0.075 g/50g Cream Topical 0.07 g/100g Patch Topical .25 mg/1 Patch Topical 025 mg/1 Plaster Topical Cream Topical 0.75 mg/1g Cream; kit Topical Cream Topical .25 mg/1g Plaster Transdermal - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US6239180 No 2001-05-29 2016-11-06 US US8889113 No 2014-11-18 2023-09-05 US US8263059 No 2012-09-11 2023-09-05 US US9226903 No 2016-01-05 2028-12-15 US US10463598 No 2019-11-05 2023-09-05 US US8821920 No 2014-09-02 2030-03-26 US US10034841 No 2018-07-31 2025-09-06 US US10869827 No 2020-12-22 2023-09-05 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 65 MSDS boiling point (°C) 210-220 MSDS water solubility Insoluble in cold water MSDS - Predicted Properties
Property Value Source logP 3.75 Chemaxon pKa (Strongest Acidic) 9.93 Chemaxon pKa (Strongest Basic) -1.4 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 58.56 Å2 Chemaxon Rotatable Bond Count 9 Chemaxon Refractivity 90.32 m3·mol-1 Chemaxon Polarizability 36.32 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 203.735976 predictedDarkChem Lite v0.1.0 [M-H]- 185.5421448 predictedDarkChem Lite v0.1.0 [M-H]- 197.010676 predictedDarkChem Lite v0.1.0 [M-H]- 203.438776 predictedDarkChem Lite v0.1.0 [M-H]- 187.47649 predictedDeepCCS 1.0 (2019) [M+H]+ 204.141476 predictedDarkChem Lite v0.1.0 [M+H]+ 180.1835656 predictedDarkChem Lite v0.1.0 [M+H]+ 197.252676 predictedDarkChem Lite v0.1.0 [M+H]+ 203.917376 predictedDarkChem Lite v0.1.0 [M+H]+ 189.83449 predictedDeepCCS 1.0 (2019) [M+Na]+ 202.995276 predictedDarkChem Lite v0.1.0 [M+Na]+ 184.8946483 predictedDarkChem Lite v0.1.0 [M+Na]+ 196.818676 predictedDarkChem Lite v0.1.0 [M+Na]+ 195.92763 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- AgonistRegulator
- General Function
- Transmembrane signaling receptor activity
- Specific Function
- Ligand-activated non-selective calcium permeant cation channel involved in detection of noxious chemical and thermal stimuli. Seems to mediate proton influx and may be involved in intracellular aci...
- Gene Name
- TRPV1
- Uniprot ID
- Q8NER1
- Uniprot Name
- Transient receptor potential cation channel subfamily V member 1
- Molecular Weight
- 94955.33 Da
References
- Wallace M, Pappagallo M: Qutenza(R): a capsaicin 8% patch for the management of postherpetic neuralgia. Expert Rev Neurother. 2011 Jan;11(1):15-27. doi: 10.1586/ern.10.182. [Article]
- Anand P, Bley K: Topical capsaicin for pain management: therapeutic potential and mechanisms of action of the new high-concentration capsaicin 8% patch. Br J Anaesth. 2011 Oct;107(4):490-502. doi: 10.1093/bja/aer260. Epub 2011 Aug 17. [Article]
- Guo A, Vulchanova L, Wang J, Li X, Elde R: Immunocytochemical localization of the vanilloid receptor 1 (VR1): relationship to neuropeptides, the P2X3 purinoceptor and IB4 binding sites. Eur J Neurosci. 1999 Mar;11(3):946-58. doi: 10.1046/j.1460-9568.1999.00503.x. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Acts as a mediator of transcriptional repression by nuclear hormone receptors via recruitment of histone deacetylases (By similarity). Functions as an estrogen receptor (ER)-selective coregulator that potentiates the inhibitory activities of antiestrogens and represses the activity of estrogens. Competes with NCOA1 for modulation of ER transcriptional activity. Probably involved in regulating mitochondrial respiration activity and in aging.
- Specific Function
- Amide binding
- Gene Name
- PHB2
- Uniprot ID
- Q99623
- Uniprot Name
- Prohibitin-2
- Molecular Weight
- 33296.06 Da
References
- Kuramori C, Azuma M, Kume K, Kaneko Y, Inoue A, Yamaguchi Y, Kabe Y, Hosoya T, Kizaki M, Suematsu M, Handa H: Capsaicin binds to prohibitin 2 and displaces it from the mitochondria to the nucleus. Biochem Biophys Res Commun. 2009 Feb 6;379(2):519-25. doi: 10.1016/j.bbrc.2008.12.103. Epub 2008 Dec 29. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Takanohashi T, Isaka M, Ubukata K, Mihara R, Bernard BK: Studies of the toxicological potential of capsinoids, XIII: inhibitory effects of capsaicin and capsinoids on cytochrome P450 3A4 in human liver microsomes. Int J Toxicol. 2010 Mar;29(2 Suppl):22S-6S. doi: 10.1177/1091581809360282. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Prostaglandin-endoperoxide synthase activity
- Specific Function
- Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Constitutively expressed in some tissues in physiological conditions, such as the endothelium, kidney and...
- Gene Name
- PTGS2
- Uniprot ID
- P35354
- Uniprot Name
- Prostaglandin G/H synthase 2
- Molecular Weight
- 68995.625 Da
References
- Park JS, Choi MA, Kim BS, Han IS, Kurata T, Yu R: Capsaicin protects against ethanol-induced oxidative injury in the gastric mucosa of rats. Life Sci. 2000 Nov 10;67(25):3087-93. [Article]
- Hwang JT, Lee YK, Shin JI, Park OJ: Anti-inflammatory and anticarcinogenic effect of genistein alone or in combination with capsaicin in TPA-treated rat mammary glands or mammary cancer cell line. Ann N Y Acad Sci. 2009 Aug;1171:415-20. doi: 10.1111/j.1749-6632.2009.04696.x. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Peroxidase activity
- Specific Function
- Part of the host defense system of polymorphonuclear leukocytes. It is responsible for microbicidal activity against a wide range of organisms. In the stimulated PMN, MPO catalyzes the production o...
- Gene Name
- MPO
- Uniprot ID
- P05164
- Uniprot Name
- Myeloperoxidase
- Molecular Weight
- 83867.71 Da
References
- Ikeura T, Kataoka Y, Wakabayashi T, Mori T, Takamori Y, Takamido S, Okazaki K, Yamada H: Effects of sensory denervation by neonatal capsaicin administration on experimental pancreatitis induced by dibutyltin dichloride. Med Mol Morphol. 2007 Sep;40(3):141-9. Epub 2007 Sep 18. [Article]
- Park JS, Choi MA, Kim BS, Han IS, Kurata T, Yu R: Capsaicin protects against ethanol-induced oxidative injury in the gastric mucosa of rats. Life Sci. 2000 Nov 10;67(25):3087-93. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInducer
- General Function
- Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP1A2
- Uniprot ID
- P05177
- Uniprot Name
- Cytochrome P450 1A2
- Molecular Weight
- 58293.76 Da
References
- Babbar S, Chanda S, Bley K: Inhibition and induction of human cytochrome P450 enzymes in vitro by capsaicin. Xenobiotica. 2010 Dec;40(12):807-16. doi: 10.3109/00498254.2010.520044. Epub 2010 Sep 23. [Article]
- Reilly CA, Ehlhardt WJ, Jackson DA, Kulanthaivel P, Mutlib AE, Espina RJ, Moody DE, Crouch DJ, Yost GS: Metabolism of capsaicin by cytochrome P450 produces novel dehydrogenated metabolites and decreases cytotoxicity to lung and liver cells. Chem Res Toxicol. 2003 Mar;16(3):336-49. doi: 10.1021/tx025599q. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...
- Gene Name
- CYP2E1
- Uniprot ID
- P05181
- Uniprot Name
- Cytochrome P450 2E1
- Molecular Weight
- 56848.42 Da
References
- Surh YJ, Lee SS: Capsaicin, a double-edged sword: toxicity, metabolism, and chemopreventive potential. Life Sci. 1995;56(22):1845-55. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Serotonin binding
- Specific Function
- Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral...
- Gene Name
- MAOA
- Uniprot ID
- P21397
- Uniprot Name
- Amine oxidase [flavin-containing] A
- Molecular Weight
- 59681.27 Da
References
- Dina OA, Khasar SG, Alessandri-Haber N, Bogen O, Chen X, Green PG, Reichling DB, Messing RO, Levine JD: Neurotoxic catecholamine metabolite in nociceptors contributes to painful peripheral neuropathy. Eur J Neurosci. 2008 Sep;28(6):1180-90. doi: 10.1111/j.1460-9568.2008.06425.x. Epub 2008 Sep 9. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- L-ascorbic acid binding
- Specific Function
- Conversion of dopamine to noradrenaline.
- Gene Name
- DBH
- Uniprot ID
- P09172
- Uniprot Name
- Dopamine beta-hydroxylase
- Molecular Weight
- 69064.45 Da
References
- Dina OA, Khasar SG, Alessandri-Haber N, Bogen O, Chen X, Green PG, Reichling DB, Messing RO, Levine JD: Neurotoxic catecholamine metabolite in nociceptors contributes to painful peripheral neuropathy. Eur J Neurosci. 2008 Sep;28(6):1180-90. doi: 10.1111/j.1460-9568.2008.06425.x. Epub 2008 Sep 9. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- General Function
- Manganese ion binding
- Specific Function
- This enzyme has 2 functions: it catalyzes the production of glutamine and 4-aminobutanoate (gamma-aminobutyric acid, GABA), the latter in a pyridoxal phosphate-independent manner (By similarity). E...
- Gene Name
- GLUL
- Uniprot ID
- P15104
- Uniprot Name
- Glutamine synthetase
- Molecular Weight
- 42064.15 Da
References
- Okere CO, Waterhouse BD: Capsaicin increases GFAP and glutamine synthetase immunoreactivity in rat arcuate nucleus and median eminence. Neuroreport. 2004 Feb 9;15(2):255-8. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Identical protein binding
- Specific Function
- Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
- Gene Name
- BCHE
- Uniprot ID
- P06276
- Uniprot Name
- Cholinesterase
- Molecular Weight
- 68417.575 Da
References
- Orhan I, Naz Q, Kartal M, Tosun F, Sener B, Choudhary MI: In vitro anticholinesterase activity of various alkaloids. Z Naturforsch C. 2007 Sep-Oct;62(9-10):684-8. [Article]
Drug created at September 14, 2010 16:21 / Updated at February 20, 2024 23:55