Identification

Name
Capsaicin
Accession Number
DB06774
Description

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
Thumb
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.

Associated Conditions
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
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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.

TargetActionsOrganism
ATransient receptor potential cation channel subfamily V member 1
agonist
Humans
UProhibitin-2Not AvailableHumans
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
Learn about our commercial Adverse Effects data.
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Toxicity

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.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
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.
DrugInteraction
AbametapirThe serum concentration of Capsaicin can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Capsaicin can be increased when combined with Abatacept.
AbirateroneThe serum concentration of Capsaicin can be increased when it is combined with Abiraterone.
AcalabrutinibThe metabolism of Acalabrutinib can be decreased when combined with Capsaicin.
AcebutololCapsaicin may increase the bradycardic activities of Acebutolol.
AcenocoumarolThe serum concentration of Acenocoumarol can be increased when it is combined with Capsaicin.
AcetaminophenThe metabolism of Capsaicin can be decreased when combined with Acetaminophen.
AcetylcholineThe risk or severity of adverse effects can be increased when Capsaicin is combined with Acetylcholine.
AclidiniumCapsaicin may increase the neuromuscular blocking activities of Aclidinium.
AcyclovirThe metabolism of Capsaicin can be decreased when combined with Acyclovir.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
No interactions found.

Products

International/Other Brands
Zostrix
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Qutenza640 ug/1cm2Cutaneous; TopicalNeurogesX, Inc.2010-03-012016-02-28US flag
QutenzaKit640 ug/1cm2Cutaneous; TopicalAcorda Therapeutics, Inc.2013-08-122020-11-30US flag
QutenzaPatch179 mgCutaneousGrunenthal Gmb H2009-05-15Not applicableEU flag
QutenzaKit640 ug/1cm2Cutaneous; TopicalAcorda Therapeutics, Inc.2013-08-122020-11-30US flag
QutenzaKit179 mg/179mgCutaneous; TopicalAveritas Pharma Inc2018-10-30Not applicableUS flag
QutenzaPatch179 mgCutaneousGrunenthal Gmb H2009-05-15Not applicableEU flag
QutenzaKit179 mg/179mgCutaneous; TopicalAveritas Pharma Inc2018-10-30Not applicableUS flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
2-Count HEAT PATCHESPatch0.025 g/100gTopicalQuality Choice (Chain Drug Marketing Association, Inc.)2017-06-01Not applicableUS flag
2-Count HEAT PATCHESPatch0.025 g/100gTopicalDiscount Drug Mart, Inc2017-06-01Not applicableUS flag
2-Count HEAT PATCHESPatch0.25 g/1gTopicalVeridian Healthcare2018-11-21Not applicableUS flag
2-Count HEAT PATCHESPatch0.025 g/100gTopicalChain Drug Consortium2017-06-01Not applicableUS flag
A2a ArthritisCream0.1 g/100gTopicalA2A Integrated Pharmaceuticals, LLC2020-04-02Not applicableUS flag
Ageranium PatchPatch0.228 mg/99.13mgTopicalEntom Co., Ltd.2017-12-29Not applicableUS flag
Antiphlogistine Rub A-535 Capsaicin GelGelTopicalChurch & Dwight Canada Corp1998-11-232007-07-23Canada flag
Antiphlogistine Rub A-535 Capsaicin LiquidLiquidTopicalCarter Horner Corp.1998-11-232001-07-18Canada flag
Arthricare for Women Extra MoisturizingLotionTopicalDel Pharmaceuticals Inc.2000-08-082005-06-20Canada flag
Arthricare for Women Quick DryingCreamTopicalDel Pharmaceuticals Inc.2002-06-172005-06-20Canada flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
1st Medxpatch With Lidocaine 4%Capsaicin (0.025 g/1) + Levomenthol (5 g/1) + Lidocaine (4 g/1) + Methyl salicylate (20 g/1)PatchTopical1ST MEDX LLC2018-03-15Not applicableUS flag
Aflexeryl-MCCapsaicin (0.0375 g/100g) + Racementhol (5 g/100g)PatchTopicalEasy Distributors, Llc2015-01-142016-01-05US flag
Alegenix Biofrequency ChipCapsaicin (0.0375 g/100g) + Levomenthol (5 g/100g)DiscTopicalSolubiomix2015-06-012016-01-13US flag
Aleveer PatchCapsaicin (0.0375 g/100g) + Levomenthol (5 g/100g)PatchTopicalPharmaceutics Corporation2013-10-012015-01-06US flag
AlivioCapsaicin (0.05 g/100g) + Levomenthol (4 g/100g)PatchTopicalGa Health And Beauty (Foshan) Co., Ltd2016-03-182016-12-31US flag
AlivioCapsaicin (0.05 g/100g) + Levomenthol (4 g/100g)PatchTopicalAble Wholesalers2014-12-302016-12-31US flag
AlivioCapsaicin (2.4 mg/8g) + Levomenthol (400 mg/8g)PatchTopicalZhejiang Bangli Medical Products Co., Ltd2015-01-152016-08-01US flag
AlivioCapsaicin (.03 g/100g) + Levomenthol (5 g/100g)PatchTopicalZhejiang Bangli Medical Products Co., Ltd2015-01-152016-09-01US flag
Alivio Medicated PainCapsaicin (.03 g/100g) + Levomenthol (5 g/100g)PatchTopicalAlivio Medical Products, Llc2015-01-21Not applicableUS flag
AllevessCapsaicin (0.05 g/100g) + Levomenthol (5 g/100g)PatchTopicalApi Solutions, Inc.2015-12-01Not applicableUS flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
1st Medxpatch With Lidocaine 4%-rxCapsaicin (0.0375 1/1) + Levomenthol (5 1/1) + Lidocaine (4 1/1) + Methyl salicylate (20 1/1)PatchTopical1ST MEDX LLC2018-03-15Not applicableUS flag
AdazinCapsaicin (0.035 g/100g) + Benzocaine (2 g/100g) + Lidocaine (2 g/100g) + Methyl salicylate (1 g/100g)CreamTopicalSterling Knight Pharmaceuticals, Llc2014-12-032018-10-01US flag
AnodyneRxCapsaicin (0.05 g/1) + Levomenthol (5 g/1) + Lidocaine (2.5 g/1)PatchTopicalGen Pak Solutions, Llc2015-04-012015-04-01US flag
AnodynzCapsaicin (0.0375 g/100g) + Levomenthol (5 1/100g)DiscTopicalSolubiomix2015-04-102015-04-21US flag
AstronicCapsaicin (0.0375 g/100g) + Levomenthol (5 g/100g)PatchTopicalPharmaco Technology Llc2015-04-012015-04-01US flag
BioachesCapsaicin (0.0375 g/1) + Levomenthol (5 g/1)PatchTopicalBIO-SANTEE CHEM2015-01-10Not applicableUS flag
CapmentCapsaicin (.00375 1/100g) + Levomenthol (.04 1/100g)PatchTopicalOriginal Patch Company Inc2015-03-24Not applicableUS flag
CapmentCapsaicin (.00375 1/100g) + Levomenthol (.04 1/100g)PatchTopicalOriginal Patch Company Inc2015-03-31Not applicableUS flag
CapsaicinCapsaicin (0.025 g/100g)CreamTopicalPhysicians Total Care, Inc.2009-03-132013-01-15US flag
CaptracinCapsaicin (0.0375 g/1) + Levomenthol (5 g/1)PatchTopicalSallus Laboratories, Llc2014-12-012015-05-13US flag

Categories

ATC Codes
M02AB01 — CapsaicinN01BX04 — Capsaicin
Drug Categories
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)

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
  1. 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. [PubMed:21852280]
  2. 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. [PubMed:21158551]
  3. 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. [PubMed:17959343]
  4. 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. [PubMed:23023032]
  5. Oleoresin Capsicum Toxicology Evaluation and Hazard Review [Link]
Human Metabolome Database
HMDB0002227
KEGG Drug
D00250
KEGG Compound
C06866
PubChem Compound
1548943
PubChem Substance
347827793
ChemSpider
1265957
BindingDB
20461
RxNav
1992
ChEBI
3374
ChEMBL
CHEMBL294199
ZINC
ZINC000001530575
PDBe Ligand
4DY
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Capsaicin
AHFS Codes
  • 84:24.04 — Basic Lotions and Liniments
PDB Entries
2n27
FDA label
Download (532 KB)
MSDS
Download (49.8 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedBasic ScienceCentral Sensitisation / Motor Disorders1
4CompletedBasic ScienceHealthy Volunteers1
4CompletedBasic ScienceOsteoarthritis of the Knee1
4CompletedDiagnosticAlopecia Areata (AA)1
4CompletedPreventionPain1
4CompletedSupportive CareDiabetic complications neurological / Diabetic Nerve Problems / Diabetic Neuropathies1
4CompletedTreatmentHealthy Controls / Idiopathic Rhinitis Patients1
4CompletedTreatmentNon-Allergic Rhinitis1
4CompletedTreatmentNon-diabetic Painful Peripheral Polyneuropathy / Peripheral Nerve Injury (PNI) / Postherpetic Neuralgia ( PHN )1
4CompletedTreatmentOr Peripheral Nerve Injury (PNI) / Peripheral Neuropathic Pain (PNP) Due to Postherpetic Neuralgia (PHN)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
PatchTopical0.025 g/100g
PatchTopical0.25 g/1g
PatchTopical0.228 mg/99.13mg
GelTopical
LiquidTopical
GelTopical0.06375 g/255g
LiquidTopical.15 g/100mL
CreamTopical0.25 mg/1mL
GelTopical0.00025 g/1g
PatchTopical1.506 mg/1
PlasterTopical0.25 g/100g
PlasterTopical70 mg/1
OilPercutaneous; Topical; Transdermal
CreamTopical0.05925 g/237mL
CreamTopical0.025 mg/1mL
LotionTopical
Cream0.075 %
CreamTopical25 g/1g
LiquidTopical0.15 g/100mL
CreamTopical1 mg/1g
CreamTopical
LiquidTopical1.5 mg/1mL
PatchTopical0.702 mg/1
CreamTopical0.025 g
CreamTopical0.001 g/1g
CreamTopical0.00035 g/1g
CreamTopical0.075 g
CreamTopical0.35 mg/1g
ClothTopical0.09 1/1
OintmentTopical0.25 g/100mL
PatchTopical249 mg/1
LiquidTopical0.025 g/100g
PatchTransdermal363 mg
CreamOral75 mg/1g
LiquidTopical0.15 g/100g
PatchTopical0.025 g/1g
LotionTopical
CreamTopical0.27 mg/1g
DiscTopical
CreamTopical0.02125 g/85g
PatchTopical0.25 mg/1g
GelTopical0.025 g/100mL
PatchTopical
GelTopical0.01425 g/57g
LinimentTopical
KitOral; Topical
GelTopical0.25 mg/1g
LiquidTopical0.25 mg/1mL
CreamTopical0.75 mg/1mL
CreamTopical0.35 mg/1mL
CreamTopical0.17 g/100g
OintmentTopical1 g
SolutionTopical
CreamTopical0.1 g/100g
LiquidTopical150 mg/100000mg
OilTopical
PatchTopical1.2 mg/1000mg
GelTopical.03 mL/5mL
GelTopical5.8 mL/960mL
CreamTopical0.025 ug/1mL
CreamTopical0.25 mg/1g
CreamTopical0.875 mg/3.5g
ClothTopical0.036 1/1
CreamTopical0.0125 g/50g
CreamTopical0.0375 g/50g
ClothTopical0.13 1/1
PatchTopical0.6 mg/1
OintmentTopical
CreamTopical0.1 g/10g
GelTopical0.02825 g/113g
CreamTopical0.0265 g/106g
CreamTopical.075 g/100g
LiquidTopical
KitOral
ClothTopical0.2 1/1
ClothTopical0.23 1/1
ClothTopical0.075 1/1
ClothTopical0.12 1/1
ClothTopical0.18 1/1
ClothTopical0.15 1/1
CreamTopical2.5 mg/1g
GelTopical0.02125 g/85g
CreamTopical0.0295 g/118mL
StickTopical
SprayTopical0.00025 g/1mL
LiquidTopical2.5 mg/1mL
SolutionTopical2.5 mg/1mL
PatchTopical0.025 mg/100mg
CreamTopical0.02825 g/113g
GelTopical0.0295 g/118mL
LiquidTopical0.0015 g/1mL
KitCutaneous; Topical179 mg/179mg
KitCutaneous; Topical640 ug/1cm2
PatchCutaneous179 mg
PatchCutaneous; Topical179 MG
OintmentTopical0.05 g/100g
SolutionTopical0.25 mg/1mL
LotionTopical0.025 mL/100mL
PatchTopical0.25 mg/1
CreamTopical3 g/100g
GelTopical0.06275 g/251mL
Solution / dropsTopical
CreamTopical.025 mg/.001g
KitTopical
GelTopical156.25 ng/1mL
CreamTopical0.025 g/100g
CreamTopical0.075 g/100g
GelTopical
GelTopical1 %
PatchTransdermal
PlasterTransdermal
PatchTopical1.75 mg/1
OilTopical0.075 g/50g
CreamTopical0.07 g/100g
PatchTopical.25 mg/1
PatchTopical025 mg/1
PlasterTopical
CreamTopical
CreamTopical0.75 mg/1g
CreamTopical.25 mg/1g
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US6239180No2001-05-292016-11-06US flag
US8889113No2014-11-182023-09-05US flag
US8263059No2012-09-112023-09-05US flag
US9226903No2016-01-052028-12-15US flag
US10463598No2019-11-052023-09-05US flag
US8821920No2014-09-022030-03-26US flag
US10034841No2018-07-312025-09-06US flag
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)65MSDS
boiling point (°C)210-220MSDS
water solubilityInsoluble in cold waterMSDS
Predicted Properties
PropertyValueSource
logP3.75ChemAxon
pKa (Strongest Acidic)9.93ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.56 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity90.32 m3·mol-1ChemAxon
Polarizability36.32 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-014i-0901000000-adba1bb6f254087febe8
LC-MS/MS Spectrum - LC-ESI-ITTOF , negativeLC-MS/MSsplash10-014i-0900000000-5be0e66854b20d7a5a03
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-014i-0900000000-4337ff26dcbd2a77725e
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-014i-0900000000-c94a246143850aa73e44
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-014r-0950000000-3d145ef428e054b3e535
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-014r-0950000000-c3ca097a6480ab798ff3
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-000i-0900000000-4e8f98d1f848f30117d7
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-000i-0900000000-58fab2fdd15893ea71e7
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-000i-0900000000-296a0cb1555da4f1ccd7
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-03di-0209000000-a91e6403d5a0c0b67c2e
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-03di-0209000000-dd0879d3f4f3a8b022c3
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-014i-0149000000-d6a9f6e70ae7cd7aec38
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-014i-0149000000-6fcf63c3bf44a4efc5bd
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-06sl-0075690000-b562b766019cc7cbd98f
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-01x3-0094560000-f354077f4cd51e45b945
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-004i-0002900000-ce1ea9819252343543cd
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-004i-0002911000-6c37470f794c89a66410
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-000i-0900000000-00619747b8012ce6aa64
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-000i-0900000000-3ca73f5212a7643b45d2
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-03dr-0956000000-d0dbf319e1bb02a1aa21
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-03dr-0958000000-a53fd50bc48a51d95c1c
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-004i-0096000000-265377cd56468981c3a3
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-004i-0096000000-da1cc255516c9c58c6f6

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
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
  1. 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. [PubMed:21158551]
  2. 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. [PubMed:21852280]
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
  1. 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. [PubMed:19116139]

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
  1. 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. [PubMed:20388821]
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
  1. 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. [PubMed:11125845]
  2. 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. [PubMed:19723084]
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
  1. 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. [PubMed:17874046]
  2. 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. [PubMed:11125845]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inducer
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
  1. 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. [PubMed:20863199]
  2. 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. [PubMed:12641434]
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
  1. Surh YJ, Lee SS: Capsaicin, a double-edged sword: toxicity, metabolism, and chemopreventive potential. Life Sci. 1995;56(22):1845-55. [PubMed:7746093]
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
  1. 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. [PubMed:18783367]
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
  1. 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. [PubMed:18783367]
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
  1. 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. [PubMed:15076747]
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
  1. 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. [PubMed:18069241]

Drug created on September 14, 2010 10:21 / Updated on September 25, 2020 15:13

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