Identification

Name
Capsaicin
Accession Number
DB06774  (DB05318)
Type
Small Molecule
Groups
Approved
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.

Structure
Thumb
Synonyms
  • (E)-8-Methyl-N-vanillyl-6-nonenamide
  • Isodecenoic acid vanillylamide
  • trans-8-Methyl-N-vanillyl-6-nonenamide
External IDs
ALGRX 4975 / ALGRX-4975 / FEMA NO. 3404 / NGX-1998 / NGX-4010 / NSC-56353
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
QutenzaKitNeuroges X2010-03-01Not applicableUs
QutenzaKitAcorda Therapeutics2013-08-12Not applicableUs
QutenzaPatch179 mgCutaneousAstellas Pharma Europe Bv2009-05-15Not applicableEu
QutenzaKitAcorda Therapeutics2013-08-12Not applicableUs
QutenzaPatch179 mgCutaneousAstellas Pharma Europe Bv2009-05-15Not applicableEu
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
2-Count HEAT PATCHESPatch4 g/100gTopicalVeridian Healthcare2017-06-01Not applicableUs
2-Count HEAT PATCHESPatch.025 g/100gTopicalDiscount Drug Mart, Inc2017-06-01Not applicableUs
2-Count HEAT PATCHESPatch.025 g/100gTopicalChain Drug Consortium2017-06-01Not applicableUs
2-Count HEAT PATCHESPatch.025 g/100gTopicalQuality Choice (Chain Drug Marketing Association, Inc.)2017-06-01Not applicableUs
Antiphlogistine Rub A-535 Capsaicin GelGel0.05 %TopicalChurch & Dwight Company, Inc.1998-11-232007-07-23Canada
Antiphlogistine Rub A-535 Capsaicin LiquidLiquid0.025 %TopicalCarter Horner Corp.1998-11-232001-07-18Canada
Arthricare for Women Extra MoisturizingLotion0.025 %TopicalDel Pharmaceuticals Inc.2000-08-082005-06-20Canada
Arthricare for Women Quick DryingCream0.025 %TopicalDel Pharmaceuticals Inc.2002-06-172005-06-20Canada
Arthritazin Pain RelievingGel.06375 g/255gTopicalConcept Laboratories2013-01-172017-10-21Us
Arthritazin Pain RelievingGel.02125 g/85gTopicalConcept Laboratories2013-01-102017-10-21Us
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
AdazinCapsaicin (.035 g/100g) + Benzocaine (2 g/100g) + Lidocaine (2 g/100g) + Methyl salicylate (1 g/100g)CreamTopicalSterling Knight Pharmaceuticals, Llc2014-12-03Not applicableUs
Aflexeryl-MCCapsaicin (.0375 g/100g) + Menthol (5 g/100g)PatchTopicalEasy Distributors, Llc2015-01-142016-10-13Us
Alegenix Biofrequency ChipCapsaicin (.0375 g/100g) + Menthol (5 g/100g)DiscTopicalSolubiomix2015-06-012030-01-01Us
AlivioCapsaicin (.03 g/100g) + Menthol (5 g/100g)PatchTopicalZhejiang Bangli Medical Products Co., Ltd2015-01-152016-10-13Us
AlivioCapsaicin (.05 g/100g) + Menthol (4 g/100g)PatchTopicalAble Wholesalers2014-12-302017-01-20Us
AlivioCapsaicin (2.4 mg/8g) + Menthol (400 mg/8g)PatchTopicalZhejiang Bangli Medical Products Co., Ltd2015-01-152016-11-01Us
Alivio Medicated PainCapsaicin (.03 g/100g) + Menthol (5 g/100g)PatchTopicalAlivio Medical Products, Llc2015-01-212017-11-04Us
AllevessCapsaicin (.05 g/100g) + Menthol (5 g/100g)PatchTopicalApi Solutions, Inc.2015-12-01Not applicableUs
Ameri PatchCapsaicin (.0375 g/100g) + Menthol (5 g/100g)PatchTopicalZhejiang Bangli Medical Products Co., Ltd2015-03-152016-10-13Us
AmeriPatchCapsaicin (.0375 g/100g) + Menthol (5 g/100g)PatchTopicalMeds Direct Rx, Inc.2015-01-31Not applicableUs
Categories
UNII
S07O44R1ZM
CAS number
404-86-4
Weight
Average: 305.4119
Monoisotopic: 305.199093735
Chemical Formula
C18H27NO3
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

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.

Structured Indications
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 mechanism in pain relief. 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
Human
UProhibitin-2Not AvailableHuman
Absorption

There is limited evidence that topical capsaicin is absorbed in any site other than the transdermal layers of the skin. It shows limited potential for absorption into tissues as it is a very lipophilic, non-water soluble compound and therefore will not diffuse into aqueous solutions.

Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AtorvastatinThe risk or severity of adverse effects can be increased when Capsaicin is combined with Atorvastatin.Approved
BromocriptineThe risk or severity of adverse effects can be increased when Bromocriptine is combined with Capsaicin.Approved, Investigational
CabergolineThe risk or severity of adverse effects can be increased when Cabergoline is combined with Capsaicin.Approved
CerivastatinThe serum concentration of Cerivastatin can be increased when it is combined with Capsaicin.Withdrawn
ClotrimazoleThe metabolism of Capsaicin can be decreased when combined with Clotrimazole.Approved, Vet Approved
Cyproterone acetateThe serum concentration of Capsaicin can be decreased when it is combined with Cyproterone acetate.Approved, Investigational
DihydroergocornineThe risk or severity of adverse effects can be increased when Dihydroergocornine is combined with Capsaicin.Approved
DihydroergocristineThe risk or severity of adverse effects can be increased when Dihydroergocristine is combined with Capsaicin.Experimental
DihydroergocryptineThe risk or severity of adverse effects can be increased when Dihydroergocryptine is combined with Capsaicin.Experimental
DihydroergotamineThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Capsaicin.Approved
ErgonovineThe risk or severity of adverse effects can be increased when Ergonovine is combined with Capsaicin.Approved
ErgotamineThe risk or severity of adverse effects can be increased when Ergotamine is combined with Capsaicin.Approved
FluvastatinThe serum concentration of Fluvastatin can be increased when it is combined with Capsaicin.Approved
HyaluronidaseThe risk or severity of adverse effects can be increased when Hyaluronidase is combined with Capsaicin.Approved, Investigational
IsoniazidThe metabolism of Capsaicin can be decreased when combined with Isoniazid.Approved
LisurideThe risk or severity of adverse effects can be increased when Lisuride is combined with Capsaicin.Approved, Investigational
LovastatinThe serum concentration of Lovastatin can be increased when it is combined with Capsaicin.Approved, Investigational
Lysergic Acid DiethylamideThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Capsaicin.Illicit, Investigational, Withdrawn
MetergolineThe risk or severity of adverse effects can be increased when Metergoline is combined with Capsaicin.Experimental
MethylergometrineThe risk or severity of adverse effects can be increased when Methylergometrine is combined with Capsaicin.Approved
MethysergideThe risk or severity of adverse effects can be increased when Methysergide is combined with Capsaicin.Approved
MevastatinThe serum concentration of Mevastatin can be increased when it is combined with Capsaicin.Experimental
NicergolineThe risk or severity of adverse effects can be increased when Nicergoline is combined with Capsaicin.Approved, Investigational
NicotineThe metabolism of Capsaicin can be decreased when combined with Nicotine.Approved
PergolideThe risk or severity of adverse effects can be increased when Pergolide is combined with Capsaicin.Approved, Investigational, Vet Approved, Withdrawn
PitavastatinThe serum concentration of Pitavastatin can be increased when it is combined with Capsaicin.Approved
PravastatinThe serum concentration of Pravastatin can be increased when it is combined with Capsaicin.Approved
RosuvastatinThe serum concentration of Rosuvastatin can be increased when it is combined with Capsaicin.Approved
SimvastatinThe serum concentration of Simvastatin can be increased when it is combined with Capsaicin.Approved
Technetium Tc-99m tilmanoceptCapsaicin may decrease effectiveness of Technetium Tc-99m tilmanocept as a diagnostic agent.Approved, Investigational
TergurideThe risk or severity of adverse effects can be increased when Terguride is combined with Capsaicin.Experimental
TiclopidineThe metabolism of Capsaicin can be decreased when combined with Ticlopidine.Approved
UbidecarenoneThe serum concentration of Ubidecarenone can be increased when it is combined with Capsaicin.Approved, Experimental
Food Interactions
No interactions found.

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]
External Links
Human Metabolome Database
HMDB02227
KEGG Drug
D00250
KEGG Compound
C06866
PubChem Compound
1548943
PubChem Substance
347827793
ChemSpider
1265957
BindingDB
20461
ChEBI
3374
ChEMBL
CHEMBL294199
HET
4DY
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Capsaicin
ATC Codes
M02AB01 — CapsaicinN01BX04 — Capsaicin
AHFS Codes
  • 84:24.04 — Basic Lotions and Liniments
PDB Entries
2n27
FDA label
Download (532 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedBasic ScienceMigraine Disorders1
0RecruitingDiagnosticAmyotrophic Lateral Sclerosis (ALS)1
0RecruitingDiagnosticOculopharyngeal Muscular Dystrophy1
0RecruitingTreatmentAmyotrophic Lateral Sclerosis (ALS)1
1CompletedSupportive CarePain1
1CompletedTreatmentHealthy Volunteers1
1CompletedTreatmentHuman Volunteers1
1CompletedTreatmentMorton's neuralgia1
1CompletedTreatmentPain1
1, 2CompletedDiagnosticCoughing1
1, 2CompletedTreatmentCoughing / Parkinson's Disease (PD)1
1, 2CompletedTreatmentInterstitial Cystitis / Vulvar Diseases1
1, 2CompletedTreatmentPeripheral Nerve Injury (PNI) / Postherpetic Neuralgia1
1, 2CompletedTreatmentPruritus1
1, 2CompletedTreatmentStroke, Ischemic1
1, 2RecruitingBasic ScienceHealthy Volunteers1
1, 2RecruitingTreatmentHypertriglyceridemias1
2CompletedTreatmentArthroplasty, Replacement, Knee / Knee Injuries1
2CompletedTreatmentFacial Pain1
2CompletedTreatmentHealthy Volunteers / Tooth Extractions1
2CompletedTreatmentHerpes Zoster / Neurocostal neuralgia / Pain / Peripheral Nervous System Diseases1
2CompletedTreatmentIntrauterine Growth Restriction1
2CompletedTreatmentLateral Epicondylitis1
2CompletedTreatmentMania1
2CompletedTreatmentNeuroma1
2CompletedTreatmentPain / Postherpetic Neuralgia1
2CompletedTreatmentPain / Pulmonary Hypertension (PH)1
2CompletedTreatmentPostherpetic Neuralgia1
2CompletedTreatmentPostoperative pain2
2CompletedTreatmentPulmonary Arterial Hypertension (PAH) / Pulmonary Hypertension (PH)1
2Not Yet RecruitingTreatmentCyclical Vomiting1
2RecruitingTreatmentNonallergic Irritant Rhinitis1
2RecruitingTreatmentPain, Neuropathic1
2TerminatedBasic ScienceHealthy Volunteers1
2WithdrawnTreatmentMyofascial Pain Syndrome1
2WithdrawnTreatmentPain, Acute1
2, 3CompletedTreatmentDiabetic Polyneuropathy1
2, 3Not Yet RecruitingTreatmentDyslipidemias / Overweight or Obesity1
2, 3RecruitingTreatmentVestibulodynia1
2, 3Unknown StatusTreatmentPainful Diabetic Neuropathy1
2, 3WithdrawnTreatmentHIV-infection/Aids / Immune Reconstitution Inflammatory Syndrome / Immune Reconstitution Syndrome / Tuberculosis1
3Active Not RecruitingTreatmentDry Eye Syndromes1
3CompletedPreventionCoronary Arteriosclerosis1
3CompletedTreatmentDiabetic Peripheral Neuropathy (DPN) / Pain1
3CompletedTreatmentHerpes Zoster / Neurocostal neuralgia / Pain / Peripheral Nervous System Diseases / Shingles2
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Pain / Peripheral Nervous System Diseases1
3CompletedTreatmentPain, Acute1
3CompletedTreatmentPainful Diabetic Peripheral Neuropathy (PDPN)1
3RecruitingSupportive CarePain1
3TerminatedTreatmentPersistent Pain After Inguinal Herniotomy1
3TerminatedTreatmentStable Angina (SA)1
3Unknown StatusPreventionCoronary Arteriosclerosis1
4CompletedBasic ScienceHealthy Volunteers1
4CompletedDiagnosticAlopecia Areata (AA)1
4CompletedPreventionPain1
4CompletedSupportive CareKnee Osteoarthritis (Knee OA)1
4CompletedTreatmentHealthy Controls / Idiopathic Rhinitis Patients1
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
4CompletedTreatmentPostherpetic Neuralgia1
4CompletedTreatmentRhinitis1
4CompletedTreatmentSub-acute Back Pain1
4RecruitingTreatmentChronic Low Back Pain (CLBP)2
4RecruitingTreatmentNon-Allergic Rhinitis1
4TerminatedTreatmentPsoriasis1
4Unknown StatusTreatmentPain, Neuropathic / Renal Failure Chronic1
4WithdrawnTreatmentInduction of Uterine contractions / Labour Pain / Pregnancy Loss1
Not AvailableActive Not RecruitingNot AvailableThoracic Pain2
Not AvailableCompletedNot AvailableCoughing1
Not AvailableCompletedNot AvailableHealthy Volunteers1
Not AvailableCompletedNot AvailableHealthy Volunteers / Hyperalgesia / Pain / Peripheral Nervous System Diseases1
Not AvailableCompletedNot AvailableMyofascial Pain Syndrome of the Upper Trapezius1
Not AvailableCompletedNot AvailablePeripheral Neuropathic Pain1
Not AvailableCompletedNot AvailablePost-operative Peripheral Neuropathic Pain1
Not AvailableCompletedNot AvailablePrimary Hyperalgesia1
Not AvailableCompletedTreatmentStings1
Not AvailableEnrolling by InvitationNot AvailableArthritis / Gout Acute / Headaches / Migraines / Muscle Spasms / Radicular syndrome / Synovitis / Tendonitis1
Not AvailableEnrolling by InvitationOtherKnee Osteoarthritis (Knee OA)1
Not AvailableRecruitingNot AvailableArteriovenous Fistulae / Pain, Neuropathic1
Not AvailableRecruitingNot AvailableParkinson's Disease (PD)1
Not AvailableRecruitingBasic ScienceDermatology/Skin - Other / Pain / Pain, Neuropathic / Pruritus1
Not AvailableRecruitingBasic SciencePain1
Not AvailableRecruitingPreventionMorbid Obesity D0097651
Not AvailableRecruitingTreatmentPain, Neuropathic / Spinal Cord Injuries (SCI)1
Not AvailableUnknown StatusNot AvailableLower Limb Amputation / Pain, Neuropathic1
Not AvailableUnknown StatusTreatmentChronic Neck Pain1
Not AvailableUnknown StatusTreatmentPain Relief1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
PatchTopical.025 g/100g
PatchTopical4 g/100g
DiscTopical
GelTopical0.05 %
LiquidTopical0.025 %
GelTopical.06375 g/255g
GelTopical.02825 g/113g
LiquidTopical.15 g/100mL
CreamTopical.25 mg/mL
PlasterTopical70 mg/1
OilPercutaneous; Topical; Transdermal
CreamTopical.05925 g/237mL
LotionTopical0.025 %
CreamTopical1 mg/g
CreamTopical0.075 %
CreamTopical0.025 %
LiquidTopical1.5 mg/mL
PatchTopical.702 mg/1
CreamTopical0.05 %
KitOral; Topical
CreamTopical.001 g/g
LiquidTopical.0015 g/mL
CreamTopical.00035 g/g
GelTopical
CreamTopical.025 %
CreamTopical.35 mg/g
OintmentTopical.25 g/100mL
PatchTopical249 mg/1
LiquidTopical.025 g/100g
CreamOral75 mg/g
PatchTopical.025 g/g
LotionTopical
CreamTopical.27 mg/g
CreamTopical.1 g/100g
CreamTopical.02125 g/85g
GelTopical.01425 g/57g
LinimentTopical
GelTopical.25 mg/g
CreamTopical.75 mg/mL
CreamTopical.35 mg/mL
CreamTopical.17 g/100g
LiquidTopical150 mg/100000mg
LiquidTopical
PatchTopical1.2 mg/1000mg
GelTopical.5 mL/90mL
GelTopical1.5 mL/240mL
CreamTopical.875 mg/3.5g
CreamTopical.0295 g/118mL
CreamTopical.0375 g/50g
PatchTopical.6 mg/1
OintmentTopical
PatchTopical
CreamTopical.1 g/10g
GelTopical.02125 g/85g
CreamTopical.0265 g/106g
CreamTopical.025 ug/mL
CreamTopical2.5 mg/g
SprayTopical.00025 g/mL
SolutionTopical2.5 mg/mL
PatchTopical.025 mg/100mg
CreamTopical.02825 g/113g
GelTopical.0295 g/118mL
Kit
PatchCutaneous179 mg
OintmentTopical.05 g/100g
LotionTopical.025 mL/100mL
CreamTopical.025 g/100g
PatchTopical.25 mg/1
CreamTopical3 g/100g
GelTopical.06275 g/251mL
Solution / dropsTopical
CreamTopical.025 mg/.001g
GelTopical156.25 ng/mL
PatchTransdermal
PlasterTransdermal
CreamTopical
SolutionTopical
OilTopical.075 g/50g
CreamTopical.07 g/100g
PatchTopical25 mg/1
PlasterTopical
CreamTopical.25 mg/g
CreamTopical.75 mg/g
Kit
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US6239180No1996-11-062016-11-06Us

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00841 mg/mLALOGPS
logP3.8ALOGPS
logP3.75ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)9.93ChemAxon
pKa (Strongest Basic)-0.52ChemAxon
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

Taxonomy

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
Methoxyphenol / Phenoxy compound / Anisole / Methoxybenzene / Phenol ether / Alkyl aryl ether / 1-hydroxy-2-unsubstituted benzenoid / Monocyclic benzene moiety / Fatty acyl / Fatty amide
show 14 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
capsaicinoid (CHEBI:3374) / Capsaicinoids and derivatives (C06866)

Targets

Kind
Protein
Organism
Human
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
Human
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
Human
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
Human
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
Human
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
Human
Pharmacological action
Unknown
Actions
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]
Kind
Protein
Organism
Human
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
Human
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
Human
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
Human
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
Human
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 November 19, 2017 20:34