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Details

Stereochemistry ACHIRAL
Molecular Formula C18H27NO3
Molecular Weight 305.4126
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of CAPSAICIN

SMILES

CC(C)/C(/[H])=C(\[H])/CCCCC(=NCc1ccc(c(c1)OC)O)O

InChI

InChIKey=YKPUWZUDDOIDPM-SOFGYWHQSA-N
InChI=1S/C18H27NO3/c1-14(2)8-6-4-5-7-9-18(21)19-13-15-10-11-16(20)17(12-15)22-3/h6,8,10-12,14,20H,4-5,7,9,13H2,1-3H3,(H,19,21)/b8-6+

HIDE SMILES / InChI

Molecular Formula C18H27NO3
Molecular Weight 305.4126
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description
Curator's Comment:: http://www.wikidoc.org/index.php/Capsaicin

Capsaicin is a topical analgesic that is FDA approved for the treatment of neuropathic pain associated with postherpetic neuralgia. Capsaicin is most often used as a topical analgesic and exists in many formulations of cream, liquid, and patch preparations of various strengths; however, it may also be found in some dietary supplements. Capsaicin is a naturally-occurring botanical irritant in chili peppers, synthetically derived for pharmaceutical formulations. Capsaicin is an agonist for the transient receptor potential vanilloid I receptor (TRPVI), which is an ion channel-receptor complex expressed on nociceptive nerve fibers in the skin. Common adverse reactions include erythema, rash, pruritus, nausea.

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
QUTENZA

Approved Use

Qutenza is indicated for the management of neuropathic pain associated with postherpetic neuralgia

Launch Date

1258329600000
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1.38 ng/mL
640 μg/cm² single, topical
dose: 640 μg/cm²
route of administration: Topical
experiment type: SINGLE
co-administered:
CAPSAICIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
4.36 ng × h/mL
640 μg/cm² single, topical
dose: 640 μg/cm²
route of administration: Topical
experiment type: SINGLE
co-administered:
CAPSAICIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1.64 h
640 μg/cm² single, topical
dose: 640 μg/cm²
route of administration: Topical
experiment type: SINGLE
co-administered:
CAPSAICIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
8 % single, topical
Recommended
dose: 8 %
route: topical
experiment_type: single
dose_type: Recommended
co-adm with
    data_source:
    https://pubmed.ncbi.nlm.nih.gov/20655809
    unhealthy, 71.6 +/-10.27
    population: unhealthy
    age: 71.6 +/-10.27
    sex: M+F
    food_status:
    n:
    data_source:
    https://pubmed.ncbi.nlm.nih.gov/20655809
    Disc. AE: Neuralgia...
    AEs leading to
    discontinuation/dose reduction:​
    Neuralgia (0.9%)

    data_source:
    https://pubmed.ncbi.nlm.nih.gov/20655809
    8 % 1 times / 3 months multiple, topical
    Recommended
    dose: 8 % 1 times / 3 months
    route: topical
    experiment_type: multiple
    dose_type: Recommended
    co-adm with
      data_source:
      https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022395lbl.pdf
      unhealthy
      population: unhealthy
      age:
      sex:
      food_status:
      n:
      data_source:
      https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022395lbl.pdf
      Other AEs: Irritation of eyes, Respiratory tract irritation...
      Other AEs:
      Irritation of eyes
      Respiratory tract irritation
      Transient blood pressure increase

      data_source:
      https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022395lbl.pdf
      AEs

      AEs

      AESignificanceDosePopulation
      Neuralgia 0.9%
      Disc. AE
      8 % single, topical
      Recommended
      dose: 8 %
      route: topical
      experiment_type: single
      dose_type: Recommended
      co-adm with
        data_source:
        https://pubmed.ncbi.nlm.nih.gov/20655809
        unhealthy, 71.6 +/-10.27
        population:
        age:
        sex:
        food_status:
        n:
        data_source:
        https://pubmed.ncbi.nlm.nih.gov/20655809
        Irritation of eyes
        8 % 1 times / 3 months multiple, topical
        Recommended
        dose: 8 % 1 times / 3 months
        route: topical
        experiment_type: multiple
        dose_type: Recommended
        co-adm with
          data_source:
          https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022395lbl.pdf
          unhealthy
          population:
          age:
          sex:
          food_status:
          n:
          data_source:
          https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022395lbl.pdf
          Respiratory tract irritation
          8 % 1 times / 3 months multiple, topical
          Recommended
          dose: 8 % 1 times / 3 months
          route: topical
          experiment_type: multiple
          dose_type: Recommended
          co-adm with
            data_source:
            https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022395lbl.pdf
            unhealthy
            population:
            age:
            sex:
            food_status:
            n:
            data_source:
            https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022395lbl.pdf
            Transient blood pressure increase
            8 % 1 times / 3 months multiple, topical
            Recommended
            dose: 8 % 1 times / 3 months
            route: topical
            experiment_type: multiple
            dose_type: Recommended
            co-adm with
              data_source:
              https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022395lbl.pdf
              unhealthy
              population:
              age:
              sex:
              food_status:
              n:
              data_source:
              https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022395lbl.pdf
              Overview

              Overview

              Drug as perpetrator​

              Drug as perpetrator​

              TargetModalityActivityMetaboliteClinical evidence
              no
              no
              no
              no
              no
              no
              unlikely [IC50 12 uM]
              unlikely [IC50 18 uM]
              unlikely [IC50 2 uM]
              unlikely [IC50 2.1 uM]
              unlikely [IC50 24 uM]
              unlikely [IC50 3.2 uM]
              unlikely [IC50 >10 uM]
              Drug as victim
              PubMed

              PubMed

              TitleDatePubMed
              The effects of intradermal fentanyl and ketamine on capsaicin-induced secondary hyperalgesia and flare reaction.
              1999 Dec
              Neurokinin-1 receptors are involved in behavioral responses to high-intensity heat stimuli and capsaicin-induced hyperalgesia in mice.
              1999 Jun
              Capsaicin-sensitive C-fiber-mediated protective responses in ozone inhalation in rats.
              1999 Mar
              Effect of sympathetic activity on capsaicin-evoked pain, hyperalgesia, and vasodilatation.
              1999 Mar 23
              Tourniquet constriction exacerbates hyperalgesia-related pain induced by intradermal capsaicin injection.
              1999 Sep
              Tachykinins in the porcine pancreas: potent exocrine and endocrine effects via NK-1 receptors.
              2000 Apr
              Involvement of glutamate in transmission of afferent constrictive inputs from the airways to the nucleus tractus solitarius in ferrets.
              2000 Apr 12
              Differential effects of systemically administered ketamine and lidocaine on dynamic and static hyperalgesia induced by intradermal capsaicin in humans.
              2000 Feb
              Antinociceptive properties of the methanolic extract and two triterpenes isolated from Epidendrum Mosenii stems (Orchidaceae).
              2000 Jan 21
              Evidence for activation of the tissue kallikrein-kinin system in nociceptive transmission and inflammatory responses of mice using a specific enzyme inhibitor.
              2000 Jul
              Activation of the somatosensory cortex during Abeta-fiber mediated hyperalgesia. A MSI study.
              2000 Jul 14
              ATP in human skin elicits a dose-related pain response which is potentiated under conditions of hyperalgesia.
              2000 Jun
              Capsaicin protects against ethanol-induced oxidative injury in the gastric mucosa of rats.
              2000 Nov 10
              Peripheral lidocaine but not ketamine inhibits capsaicin-induced hyperalgesia in humans.
              2000 Oct
              Influence of thermode size for detecting heat pain dysfunction in a capsaicin model of epidermal nerve fiber loss.
              2001 Apr
              Influence of capsaicin cream in rats with peripheral neuropathy.
              2001 Aug
              Comparative effect of Phoneutria nigriventer spider venom and capsaicin on the rat paw oedema.
              2001 Aug 17
              Improvement of preservation with cardioplegic solution by nitroglycerin-induced delayed preconditioning is mediated by calcitonin gene-related peptide.
              2001 Dec
              Chronic tobacco smoke exposure increases airway sensitivity to capsaicin in awake guinea pigs.
              2001 Feb
              Antinociceptive effects of delta-opioid agonists in Rhesus monkeys: effects on chemically induced thermal hypersensitivity.
              2001 Mar
              Monophosphoryl lipid A-induced delayed preconditioning is mediated by calcitonin gene-related peptide.
              2001 May 25
              Cannabinoids attenuate capsaicin-evoked hyperalgesia through spinal and peripheral mechanisms.
              2001 Sep
              Antihyperalgesic effects of the muscarinic receptor ligand vedaclidine in models involving central sensitization in rats.
              2001 Sep
              Effect of systemic adenosine on pain and secondary hyperalgesia associated with the heat/capsaicin sensitization model in healthy volunteers.
              2001 Sep-Oct
              Ischemia/reperfusion-induced increase in the hepatic level of prostacyclin is mainly mediated by activation of capsaicin-sensitive sensory neurons in rats.
              2002 Apr
              Delayed cardioprotection induced by nitroglycerin is mediated by alpha-calcitonin gene-related peptide.
              2002 Apr
              Suppression of phorbol ester-induced NF-kappaB activation by capsaicin in cultured human promyelocytic leukemia cells.
              2002 Aug
              Pharmacological characterisation of the somatostatin analogue TT-232: effects on neurogenic and non-neurogenic inflammation and neuropathic hyperalgesia.
              2002 Aug
              Role of bradykinin in acid-induced mesenteric hyperemia and duodenal villous damage.
              2002 Jan 4
              Acupuncture modulation of capsaicin-induced inflammation: effect of intraperitoneal and local administration of naloxone in rats. A blinded controlled study.
              2002 Jun
              Cell death of primary afferent nerve cells in neonatal mice treated with capsaicin.
              2002 Mar
              Postdelivery of alfentanil and ketamine has no effect on intradermal capsaicin-induced pain and hyperalgesia.
              2002 Nov-Dec
              Pain activation of human supraspinal opioid pathways as demonstrated by [11C]-carfentanil and positron emission tomography (PET).
              2002 Oct
              The role of the gastric afferent vagal nerve in ghrelin-induced feeding and growth hormone secretion in rats.
              2002 Oct
              The effect of chronic oral desipramine on capsaicin-induced allodynia and hyperalgesia: a double-blinded, placebo-controlled, crossover study.
              2002 Oct
              High affinity antagonists of the vanilloid receptor.
              2002 Oct
              Deficits in visceral pain and referred hyperalgesia in Nav1.8 (SNS/PN3)-null mice.
              2002 Oct 1
              Capsaicin regulates vascular endothelial cell growth factor expression by modulation of hypoxia inducing factor-1alpha in human malignant melanoma cells.
              2002 Sep
              Capsaicin-induced muscle pain alters the excitability of the human jaw-stretch reflex.
              2002 Sep
              Opioid-insensitive hypoalgesia to mechanical stimuli at sites ipsilateral and contralateral to experimental muscle pain in human volunteers.
              2002 Sep
              Phosphorylation of extracellular signal-regulated kinase in primary afferent neurons by noxious stimuli and its involvement in peripheral sensitization.
              2002 Sep 1
              Prostaglandin and protein kinase A-dependent modulation of vanilloid receptor function by metabotropic glutamate receptor 5: potential mechanism for thermal hyperalgesia.
              2002 Sep 1
              Roles of JNK-1 and p38 in selective induction of apoptosis by capsaicin in ras-transformed human breast epithelial cells.
              2003 Feb 10
              A comparison of hyperalgesia and neurogenic inflammation induced by melittin and capsaicin in humans.
              2003 Feb 13
              Patents

              Sample Use Guides

              The recommended dose of Qutenza is a single, 60-minute application of up to four patches. Qutenza patch contains 8% capsaicin (640 mcg/cm2).
              Route of Administration: Topical
              In Vitro Use Guide
              In isolated perfused globally ischemic rat hearts, antiischemic efficacy was assessed as a significant extension (36% and 50%) in time to contracture with 30 microM capsaicin and 1 microM diltiazem, respectively.
              Substance Class Chemical
              Created
              by admin
              on Fri Jun 25 20:59:41 UTC 2021
              Edited
              by admin
              on Fri Jun 25 20:59:41 UTC 2021
              Record UNII
              S07O44R1ZM
              Record Status Validated (UNII)
              Record Version
              • Download
              Name Type Language
              CAPSAICIN
              DASH   EMA EPAR   HSDB   INCI   INN   JAN   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
              INN   INCI  
              Official Name English
              CAPSAICIN [MART.]
              Common Name English
              CAPSAICIN [JAN]
              Common Name English
              OVOCAP
              Common Name English
              CNTX-4975
              Common Name English
              CAPSAICIN [EMA EPAR]
              Common Name English
              AUSANIL
              Common Name English
              TRANS-CAPSAICIN
              Common Name English
              (E)-8-METHYL-N-VANILLYL-6-NONENAMIDE
              Systematic Name English
              CAPSAICIN [INN]
              Common Name English
              NGX-4010
              Code English
              RATDEN PE 40
              Common Name English
              NSC-56353
              Code English
              CAPSAICIN [ORANGE BOOK]
              Common Name English
              QUTENZA
              Brand Name English
              6-NONENAMIDE, (E)-N-((4-HYDROXY-3-METHOXY-PHENYL)METHYL)-8-METHYL
              Common Name English
              ZOSTRIX
              Common Name English
              CAPSAICIN (CONSTITUENT OF CAPSICUM) [DSC]
              Common Name English
              CAPSAICIN [HSDB]
              Common Name English
              TOGARASHI ORENJI
              Common Name English
              FEMA NO. 3404
              Code English
              CAPSAICIN [WHO-DD]
              Common Name English
              CAPSAICIN [USP MONOGRAPH]
              Common Name English
              CAPSAICIN [INCI]
              Common Name English
              N-(4-HYDROXY-3-METHOXYBENZYL)-8-METHYL-6-NONENAMIDE [FHFI]
              Common Name English
              ALGRX-4975
              Code English
              MIOTON
              Common Name English
              CAPSAICIN [USP-RS]
              Common Name English
              ALGRX 4975
              Code English
              CAPSAICIN [MI]
              Common Name English
              NGX-1998
              Code English
              CAPSAICIN [VANDF]
              Common Name English
              CAPZASIN-HP
              Common Name English
              DOLENON
              Common Name English
              AXSAIN
              Common Name English
              Classification Tree Code System Code
              EPA PESTICIDE CODE 70701
              Created by admin on Fri Jun 25 20:59:41 UTC 2021 , Edited by admin on Fri Jun 25 20:59:41 UTC 2021
              FDA ORPHAN DRUG 269508
              Created by admin on Fri Jun 25 20:59:41 UTC 2021 , Edited by admin on Fri Jun 25 20:59:41 UTC 2021
              NCI_THESAURUS C68530
              Created by admin on Fri Jun 25 20:59:41 UTC 2021 , Edited by admin on Fri Jun 25 20:59:41 UTC 2021
              FDA ORPHAN DRUG 165502
              Created by admin on Fri Jun 25 20:59:41 UTC 2021 , Edited by admin on Fri Jun 25 20:59:41 UTC 2021
              WHO-VATC QM02AB01
              Created by admin on Fri Jun 25 20:59:41 UTC 2021 , Edited by admin on Fri Jun 25 20:59:41 UTC 2021
              EMA ASSESSMENT REPORTS QUTENZA (AUTHORIZED: NEURALGIA)
              Created by admin on Fri Jun 25 20:59:41 UTC 2021 , Edited by admin on Fri Jun 25 20:59:41 UTC 2021
              FDA ORPHAN DRUG 158202
              Created by admin on Fri Jun 25 20:59:41 UTC 2021 , Edited by admin on Fri Jun 25 20:59:41 UTC 2021
              WHO-ATC N01BX04
              Created by admin on Fri Jun 25 20:59:41 UTC 2021 , Edited by admin on Fri Jun 25 20:59:41 UTC 2021
              WHO-ATC M02AB01
              Created by admin on Fri Jun 25 20:59:41 UTC 2021 , Edited by admin on Fri Jun 25 20:59:41 UTC 2021
              FDA ORPHAN DRUG 222506
              Created by admin on Fri Jun 25 20:59:41 UTC 2021 , Edited by admin on Fri Jun 25 20:59:41 UTC 2021
              DSLD 3807 (Number of products:4)
              Created by admin on Fri Jun 25 20:59:41 UTC 2021 , Edited by admin on Fri Jun 25 20:59:41 UTC 2021
              NCI_THESAURUS C2198
              Created by admin on Fri Jun 25 20:59:41 UTC 2021 , Edited by admin on Fri Jun 25 20:59:41 UTC 2021
              EU-Orphan Drug Capsaicin
              Created by admin on Fri Jun 25 20:59:41 UTC 2021 , Edited by admin on Fri Jun 25 20:59:41 UTC 2021
              WHO-VATC QN01BX04
              Created by admin on Fri Jun 25 20:59:41 UTC 2021 , Edited by admin on Fri Jun 25 20:59:41 UTC 2021
              FDA ORPHAN DRUG 205705
              Created by admin on Fri Jun 25 20:59:41 UTC 2021 , Edited by admin on Fri Jun 25 20:59:41 UTC 2021
              Code System Code Type Description
              IUPHAR
              2486
              Created by admin on Fri Jun 25 20:59:41 UTC 2021 , Edited by admin on Fri Jun 25 20:59:41 UTC 2021
              PRIMARY
              HSDB
              954
              Created by admin on Fri Jun 25 20:59:41 UTC 2021 , Edited by admin on Fri Jun 25 20:59:41 UTC 2021
              PRIMARY
              DRUG CENTRAL
              3064
              Created by admin on Fri Jun 25 20:59:41 UTC 2021 , Edited by admin on Fri Jun 25 20:59:41 UTC 2021
              PRIMARY
              RXCUI
              1992
              Created by admin on Fri Jun 25 20:59:41 UTC 2021 , Edited by admin on Fri Jun 25 20:59:41 UTC 2021
              PRIMARY RxNorm
              EVMPD
              SUB13229MIG
              Created by admin on Fri Jun 25 20:59:41 UTC 2021 , Edited by admin on Fri Jun 25 20:59:41 UTC 2021
              PRIMARY
              FDA UNII
              S07O44R1ZM
              Created by admin on Fri Jun 25 20:59:41 UTC 2021 , Edited by admin on Fri Jun 25 20:59:41 UTC 2021
              PRIMARY
              USP_CATALOG
              1091108
              Created by admin on Fri Jun 25 20:59:41 UTC 2021 , Edited by admin on Fri Jun 25 20:59:41 UTC 2021
              PRIMARY USP-RS
              ECHA (EC/EINECS)
              206-969-8
              Created by admin on Fri Jun 25 20:59:41 UTC 2021 , Edited by admin on Fri Jun 25 20:59:41 UTC 2021
              PRIMARY
              WIKIPEDIA
              CAPSAICIN
              Created by admin on Fri Jun 25 20:59:41 UTC 2021 , Edited by admin on Fri Jun 25 20:59:41 UTC 2021
              PRIMARY
              CAS
              404-86-4
              Created by admin on Fri Jun 25 20:59:41 UTC 2021 , Edited by admin on Fri Jun 25 20:59:41 UTC 2021
              PRIMARY
              MERCK INDEX
              M3040
              Created by admin on Fri Jun 25 20:59:41 UTC 2021 , Edited by admin on Fri Jun 25 20:59:41 UTC 2021
              PRIMARY Merck Index
              MESH
              D002211
              Created by admin on Fri Jun 25 20:59:41 UTC 2021 , Edited by admin on Fri Jun 25 20:59:41 UTC 2021
              PRIMARY
              INN
              10145
              Created by admin on Fri Jun 25 20:59:41 UTC 2021 , Edited by admin on Fri Jun 25 20:59:41 UTC 2021
              PRIMARY
              PUBCHEM
              1548943
              Created by admin on Fri Jun 25 20:59:41 UTC 2021 , Edited by admin on Fri Jun 25 20:59:41 UTC 2021
              PRIMARY
              EPA CompTox
              404-86-4
              Created by admin on Fri Jun 25 20:59:41 UTC 2021 , Edited by admin on Fri Jun 25 20:59:41 UTC 2021
              PRIMARY
              DRUG BANK
              DB06774
              Created by admin on Fri Jun 25 20:59:41 UTC 2021 , Edited by admin on Fri Jun 25 20:59:41 UTC 2021
              PRIMARY
              ChEMBL
              CHEMBL294199
              Created by admin on Fri Jun 25 20:59:41 UTC 2021 , Edited by admin on Fri Jun 25 20:59:41 UTC 2021
              PRIMARY
              NCI_THESAURUS
              C339
              Created by admin on Fri Jun 25 20:59:41 UTC 2021 , Edited by admin on Fri Jun 25 20:59:41 UTC 2021
              PRIMARY
              Related Record Type Details
              PARENT -> CONSTITUENT ALWAYS PRESENT
              48.6% of Capsaicinoid components.
              PARENT -> CONSTITUENT ALWAYS PRESENT
              48.6% of Capsaicinoid components.
              PARENT -> CONSTITUENT ALWAYS PRESENT
              48.6% of Capsaicinoid components.
              PARENT -> CONSTITUENT ALWAYS PRESENT
              48.6% of Capsaicinoid components.
              METABOLIC ENZYME -> SUBSTRATE
              EXCRETED UNCHANGED
              There is no human excretion information available for capsaicin
              METABOLIC ENZYME -> SUBSTRATE
              WEAK
              TARGET -> AGONIST
              PARENT -> CONSTITUENT ALWAYS PRESENT
              48.6% of Capsaicinoid components.
              METABOLIC ENZYME -> SUBSTRATE
              WEAK
              METABOLIC ENZYME -> SUBSTRATE
              METABOLIC ENZYME -> SUBSTRATE
              WEAK
              Related Record Type Details
              PRODRUG -> METABOLITE ACTIVE
              HYDROLYSIS INDEPENDENT OF ENZYME
              METABOLITE -> PARENT
              In incubation medium and skin vanillic acid ranged from 0.11 to 7.97% of the radioactivity in each sample at all concentrations.
              SKIN
              METABOLITE -> PARENT
              MINOR
              PLASMA
              METABOLITE -> PARENT
              In incubation medium and skin vanillylamine ranged from 4.37 to 19.8% of the radioactivity in each sample at all concentrations.
              SKIN
              Related Record Type Details
              ACTIVE MOIETY