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Drug

D0325 | Capsaicin

Molecular Formula C18H27NO3
Molecular Weight 305.4
Structure
State solid
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 [A32319].
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 [A32319]. Following topical application of 3% solution of capsaicin, the half-life of capsaicin was approximately 24 h [A32319]. The mean population elimination half-life was 1.64 h following application of a topical patch containing 179 mg of capsaicin [A32319].
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 [A32319]. The peak blood concentration can be reached within 1 hour following administration [A32319]. 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 [A32319]. **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 [A32319]. **Topical**: Topical capsaicin in humans is rapidly and well absorbed through the skin, however systemic absorption following topical or transdermal administration is unlikely [A32319]. 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 [A32319].
Description Class C Complex I inhibitors; quinol antagonist; active component of chili peppers; topical analgesic; capsaicinoids; TRPV1 agonist

N

M

N01BX04 Capsaicin


[N01BX] Other local anesthetics


[N01B] ANESTHETICS, LOCAL


[N01] ANESTHETICS


[N] Nervous system

M02AB01 Capsaicin


[M02AB] Capsaicin and similar agents


[M02A] TOPICAL PRODUCTS FOR JOINT AND MUSCULAR PAIN


[M02] TOPICAL PRODUCTS FOR JOINT AND MUSCULAR PAIN


[M] Musculoskeletal system

Toxicity Dose Time Species Model Method Action Positive criterion Reference
MEMBRANE POTENTIAL 275 µM 30 mins mouse liver mitochondria Rh123 fluorescence (excitation 485 nm, emission 535 nm) are recorded using a fluorescence multi-well plate reader (mCICCP (20 µM) treatments was considered as the 100% baseline for ΔΨm loss) decrease EC20 36
RESPIRATION 15 µM 60 mins mouse liver mitochondria Oxygen consumption was monitored with 50nM MitoXpress ( an oxygen-sensitive phosphorescent dye) using a spectrofluorimeter (Tecan Infinite 200; λExcitation 380nm; λEmission 650nm). Rotenone (2µM) was used as 100% baseline for complex I inhibition. decrease EC20 36
RESPIRATION 15.7 µM 60 mins mouse liver mitochondria Oxygen consumption was monitored with 50nM MitoXpress ( an oxygen-sensitive phosphorescent dye) using a spectrofluorimeter (Tecan Infinite 200; λExcitation 380nm; λEmission 650nm). Oligomycin A (1µM) was used as 100% baseline for complex II inhibition. decrease EC20 36
ELECTRON TRANSPORT CHAIN 20–30 μM bovine mitochondria NADH–Q decrease IC50 102
ELECTRON TRANSPORT CHAIN 20–30 μM bovine mitochondria NADH:O2 decrease IC50 102
GLUCOSE GALACTOSE IC50 RATIO permeabilized LUHMES cells Assessment of the function of individual mitochondrial complexes using Agilent Seahorse XFe24 Negative EC25(NA) [Glc/Gal] 326
SWELLING > 200 µM 30 mins mouse liver mitochondria swelling assay: Absorbance at 545 nm using a fluorescence multi-well plate reader (CaCl2 (50 µM) was considered as the 100% baseline for the swelling ) increase EC20 36

Target Dose Time Species Model Method Action Positive criterion Reference
NADH:ubiquinone reductase 20–30 μM bovine mitochondria NADH–Q inhibitor IC50 102
NADH:ubiquinone reductase 20–30 μM bovine mitochondria NADH:O2 inhibitor IC50 102
NADH:ubiquinone reductase 15 µM 60 mins mouse liver mitochondria Oxygen consumption was monitored with 50nM MitoXpress ( an oxygen-sensitive phosphorescent dye) using a spectrofluorimeter (Tecan Infinite 200; λExcitation 380nm; λEmission 650nm). Rotenone (2µM) was used as 100% baseline for complex I inhibition. inhibit EC20 36
Succinate dehydrogenase 15.7 µM 60 mins mouse liver mitochondria Oxygen consumption was monitored with 50nM MitoXpress ( an oxygen-sensitive phosphorescent dye) using a spectrofluorimeter (Tecan Infinite 200; λExcitation 380nm; λEmission 650nm). Oligomycin A (1µM) was used as 100% baseline for complex II inhibition. inhibit EC20 36
Cytochrome c > 200 µM 30 mins mouse liver mitochondria Cytochrome c release was evaluated using ELISA kit ( 20 µg/ml Alamethicin was used as 100% baseline) release EC20 36

Pictogram Signal Statements Precautionary Statement Codes
Danger

Aggregated GHS information provided by 1662 companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.


H301 (22.14%): Toxic if swallowed [Danger Acute toxicity, oral]


H302 (77.8%): Harmful if swallowed [Warning Acute toxicity, oral]


H315 (99.76%): Causes skin irritation [Warning Skin corrosion/irritation]


H318 (97.23%): Causes serious eye damage [Danger Serious eye damage/eye irritation]


Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.


 P264, P270, P280, P301+P310, P301+P312, P302+P352, P305+P351+P338, P310, P321, P330, P332+P313, P362, P405, and P501; (The corresponding statement to each P-code can be found at the GHS Classification page.)
Danger

H301: Toxic if swallowed [Danger Acute toxicity, oral]


H315: Causes skin irritation [Warning Skin corrosion/irritation]


H317: May cause an allergic skin reaction [Warning Sensitization, Skin]


H319: Causes serious eye irritation [Warning Serious eye damage/eye irritation]


H334: May cause allergy or asthma symptoms or breathing difficulties if inhaled [Danger Sensitization, respiratory]


H335: May cause respiratory irritation [Warning Specific target organ toxicity, single exposure


Respiratory tract irritation]


 P261, P264, P270, P271, P272, P280, P285, P301+P310, P302+P352, P304+P340, P304+P341, P305+P351+P338, P312, P321, P330, P332+P313, P333+P313, P337+P313, P342+P311, P362, P363, P403+P233, P405, and P501; (The corresponding statement to each P-code can be found at the GHS Classification page.)

  • Diabetes mellitus

  • Neuralgia

  • Pain

  • Post herpetic neuralgia

  • Pruritus (2e-04)

  • Application site dryness

  • Application site erythema

  • Application site oedema

  • Application site pain

  • Application site papules

  • Application site pruritus

  • Application site swelling

  • Bronchitis

  • Hypertension

  • Instillation site pain

  • Nasopharyngitis

  • Nausea

  • Sinusitis

  • Vomiting

    • (6E)-N-(4-Hydroxy-3-methoxybenzyl)-8-methyl-6-nonenamide # (6E)-N-(4-hydroxy-3-methoxybenzyl)-8-methylnon-6-enamide (6E)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnon-6-enamide
    (6E)-N-{[4-hydroxy-3-(methyloxy)phenyl]methyl}-8-methylnon-6-enamide (E)-8-Methyl-N-vanillyl-6-nonenamide (E)-8-Methyl-N-vanillyl-6-nonenamide(8cl)
    (E)-Capsaicin (E)-N-((4-Hydroxy-3-methoxyphenyl)-methyl)-8-methyl-6-nonenamide (E)-N-[(4-HYDROXY-3-METHOXYPHENYL)METHYL]-8-METHYL-6-NONENAMIDE
    (E)-N-[(4-Hydroxy-3-methoxyphenyl)-methyl]-8-methyl-6-nonenamide (E)-N-[(4-Hydroxy-3-methoxyphenyl)methyl]-8-methyl-6-nonenamide. (E)-N-[(4-hydroxy-3-methoxy-phenyl)methyl]-8-methyl-non-6-enamide
    (E)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnon-6-enamide (E)8-methyl-N-vanillyl-6-Nonenamide (e)-n-(4-hydroxy-3-methoxybenzyl)-8-methylnon-6-enamide
    1217899-52-9 404-86-4 4CH-016296
    6-Nonenamide, (E)- 6-Nonenamide, (E)-N-((4-hydroxy-3-methoxy-phenyl)methyl)-8-methyl 6-Nonenamide, 8-methyl-N-vanillyl-, (E)-
    6-Nonenamide, 8-methyl-N-vanillyl-, (E)- (8CI) 6-Nonenamide, N-((4-hydroxy-3-methoxyphenyl)methyl)-8-methyl-, (6E)- 6-Nonenamide, N-((4-hydroxy-3-methoxyphenyl)methyl)-8-methyl-, (E)-
    6-Nonenamide, N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methyl-, (6E)- 6-Nonenamide, N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methyl-, (E)- 8-Methyl-N-Vanillyl-6-Nonenamide
    8-Methyl-N-vanillyl-6-nonenamide, (E)- 8-Methyl-N-vanillyl-6E-nonenamide 8-Methyl-N-vanillyl-trans-6-nonenamide
    AB00053098-11 AB00053098_12 AC-10114
    AKOS007930159 ALGRX 4975 Adlea
    Ausanil Axsain BBL027836
    BDBM20461 BDBM86537 BPBio1_001053
    BRD-K37056290-001-01-1 BRD-K50590187-001-06-6 BRN 2816484
    BSPBio_000957 BSPBio_001548 BSPBio_002917
    Bitter orange extract 30% C06866 C18H27NO3
    CAPSAICIN (2444-46-4 NONIVAMIDE (SYNTHETIC CAPSAICIN)) CAPSAICIN, NATURAL CAPSAICINE
    CAPSAICINOIDS CAS-404-86-4 CAS_404-86-4
    CC0144 CCG-39908 CCRIS 1588
    CHEBI:3374 CHEBI:94524 CHEMBL294199
    CITRUS AURANTIUM PE CS-1518 Capsaicin
    Capsaicin (8-Methyl-N-vanillyl-6-nonenamide) Capsaicin (JAN/USP) Capsaicin (Natural)
    Capsaicin (in oleoresin of capsicum) Capsaicin Patch Capsaicin [USAN]
    Capsaicin [USP:INN] Capsaicin [in oleoresin of capsicum] Capsaicin(Qutenza)
    Capsaicin(Vanilloid) Capsaicin, >=95%, from Capsicum sp. Capsaicin, European Pharmacopoeia (EP) Reference Standard
    Capsaicin, Pharmaceutical Secondary Standard Capsaicin, United States Pharmacopeia (USP) Reference Standard Capsaicin, analytical standard
    Capsaicin, certified reference material, TraceCERT(R) Capsaicin, from Capsicum sp., >=50% (HPLC) Capsaicin, from natural source
    Capsaicin,(S) Caswell No. 158 Certified Reference Material
    Citrus Aurantium 30% Citrus Aurantium Extract D00250
    DB06774 DSSTox_CID_241 DSSTox_GSID_20241
    DSSTox_RID_75455 DTXSID9020241 E-CAPSAICIN
    EI-125 EINECS 206-969-8 EPA Pesticide Chemical Code 070701
    FEMA No. 3404 FT-0082538 GTPL2486
    HMS1361N10 HMS1570P19 HMS1791N10
    HMS1921H11 HMS1989N10 HMS2089N11
    HMS2092D21 HMS2097P19 HMS2230O23
    HMS3402N10 HMS3414F11 HMS3649N15
    HMS3678F11 HMS501B16 HSDB 954
    HY-10448 IDI1_000354 IDI1_034018
    Isodecenoate Isodecenoic acid vanillylamide KS-5181
    LMFA08020085 LS-2138 M1149
    MCULE-8056866140 MEGxp0_001448 MFCD00017259
    MLS002154049 MR3H3 Mioton
    N-((4-Hydroxy-3-methoxyphenyl)methyl)-8-methyl-6-nonenamide N-((4-Hydroxy-3-methoxyphenyl)methyl)-8-methyl-6-nonenamide, (E)- N-(3-Methoxy-4-hydroxybenzyl)-8-methyl-6-nonenamide
    N-(4-Hydroxy-3-methoxybenzyl)-8-methylnon-trans-6-enamide N-(4-hydroxy-3-methoxybenzyl)-8-methylnon-6-enamide N-[(4-Hydroxy-3-methoxyphenyl)methyl]-8-methyl-6-nonenamide
    N-[(4-hydroxy-3-methoxy-phenyl)methyl]nonanamide N-[(4-hydroxy-3-methoxyphenyl)methyl]-6E-8-methyl-nonenamide N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnon-6-enamide
    N0C781 N1667 N735
    NCGC00017337-02 NCGC00017337-03 NCGC00017337-04
    NCGC00017337-05 NCGC00017337-06 NCGC00017337-07
    NCGC00017337-08 NCGC00017337-09 NCGC00017337-10
    NCGC00017337-11 NCGC00017337-12 NCGC00017337-13
    NCGC00017337-18 NCGC00090853-01 NCGC00090853-02
    NCGC00090853-03 NCGC00090853-04 NCGC00090853-06
    NCGC00090853-07 NCGC00090853-08 NCGC00090853-09
    NCGC00090853-10 NCGC00090853-11 NCGC00090853-12
    NCGC00257869-01 NCI-C56564 NGX 4010
    NGX-1998 NGX-3781 NGX-4010
    NGX-7325 NSC 56353 NSC-56353
    NSC-757844 NSC56353 NSC757844
    NSC_2548 Nonenamide, 8-methyl-N-vanillyl-, (E)- Nonenamide, N-((4-hydroxy-3-methoxyphenyl)methyl)-8 -methyl-, (E)-
    Pharmakon1600-01501128 Prestwick2_000879 Prestwick3_000879
    Prestwick_204 Q273169 Qutenza
    Qutenza;Vanilloid RTC-030399 S07O44R1ZM
    SBI-0052593.P002 SC-19636 SCHEMBL8085
    SCHEMBL8086 SDCCGMLS-0066678.P001 SMP2_000337
    SMR000718774 SPECTRUM1501128 SR-05000001861
    SR-05000001861-1 SR-05000001861-4 SR-05000001861-5
    SR-05000001861-6 SR-05000001861-9 ST057183
    STL372889 Spectrum5_000538 Styptysat
    TC-030399 TNP00277 TQ-1018
    Tox21_110817 Tox21_200315 Transacin
    UNII-S07O44R1ZM UNII-UW86K581WY component YKPUWZUDDOIDPM-SOFGYWHQSA-N UPCMLD-DP092
    UPCMLD-DP092:001 UPCMLD-DP092:002 Vanilloid
    W-5044 YKPUWZUDDOIDPM-SOFGYWHQSA-N ZINC1530575
    ZOSTRIX (TN) Zostrix Zostrix HP
    [(E)-N-(4-Hydroxy-3-methoxyphenyl)methyl]-8-methyl-6-nonenamide capsacin(E) depletes Substance P
    epsilon-capsaicin n-(4-hydroxy-3-methoxybenzyl)-8-methyl-6-nonenamide neurotoxic
    trans-8-Methyl-N-vanillyl-6-nonenamide trans-Capsaicin trans-Capsaicin-d3
    trans-N-((4-Hydroxy-3-methoxyphenyl)methyl)-8-methyl-6-nonenamide

    DrugBank Name Capsaicin
    DrugBank DB06774
    CAS Number 1217899-52-9, 25775-90-0, 404-86-4, 7553-53-9
    PubChem Compound 1548943
    KEGG Compound ID C06866
    KEGG Drug D00250
    PubChem.Substance 347827793
    ChEBI 3374
    ChemSpider 1265957
    BindingDB 20461.0
    Wikipedia Capsaicin
    HET 4DY
    DPD 3610