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Drug

D0859 | curcumin

Molecular Formula C21H20O6
Molecular Weight 368.4
Structure
State solid
Clearance No pharmacokinetic data available.
Volume of distribution Following oral administration of radio-labelled curcumin to rats, radioactivity was detected in the liver and kidneys [F114].
Route of elimination Following oral administration of curcumin to rats at a dose of 1 g/kg bw, about 75% of dose was excreted in the faeces and only traces of the compound was detected in the urine [F114]. When a single 400 mg dose of curcumin was administered orally to rats, about 60% was absorbed and 40% was excreted unchanged in the faeces over an period of 5 days [F114]. Intraperitoneal administration resulted in fecal excretion of 73% and biliary excretion of 11% [F114].
Protein binding No pharmacokinetic data available.
Half life No pharmacokinetic data available.
Absorption Curcumin displays poor absorption into the gastrointestinal tract. In a rat study, oral administration of a single dose of 2 g of curcumin resulted in a plasma concentration of less than 5 μg/mL, indicating poor absorption from the gut [F114].

Toxicity Dose Time Species Model Method Action Positive criterion Reference
MEMBRANE POTENTIAL 1.31±1.03 human qHTS-HepG2 MMP assay decrease IC50 163
MEMBRANE POTENTIAL 2.51 human HepG2 MMP assay decrease IC50 163
MEMBRANE POTENTIAL 11.60±9.87 rat hepatocytes MMP assay decrease IC50 163
MEMBRANE POTENTIAL > 200 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 > 200 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 > 200 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
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 > 200 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 > 200 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 54 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.


H304 (100%): May be fatal if swallowed and enters airways [Danger Aspiration hazard]


H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]


H412 (100%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]


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.


 P261, P272, P273, P280, P301+P310, P302+P352, P321, P331, P333+P313, P363, P405, and P501; (The corresponding statement to each P-code can be found at the GHS Classification page.)
Warning

Aggregated GHS information provided by 285 companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.


Reported as not meeting GHS hazard criteria by 12 of 285 companies. For more detailed information, please visit ECHA C&L website


Of the 9 notification(s) provided by 273 of 285 companies with hazard statement code(s):


H315 (99.63%): Causes skin irritation [Warning Skin corrosion/irritation]


H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]


H335 (99.27%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure


Respiratory tract 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.


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

Organism Test type Route Dose (normalized dose) Effect Source
mouse LD50 intraperitoneal 540mg/kg (540mg/kg) Yakugaku Zasshi. Journal of Pharmacy. Vol. 81, Pg. 659, 1961.
rat LD50 oral 1650mg/kg (1650mg/kg) Toxicology and Applied Pharmacology. Vol. 1, Pg. 240, 1959.
rat LD50 intraperitoneal 634mg/kg (634mg/kg) Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 62, Pg. 11, 1966.
dog LDLo intravenous 260mg/kg (260mg/kg) National Technical Information Service. Vol. PB282-666,
hamster LD50 oral 1690mg/kg (1690mg/kg) Pharmazie. Vol. 8, Pg. 572, 1953.
mouse LD50 oral 866mg/kg (866mg/kg) Arzneimittel-Forschung. Drug Research. Vol. 28, Pg. 1644, 1978.
mouse LC50 inhalation 33900mg/m3 (33900mg/m3) Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 34(10), Pg. 36, 1969.
guinea pig LD50 oral 1870mg/kg (1870mg/kg) lungs, thorax, or respiration: respiratory depression Toxicology and Applied Pharmacology. Vol. 2, Pg. 23, 1960.
rabbit LD50 subcutaneous 1gm/kg (1000mg/kg) behavioral: convulsions or effect on seizure threshold Arzneimittel-Forschung. Drug Research. Vol. 21, Pg. 719, 1971.
mouse LD50 subcutaneous 1625mg/kg (1625mg/kg) Arzneimittel-Forschung. Drug Research. Vol. 8, Pg. 25, 1958.
man LDLo unreported 74mg/kg (74mg/kg) "Poisoning; Toxicology, Symptoms, Treatments," 2nd ed., Arena, J.M., Springfield, IL, C.C. Thomas, 1970Vol. 2, Pg. 73, 1970.
rabbit LD50 oral 2500mg/kg (2500mg/kg) Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 21(9), Pg. 53, 1977.


  • ((E,E)-1,7-bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione) (1E,4Z,6E)-5-Hydroxy-1,7-bis-(4-hydroxy-3-methoxy-phenyl)-hepta-1,4,6-trien-3-one (1E,6E)-1,7-Bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione
    (1E,6E)-1,7-Bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione # (1E,6E)-1,7-Bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione (1E,6E)-1,7-Bis-(4-hydroxy-3-methoxy-phenyl)-hepta-1,6-diene-3,5-dione
    (1E,6E)-1,7-bis(3-methoxy-4-oxidanyl-phenyl)hepta-1,6-diene-3,5-dione (1E,6E)-1,7-bis(4-hydroxy-3-methoxy-phenyl)hepta-1,6-diene-3,5-dione (1E,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione.
    (1E,6E)-1,7-bis[4-hydroxy-3-(methyloxy)phenyl]hepta-1,6-diene-3,5-dione (1Z,6E)-1,7-Bis-(4-hydroxy-3-methoxy-phenyl)-hepta-1,6-diene-3,5-dione (E,E)-1,7-bis(4-Hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione
    1,3-Di(3-methoxy-4-hydroxystyryl)propanedial 1,5-Di(vanillyliden)acetylaceton 1,5-Divanillyliden-2,4-pentandion
    1,5-dione, 1,7-bis(4-hydroxy-3-methoxyphenyl)- 1,6-Heptadiene-3,5-dione, 1,7-bis(4-hydroxy-3-methoxyphenyl)- 1,6-Heptadiene-3,5-dione, 1,7-bis(4-hydroxy-3-methoxyphenyl)-, (1E,6E)-
    1,6-Heptadiene-3,5-dione, 1,7-bis(4-hydroxy-3-methoxyphenyl)-, (E,E)- 1,7-Bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione 1,7-Bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione
    1,7-Bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione, (E,E)- 1,7-Bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione 1,7-Bis-(4-hydroxy-3-methoxy-phenyl)-hepta-1,6-diene-3,5-dione
    1,7-DI(4-HYDROXY-3-METHOXYPHENYL)HEPTA-1,6-DIENE-3 1,7-bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadien-3,5-dione 1,7-bis(4-hydroxy-3-methoxyphenyl)1,6-heptadiene-3,5-dione
    1,7-bis-(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione 1,9-Bis(4-hydroxy-3-methoxyphenyl)-2,7-nonadiene-4,6-dione 1790-EP2305629A1
    1790-EP2308861A1 2,7-Nonadiene-4,6-dione, 1,9-bis(4-hydroxy-3-methoxyphenyl)- 4-08-00-03697 (Beilstein Handbook Reference)
    458-37-7 458C377 5-Hydroxy-1,7-bis-(4-hydroxy-3-methoxy-phenyl)-hepta-1,4,6-trien-3-one
    5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)-1,4,6-heptatrien-3-one 8024-37-1 91884-86-5
    98% curcurmin) AC-24238 AKOS001305497
    AS-72202 BBL027711 BB_NC-01422
    BCP04695 BCP0726000035 BCP9000557
    BDBM29532 BDBM50067040 BDBM50140172
    BG0601 BIC8500 BIDD:ER0479
    BRD-K07572174-001-02-2 BRD-K07572174-001-19-6 BRD-K07572174-001-22-0
    BRN 2306965 C-230 C.I. 75300
    C.I. Natural Yellow 3 C21H20O6 CAS-458-37-7
    CC0179 CCG-36020 CCG-36107
    CCRIS 3257 CCRIS 5804 CHEBI:3962
    CHEMBL140 CI 75300 CI Natural Yellow 3
    CS-1490 CU-01000001305-2 CURCUMIN (SEE ALSO TUMERIC, OLEORESIN (10105-J))
    Cucurmin Curcuma Curcuma
    Curcuma longa l. oil Curcuma longa l. oleoresin Curcuma longa l. root oil
    Curcuma longa l. root oleoresin Curcuma longa oils Curcuma oil
    Curcuma oil (Curcuma longa) Curcumin Curcumin (Synthetic), 98%
    Curcumin (mixture of curcumin, demethoxycurcumin, and bisdemethoxycurcumin), 98+% Curcumin I Curcumin solution, ~0.1 % (w/v) (in ethanol with 2M HCl (99:1 v/v)), for TLC derivatization;
    Curcumin, >=94% (curcuminoid content), >=80% (Curcumin) Curcumin, United States Pharmacopeia (USP) Reference Standard Curcumin, analytical standard
    Curcumin, from Curcuma longa (Turmeric), powder Curcumin, matrix substance for MALDI-MS, >=99.5% (HPLC) Curcumin, primary pharmaceutical reference standard
    Curcumin,(S) Curcumine Curcurmin
    DB-002681 DB11672 DSSTox_CID_1421
    DSSTox_GSID_31077 DSSTox_RID_78861 DTXSID8031077
    Diferaloylmethane Diferuloylmethane E 100
    E 100 (Dye) EINECS 207-280-5 FEMA No. 3085
    FEMA No. 3086 GP8291 GTPL7000
    Gelbwurz Golden seal HMS2233K04
    HMS3649K06 HSDB 4334 HY-N0005
    Haidr Halad Haldar
    Haldar, Souchet Halud Hydrastis
    IT942ZTH98 Indian saffron Indian turmeric
    J10108 K00009 Kacha haldi
    Kurkumin Kurkumin [Czech] LS-125
    LS-2189 M212 MFCD00008365
    MLS000069631 MLS001148449 Merita earth
    N1839 NCGC00017159-04 NCGC00017159-05
    NCGC00017159-06 NCGC00017159-07 NCGC00017159-09
    NCGC00017159-10 NCGC00017159-11 NCGC00017159-12
    NCGC00023332-03 NCGC00023332-04 NCGC00023332-05
    NCGC00258668-01 NCI-C61325 NSC 32982
    NSC 687842 NSC-32982 NSC32982
    NSC687842 Natural yellow 3 OR24598
    Oil of turmeric Oils, curcuma Opera_ID_1627
    Orange Root PREVENTION 4 (CURCUMIN) (SEE ALSO TUMERIC, OLEORESIN (10105-J)) Q312266
    RTR-032605 SB17248 SBB006495
    SC-17381 SCHEMBL13521974 SCHEMBL8440
    SCHEMBL8441 SMR000058237 SR-01000000149
    SR-01000000149-2 SR-01000000149-5 ST055629
    STL371943 Safran d'Inde Souchet
    TR-032605 TURMERIC, OLEORESIN (CURCUMIN) (SEE ALSO CURCURMIN (458-37-7)) Terra Merita
    Tox21_110803 Tox21_111505 Tox21_201116
    Tu rmeric root oil Tumeric oleoresin Tumeric yellow
    Turmeric Turmeric Turmeric (>98% curcurmin)
    Turmeric extract Turmeric extract (Curcuma longa L.) Turmeric oil
    Turmeric oil (Curcuma longa L.) Turmeric oleoresin Turmeric oleoresin (79%-85% curcumin)
    Turmeric root oil Turmeric root oleoresin Turmeric yellow
    Turmeric, oleoresin UNII-IT942ZTH98 VFLDPWHFBUODDF-FCXRPNKRSA-N
    W-5038 WLN: 1OR BQ E1U1V1V1U1R DQ CO1 Yellow Ginger
    Yellow Root Yellow puccoon Yo-Kin
    ZINC899824 ZX-AT003872 Zlut prirodni 3
    Zlut prirodni 3 [Czech] cMAP_000052 cid_5281767
    cid_969516 curcuma longa l. root oil CO2 extract curcuma longa l. root oil hydrodistilled
    curcumin curouma diferuloylmethan
    kachs haldi safra d'inde trans,trans-Curcumin
    turmeric root oil CO2 extract turmeric root oil hydrodistilled

    DrugBank Name curcumin
    DrugBank DB11672
    CAS Number 1246833-26-0, 458-37-7, 62-44-2, 8024-37-1, 91884-86-5, 94875-80-6
    PubChem Compound 969516
    KEGG Compound ID C10443
    ChEBI 3962
    PharmGKB PA151958596