U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

Details

Stereochemistry ACHIRAL
Molecular Formula C21H20O6
Molecular Weight 368.3799
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of CURCUMIN

SMILES

COC1=CC(\C=C\C(=O)CC(=O)\C=C\C2=CC(OC)=C(O)C=C2)=CC=C1O

InChI

InChIKey=VFLDPWHFBUODDF-FCXRPNKRSA-N
InChI=1S/C21H20O6/c1-26-20-11-14(5-9-18(20)24)3-7-16(22)13-17(23)8-4-15-6-10-19(25)21(12-15)27-2/h3-12,24-25H,13H2,1-2H3/b7-3+,8-4+

HIDE SMILES / InChI

Molecular Formula C21H20O6
Molecular Weight 368.3799
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 2
Optical Activity NONE

Curcumin is a bright yellow chemical produced by some plants, for example, it is the principal curcuminoid of turmeric. It is sold as a food flavoring, food colorant, herbal supplement, and cosmetic ingredient. Although curcumin has been widely studied it has not been officially endorsed for any pharmaceutical use due to issues of stability and bioavailability; although it continues to b marketed as a health supplement. Curcumin has been investigated for the treatment of a number of cancers, asthma, mucositis, schizophrenia, mild cognitive impairment, and depression.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P11473
Gene ID: 7421.0
Gene Symbol: VDR
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
87.7 ng/mL
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CURCUMIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
1360 ng × h/mL
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CURCUMIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
6.01 h
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CURCUMIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
12 g single, oral
Studied dose
Dose: 12 g
Route: oral
Route: single
Dose: 12 g
Sources:
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: M+F
Food Status: FED
Sources:
Other AEs: Diarrhea...
Other AEs:
Diarrhea (1, 1 pt)
Sources:
8 g 1 times / day multiple, oral
Studied dose
Dose: 8 g, 1 times / day
Route: oral
Route: multiple
Dose: 8 g, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Other AEs: Cardiac disorders, Gastrointestinal disorders...
Other AEs:
Cardiac disorders (serious, 4 patients)
Gastrointestinal disorders (serious, 11 patient)
General disorders (serious, 4 patients)
Infection (serious, 1 patient)
Metabolism and nutrition disorders (serious, 3 patients)
Musculoskeletal and connective tissue disorders (serious, 1 patient)
Nervous system disorders (serious, 3 patients)
Renal and urinary disorders (serious, 1 patient)
Sources:
1000 mg 1 times / day steady, oral
Studied dose
Dose: 1000 mg, 1 times / day
Route: oral
Route: steady
Dose: 1000 mg, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: FASTED
Sources:
180 mg 2 times / day steady, oral
Studied dose
Dose: 180 mg, 2 times / day
Route: oral
Route: steady
Dose: 180 mg, 2 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
500 mg 2 times / day steady, oral
Studied dose
Dose: 500 mg, 2 times / day
Route: oral
Route: steady
Dose: 500 mg, 2 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Sources:
Other AEs: Nausea, Headache...
Other AEs:
Nausea (not serious, 1 patient)
Headache (not serious, 1 patient)
Blood bilirubin increased (not serious, 1 patient)
Sources:
AEs

AEs

AESignificanceDosePopulation
Diarrhea 1, 1 pt
12 g single, oral
Studied dose
Dose: 12 g
Route: oral
Route: single
Dose: 12 g
Sources:
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: M+F
Food Status: FED
Sources:
Infection serious, 1 patient
8 g 1 times / day multiple, oral
Studied dose
Dose: 8 g, 1 times / day
Route: oral
Route: multiple
Dose: 8 g, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Musculoskeletal and connective tissue disorders serious, 1 patient
8 g 1 times / day multiple, oral
Studied dose
Dose: 8 g, 1 times / day
Route: oral
Route: multiple
Dose: 8 g, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Renal and urinary disorders serious, 1 patient
8 g 1 times / day multiple, oral
Studied dose
Dose: 8 g, 1 times / day
Route: oral
Route: multiple
Dose: 8 g, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Gastrointestinal disorders serious, 11 patient
8 g 1 times / day multiple, oral
Studied dose
Dose: 8 g, 1 times / day
Route: oral
Route: multiple
Dose: 8 g, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Metabolism and nutrition disorders serious, 3 patients
8 g 1 times / day multiple, oral
Studied dose
Dose: 8 g, 1 times / day
Route: oral
Route: multiple
Dose: 8 g, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Nervous system disorders serious, 3 patients
8 g 1 times / day multiple, oral
Studied dose
Dose: 8 g, 1 times / day
Route: oral
Route: multiple
Dose: 8 g, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Cardiac disorders serious, 4 patients
8 g 1 times / day multiple, oral
Studied dose
Dose: 8 g, 1 times / day
Route: oral
Route: multiple
Dose: 8 g, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
General disorders serious, 4 patients
8 g 1 times / day multiple, oral
Studied dose
Dose: 8 g, 1 times / day
Route: oral
Route: multiple
Dose: 8 g, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Blood bilirubin increased not serious, 1 patient
500 mg 2 times / day steady, oral
Studied dose
Dose: 500 mg, 2 times / day
Route: oral
Route: steady
Dose: 500 mg, 2 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Sources:
Headache not serious, 1 patient
500 mg 2 times / day steady, oral
Studied dose
Dose: 500 mg, 2 times / day
Route: oral
Route: steady
Dose: 500 mg, 2 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Sources:
Nausea not serious, 1 patient
500 mg 2 times / day steady, oral
Studied dose
Dose: 500 mg, 2 times / day
Route: oral
Route: steady
Dose: 500 mg, 2 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Sources:
OverviewDrug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
moderate [IC50 24.5 uM]
moderate [IC50 40 uM]
moderate [IC50 50.3 uM]
no
no
no
weak [IC50 172.05 uM]
yes [IC50 1.63 uM]
yes [IC50 10.0916 uM]
yes [IC50 16.3 uM]
yes [IC50 2.2 uM]
yes [IC50 2.6 uM]
yes [IC50 4.3 uM]
yes [IC50 62 uM]
yes [Inhibition 10 uM]
yes [Inhibition 10 uM]
yes
Drug as victimTox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Effects of Curcuma Longa on proliferation of cultured bovine smooth muscle cells and on expression of low density lipoprotein receptor in cells.
1999 Apr
Pulmonary protective effects of curcumin against paraquat toxicity.
2000
Synthesis and HIV-1 integrase inhibitory activities of caffeoylglucosides.
2000 Aug 21
Curcumin prevents adriamycin nephrotoxicity in rats.
2000 Jan
Steroid hormone activity of flavonoids and related compounds.
2000 Jul
Arsenite induces apoptosis of murine T lymphocytes through membrane raft-linked signaling for activation of c-Jun amino-terminal kinase.
2000 Oct 15
Curcuma longa (turmeric). Monograph.
2001 Sep
Hepatobiliary clearance of labelled mebrofenin in normal and D-galactosamine HCl-induced hepatitis rats and the protective effect of turmeric extract.
2003 Jul
Hepatoprotective effect of sesquiterpenes in turmeric.
2004
Curcumin, a major constituent of turmeric, corrects cystic fibrosis defects.
2004 Apr 23
[Modulation of intestinal mucosal inflammatory factors by curcumin in rats with colitis].
2004 Dec
All-trans retinoic acid potentiates Taxotere-induced cell death mediated by Jun N-terminal kinase in breast cancer cells.
2004 Jan 15
Curcumin-induced apoptosis in scleroderma lung fibroblasts: role of protein kinase cepsilon.
2004 Jul
Induction of manganese-superoxide dismutase by YS 51, a synthetic 1-(beta-naphtylmethyl)6,7-dihydroxy- 1,2,3,4-tetrahydroisoquinoline alkaloid: implication for anti-inflammatory actions.
2004 Jun
Therapeutic potential of curcumin in prostate cancer--V: Interference with the osteomimetic properties of hormone refractory C4-2B prostate cancer cells.
2004 Jun 15
Anti-apoptotic effects of curcumin on photosensitized human epidermal carcinoma A431 cells.
2004 May 1
Curcumin inhibits formation of amyloid beta oligomers and fibrils, binds plaques, and reduces amyloid in vivo.
2005 Feb 18
Curcuminoids and sesquiterpenoids in turmeric (Curcuma longa L.) suppress an increase in blood glucose level in type 2 diabetic KK-Ay mice.
2005 Feb 23
Indomethacin inactivates gastric peroxidase to induce reactive-oxygen-mediated gastric mucosal injury and curcumin protects it by preventing peroxidase inactivation and scavenging reactive oxygen.
2006 Apr 15
Curcuminoids purified from turmeric powder modulate the function of human multidrug resistance protein 1 (ABCC1).
2006 Feb
Amyloid-beta peptide binds with heme to form a peroxidase: relationship to the cytopathologies of Alzheimer's disease.
2006 Feb 28
Turmeric and curcumin modulate the conjugation of 1-naphthol in Caco-2 cells.
2006 Jul
Turmeric extracts containing curcuminoids prevent experimental rheumatoid arthritis.
2006 Mar
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.
2006 Nov
Protective effect of dietary curcumin and capsaicin on induced oxidation of low-density lipoprotein, iron-induced hepatotoxicity and carrageenan-induced inflammation in experimental rats.
2006 Oct
TPA-induced up-regulation of activator protein-1 can be inhibited or enhanced by analogs of the natural product curcumin.
2006 Oct 16
Curcumin inhibits neurotensin-mediated interleukin-8 production and migration of HCT116 human colon cancer cells.
2006 Sep 15
Increased expression of the MGMT repair protein mediated by cysteine prodrugs and chemopreventative natural products in human lymphocytes and tumor cell lines.
2007 Feb
Curcumin induces changes in expression of genes involved in cholesterol homeostasis.
2007 Feb
Disruption of transforming growth factor-beta signaling by curcumin induces gene expression of peroxisome proliferator-activated receptor-gamma in rat hepatic stellate cells.
2007 Jan
Patents

Sample Use Guides

Patients with a history of stable persistent asthma and allergic sensitivities received oral supplementation of 2000 mg of curcumin.
Route of Administration: Oral
Human colorectal adenocarcinoma cells (Caco-2) were grown at 37 deg-C under a 5% CO2 were plated at a density of 40,000 cells per well in minimum essential medium, supplemented with 20% fetal bovine serum, 1 mM sodium pyruvate, 0.1 mM nonessential amino acids, 100 units/mL penicillin and 100 micro-g/mL streptomycin. Transfection was conducted with each well receiving 1 μL of Lipofectamine Reagent, 2 μL of Plus Reagent, 500 ng of pTZ18U carrier DNA plasmid, and 20 ng of pRL-null. Each well also received 250 ng of pLuc-MCS plasmid containing an oligonucleotide with two copies of a nuclear receptor responsive element upstream of the firefly luciferase gene. In addition to the responsive element reporter constructs, cells were also cotransfected with 50 ng of a pSG5-based expression plasmid containing the appropriate nuclear receptor. The cells received both 50 ng of pSG5-VDR (vitamin D receptor), and 20 ng of pSG5-RXRα when the VDRE-containing reporter was employed. The cells were treated with known nuclear receptor ligands or curcumin (6.7 and 10 microM), 18 hours after completion of transfection; treatment times ranged from 24 to 30 hours. After incubation with ligands, cells were collected and the amount of reporter gene product (luciferase) produced in the cells was measured using the Dual-Luciferase® Reporter Assay System. Cells treated with 6.7 and 10 microM curcumin demonstrated a dose-dependent increase in the level of transcription of the VDRE-reporter plasmid of 2.1 and 5.0 fold respectively.
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:48:46 GMT 2025
Edited
by admin
on Mon Mar 31 17:48:46 GMT 2025
Record UNII
IT942ZTH98
Record Status Validated (UNII)
Record Version
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Name Type Language
CI 75300
INCI  
INCI  
Preferred Name English
CURCUMIN
HSDB   INCI   MART.   MI   USP-RS   WHO-DD  
INCI  
Official Name English
CURCUMIN [MI]
Common Name English
CURCUMIN [USP-RS]
Common Name English
(1E,6E)-1,7-BIS(4-HYDROXY-3-METHOXYPHENYL)-1,6-HEPTADIENE-3,5-DIONE
Systematic Name English
C.I. NATURAL YELLOW 3
Common Name English
E-100
Code English
MERITA EARTH
Common Name English
C.I. 75300
Common Name English
E 100
Code English
TURMERIC YELLOW
Common Name English
HALDAR
Common Name English
JIANGHUANGSU
Common Name English
INS-100(I)
Code English
Curcumin [WHO-DD]
Common Name English
CURCUMIN [HSDB]
Common Name English
KURKUM
Common Name English
E100
Code English
NANOCURC
Common Name English
NSC-687842
Code English
LIPOCURC
Common Name English
KACHA HALDI
Common Name English
CURCUMIN (CONSTITUENT OF TURMERIC) [DSC]
Common Name English
INS NO. 100(I)
Code English
1,7-BIS-(4-HYDROXY-3-METHOXYPHENYL)-HEPTA-1,6-DIENE-3,5-DIONE
Systematic Name English
CURCUMIN E100
Common Name English
CURCUMIN [MART.]
Common Name English
DIFERULOYLMETHANE
Common Name English
NSC-32982
Code English
Classification Tree Code System Code
FDA ORPHAN DRUG 167603
Created by admin on Mon Mar 31 17:48:46 GMT 2025 , Edited by admin on Mon Mar 31 17:48:46 GMT 2025
NCI_THESAURUS C1323
Created by admin on Mon Mar 31 17:48:46 GMT 2025 , Edited by admin on Mon Mar 31 17:48:46 GMT 2025
CODEX ALIMENTARIUS (GSFA) INS-100(I)
Created by admin on Mon Mar 31 17:48:46 GMT 2025 , Edited by admin on Mon Mar 31 17:48:46 GMT 2025
JECFA EVALUATION INS-100(I)
Created by admin on Mon Mar 31 17:48:46 GMT 2025 , Edited by admin on Mon Mar 31 17:48:46 GMT 2025
DSLD 2377 (Number of products:310)
Created by admin on Mon Mar 31 17:48:46 GMT 2025 , Edited by admin on Mon Mar 31 17:48:46 GMT 2025
NCI_THESAURUS C1967
Created by admin on Mon Mar 31 17:48:46 GMT 2025 , Edited by admin on Mon Mar 31 17:48:46 GMT 2025
Code System Code Type Description
WIKIPEDIA
CURCUMIN
Created by admin on Mon Mar 31 17:48:46 GMT 2025 , Edited by admin on Mon Mar 31 17:48:46 GMT 2025
PRIMARY
CAS
458-37-7
Created by admin on Mon Mar 31 17:48:46 GMT 2025 , Edited by admin on Mon Mar 31 17:48:46 GMT 2025
PRIMARY
EU FOOD ADDITIVES
E100(I)
Created by admin on Mon Mar 31 17:48:46 GMT 2025 , Edited by admin on Mon Mar 31 17:48:46 GMT 2025
PRIMARY
MESH
D003474
Created by admin on Mon Mar 31 17:48:46 GMT 2025 , Edited by admin on Mon Mar 31 17:48:46 GMT 2025
PRIMARY
EPA CompTox
DTXSID8031077
Created by admin on Mon Mar 31 17:48:46 GMT 2025 , Edited by admin on Mon Mar 31 17:48:46 GMT 2025
PRIMARY
NCI_THESAURUS
C401
Created by admin on Mon Mar 31 17:48:46 GMT 2025 , Edited by admin on Mon Mar 31 17:48:46 GMT 2025
PRIMARY
DRUG BANK
DB11672
Created by admin on Mon Mar 31 17:48:46 GMT 2025 , Edited by admin on Mon Mar 31 17:48:46 GMT 2025
PRIMARY
GRAS Notification (GRN No.)
822
Created by admin on Mon Mar 31 17:48:46 GMT 2025 , Edited by admin on Mon Mar 31 17:48:46 GMT 2025
PRIMARY
DAILYMED
IT942ZTH98
Created by admin on Mon Mar 31 17:48:46 GMT 2025 , Edited by admin on Mon Mar 31 17:48:46 GMT 2025
PRIMARY
ECHA (EC/EINECS)
207-280-5
Created by admin on Mon Mar 31 17:48:46 GMT 2025 , Edited by admin on Mon Mar 31 17:48:46 GMT 2025
PRIMARY
SMS_ID
100000093154
Created by admin on Mon Mar 31 17:48:46 GMT 2025 , Edited by admin on Mon Mar 31 17:48:46 GMT 2025
PRIMARY
RXCUI
2955
Created by admin on Mon Mar 31 17:48:46 GMT 2025 , Edited by admin on Mon Mar 31 17:48:46 GMT 2025
PRIMARY RxNorm
GRAS Notification (GRN No.)
686
Created by admin on Mon Mar 31 17:48:46 GMT 2025 , Edited by admin on Mon Mar 31 17:48:46 GMT 2025
PRIMARY
CHEBI
3962
Created by admin on Mon Mar 31 17:48:46 GMT 2025 , Edited by admin on Mon Mar 31 17:48:46 GMT 2025
PRIMARY
EU FOOD ADDITIVES
E 100
Created by admin on Mon Mar 31 17:48:46 GMT 2025 , Edited by admin on Mon Mar 31 17:48:46 GMT 2025
PRIMARY
MERCK INDEX
m3933
Created by admin on Mon Mar 31 17:48:46 GMT 2025 , Edited by admin on Mon Mar 31 17:48:46 GMT 2025
PRIMARY Merck Index
NSC
687842
Created by admin on Mon Mar 31 17:48:46 GMT 2025 , Edited by admin on Mon Mar 31 17:48:46 GMT 2025
PRIMARY
NSC
32982
Created by admin on Mon Mar 31 17:48:46 GMT 2025 , Edited by admin on Mon Mar 31 17:48:46 GMT 2025
PRIMARY
PUBCHEM
969516
Created by admin on Mon Mar 31 17:48:46 GMT 2025 , Edited by admin on Mon Mar 31 17:48:46 GMT 2025
PRIMARY
FDA UNII
IT942ZTH98
Created by admin on Mon Mar 31 17:48:46 GMT 2025 , Edited by admin on Mon Mar 31 17:48:46 GMT 2025
PRIMARY
RS_ITEM_NUM
1151855
Created by admin on Mon Mar 31 17:48:46 GMT 2025 , Edited by admin on Mon Mar 31 17:48:46 GMT 2025
PRIMARY
EVMPD
SUB29071
Created by admin on Mon Mar 31 17:48:46 GMT 2025 , Edited by admin on Mon Mar 31 17:48:46 GMT 2025
PRIMARY
HSDB
4334
Created by admin on Mon Mar 31 17:48:46 GMT 2025 , Edited by admin on Mon Mar 31 17:48:46 GMT 2025
PRIMARY
Related Record Type Details
DERIVATIVE -> PARENT
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
Related Record Type Details
METABOLITE -> PARENT
IN-VIVO
PLASMA
METABOLITE -> PARENT
IN-VIVO
URINE
METABOLITE -> PARENT
Significant Metabolite
METABOLITE -> PARENT
IN-VIVO
PLASMA
METABOLITE -> PARENT
Significant Metabolite
METABOLITE -> PARENT
Significant Metabolite
METABOLITE -> PARENT
IN-VIVO
METABOLITE -> PARENT
Significant Metabolite
METABOLITE -> PARENT
Unit: mcg/mL; Fraction of curcumin glucuronide in plasma at Cmax after administration of 10g curcumin (n=6); Total curcumin: 3.10 +/- 0.60 mcg/mL
IN-VIVO
PLASMA
METABOLITE -> PARENT
IN-VIVO
METABOLITE -> PARENT
Unit: mcg/mL; Fraction of curcumin sulfate in plasma at Cmax after administration of 12 g curcumin; Total curcumin: 2.27 +/- 1.17 mcg/mL
IN-VIVO
PLASMA
Related Record Type Details
ACTIVE MOIETY