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
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+
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
Primary Target | Pharmacology | Condition | Potency |
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Target ID: P11473 Gene ID: 7421.0 Gene Symbol: VDR Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/20153625 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Oral administration of a turmeric extract inhibits LDL oxidation and has hypocholesterolemic effects in rabbits with experimental atherosclerosis. | 1999 Dec |
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The effect of curcumin on glutathione-linked enzymes in K562 human leukemia cells. | 1999 Sep 20 |
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Pulmonary protective effects of curcumin against paraquat toxicity. | 2000 |
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Therapeutic potential of curcumin in human prostate cancer-I. curcumin induces apoptosis in both androgen-dependent and androgen-independent prostate cancer cells. | 2000 Aug |
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Differential and special properties of the major human UGT1-encoded gastrointestinal UDP-glucuronosyltransferases enhance potential to control chemical uptake. | 2004 Jan 9 |
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Evidence against the rescue of defective DeltaF508-CFTR cellular processing by curcumin in cell culture and mouse models. | 2004 Sep 24 |
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Gene expression profiling identifies activating transcription factor 3 as a novel contributor to the proapoptotic effect of curcumin. | 2005 Feb |
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Inhibition of multidrug resistance proteins MRP1 and MRP2 by a series of alpha,beta-unsaturated carbonyl compounds. | 2005 Jun 15 |
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Preventive and therapeutic effects of NF-kappaB inhibitor curcumin in rats colitis induced by trinitrobenzene sulfonic acid. | 2005 Mar 28 |
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Expression profiles of apoptotic genes induced by curcumin in human breast cancer and mammary epithelial cell lines. | 2005 Sep-Oct |
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Curcumin inhibits trinitrobenzene sulphonic acid-induced colitis in rats by activation of peroxisome proliferator-activated receptor gamma. | 2006 Aug |
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Piceatannol upregulates endothelial heme oxygenase-1 expression via novel protein kinase C and tyrosine kinase pathways. | 2006 Feb |
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Curcumin protects against radiation-induced acute and chronic cutaneous toxicity in mice and decreases mRNA expression of inflammatory and fibrogenic cytokines. | 2006 Jul 1 |
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Regulation of LDL receptor expression by the effect of curcumin on sterol regulatory element pathway. | 2006 Jul-Aug |
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Silencing of the human microsomal glucose-6-phosphate translocase induces glioma cell death: potential new anticancer target for curcumin. | 2006 Jun 26 |
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Inhibition of homodimerization of Toll-like receptor 4 by curcumin. | 2006 Jun 28 |
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Immediate and delayed treatments with curcumin prevents forebrain ischemia-induced neuronal damage and oxidative insult in the rat hippocampus. | 2006 May |
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Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods. | 2006 Nov |
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Increased expression of the MGMT repair protein mediated by cysteine prodrugs and chemopreventative natural products in human lymphocytes and tumor cell lines. | 2007 Feb |
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Curcumin induces changes in expression of genes involved in cholesterol homeostasis. | 2007 Feb |
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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
In Vivo Use Guide
Sources: https://clinicaltrials.gov/ct2/show/NCT01179256
Patients with a history of stable persistent asthma and allergic sensitivities received oral supplementation of 2000 mg of curcumin.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20153625
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.
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Classification Tree | Code System | Code | ||
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FDA ORPHAN DRUG |
167603
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NCI_THESAURUS |
C1323
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CODEX ALIMENTARIUS (GSFA) |
INS-100(I)
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JECFA EVALUATION |
INS-100(I)
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DSLD |
2377 (Number of products:310)
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NCI_THESAURUS |
C1967
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CURCUMIN
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458-37-7
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E100(I)
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D003474
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DTXSID8031077
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C401
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DB11672
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IT942ZTH98
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207-280-5
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100000093154
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2955
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686
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E 100
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m3933
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687842
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32982
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IT942ZTH98
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1151855
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SUB29071
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4334
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