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+
| 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
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
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 |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| 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 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
87.7 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30666922/ |
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1360 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30666922/ |
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
6.01 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30666922/ |
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
| Dose | Population | Adverse 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... |
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) Sources: 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) |
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) Sources: Headache (not serious, 1 patient) Blood bilirubin increased (not serious, 1 patient) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| 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: |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| moderate [IC50 24.5 uM] | ||||
| moderate [IC50 40 uM] | ||||
| moderate [IC50 50.3 uM] | ||||
Page: 103.0 |
no | |||
Page: 735.0 |
no | |||
Page: 275.0 |
no | |||
| weak [IC50 172.05 uM] | ||||
Page: 16.0 |
yes [IC50 1.63 uM] | |||
Page: 58.0 |
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 victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
Page: 146 | 731 |
inconclusive | |||
| major | ||||
| major | ||||
| major | ||||
| minor | ||||
| minor | ||||
| minor | ||||
| no | ||||
| weak | ||||
| weak | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes |
Tox targets
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
Page: 26.0 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Increased expression of the MGMT repair protein mediated by cysteine prodrugs and chemopreventative natural products in human lymphocytes and tumor cell lines. | 2007-02 |
|
| Curcumin induces changes in expression of genes involved in cholesterol homeostasis. | 2007-02 |
|
| Disruption of transforming growth factor-beta signaling by curcumin induces gene expression of peroxisome proliferator-activated receptor-gamma in rat hepatic stellate cells. | 2007-01 |
|
| Curcumin regulates signal transducer and activator of transcription (STAT) expression in K562 cells. | 2006-11-30 |
|
| Curcumin inhibits hypoxia-inducible factor-1 by degrading aryl hydrocarbon receptor nuclear translocator: a mechanism of tumor growth inhibition. | 2006-11 |
|
| Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods. | 2006-11 |
|
| Inhibitory effect of curcumin on nitric oxide production from lipopolysaccharide-activated primary microglia. | 2006-10-19 |
|
| TPA-induced up-regulation of activator protein-1 can be inhibited or enhanced by analogs of the natural product curcumin. | 2006-10-16 |
|
| Protective effect of dietary curcumin and capsaicin on induced oxidation of low-density lipoprotein, iron-induced hepatotoxicity and carrageenan-induced inflammation in experimental rats. | 2006-10 |
|
| Jak3- and JNK-dependent vascular endothelial growth factor expression in cutaneous T-cell lymphoma. | 2006-10 |
|
| Curcumin sensitizes tumor necrosis factor-related apoptosis-inducing ligand (TRAIL)-mediated apoptosis through CHOP-independent DR5 upregulation. | 2006-10 |
|
| Curcumin inhibits neurotensin-mediated interleukin-8 production and migration of HCT116 human colon cancer cells. | 2006-09-15 |
|
| Hydrogen peroxide-mediated downregulation of matrix metalloprotease-2 in indomethacin-induced acute gastric ulceration is blocked by melatonin and other antioxidants. | 2006-09-15 |
|
| Modification by curcumin of mutagenic activation of carcinogenic N-nitrosamines by extrahepatic cytochromes P-450 2B1 and 2E1 in rats. | 2006-09 |
|
| Curcumin regulated shift from Th1 to Th2 in trinitrobenzene sulphonic acid-induced chronic colitis. | 2006-08 |
|
| Curcumin inhibits trinitrobenzene sulphonic acid-induced colitis in rats by activation of peroxisome proliferator-activated receptor gamma. | 2006-08 |
|
| Curcumin protects against radiation-induced acute and chronic cutaneous toxicity in mice and decreases mRNA expression of inflammatory and fibrogenic cytokines. | 2006-07-01 |
|
| A specific method for measurement of equine active myeloperoxidase in biological samples and in in vitro tests. | 2006-07 |
|
| Turmeric and curcumin modulate the conjugation of 1-naphthol in Caco-2 cells. | 2006-07 |
|
| Curcumin decreases binding of Shiga-like toxin-1B on human intestinal epithelial cell line HT29 stimulated with TNF-alpha and IL-1beta: suppression of p38, JNK and NF-kappaB p65 as potential targets. | 2006-07 |
|
| Curcumin-attenuated trinitrobenzene sulphonic acid induces chronic colitis by inhibiting expression of cyclooxygenase-2. | 2006-06-28 |
|
| Inhibition of homodimerization of Toll-like receptor 4 by curcumin. | 2006-06-28 |
|
| Silencing of the human microsomal glucose-6-phosphate translocase induces glioma cell death: potential new anticancer target for curcumin. | 2006-06-26 |
|
| Curcumin attenuates thermal hyperalgesia in a diabetic mouse model of neuropathic pain. | 2006-05-01 |
|
| Immediate and delayed treatments with curcumin prevents forebrain ischemia-induced neuronal damage and oxidative insult in the rat hippocampus. | 2006-05 |
|
| Indomethacin inactivates gastric peroxidase to induce reactive-oxygen-mediated gastric mucosal injury and curcumin protects it by preventing peroxidase inactivation and scavenging reactive oxygen. | 2006-04-15 |
|
| Selective protection of curcumin against carbon tetrachloride-induced inactivation of hepatic cytochrome P450 isozymes in rats. | 2006-04-04 |
|
| The antioxidants curcumin and quercetin inhibit inflammatory processes associated with arthritis. | 2006-04 |
|
| Interleukin-18 induces the production of vascular endothelial growth factor (VEGF) in rheumatoid arthritis synovial fibroblasts via AP-1-dependent pathways. | 2006-03-15 |
|
| Turmeric extracts containing curcuminoids prevent experimental rheumatoid arthritis. | 2006-03 |
|
| Amyloid-beta peptide binds with heme to form a peroxidase: relationship to the cytopathologies of Alzheimer's disease. | 2006-02-28 |
|
| Piceatannol upregulates endothelial heme oxygenase-1 expression via novel protein kinase C and tyrosine kinase pathways. | 2006-02 |
|
| Curcuminoids purified from turmeric powder modulate the function of human multidrug resistance protein 1 (ABCC1). | 2006-02 |
|
| Curcumin (diferuloylmethane) down-regulates expression of cell proliferation and antiapoptotic and metastatic gene products through suppression of IkappaBalpha kinase and Akt activation. | 2006-01 |
|
| Synergistic inhibitory effects of curcumin and 5-fluorouracil on the growth of the human colon cancer cell line HT-29. | 2006 |
|
| Induction of cytotoxicity and apoptosis and inhibition of cyclooxygenase-2 gene expression, by curcumin and its analog, alpha-diisoeugenol. | 2005-11-29 |
|
| Inhibition of nuclear translocation of nuclear factor-kappaB despite lack of functional IkappaBalpha protein overcomes multiple defects in apoptosis signaling in human B-cell malignancies. | 2005-11-15 |
|
| Regulation of LDL receptor expression by the effect of curcumin on sterol regulatory element pathway. | 2005-11-03 |
|
| Effect of artemisinin/artesunate as inhibitors of hepatitis B virus production in an "in vitro" replicative system. | 2005-11 |
|
| Curcumin suppresses the paclitaxel-induced nuclear factor-kappaB pathway in breast cancer cells and inhibits lung metastasis of human breast cancer in nude mice. | 2005-10-15 |
|
| Effects of nuclear factor-kappaB inhibitors and its implication on natural killer T-cell lymphoma cells. | 2005-10 |
|
| Curcumin (diferuloylmethane) inhibits constitutive NF-kappaB activation, induces G1/S arrest, suppresses proliferation, and induces apoptosis in mantle cell lymphoma. | 2005-09-01 |
|
| Expression profiles of apoptotic genes induced by curcumin in human breast cancer and mammary epithelial cell lines. | 2005-08-17 |
|
| Combined effects of GSTP1 and MRP1 in melanoma drug resistance. | 2005-07-25 |
|
| Antitumor effects of curcumin, alone or in combination with cisplatin or doxorubicin, on human hepatic cancer cells. Analysis of their possible relationship to changes in NF-kB activation levels and in IAP gene expression. | 2005-06-16 |
|
| Inhibition of multidrug resistance proteins MRP1 and MRP2 by a series of alpha,beta-unsaturated carbonyl compounds. | 2005-06-15 |
|
| CSN5/Jab1 is involved in ligand-dependent degradation of estrogen receptor {alpha} by the proteasome. | 2005-06 |
|
| Antioxidant and antigenotoxic effects of plant cell wall hydroxycinnamic acids in cultured HT-29 cells. | 2005-06 |
|
| Preventive and therapeutic effects of NF-kappaB inhibitor curcumin in rats colitis induced by trinitrobenzene sulfonic acid. | 2005-03-28 |
|
| Protective role of aqueous turmeric extract against mutagenicity of direct-acting carcinogens as well as benzo [alpha] pyrene-induced genotoxicity and carcinogenicity. | 1992 |
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.
| Substance Class |
Chemical
Created
by
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on
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Mon Mar 31 17:48:46 GMT 2025
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on
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| Record UNII |
IT942ZTH98
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| Record Status |
Validated (UNII)
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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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| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
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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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822
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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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3962
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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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969516
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IT942ZTH98
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1151855
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SUB29071
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4334
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DERIVATIVE -> PARENT |
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TRANSPORTER -> INHIBITOR | |||
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TRANSPORTER -> INHIBITOR | |||
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TRANSPORTER -> INHIBITOR |
| Related Record | Type | Details | ||
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METABOLITE -> PARENT |
IN-VIVO
PLASMA
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METABOLITE -> PARENT |
IN-VIVO
URINE
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METABOLITE -> PARENT |
Significant Metabolite
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METABOLITE -> PARENT |
IN-VIVO
PLASMA
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METABOLITE -> PARENT |
Significant Metabolite
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METABOLITE -> PARENT |
Significant Metabolite
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METABOLITE -> PARENT |
IN-VIVO
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METABOLITE -> PARENT |
Significant Metabolite
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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
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METABOLITE -> PARENT |
IN-VIVO
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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
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ACTIVE MOIETY |