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 |
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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 |
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 |
---|---|---|
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 |
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Curcumin prevents adriamycin nephrotoxicity in rats. | 2000 Jan |
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Steroid hormone activity of flavonoids and related compounds. | 2000 Jul |
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Arsenite induces apoptosis of murine T lymphocytes through membrane raft-linked signaling for activation of c-Jun amino-terminal kinase. | 2000 Oct 15 |
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Curcuma longa (turmeric). Monograph. | 2001 Sep |
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Hepatobiliary clearance of labelled mebrofenin in normal and D-galactosamine HCl-induced hepatitis rats and the protective effect of turmeric extract. | 2003 Jul |
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Hepatoprotective effect of sesquiterpenes in turmeric. | 2004 |
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Curcumin, a major constituent of turmeric, corrects cystic fibrosis defects. | 2004 Apr 23 |
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[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 |
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Curcumin-induced apoptosis in scleroderma lung fibroblasts: role of protein kinase cepsilon. | 2004 Jul |
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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 |
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Anti-apoptotic effects of curcumin on photosensitized human epidermal carcinoma A431 cells. | 2004 May 1 |
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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 |
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Amyloid-beta peptide binds with heme to form a peroxidase: relationship to the cytopathologies of Alzheimer's disease. | 2006 Feb 28 |
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Turmeric and curcumin modulate the conjugation of 1-naphthol in Caco-2 cells. | 2006 Jul |
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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 |
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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
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
admin
on
Edited
Mon Mar 31 17:48:46 GMT 2025
by
admin
on
Mon Mar 31 17:48:46 GMT 2025
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Record UNII |
IT942ZTH98
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Record Status |
Validated (UNII)
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Record Version |
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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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PRIMARY | RxNorm | ||
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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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Related Record | Type | Details | ||
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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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Related Record | Type | Details | ||
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ACTIVE MOIETY |