Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C20H18O5 |
| Molecular Weight | 338.3539 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 2 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=C(O)C=CC(\C=C\C(=O)CC(=O)\C=C\C2=CC=C(O)C=C2)=C1
InChI
InChIKey=HJTVQHVGMGKONQ-LUZURFALSA-N
InChI=1S/C20H18O5/c1-25-20-12-15(6-11-19(20)24)5-10-18(23)13-17(22)9-4-14-2-7-16(21)8-3-14/h2-12,21,24H,13H2,1H3/b9-4+,10-5+
| Molecular Formula | C20H18O5 |
| Molecular Weight | 338.3539 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 2 |
| Optical Activity | NONE |
DescriptionCurator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/27503249 | https://www.ncbi.nlm.nih.gov/pubmed/22546674 | https://www.ncbi.nlm.nih.gov/pubmed/9301668 | https://clinicaltrials.gov/ct2/show/NCT02724202
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/27503249 | https://www.ncbi.nlm.nih.gov/pubmed/22546674 | https://www.ncbi.nlm.nih.gov/pubmed/9301668 | https://clinicaltrials.gov/ct2/show/NCT02724202
Demethoxycurcumin is a derivative or curcumin and represents one of the major active components of curcumin products isolated from Curcumae sp. In preclinical models, Demethoxycurcumin inhibits LPS-induced nitric oxide (NO) production, and expression of iNOS and COX2 in RAW264.7 cells by blocking NF-kB activation. Demethoxycurcumin also inhibits NF-kB dependent iNOS, TNFα and IL-1β expression in LPS-treated rat microglial cells. Demethoxycurcumin suppresses the expression of MMPs and ICAM-1 in MDA-MB-231 human breast cancer cells by inhibition of NF-kB. Demethoxycurcumin is currently in Phase I clinical trials.
Originator
Approval Year
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
85.8 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21856253 |
44.25 mg/kg single, oral dose: 44.25 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
DEMETHOXYCURCUMIN tumor | Mus musculus population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
506.6 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21856253 |
44.25 mg/kg single, oral dose: 44.25 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
DEMETHOXYCURCUMIN tumor | Mus musculus population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
39.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21856253 |
44.25 mg/kg single, oral dose: 44.25 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
DEMETHOXYCURCUMIN tumor | Mus musculus population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Curcumin analogs with altered potencies against HIV-1 integrase as probes for biochemical mechanisms of drug action. | 1997 Sep 12 |
|
| 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 |
|
| Inhibition of multidrug resistance proteins MRP1 and MRP2 by a series of alpha,beta-unsaturated carbonyl compounds. | 2005 Jun 15 |
|
| Curcuminoids purified from turmeric powder modulate the function of human multidrug resistance protein 1 (ABCC1). | 2006 Feb |
|
| Regulation of heme oxygenase-1 expression by demethoxy curcuminoids through Nrf2 by a PI3-kinase/Akt-mediated pathway in mouse beta-cells. | 2007 Sep |
|
| Comparison of suppressive effects of demethoxycurcumin and bisdemethoxycurcumin on expressions of inflammatory mediators in vitro and in vivo. | 2008 Apr |
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| Opposing effects of curcuminoids on serum stimulated and unstimulated angiogenic response. | 2008 Apr |
|
| Comparison of inhibitory potency of three different curcuminoid pigments on nitric oxide and tumor necrosis factor production of rat primary microglia induced by lipopolysaccharide. | 2008 Dec 5 |
|
| Effect of pure curcumin, demethoxycurcumin, and bisdemethoxycurcumin on WT1 gene expression in leukemic cell lines. | 2008 Sep |
|
| Optimized turmeric extracts have potent anti-amyloidogenic effects. | 2009 Dec |
|
| Inhibitory effect of curcuminoids on acetylcholinesterase activity and attenuation of scopolamine-induced amnesia may explain medicinal use of turmeric in Alzheimer's disease. | 2009 Feb |
|
| Curcumin, demethoxycurcumin and bisdemethoxycurcumin differentially inhibit cancer cell invasion through the down-regulation of MMPs and uPA. | 2009 Feb |
|
| Induction of antioxidant enzymes by curcumin and its analogues in human islets: implications in transplantation. | 2009 May |
|
| Isoxazole analogs of curcuminoids with highly potent multidrug-resistant antimycobacterial activity. | 2010 Oct |
|
| Curcuminoids distinctly exhibit antioxidant activities and regulate expression of scavenger receptors and heme oxygenase-1. | 2013 Sep |
|
| Suppression effects of O-demethyldemethoxycurcumin on thapsigargin triggered on endoplasmic reticulum stress in SK-N-SH cells. | 2015 Sep |
Patents
Sample Use Guides
500 mg (95% curcumin, 5% desmethoxycurcumin) twice per day for 2 weeks.
Route of Administration:
Oral
Cytotoxicity of compound 7 (Demethoxycurcumin) were evaluated against a panel of 8 cancer cell lines; lung (A549), prostate (DU-145), skin (SK-MEL-5), pancreatic (BxPC-3), liver (Hep G2), colon (HT-29), breast (MCF-7) and (MDA-MB-231). Cell lines were cultured in DMEM media supplemented with 2 mM L-glutamine, 10% fetal bovine serum, 50 mkg/ml gentamycin and 2.5 mkg/ml amphotericin B, maintained in a 37 C humid atmosphere of 5% CO2 cell incubator. Samples and drug standards (cisplatin and vinblastine sulfate) were dissolved in DMSO and immediately diluted with DMEM media to yield a final DMSO concentration of less than 0.5% v/v. Cells were plated into 96-well microplates at 5,000–10,000 cells per well and maintained in the cell incubator for 24 h. Then, 100 mkL of samples were introduced in triplicates to a final concentration of 15–150 mkM. Drug standards were also introduced to a final concentration of 0.03–2000 mkM (cisplatin) and 0.002–100 mkM (vinblastine sulfate). Cells were further incubated for 48 h and then, cell viability was determined according to the manufacturer protocol of a commercial MTS assay kit
| Substance Class |
Chemical
Created
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admin
on
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Fri Dec 15 15:59:08 UTC 2023
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| Record UNII |
W2F8059T80
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| Record Status |
Validated (UNII)
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3710 (Number of products:81)
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33171-16-3
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65737
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5469424
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1173100
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DESMETHOXYCURCUMIN
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300000009706
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