Page last updated: 2024-11-13

curcumin glucuronide

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

curcumin glucuronide: a curcumin metabolite [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID71315012
CHEMBL ID4065571
CHEBI ID189745
MeSH IDM000597463

Synonyms (35)

Synonym
227466-72-0
(2s,3s,4s,5r,6s)-3,4,5-trihydroxy-6-[4-[(1e,6e)-7-(4-hydroxy-3-methoxyphenyl)-3,5-dioxohepta-1,6-dienyl]-2-methoxyphenoxy]oxane-2-carboxylic acid
curcumin glucuronide
CHEBI:189745
curcumin |a-d-glucuronide
4-((1e,6e)-7-(4-hydroxy-3-methoxyphenyl)-3,5-dioxo-1,6-heptadien-1-yl)-2-methoxyphenyl beta-d-glucopyranosiduronic acid
unii-be1pk7rl4m
curcumin beta-o-glucuronide
beta-d-glucopyranosiduronic acid, 4-((1e,6e)-7-(4-hydroxy-3-methoxyphenyl)-3,5-dioxo-1,6-heptadien-1-yl)-2-methoxyphenyl
beta-d-glucopyranosiduronic acid, 4-((1e,6e)-7-(4-hydroxy-3-methoxyphenyl)-3,5-dioxo-1,6-heptadienyl)-2-methoxyphenyl
curcumin beta-d-glucuronide
(2s,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(4-((1e,4z,6e)-5-hydroxy-7-(4-hydroxy-3-methoxyphenyl)-3-oxohepta-1,4,6-trien-1-yl)-2-methoxyphenoxy)tetrahydro-2h-pyran-2-carboxylic acid
BE1PK7RL4M ,
.beta.-d-glucopyranosiduronic acid, 4-((1e,6e)-7-(4-hydroxy-3-methoxyphenyl)-3,5-dioxo-1,6-heptadien-1-yl)-2-methoxyphenyl
curcumin .beta.-d-glucuronide
.beta.-d-glucopyranosiduronic acid, 4-((1e,6e)-7-(4-hydroxy-3-methoxyphenyl)-3,5-dioxo-1,6-heptadienyl)-2-methoxyphenyl
4-((1e,6e)-7-(4-hydroxy-3-methoxyphenyl)-3,5-dioxo-1,6-heptadien-1-yl)-2-methoxyphenyl .beta.-d-glucopyranosiduronic acid
curcumin .beta.-o-glucuronide
(2s,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(4-((1e,6e)-7-(4-hydroxy-3-methoxyphenyl)-3,5-dioxohepta-1,6-dienyl)-2-methoxyphenoxy)oxane-2-carboxylic acid
DTXSID20747384
curcumin alpha-d-glucuronide
J-014841
curcumin-beta-d-glucuronide
EX-A7619
CHEMBL4065571
Q27274613
MS-30002
discontinued. please see c838505.
curcumin ?-d-glucuronide
CS-0168489
curcumin-|a-d-glucuronide
HY-138795
4-[(1e,6e)-7-(4-hydroxy-3-methoxyphenyl)-3,5-dioxo-1,6-heptadien-1-yl]-2-methoxyphenyl beta-dglucopyranosiduronic acid;
curcumin beta -d-glucuronide
curcumin-4-o-beta-d-glucuronide

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
" Physiologically based pharmacokinetic modeling (PBPK) and simulation using Simcyp correlated well with the observed data."( Pharmacokinetics, Pharmacodynamics, and PKPD Modeling of Curcumin in Regulating Antioxidant and Epigenetic Gene Expression in Healthy Human Volunteers.
Brunetti, L; Cheng, D; Hudlikar, R; Kong, AN; Li, W; Lin, T; Ondar, P; Poiani, G; Wang, L; Wassef, A, 2019
)
0.51
" The purpose of this preclinical study is to investigate the acute pharmacokinetic and pharmacodynamic (PK/PD) profiles of two commercially marketed CUR products (GNC and Vitamin Shoppe) and a CUR powder from Sigma in female rats."( Pharmacokinetics and pharmacodynamics of three oral formulations of curcumin in rats.
Buckley, B; Cheng, D; Guo, Y; Hudlikar, R; Kong, AN; Kuo, HC; Li, S; Li, W; Wang, L; Wu, R; Yang, H; Yin, R, 2020
)
0.56
"This study aimed to investigate the potential pharmacokinetic interactions between curcumin, imatinib and bosutinib, combining In Vitro and in silico methods."( Physiologically-Based Pharmacokinetic Predictions of the Effect of Curcumin on Metabolism of Imatinib and Bosutinib: In Vitro and In Vivo Disconnect.
Adiwidjaja, J; Boddy, AV; McLachlan, AJ, 2020
)
0.56
" A physiologically-based pharmacokinetic (PBPK) model for curcumin formulated as solid lipid nanoparticles (SLN) was constructed using In Vitro glucuronidation kinetics and published clinical pharmacokinetic data."( Physiologically-Based Pharmacokinetic Predictions of the Effect of Curcumin on Metabolism of Imatinib and Bosutinib: In Vitro and In Vivo Disconnect.
Adiwidjaja, J; Boddy, AV; McLachlan, AJ, 2020
)
0.56

Bioavailability

ExcerptReferenceRelevance
" The systemic bioavailability of curcumin is low, so that its pharmacological activity may be mediated, in part, by curcumin metabolites."( Characterization of metabolites of the chemopreventive agent curcumin in human and rat hepatocytes and in the rat in vivo, and evaluation of their ability to inhibit phorbol ester-induced prostaglandin E2 production.
Gescher, A; Howells, L; Ireson, C; Jones, DJ; Jukes, R; Lim, CK; Luo, JL; Orr, S; Plummer, S; Steward, WP; Verschoyle, R; Williams, M, 2001
)
0.31
" Firstly, we orally administered highly bioavailable curcumin to rats to elucidate its kinetics, and observed not only the free-form of curcumin, but also, curcumin in a conjugated form, within the portal vein."( Curcumin β-D-Glucuronide Plays an Important Role to Keep High Levels of Free-Form Curcumin in the Blood.
Hashimoto, T; Imaizumi, A; Kakeya, H; Kanai, M; Makino, Y; Ozawa, H; Sumi, Y; Takahashi, N; Tsuda, T, 2017
)
0.46
" Taken together, these results show that the bioavailability of the parent curcumin compound is low, and oral administration of curcumin can still deliver detectable levels of curcumin glucuronide metabolite."( Pharmacokinetics, Pharmacodynamics, and PKPD Modeling of Curcumin in Regulating Antioxidant and Epigenetic Gene Expression in Healthy Human Volunteers.
Brunetti, L; Cheng, D; Hudlikar, R; Kong, AN; Li, W; Lin, T; Ondar, P; Poiani, G; Wang, L; Wassef, A, 2019
)
0.71
" Yet, a significant amount of the orally dosed compound is eliminated in the feces, and a major fraction of the absorbed compound is metabolized to inactive glucuronides, resulting in poor bioavailability (<1%)."( Chemopreventive efficacy of oral curcumin: a prodrug hypothesis.
Grill, A; Khanna, V; Kirtane, A; Liu, G; Panyam, J, 2019
)
0.51

Dosage Studied

ExcerptRelevanceReference
" Yet, a significant amount of the orally dosed compound is eliminated in the feces, and a major fraction of the absorbed compound is metabolized to inactive glucuronides, resulting in poor bioavailability (<1%)."( Chemopreventive efficacy of oral curcumin: a prodrug hypothesis.
Grill, A; Khanna, V; Kirtane, A; Liu, G; Panyam, J, 2019
)
0.51
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
diarylheptanoidA family of plant metabolites with a common 1,7-diphenylheptane structural skeleton, carrying various substituents. They are mainly distributed in the roots, rhizomes and bark of Alpinia, Zingiber, Curcuma and Alnus species.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (5)

Assay IDTitleYearJournalArticle
AID1440512Plasma concentration in human at 2 to 4 g, po administered twice daily capsule for 24 weeks by HPLC method2017Journal of medicinal chemistry, 03-09, Volume: 60, Issue:5
The Essential Medicinal Chemistry of Curcumin.
AID1615169Prodrug conversion assessed as recombinant human alpha-klotho mediated curcumin-glucuronide hydrolysis incubated for 24 hrs by LC-MS analysis2019Journal of natural products, 03-22, Volume: 82, Issue:3
Beta-Glucuronidase Catalyzes Deconjugation and Activation of Curcumin-Glucuronide in Bone.
AID1615167Prodrug conversion in C57BL/6J mouse bone marrow assessed as beta-glucuronidase mediated stabilization of aglycone curcumin at 0.5 uM administered via oral gavage incubated for 30 mins followed by resuspension in sodium acetate buffer at pH 5 measured aft2019Journal of natural products, 03-22, Volume: 82, Issue:3
Beta-Glucuronidase Catalyzes Deconjugation and Activation of Curcumin-Glucuronide in Bone.
AID1615148Inhibition of RANKL-induced osteoclastogenesis in murine RAW264.7 cells assessed as formation of TRAP positive multinucleated osteoclasts at 30 uM pretreated for 4 hrs followed by RANKL addition measured after 72 hrs2019Journal of natural products, 03-22, Volume: 82, Issue:3
Beta-Glucuronidase Catalyzes Deconjugation and Activation of Curcumin-Glucuronide in Bone.
AID1615168Prodrug conversion assessed as recombinant human C-terminal His6-tagged beta-glucuronidase mediated curcumin-glucuronide hydrolysis incubated for 24 hrs by LC-MS analysis2019Journal of natural products, 03-22, Volume: 82, Issue:3
Beta-Glucuronidase Catalyzes Deconjugation and Activation of Curcumin-Glucuronide in Bone.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (17)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's1 (5.88)29.6817
2010's10 (58.82)24.3611
2020's6 (35.29)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 22.49

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index22.49 (24.57)
Research Supply Index2.89 (2.92)
Research Growth Index6.08 (4.65)
Search Engine Demand Index18.60 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (22.49)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (5.88%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other16 (94.12%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]