retinoyl glucuronide: metabolite of retinoic acid in bile
9-cis-retinoyl-beta-D-glucuronide : A retinoid that is 9-cis-retinoic acid in which the carboxy proton has been replaced by a beta-D-glucuronyl group. It is a major metabolite of 9-cis-retinoic acid.
ID Source | ID |
---|---|
PubMed CID | 5281877 |
CHEBI ID | 28870 |
MeSH ID | M0087629 |
Synonym |
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retinoyl b-glucuronide |
401-10-5 |
all-trans-retinoyl-beta-glucuronide |
glucuronide |
retinoyl glucuronide |
o(15)-[(2s,3r,4s,5s,6s)-6-carboxy-3,4,5-trihydroxytetrahydro-2h-pyran-2-yl]retinoic acid |
CHEBI:28870 |
1-o-[(2e,4e,6e,8e)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoyl]-beta-d-glucopyranuronic acid |
all-trans-retinoyl-beta-d-glucuronide |
9-cis-retinoyl-beta-d-glucuronide |
retinoyl-beta-glucuronide |
beta-d-glucopyranuronic acid, 1-retinoate |
13-cis-retinoyl glucuronide |
beta-d-glucopyranuronic acid, 1-ester with retinoic acid |
retinoic acid beta-d-glucuronide |
retinoyl beta-glucuronide |
all-trans retinoyl |a-d-glucuronide, >85% by hplc |
(2s,3s,4s,5r,6s)-6-[(2e,4e,6e,8e)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoyl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid |
unii-xb6rq16y55 |
trans-retinoyl glucuronide |
xb6rq16y55 , |
W-201374 |
13-cis-retinoyl b-d-glucuronide |
9-cis-retinoyl b-d-glucuronide |
W-203796 |
W-202656 |
e-retinoyl b-glucuronide |
retinoyl .beta.-glucuronide |
all-trans-retinoyl .beta.-d-glucuronide |
glucopyranosiduronic acid, 1-retinoate, .beta.-d- |
all-trans-retinoyl glucuronide |
1004517-36-5 |
retinoyl glucuronide, all-trans |
retinoic acid, 1-ester with glucopyranuronic acid |
retinoic acid, .beta.-d-glucuronosyl ester |
.beta.-d-glucopyranuronic acid, 1-retinoate |
retinoic acid, 1-ester with .beta.-d-glucopyranosiduronic acid |
(2s,3s,4s,5r,6s)-6-{[(2e,4e,6e,8e)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid |
DTXSID40274187 |
13-cis-retinoic acid acyl beta-d-glucuronide |
13-cis-retinoic acid acyl beta-delta-glucuronide |
13-cis-retinoyl-beta-d-glucuronide |
all-trans-retinoyl-beta-delta-glucuronide |
9-cis-retinoyl-beta-delta-glucuronide |
13-cis-retinoyl-beta-delta-glucuronide |
retinoic acid beta-delta-glucuronide |
MTGFYEHKPMOVNE-NEFMKCFNSA-N |
Q27103934 |
all-trans retinoyl beta-d-glucuronide, >85per cent by hplc |
e-retinoylb-glucuronide |
all-trans retinoyl ?-d-glucuronide, (>80%) |
all-trans retinoyl ?-d-glucuronide |
all-trans retinoyl ??-d-glucuronide |
AKOS040754950 |
Excerpt | Reference | Relevance |
---|---|---|
" Thereafter, RAG was eliminated through a first-order process, in accord with a typical two-compartment first order pharmacokinetic profile." | ( Pharmacokinetic study of all-trans-retinoyl-beta-D-glucuronide in Sprague-Dawley rats after single and multiple intravenous administration(s). Barua, AB; Chan, SY; Ho, PC; Lin, HS; Low, KS; Olson, JA; Shoon, ML, 2001) | 0.31 |
Excerpt | Relevance | Reference |
---|---|---|
"In order to compare the disposition and metabolism of 13-cis-retinoic acid (13-cis-RA) and all-trans-retinoic acid (all-trans-RA) in the nonpregnant female cynomolgus monkey, the plasma concentrations of the parent compound, the oxidized metabolites 4-oxo-13-cis-retinoic acid and 4-oxo-all-trans-retinoic acid, and the conjugate metabolites 13-cis-retinoyl-beta-glucuronide (13-cis-RAG) and all trans-retinoyl-beta-glucuronide (all-trans-RAG), were determined on day 1 and day 10 after oral dosing of 2 and 10 mg 13-cis- and all-trans-RA/kg/day." | ( Plasma pharmacokinetics and metabolism of 13-cis- and all-trans-retinoic acid in the cynomolgus monkey and the identification of 13-cis- and all-trans-retinoyl-beta-glucuronides. A comparison to one human case study with isotretinoin. Bailey, JR; Fischer, B; Kraft, JC; Nau, H; Roberts, LG; Slikker, W; Wittfoht, W, ) | 0.13 |
" Since 13-cis-retinoyl-beta-glucuronide and 13-cis- and all-trans-retinoic acid were detected in the embryo after this multiple dosing schedule, any of the three or their combinations may have been involved in the induction of malformations, but all-trans-retinoic acid, a well-known potent teratogen detected at concentrations of between 590 and 80 ng/g for 10 critical hours during gestation, could have been the major component." | ( Isotretinoin (13-cis-retinoic acid) metabolism, cis-trans isomerization, glucuronidation, and transfer to the mouse embryo: consequences for teratogenicity. Bochert, G; Chahoud, I; Creech Kraft, J; Eckhoff, C; Kochhar, DM; Nau, H, 1991) | 0.28 |
"The liver and intestinal metabolites of orally dosed 13-cis-[11-3H]retinoic acid were analyzed in normal and 13-cis-retinoic acid treated rats 3 h after administration of the radiolabeled retinoid." | ( 13-cis-retinoic acid metabolism in vivo. The major tissue metabolites in the rat have the all-trans configuration. Kroll, KD; McCormick, AM; Napoli, JL, 1983) | 0.27 |
" In contrast, dosing with 13-cis-RA yielded much higher plasma retinoid levels." | ( Metabolism of oral 9-cis-retinoic acid in the human. Identification of 9-cis-retinoyl-beta-glucuronide and 9-cis-4-oxo-retinoyl-beta-glucuronide as urinary metabolites. Masgrau, E; Nau, H; Sass, JO; Saurat, JH, 1995) | 0.29 |
" Taken together, our findings that chronic dosing with RAG produces sustained levels of both the parent compound and the RA hydrolysis product, combined with the apparent low toxicity of RAG, suggest that RAG could be a safe and useful alternative to some retinoids which are presently being utilized in the clinic." | ( Pharmacokinetics of chronically administered all-trans-retinoyl-beta-glucuronide in mice. Barua, AB; Connor, MJ; Olson, JA; Sawatsri, S; Sidell, N; Wada, RK, 2000) | 0.31 |
" Therefore, long-term daily dosing of RAG seemed to decrease its distribution profile." | ( Pharmacokinetic study of all-trans-retinoyl-beta-D-glucuronide in Sprague-Dawley rats after single and multiple intravenous administration(s). Barua, AB; Chan, SY; Ho, PC; Lin, HS; Low, KS; Olson, JA; Shoon, ML, 2001) | 0.31 |
" In orally dosed rats (n = 6), neither RAG nor its products, except for occasional traces of the lactone, were detected." | ( Pharmacokinetics of all-trans retinoyl beta-glucuronide in rats following intraperitoneal and oral administration. Barua, AB; Olson, JA; Romans, DA, 2003) | 0.61 |
"1 mmol) was orally dosed to fasting well-nourished young men." | ( Intestinal absorption and metabolism of retinoyl beta-glucuronide in humans, and of 15-[14C]-retinoyl beta-glucuronide in rats of different vitamin A status. Barua, AB; Goswami, BC; Ivanoff, KD; Olson, JA; Reida, AK, 2003) | 0.59 |
" Blood was collected from the children in Group I (n 19) who were not dosed with RAG." | ( A new approach to the assessment of marginal vitamin A deficiency in children in suburban Guwahati, India: hydrolysis of retinoyl glucuronide to retinoic acid. Barua, AB; Bhattacharjee, H; Gogoi, K; Goswami, BC; Sarma, PC, 2009) | 0.35 |
" These included dose-response tests and isotope dilution assays." | ( Vitamin A: biomarkers of nutrition for development. Tanumihardjo, SA, 2011) | 0.37 |
Role | Description |
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human metabolite | Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens). |
[role 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] |
Class | Description |
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glucuronic acids | |
retinoid | Oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof. |
[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] |
Pathway | Proteins | Compounds |
---|---|---|
Retinol Metabolism | 37 | 30 |
Vitamin A Deficiency | 37 | 30 |
Timeframe | Studies, This Drug (%) | All Drugs % |
---|---|---|
pre-1990 | 22 (34.38) | 18.7374 |
1990's | 28 (43.75) | 18.2507 |
2000's | 13 (20.31) | 29.6817 |
2010's | 1 (1.56) | 24.3611 |
2020's | 0 (0.00) | 2.80 |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |
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 weak demand-to-supply ratio for research on this compound.
| This Compound (9.91) All Compounds (24.57) |
Publication Type | This drug (%) | All Drugs (%) |
---|---|---|
Trials | 3 (4.41%) | 5.53% |
Reviews | 6 (8.82%) | 6.00% |
Case Studies | 0 (0.00%) | 4.05% |
Observational | 0 (0.00%) | 0.25% |
Other | 59 (86.76%) | 84.16% |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |