daunorubicinol: main metabolite of daunomycin [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
(13S)-13-dihydrodaunorubicin : The (13S)-diastereomer of 13-dihydrodaunorubicin. [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]
ID Source | ID |
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PubMed CID | 443832 |
CHEBI ID | 31031 |
MeSH ID | M0040806 |
Synonym |
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dihydrodaunomycin |
5,12-naphthacenedione, 7,8,9,10-tetrahydro-10-((3-amino-2,3,6-trideoxy-alpha-l-lyxohexopyranosyl)oxy)-8-(1-hydroxyethyl)-1-methoxy-6,8,11-trihydroxy- |
13-dihydrodaunomycin |
brn 3641654 |
duborimycin |
leukaemomycin d |
5,12-naphthacenedione, 10-((3-amino-2,3,6-trideoxy-alpha-l-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-((1s)-1-hydroxyethyl)-1-methoxy-, (8s,10s)- |
antibiotic 20-798rp |
daunorubicinol |
(13s)-13-dihydrodaunorubicin |
LMPK13050005 |
(7s,9s)-7-[(2r,4s,5s,6s)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-[(1s)-1-hydroxyethyl]-4-methoxy-8,10-dihydro-7h-tetracene-5,12-dione |
unii-ydu8yip30l |
ydu8yip30l , |
(1s,3s)-3,5,12-trihydroxy-3-[(1s)-1-hydroxyethyl]-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-alpha-l-lyxo-hexopyranoside |
CHEBI:31031 |
5,12-naphthacenedione, 10-((3-amino-2,3,6-trideoxy-.alpha.-l-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-((1s)-1-hydroxyethyl)-1-methoxy-, (8s,10s)- |
AKOS027326518 |
Q27114084 |
(8s,10s)-10-(((2r,4s,5s,6s)-4-amino-5-hydroxy-6-methyltetrahydro-2h-pyran-2-yl)oxy)-6,8,11-trihydroxy-8-((s)-1-hydroxyethyl)-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione |
Daunorubicinol may make an important contribution to the pathogenesis of cardiotoxicity. Its direct effect on cardiac function has never been evaluated in preclinical models.
Excerpt | Reference | Relevance |
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"If daunorubicinol has equivalent or greater potency than daunorubicin in causing impairment of myocardial function, it may make an important contribution to the pathogenesis of cardiotoxicity." | ( Daunorubicin and daunorubicinol pharmacokinetics in plasma and tissues in the rat. Cusack, BJ; Olson, RD; Young, SP, 1995) | 1.14 |
"Daunorubicinol has been assumed also to be more cardiotoxic than unchanged daunorubicin but its direct effect on cardiac function has never been evaluated in preclinical models." | ( Role of daunorubicinol in daunorubicin-induced cardiotoxicity as evaluated with the model of isolated perfused rat heart. Bonoron-Adèle, S; Platel, D; Robert, J, 2001) | 1.47 |
Excerpt | Reference | Relevance |
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" Other CBR substrates such as menadione, phenanthrenequinone, and doxorubicin were equally toxic to both the CBR expresser cells and the control cells under the conditions tested." | ( Protection against daunorubicin cytotoxicity by expression of a cloned human carbonyl reductase cDNA in K562 leukemia cells. Akman, S; Doroshow, J; Forrest, GL; Gonzalez, B; Kaplan, WD; Rivera, H, 1995) | 0.29 |
"Cardiotoxicity is the major side-effect and limits the clinical use of the anthracyclines, doxorubicin and daunorubicin." | ( Role of daunorubicinol in daunorubicin-induced cardiotoxicity as evaluated with the model of isolated perfused rat heart. Bonoron-Adèle, S; Platel, D; Robert, J, 2001) | 0.74 |
"The role of metabolism in daunorubicin (DAUN)- and doxorubicin (DOX)-associated toxicity in cancer patients is dependent on whether the parent drugs or major metabolites, doxorubicinol (DOXol) and daunorubicinol (DAUNol), are the more toxic species." | ( A correlation between cytotoxicity and reductase-mediated metabolism in cell lines treated with doxorubicin and daunorubicin. Bains, OS; Cragg, GE; Grigliatti, TA; Lubieniecka, JM; Reid, RE; Riggs, KW; Szeitz, A, 2013) | 0.58 |
The apparent elimination half-life of daunorubicinol was longer than that ofdaunorubsicin in most tissues, including the plasma (23.5 hours) The study was an attempt to identify pharmacokinetic factors that determine the response of acute myeloid leukemia patients to induction chemotherapy.
Excerpt | Relevance | Reference |
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" Based on our in vitro studies, a dose-response curve was found between increasing intracellular DNR and incorporation of 3H-thymidine." | ( Kinetics and sensitivity of daunorubicin in patients with acute leukemia. DeGregorio, MW; Holleran, WM; Linker, CA; Macher, BA; Wilbur, JR, 1984) | 0.27 |
"3HCl dosing regimen led to concentrations in excess of the IC(90) (169." | ( Population pharmacokinetic model for daunorubicin and daunorubicinol coadministered with zosuquidar.3HCl (LY335979). Aarons, L; Burgess, M; Callies, S; de Alwis, DP; Mehta, A, 2004) | 0.57 |
Class | Description |
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13-dihydrodaunorubicin | An aminoglycoside antibiotic that is (1S,3S)-3,5,12-trihydroxy-3-(1-hydroxyethyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracene having a 3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl residue attached at position 1 via a glycosidic linkage. |
[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] |
Timeframe | Studies, This Drug (%) | All Drugs % |
---|---|---|
pre-1990 | 22 (31.43) | 18.7374 |
1990's | 17 (24.29) | 18.2507 |
2000's | 17 (24.29) | 29.6817 |
2010's | 11 (15.71) | 24.3611 |
2020's | 3 (4.29) | 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 moderate demand-to-supply ratio for research on this compound.
| This Compound (17.62) All Compounds (24.57) |
Publication Type | This drug (%) | All Drugs (%) |
---|---|---|
Trials | 9 (12.16%) | 5.53% |
Reviews | 0 (0.00%) | 6.00% |
Case Studies | 1 (1.35%) | 4.05% |
Observational | 0 (0.00%) | 0.25% |
Other | 64 (86.49%) | 84.16% |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |