Page last updated: 2024-12-08

daunorubicinol

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

Description

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]

Cross-References

ID SourceID
PubMed CID443832
CHEBI ID31031
MeSH IDM0040806

Synonyms (20)

Synonym
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

Research Excerpts

Effects

Daunorubicinol may make an important contribution to the pathogenesis of cardiotoxicity. Its direct effect on cardiac function has never been evaluated in preclinical models.

ExcerptReferenceRelevance
"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

Toxicity

ExcerptReferenceRelevance
" 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

Pharmacokinetics

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.

ExcerptReferenceRelevance
" Calculated inhibitory concentrations 50 (IC50) were compared to maximal concentrations determined by pharmacokinetic studies."( Pharmacokinetics of daunorubicin and daunorubicinol in plasma, P388 and B16 tumours. Comparison with in vitro cytotoxicity data.
Abikhalil, F; Arnould, R; Atassi, G; Dubois, J; Hanocq, M,
)
0.4
"In an attempt to identify pharmacokinetic factors that determine the response of acute myeloid leukemia (AML) patients to induction chemotherapy, we determined the concentrations of daunorubicin (DNR) and the main metabolite daunorubicinol (DOL) in vivo and particularly evaluated the concentrations in blood and bone marrow nucleated cells."( Cellular pharmacokinetics of daunorubicin: relationships with the response to treatment in patients with acute myeloid leukemia.
Hagenbeek, A; Kokenberg, E; Löwenberg, B; Sizoo, W; Sonneveld, P, 1988
)
0.46
" Pharmacokinetic parameters of DOL obtained after injection of DOL were different from those calculated for DNR and those calculated for DOL after injection of DNR."( Pharmacokinetics of daunorubicinol in the rabbit: comparison with daunorubicin.
Baurain, R; Lesne, M; Maniez-Devos, DM; Trouet, A,
)
0.45
" However, the apparent elimination half-life of daunorubicinol was longer than that of daunorubicin in most tissues, including the plasma (23."( Daunorubicin and daunorubicinol pharmacokinetics in plasma and tissues in the rat.
Cusack, BJ; Olson, RD; Young, SP, 1995
)
0.89
" There were no significant differences between patients who went into complete remission (12/23) compared with those who did not respond for the following pharmacokinetic parameters: DNR and DOL plasma AUC (area under the curve) and DNR plasma half-life and clearance."( Daunorubicin pharmacokinetics and the correlation with P-glycoprotein and response in patients with acute leukaemia.
Boutagy, J; Galettis, P; Ma, DD, 1994
)
0.29
" Although idarubicin was given in one-fifth of the dose, the intracellular peak concentration was 70% of that of daunorubicin."( Comparison of the intracellular pharmacokinetics of daunorubicin and idarubicin in patients with acute leukemia.
Paul, C; Sundman-Engberg, B; Tidefelt, U, 1994
)
0.29
"Our data show that there are no significant differences in the pharmacokinetic parameters of daunorubicin in patients receiving DaunoXome in combination with indinavir and ritonavir compared with those in patients not receiving PIs."( The pharmacokinetics of liposomal encapsulated daunorubicin are not modified by HAART in patients with HIV-associated Kaposi's sarcoma.
Careddu, A; D'Incalci, M; Fumagalli, L; Lazzarin, A; Parisi, I; Viganò, MG; Zecca, B; Zucchetti, M, 2000
)
0.31
" Pharmacokinetic and pharmacodynamic properties of zosuquidar."( 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
"A three-compartment pharmacokinetic model adequately described daunorubicin concentration-time profiles."( 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
"There is an extreme paucity of pharmacokinetic data for anticancer agents in infants."( Pharmacokinetics of daunorubicin and daunorubicinol in infants with leukemia treated in the interfant 99 protocol.
Barisone, E; Boos, J; De Lorenzo, P; de Rossi, G; Hempel, G; Pieters, R; Relling, MV; Stary, J; Valsecchi, MG, 2010
)
0.63
"8 years), who received daunorubicin in an earlier investigation, were used for pharmacokinetic model building using the software NONMEM."( Pharmacokinetics of daunorubicin and daunorubicinol in infants with leukemia treated in the interfant 99 protocol.
Barisone, E; Boos, J; De Lorenzo, P; de Rossi, G; Hempel, G; Pieters, R; Relling, MV; Stary, J; Valsecchi, MG, 2010
)
0.63
" No age-dependency in any of the BSA-normalized pharmacokinetic parameters was observed."( Pharmacokinetics of daunorubicin and daunorubicinol in infants with leukemia treated in the interfant 99 protocol.
Barisone, E; Boos, J; De Lorenzo, P; de Rossi, G; Hempel, G; Pieters, R; Relling, MV; Stary, J; Valsecchi, MG, 2010
)
0.63

Dosage Studied

ExcerptRelevanceReference
" 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
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
13-dihydrodaunorubicinAn 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]

Research

Studies (70)

TimeframeStudies, This Drug (%)All Drugs %
pre-199022 (31.43)18.7374
1990's17 (24.29)18.2507
2000's17 (24.29)29.6817
2010's11 (15.71)24.3611
2020's3 (4.29)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 17.62

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 Index17.62 (24.57)
Research Supply Index4.43 (2.92)
Research Growth Index4.42 (4.65)
Search Engine Demand Index15.26 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (17.62)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials9 (12.16%)5.53%
Reviews0 (0.00%)6.00%
Case Studies1 (1.35%)4.05%
Observational0 (0.00%)0.25%
Other64 (86.49%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]