MedKoo Cat#: 598682 | Name: Daunorubicinol

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Daunorubicinol is the main metabolite of daunomycin.

Chemical Structure

Daunorubicinol
Daunorubicinol
CAS#28008-55-1

Theoretical Analysis

MedKoo Cat#: 598682

Name: Daunorubicinol

CAS#: 28008-55-1

Chemical Formula: C27H31NO10

Exact Mass: 529.1948

Molecular Weight: 529.54

Elemental Analysis: C, 61.24; H, 5.90; N, 2.65; O, 30.21

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Daunorubicinol; Duborimycin; Antibiotic 20-798RP;
IUPAC/Chemical Name
(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
InChi Key
HJEZFVLKJYFNQW-PRFXOSGESA-N
InChi Code
InChI=1S/C27H31NO10/c1-10-22(30)14(28)7-17(37-10)38-16-9-27(35,11(2)29)8-13-19(16)26(34)21-20(24(13)32)23(31)12-5-4-6-15(36-3)18(12)25(21)33/h4-6,10-11,14,16-17,22,29-30,32,34-35H,7-9,28H2,1-3H3/t10-,11-,14-,16-,17-,22+,27-/m0/s1
SMILES Code
COc1c2c(C(c3c(C2=O)c(O)c4c(C[C@](C[C@@H]4O[C@H]5C[C@@H]([C@@H]([C@@H](O5)C)O)N)([C@@H](O)C)O)c3O)=O)ccc1
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 529.54 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
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Metabolism of the anthracycline antibiotic daunorubicin to daunorubicinol and deoxydaunorubicinol aglycone in hepatocytes isolated from the rat and the rabbit. Biochem Pharmacol. 1986 Nov 15;35(22):4059-64. PubMed PMID: 3778526. 6: Cusack BJ, Mushlin PS, Voulelis LD, Li X, Boucek RJ Jr, Olson RD. Daunorubicin-induced cardiac injury in the rabbit: a role for daunorubicinol? Toxicol Appl Pharmacol. 1993 Feb;118(2):177-85. PubMed PMID: 8441996. 7: Olson RD, Li X, Palade P, Shadle SE, Mushlin PS, Gambliel HA, Fill M, Boucek RJ Jr, Cusack BJ. Sarcoplasmic reticulum calcium release is stimulated and inhibited by daunorubicin and daunorubicinol. Toxicol Appl Pharmacol. 2000 Dec 1;169(2):168-76. PubMed PMID: 11097869. 8: Hoefer CC, Blair RH, Blanco JG. Development of a CART Model to Predict the Synthesis of Cardiotoxic Daunorubicinol in Heart Tissue Samples From Donors With and Without Down Syndrome. J Pharm Sci. 2016 Jun;105(6):2005-2008. doi: 10.1016/j.xphs.2016.03.013. Epub 2016 Apr 23. 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Nuclear binding as a determinant of tissue distribution of adriamycin, daunomycin, adriamycinol, daunorubicinol and actinomycin D. J Pharmacobiodyn. 1984 May;7(5):269-77. PubMed PMID: 6470925. 13: Zucchetti M, Boiardi A, Silvani A, Parisi I, Piccolrovazzi S, D'Incalci M. Distribution of daunorubicin and daunorubicinol in human glioma tumors after administration of liposomal daunorubicin. Cancer Chemother Pharmacol. 1999;44(2):173-6. PubMed PMID: 10412954. 14: Griese N, Blaschke G, Boos J, Hempel G. Determination of free and liposome-associated daunorubicin and daunorubicinol in plasma by capillary electrophoresis. J Chromatogr A. 2002 Dec 6;979(1-2):379-88. PubMed PMID: 12498269. 15: Albrecht KW, de Witt Hamer PC, Leenstra S, Bakker PJ, Beijnen JH, Troost D, Kaaijk P, Bosch AD. High concentration of Daunorubicin and Daunorubicinol in human malignant astrocytomas after systemic administration of liposomal Daunorubicin. J Neurooncol. 2001 Jul;53(3):267-71. PubMed PMID: 11718259. 16: Charlier HA Jr, Olson RD, Thornock CM, Mercer WK, Olson DR, Broyles TS, Muhlestein DJ, Larson CL, Cusack BJ, Shadle SE. Investigations of calsequestrin as a target for anthracyclines: comparison of functional effects of daunorubicin, daunorubicinol, and trifluoperazine. Mol Pharmacol. 2005 May;67(5):1505-12. Epub 2005 Feb 10. PubMed PMID: 15705743. 17: Eksborg S, Ehrsson H, Andersson B, Beran M. Liquid chromatographic determination of daunorubicin and daunorubicinol in plasma from leukemic patients. J Chromatogr. 1978 Jun 1;153(1):211-8. PubMed PMID: 659557. 18: Dubois J, Hanocq M, Atassi G, Arnould R, Abikhalil F. Pharmacokinetics of daunorubicin and daunorubicinol in plasma, P388 and B16 tumours. Comparison with in vitro cytotoxicity data. Eur J Drug Metab Pharmacokinet. 1991 Apr-Jun;16(2):119-27. PubMed PMID: 1936071. 19: Furlanut M, de Manzoni G, Pasini F, Tasselli S, Tomezzoli A, Poz D, Franceschi L. Daunorubicin and daunorubicinol tissue concentrations in gastric cancer patients after local administration of a liposomal preparation. Pharmacol Res. 2007 Oct;56(4):344-9. Epub 2007 Aug 24. PubMed PMID: 17904378. 20: Hulhoven R, Desager JP. HPLC determination of daunorubicin and daunorubicinol in human plasma. Biomedicine. 1977 Apr;27(3):102-4. PubMed PMID: 890014.