Daunorubicinol

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

MedKoo CAT#: 598682

CAS#: 28008-55-1

Description: Daunorubicinol is the main metabolite of daunomycin.

Chemical Structure

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Daunorubicinol
CAS# 28008-55-1
Instruction

Theoretical Analysis

MedKoo Cat#: 598682
Name: Daunorubicinol
CAS#: 28008-55-1
Chemical Formula: C27H31NO10
Exact Mass: 529.19
Molecular Weight: 529.540
Elemental Analysis: C, 61.24; H, 5.90; N, 2.65; O, 30.21

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

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:

Biological target:
In vitro activity:
In vivo activity:

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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Cusack BJ, Young SP, Vestal RE, Olson RD. Age-related pharmacokinetics of daunorubicin and daunorubicinol following intravenous bolus daunorubicin administration in the rat. Cancer Chemother Pharmacol. 1997;39(6):505-12. PubMed PMID: 9118462.

2: Cusack BJ, Young SP, Olson RD. Daunorubicin and daunorubicinol pharmacokinetics in plasma and tissues in the rat. Cancer Chemother Pharmacol. 1995;35(3):213-8. PubMed PMID: 7805179.

3: Platel D, Bonoron-Adèle S, Robert J. Role of daunorubicinol in daunorubicin-induced cardiotoxicity as evaluated with the model of isolated perfused rat heart. Pharmacol Toxicol. 2001 May;88(5):250-4. PubMed PMID: 11393585.

4: Callies S, de Alwis DP, Mehta A, Burgess M, Aarons L. Population pharmacokinetic model for daunorubicin and daunorubicinol coadministered with zosuquidar.3HCl (LY335979). Cancer Chemother Pharmacol. 2004 Jul;54(1):39-48. Epub 2004 Mar 24. PubMed PMID: 15045528.

5: Gewirtz DA, Yanovich S. 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. PubMed PMID: 27112290; PubMed Central PMCID: PMC4885781.

9: Hempel G, Relling MV, de Rossi G, Stary J, De Lorenzo P, Valsecchi MG, Barisone E, Boos J, Pieters R. Pharmacokinetics of daunorubicin and daunorubicinol in infants with leukemia treated in the interfant 99 protocol. Pediatr Blood Cancer. 2010 Mar;54(3):355-60. doi: 10.1002/pbc.22266. PubMed PMID: 19731319.

10: Slupe A, Williams B, Larson C, Lee LM, Primbs T, Bruesch AJ, Bjorklund C, Warner DL, Peloquin J, Shadle SE, Gambliel HA, Cusack BJ, Olson RD, Charlier HA Jr. Reduction of 13-deoxydoxorubicin and daunorubicinol anthraquinones by human carbonyl reductase. Cardiovasc Toxicol. 2005 Fall;5(4):365-76. PubMed PMID: 16382174.

11: Hempel G, Schulze-Westhoff P, Flege S, Boos J. Quantification of daunorubicin and daunorubicinol in plasma by capillary electrophoresis. J Chromatogr B Biomed Sci Appl. 2001 Jul 15;758(2):221-8. PubMed PMID: 11486832.

12: Terasaki T, Iga T, Sugiyama Y, Sawada Y, Hanano M. 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.