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MedKoo Cat#: 125468 | Name: Doxorubicinol HCl

Description:

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

Doxorubicinol is the primary circulating metabolite of doxorubicin which may be used as an antineoplastic.

Chemical Structure

Doxorubicinol HCl
Doxorubicinol HCl
CAS#63950-05-0 (HCl)

Theoretical Analysis

MedKoo Cat#: 125468

Name: Doxorubicinol HCl

CAS#: 63950-05-0 (HCl)

Chemical Formula: C27H32ClNO11

Exact Mass: 581.1700

Molecular Weight: 582.00

Elemental Analysis: C, 55.72; H, 5.54; Cl, 6.09; N, 2.41; O, 30.24

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 #
63950-05-0 (HCl) 54193-28-1 (free base)
Synonym
Doxorubicinol hydrochloride; 13-Dihydroadriamycin; 13-Dihydroadriamycin hydrochloride; 63950-05-0; 9LVW1H75S7
IUPAC/Chemical Name
(8S,10S)-10-(((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-8-((S)-1,2-dihydroxyethyl)-6,8,11-trihydroxy-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione hydrochloride
InChi Key
ORLHIGGRLIJIIM-PNOIAXSSSA-N
InChi Code
InChI=1S/C27H31NO11.ClH/c1-10-22(31)13(28)6-17(38-10)39-15-8-27(36,16(30)9-29)7-12-19(15)26(35)21-20(24(12)33)23(32)11-4-3-5-14(37-2)18(11)25(21)34;/h3-5,10,13,15-17,22,29-31,33,35-36H,6-9,28H2,1-2H3;1H/t10-,13-,15-,16-,17-,22+,27-;/m0./s1
SMILES Code
Cl.[H][C@@]1(C[C@H](N)[C@H](O)[C@H](C)O1)O[C@H]2C[C@@](O)(CC3=C(O)C4=C(C(=O)C5=C(OC)C=CC=C5C4=O)C(O)=C23)[C@@H](O)CO
Appearance
To be determined
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 582.00 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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Population pharmacokinetics of doxorubicin and doxorubicinol in patients diagnosed with non-Hodgkin's lymphoma. Br J Clin Pharmacol. 2016 Dec;82(6):1517-1527. doi: 10.1111/bcp.13070. Epub 2016 Sep 6. PubMed PMID: 27447545; PubMed Central PMCID: PMC5099548. 4: Salvatorelli E, Menna P, Paz OG, Chello M, Covino E, Singer JW, Minotti G. The novel anthracenedione, pixantrone, lacks redox activity and inhibits doxorubicinol formation in human myocardium: insight to explain the cardiac safety of pixantrone in doxorubicin-treated patients. J Pharmacol Exp Ther. 2013 Feb;344(2):467-78. doi: 10.1124/jpet.112.200568. Epub 2012 Nov 28. PubMed PMID: 23192654. 5: Sottani C, Poggi G, Melchiorre F, Montagna B, Minoia C. Simultaneous measurement of doxorubicin and reduced metabolite doxorubicinol by UHPLC-MS/MS in human plasma of HCC patients treated with TACE. J Chromatogr B Analyt Technol Biomed Life Sci. 2013 Feb 1;915-916:71-8. doi: 10.1016/j.jchromb.2012.12.012. Epub 2012 Dec 22. 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PubMed PMID: 11448472. 10: Salvatorelli E, Menna P, Cascegna S, Liberi G, Calafiore AM, Gianni L, Minotti G. Paclitaxel and docetaxel stimulation of doxorubicinol formation in the human heart: implications for cardiotoxicity of doxorubicin-taxane chemotherapies. J Pharmacol Exp Ther. 2006 Jul;318(1):424-33. Epub 2006 Apr 13. PubMed PMID: 16614166. 11: Mushlin PS, Cusack BJ, Boucek RJ Jr, Andrejuk T, Li X, Olson RD. Time-related increases in cardiac concentrations of doxorubicinol could interact with doxorubicin to depress myocardial contractile function. Br J Pharmacol. 1993 Nov;110(3):975-82. PubMed PMID: 8298821; PubMed Central PMCID: PMC2175809. 12: Liu Y, Yang Y, Liu X, Jiang T. Quantification of pegylated liposomal doxorubicin and doxorubicinol in rat plasma by liquid chromatography/electrospray tandem mass spectroscopy: Application to preclinical pharmacokinetic studies. Talanta. 2008 Jan 15;74(4):887-95. doi: 10.1016/j.talanta.2007.07.022. Epub 2007 Jul 31. 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Doxorubicin and doxorubicinol-induced alterations in human polymorphonuclear leukocyte oxygen metabolite generation. J Pharmacol Exp Ther. 1986 Jul;238(1):19-25. PubMed PMID: 3088258. 17: Jacquet JM, Bressolle F, Galtier M, Bourrier M, Donadio D, Jourdan J, Rossi JF. Doxorubicin and doxorubicinol: intra- and inter-individual variations of pharmacokinetic parameters. Cancer Chemother Pharmacol. 1990;27(3):219-25. PubMed PMID: 2265458. 18: Danesi R, del Tacca M, Bernardini C, Penco S. Exogenous doxorubicinol induces cardiotoxic effects in rats. Eur J Cancer Clin Oncol. 1987 Jul;23(7):907-13. PubMed PMID: 3665998. 19: de Bruijn P, Verweij J, Loos WJ, Kolker HJ, Planting AS, Nooter K, Stoter G, Sparreboom A. Determination of doxorubicin and doxorubicinol in plasma of cancer patients by high-performance liquid chromatography. Anal Biochem. 1999 Jan 15;266(2):216-21. PubMed PMID: 9888978. 20: Johansen PB, Jensen SE, Rasmussen SN, Dalmark M. 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