MedKoo Cat#: 591217 | Name: Adriamycin Aglycone
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Description:

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

Adriamycin Aglycone, also known as Doxorubicinone, is an oncolytic agent. It is a metabolite of Doxorubicin which binds to the DNA minor-groove.

Chemical Structure

Adriamycin Aglycone
CAS#24385-10-2

Theoretical Analysis

MedKoo Cat#: 591217

Name: Adriamycin Aglycone

CAS#: 24385-10-2

Chemical Formula: C21H18O9

Exact Mass: 414.0951

Molecular Weight: 414.37

Elemental Analysis: C, 60.87; H, 4.38; O, 34.75

Price and Availability

Size Price Availability Quantity
1mg USD 350.00 2 weeks
5mg USD 985.00 2 weeks
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Related CAS #
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Synonym
Adriamycinone, Adriamycin Aglycone; Doxorubicin Aglycone, Doxorubicinone
IUPAC/Chemical Name
5,12-Naphthacenedione, 7,8,9,10-tetrahydro-6,8,10,11-tetrahydroxy-8-(hydroxyacetyl)-1-methoxy-, (8S-cis)-
InChi Key
IBZGBXXTIGCACK-UZJPJQLHSA-N
InChi Code
InChI=1S/C21H18O9/c1-30-11-4-2-3-8-14(11)20(28)16-15(17(8)25)18(26)9-5-21(29,12(24)7-22)6-10(23)13(9)19(16)27/h2-4,10,22-23,26-27,29H,5-7H2,1H3/t10-,21+/m1/s1
SMILES Code
O=C(C1=C2C(O)=C3[C@H](O)C[C@@](C(CO)=O)(O)CC3=C1O)C4=CC=CC(OC)=C4C2=O
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
>2 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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 414.37 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
1: Sokolove PM. Interactions of adriamycin aglycones with mitochondria may mediate adriamycin cardiotoxicity. Int J Biochem. 1994 Dec;26(12):1341-50. doi: 10.1016/0020-711x(94)90176-7. PMID: 7890113. 2: Sokolove PM, Shinaberry RG. Na+-independent release of Ca2+ from rat heart mitochondria. Induction by adriamycin aglycone. Biochem Pharmacol. 1988 Mar 1;37(5):803-12. doi: 10.1016/0006-2952(88)90165-7. PMID: 3345198. 3: Takanashi S, Bachur NR. Adriamycin metabolism in man. Evidence from urinary metabolites. Drug Metab Dispos. 1976 Jan-Feb;4(1):79-87. PMID: 3405. 4: Tartakoff SS, Finan JM, Curtis EJ, Anchukaitis HM, Couture DJ, Glazier S. Investigations into the DNA-binding mode of doxorubicinone. Org Biomol Chem. 2019 Feb 13;17(7):1992-1998. doi: 10.1039/c8ob02344a. PMID: 30406253. 5: Sokolove PM. Oxidation of mitochondrial pyridine nucleotides by aglycone derivatives of adriamycin. Arch Biochem Biophys. 1991 Feb 1;284(2):292-7. doi: 10.1016/0003-9861(91)90298-w. PMID: 1846520. 6: Benjamin RS, Riggs CE Jr, Bachur NR. Plasma pharmacokinetics of adriamycin and its metabolites in humans with normal hepatic and renal function. Cancer Res. 1977 May;37(5):1416-20. PMID: 856462. 7: Singer A, Tresley J, Velazquez-Vega J, Yepes M. Unusual aggressive breast cancer: metastatic malignant phyllodes tumor. J Radiol Case Rep. 2013 Feb 1;7(2):24-37. doi: 10.3941/jrcr.v7i2.1430. PMID: 23705037; PMCID: PMC3661309. 8: Mahdadi R, Lhermitte M, Lafitte JJ. Determination of adriamycin and its fluorescent metabolites in human plasma by HPLC. Biomed Chromatogr. 1987 Feb;2(1):38-40. doi: 10.1002/bmc.1130020111. PMID: 3508093. 9: Cummings J, Stuart JF, Calman KC. Determination of adriamycin, adriamycinol and their 7-deoxyaglycones in human serum by high-performance liquid chromatography. J Chromatogr. 1984 Nov 9;311(1):125-33. doi: 10.1016/s0378-4347(00)84698-8. PMID: 6520153. 10: Bailey-Wood R, Dallimore CM, Whittaker JA. Effect of adriamycin on CFUGM at plasma concentrations found following therapeutic infusions. Br J Cancer. 1984 Sep;50(3):351-5. doi: 10.1038/bjc.1984.182. PMID: 6466545; PMCID: PMC1976788. 11: Ehninger G, Stocker HJ, Proksch B, Wilms K. Die Pharmakokinetik von Adriamycin und Adriamycin-Metaboliten [The pharmacokinetics of adriamycin and adriamycin-metabolites (author's transl)]. Klin Wochenschr. 1980 Sep 15;58(18):927-34. German. doi: 10.1007/BF01477050. PMID: 7206588. 12: Ozols RF, Willson JK, Weltz MD, Grotzinger KR, Myers CE, Young RC. Inhibition of human ovarian cancer colony formation by adriamycin and its major metabolites. Cancer Res. 1980 Nov;40(11):4109-12. PMID: 7471054. 13: Nohl H, Gille L, Staniek K. The exogenous NADH dehydrogenase of heart mitochondria is the key enzyme responsible for selective cardiotoxicity of anthracyclines. Z Naturforsch C J Biosci. 1998 Mar-Apr;53(3-4):279-85. doi: 10.1515/znc-1998-3-419. PMID: 9618942. 14: Lazo JS, Schwartz PE. Rapid distribution of adriamycin in the ascitic and pleural fluid of women with ovarian carcinomas. Gynecol Oncol. 1985 May;21(1):65-72. doi: 10.1016/0090-8258(85)90233-1. PMID: 3988127. 15: Saito K, Fujieda T, Yoshioka H. Feasibility of simple chitosan sheet as drug delivery carrier. Eur J Pharm Biopharm. 2006 Oct;64(2):161-6. doi: 10.1016/j.ejpb.2006.04.008. Epub 2006 Jun 23. PMID: 16884897. 16: Sokolove PM, Kester MB, Haynes J. Interaction of adriamycin aglycones with isolated mitochondria. Effect of selenium deficiency. Biochem Pharmacol. 1993 Aug 17;46(4):691-7. doi: 10.1016/0006-2952(93)90556-c. PMID: 8363643. 17: Farina A, Quaglia MG, Bossù E, Melchiorre P. Analysis of iododoxorubicin and its major impurity. J Pharm Biomed Anal. 1991;9(10-12):1165-8. doi: 10.1016/0731-7085(91)80061-d. PMID: 1822190. 18: Sokolove PM. Inhibition by cyclosporin A and butylated hydroxytoluene of the inner mitochondrial membrane permeability transition induced by adriamycin aglycones. Biochem Pharmacol. 1990 Dec 15;40(12):2733-6. doi: 10.1016/0006-2952(90)90595-c. PMID: 2260996. 19: Zorić L, Drinković N, Micek V, Frkanec L, Türeli AE, Günday-Türeli N, Vinković Vrček I, Frkanec R. High-Throughput Method for the Simultaneous Determination of Doxorubicin Metabolites in Rat Urine after Treatment with Different Drug Nanoformulations. Molecules. 2022 Feb 9;27(4):1177. doi: 10.3390/molecules27041177. PMID: 35208967; PMCID: PMC8877250. 20: Averbuch SD, Gaudiano G, Koch TH, Bachur NR. Radical dimer rescue of toxicity and improved therapeutic index of adriamycin in tumor-bearing mice. Cancer Res. 1985 Dec;45(12 Pt 1):6200-4. PMID: 4063971.