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MedKoo Cat#: 146034 | Name: Epirubicinol

Description:

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

Epirubicinol is a metabolite of the chemotherapeutic agent epirubicin, used in the treatment of various cancers, including breast cancer, lung cancer, and certain types of leukemia. It works by intercalating into DNA, inhibiting topoisomerase II, and generating free radicals, which ultimately leads to DNA damage and cancer cell death. As a potent antitumor agent, epirubicinol shares similar mechanisms with its parent compound, epirubicin, but may have a different pharmacological profile. It is typically administered in a clinical setting as part of chemotherapy regimens to reduce tumor growth and improve survival outcomes.

Chemical Structure

Epirubicinol
Epirubicinol
CAS#76155-56-1

Theoretical Analysis

MedKoo Cat#: 146034

Name: Epirubicinol

CAS#: 76155-56-1

Chemical Formula: C27H31NO11

Exact Mass: 545.1900

Molecular Weight: 545.54

Elemental Analysis: C, 59.45; H, 5.73; N, 2.57; O, 32.26

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
Epirubicinol; Epidoxorubicinol;
IUPAC/Chemical Name
(8S,10S)-10-(((2R,4S,5R,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
InChi Key
NKZRZOVSJNSBFR-QXAZHNFISA-N
InChi Code
1S/C27H31NO11/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/t10-,13-,15-,16-,17-,22-,27-/m0/s1
SMILES Code
[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 545.54 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
1: Robert J. Clinical pharmacokinetics of epirubicin. Clin Pharmacokinet. 1994 Jun;26(6):428-38. doi: 10.2165/00003088-199426060-00002. PMID: 8070217. 2: Dodde WI, Maring JG, Hendriks G, Wachters FM, Groen HJ, de Vries EG, Uges DR. Determination of epirubicin and its metabolite epirubicinol in saliva and plasma by HPLC. Ther Drug Monit. 2003 Aug;25(4):433-40. doi: 10.1097/00007691-200308000-00003. PMID: 12883225. 3: Salvatorelli E, Menna P, Gianni L, Minotti G. Defective taxane stimulation of epirubicinol formation in the human heart: insight into the cardiac tolerability of epirubicin-taxane chemotherapies. J Pharmacol Exp Ther. 2007 Feb;320(2):790-800. doi: 10.1124/jpet.106.116160. Epub 2006 Nov 29. PMID: 17135345. 4: Robert J. Epirubicin. Clinical pharmacology and dose-effect relationship. Drugs. 1993;45 Suppl 2:20-30. doi: 10.2165/00003495-199300452-00005. PMID: 7693418. 5: Fogli S, Danesi R, Gennari A, Donati S, Conte PF, Del Tacca M. Gemcitabine, epirubicin and paclitaxel: pharmacokinetic and pharmacodynamic interactions in advanced breast cancer. Ann Oncol. 2002 Jun;13(6):919-27. doi: 10.1093/annonc/mdf164. PMID: 12123338. 6: Danesi R, Innocenti F, Fogli S, Gennari A, Baldini E, Di Paolo A, Salvadori B, Bocci G, Conte PF, Del Tacca M. Pharmacokinetics and pharmacodynamics of combination chemotherapy with paclitaxel and epirubicin in breast cancer patients. Br J Clin Pharmacol. 2002 May;53(5):508-18. doi: 10.1046/j.1365-2125.2002.01579.x. PMID: 11994057; PMCID: PMC1874362. 7: Jamieson D, Lee J, Cresti N, Jackson R, Griffin M, Sludden J, Verrill M, Boddy AV. Pharmacogenetics of adjuvant breast cancer treatment with cyclophosphamide, epirubicin and 5-fluorouracil. Cancer Chemother Pharmacol. 2014 Oct;74(4):667-74. doi: 10.1007/s00280-014-2541-6. Epub 2014 Jul 24. PMID: 25055937. 8: Danesi R, Conte PF, Del Tacca M. Pharmacokinetic optimisation of treatment schedules for anthracyclines and paclitaxel in patients with cancer. Clin Pharmacokinet. 1999 Sep;37(3):195-211. doi: 10.2165/00003088-199937030-00002. PMID: 10511918. 9: Mross K, Hamm K, Hossfeld DK. Effects of verapamil on the pharmacokinetics and metabolism of epirubicin. Cancer Chemother Pharmacol. 1993;31(5):369-75. doi: 10.1007/BF00686150. PMID: 8431970. 10: Conte PF, Baldini E, Gennari A, Michelotti A, Salvadori B, Tibaldi C, Danesi R, Innocenti F, Gentile A, Dell'Anna R, Biadi O, Mariani M, Del Tacca M. Dose- finding study and pharmacokinetics of epirubicin and paclitaxel over 3 hours: a regimen with high activity and low cardiotoxicity in advanced breast cancer. J Clin Oncol. 1997 Jul;15(7):2510-7. doi: 10.1200/JCO.1997.15.7.2510. PMID: 9215819. 11: Jakobsen P, Steiness E, Bastholt L, Dalmark M, Lorenzen A, Petersen D, Gjedde SB, Sandberg E, Rose C, Nielsen OS, et al. Multiple-dose pharmacokinetics of epirubicin at four different dose levels: studies in patients with metastatic breast cancer. Cancer Chemother Pharmacol. 1991;28(1):63-8. doi: 10.1007/BF00684959. PMID: 2040035. 12: Jakobsen P, Bastholt L, Dalmark M, Pfeiffer P, Petersen D, Gjedde SB, Sandberg E, Rose C, Nielsen OS, Mouridsen HT. A randomized study of epirubicin at four different dose levels in advanced breast cancer. Feasibility of myelotoxicity prediction through single blood-sample measurement. Cancer Chemother Pharmacol. 1991;28(6):465-9. doi: 10.1007/BF00685824. PMID: 1934250. 13: Robert J, Vrignaud P, Nguyen-Ngoc T, Iliadis A, Mauriac L, Hurteloup P. Comparative pharmacokinetics and metabolism of doxorubicin and epirubicin in patients with metastatic breast cancer. Cancer Treat Rep. 1985 Jun;69(6):633-40. PMID: 3893693. 14: Mross K, Maessen P, van der Vijgh WJ, Gall H, Boven E, Pinedo HM. Pharmacokinetics and metabolism of epidoxorubicin and doxorubicin in humans. J Clin Oncol. 1988 Mar;6(3):517-26. doi: 10.1200/JCO.1988.6.3.517. PMID: 3162516. 15: Ramanathan-Girish S, Boroujerdi M. Contradistinction between doxorubicin and epirubicin: in-vivo metabolism, pharmacokinetics and toxicodynamics after single- and multiple-dosing in rats. J Pharm Pharmacol. 2001 Jul;53(7):987-97. doi: 10.1211/0022357011776234. PMID: 11480551. 16: Conte PF, Gennari A, Salvadori B, Pazzagli C, Bengala C. Paclitaxel plus epirubicin in advanced breast cancer. Oncology (Williston Park). 1998 Jan;12(1 Suppl 1):40-4. PMID: 9516603. 17: Maring JG, Wachters FM, Maurer M, Uges DR, de Vries EG, Groen HJ. Gemcitabine and epirubicin plasma concentration-related excretion in saliva in patients with non-small cell lung cancer. Ther Drug Monit. 2010 Jun;32(3):364-8. doi: 10.1097/FTD.0b013e3181d631a6. PMID: 20335827. 18: Camaggi CM, Comparsi R, Strocchi E, Testoni F, Pannuti F. HPLC analysis of doxorubicin, epirubicin and fluorescent metabolites in biological fluids. Cancer Chemother Pharmacol. 1988;21(3):216-20. doi: 10.1007/BF00262773. PMID: 3162848. 19: Verscheure E, Struys I, Creta M, Poels K, Vanoirbeek J, Lenaerts L, Amant F, Ghosh M, Godderis L. Development and validation of an UPLC-ESI-MS/MS method for simultaneous quantification of antineoplastic agents and their metabolites in human plasma after unintentional exposure. Arch Toxicol. 2025 Jan;99(1):259-270. doi: 10.1007/s00204-024-03900-5. Epub 2024 Oct 31. PMID: 39480547. 20: Barker IK, Crawford SM, Fell AF. Determination of plasma concentrations of epirubicin and its metabolites by high-performance liquid chromatography during a 96-h infusion in cancer chemotherapy. J Chromatogr B Biomed Appl. 1996 Jun 7;681(2):323-9. doi: 10.1016/0378-4347(96)00030-8. PMID: 8811443.

View History

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