Detorubicin Free Base | CAS# 66211-92-5 (free base) | anthracycline antineoplastic antibiotic daunorubicin

MedKoo Cat#: 413591 | Name: Detorubicin Free Base

Description:

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

Detorubicin Free Base is a semi-synthetic derivative of the anthracycline antineoplastic antibiotic daunorubicin. Detorubicin intercalates into DNA and interacts with topoisomerase II, thereby inhibiting DNA replication and repair and RNA and protein synthesis. This agent also produces toxic free-radical intermediates and interacts with cell membrane lipids causing lipid peroxidation. Detorubicin is less toxic than daunorubicin.

Chemical Structure

Detorubicin Free Base

CAS#66211-92-5 (free base)

Theoretical Analysis

MedKoo Cat#: 413591

Name: Detorubicin Free Base

CAS#: 66211-92-5 (free base)

Chemical Formula: C33H39NO14

Exact Mass: 673.2371

Molecular Weight: 673.67

Elemental Analysis: C, 58.84; H, 5.84; N, 2.08; O, 33.25

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 #

64291-45-8 (HCl) 66211-92-5 (free base)

Synonym

Detorubicin Free Base; RP33921; RP-33921; RP 33921

IUPAC/Chemical Name

2-((2S,4S)-4-(((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-2-yl)-2-oxoethyl 2,2-diethoxyacetate

InChi Key

XZSRRNFBEIOBDA-CFNBKWCHSA-N

InChi Code

InChI=1S/C33H39NO14/c1-5-44-32(45-6-2)31(41)46-13-20(35)33(42)11-16-23(19(12-33)48-21-10-17(34)26(36)14(3)47-21)30(40)25-24(28(16)38)27(37)15-8-7-9-18(43-4)22(15)29(25)39/h7-9,14,17,19,21,26,32,36,38,40,42H,5-6,10-13,34H2,1-4H3/t14-,17-,19-,21-,26+,33-/m0/s1

SMILES Code

CCOC(C(OCC([C@]1(C[C@@H](c2c(C1)c(O)c3c(C(c4c(C3=O)cccc4OC)=O)c2O)O[C@H]5C[C@@H]([C@@H]([C@@H](O5)C)O)N)O)=O)=O)OCC

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

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 673.67 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.

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: Chawla SP, Legha SS, Benjamin RS. Detorubicin--an active anthracycline in untreated metastatic melanoma. J Clin Oncol. 1985 Nov;3(11):1529-34. doi: 10.1200/JCO.1985.3.11.1529. PMID: 4056844. 2: Deprez-de Campeneere D, Baurain R, Trouet A. Pharmacokinetic, toxicologic, and chemotherapeutic properties of detorubicin in mice: a comparative study with daunorubicin and adriamycin. Cancer Treat Rep. 1979 May;63(5):861-7. PMID: 455327. 3: Dantchev D, Slioussartchouk V, Paintrand M, Hayat M, Bourut C, Mathé G. Electron microscopic studies of the heart and light microscopic studies of the skin after treatment of golden hamsters with adriamycin, detorubicin, AD-32, and aclacinomycin. Cancer Treat Rep. 1979 May;63(5):875-88. PMID: 455329. 4: Chauvergne J, Bui NB, Cappelaere P, Gary-Bobo J, Guerrin J, Armand JP, Durand M. Chimiothérapie des mélanomes malins évolués. Résultats d'un essai contrôlé comparant l'association de détorubicine et de dacarbazine (DTIC) à la dacarbazine seule [Chemotherapy in advanced malignant melanoma. Results of a controlled trial comparing a combination of dacarbazine (DTIC) and detorubicin with dacarbazine alone]. Sem Hop. 1982 Dec 16;58(46):2697-701. French. PMID: 6297068. 5: Sørensen JB. Current concepts in chemotherapy for malignant pleural mesothelioma. Clin Respir J. 2008 Apr;2(2):74-9. doi: 10.1111/j.1752-699X.2008.00046.x. PMID: 20298310. 6: Jacquillat C, Auclerc MF, Weil M, Maral J, Degos L, Auclerc G, Tobelem G, Schaison G, Bernard J. Clinical activity of detorubicin: a new anthracycline derivative. Cancer Treat Rep. 1979 May;63(5):889-93. PMID: 455330. 7: Ong ST, Vogelzang NJ. Chemotherapy in malignant pleural mesothelioma. A review. J Clin Oncol. 1996 Mar;14(3):1007-17. doi: 10.1200/JCO.1996.14.3.1007. PMID: 8622005. 8: Preliminary results of a phase II trial on solid tumors of detorubicin, a new anthracyclin. Cancer Clin Trials. 1980 Summer;3(2):115-20. PMID: 7428135. 9: Zenebergh A, Baurain R, Trouet A. Cellular pharmacology of detorubicin and doxorubicin in L1210 cells. Eur J Cancer Clin Oncol. 1984 Jan;20(1):115-21. doi: 10.1016/0277-5379(84)90042-7. PMID: 6537910. 10: Clinical study of detorubicin. EORTC Clinical Screening Group. Recent Results Cancer Res. 1980;74:184-91. PMID: 7444139.