Detorubicin HCl

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

MedKoo CAT#: 206062

CAS#: 64291-45-8 (HCl)

Description: Detorubicin 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.


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Detorubicin HCl is not in stock, but may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 206062
Name: Detorubicin HCl
CAS#: 64291-45-8 (HCl)
Chemical Formula: C33H40ClNO14
Exact Mass: 673.23705
Molecular Weight: 710.126
Elemental Analysis: C, 55.82; H, 5.68; Cl, 4.99; N, 1.97; O, 31.54


Related CAS #: 64291-45-8 (HCl)   66211-92-5 (free base)    

Synonym: Detorubicin; MCMC 4777; NSC 292652; 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 hydrochloride

InChi Key: PJODMULXZJQLDJ-NMELVCTCSA-N

InChi Code: InChI=1S/C33H39NO14.ClH/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;1H/t14-,17-,19-,21-,26+,33-;/m0./s1

SMILES Code: O=C(OCC([C@@]1(O)C[C@H](O[C@H]2C[C@H](N)[C@H](O)[C@H](C)O2)C3=C(O)C4=C(C(C5=CC=CC(OC)=C5C4=O)=O)C(O)=C3C1)=O)C(OCC)OCC.[H]Cl


Technical Data

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, not in water

Shelf Life:
>5 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).

Harmonized System Code:
293490


Additional Information

  
 
 
 


References

1: Zijlstra JG, Meijer C, Timmer-Bosscha H, Le TK, de Vries EG, Mulder NH. Activity of (7) anthracycline related compounds in an doxorubicin sensitive human small cell lung cancer line and its doxorubicin resistant descendant. Activity of doxorubicin, daunorubicin, 4-deoxyrubicin, 4-demethoxydaunorubicin, detorubicin, 4'-epidoxorubicin and mitoxantrone. Eur J Respir Dis Suppl. 1987;149:53-5. PubMed PMID: 3034649.

2: Chawla SP, Legha SS, Benjamin RS. Detorubicin--an active anthracycline in untreated metastatic melanoma. J Clin Oncol. 1985 Nov;3(11):1529-34. PubMed PMID: 4056844.

3: Colbert N, Vannetzel JM, Izrael V, Schlienger M, Milleron B, Blanchon F, Herman D, Akoun G, Roland J, Chatelet F, et al. A prospective study of detorubicin in malignant mesothelioma. Cancer. 1985 Nov 1;56(9):2170-4. PubMed PMID: 3902205.

4: 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. PubMed PMID: 6537910.

5: Chauvergne J, Bui NB, Cappelaere P, Gary-Bobo J, Guerrin J, Armand JP, Durand M. [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. PubMed PMID: 6297068.

6: Cappelaere P, Chauvergne J, Klein T, Gary-Bobo J, Guerrin J, Meeus L. [Randomized trial of vincristin-methotrexate-bleomycin and cis-platin or detorubicin for advanced head and neck cancer (author's transl)]. Bull Cancer. 1981;68(5):422-7. French. PubMed PMID: 6174165.

7: Huybrechts M, Trouet A. Comparative toxicity of detorubicin and doxorubicin, free and DNA-bound, for hemopoietic stem cells. Cancer Chemother Pharmacol. 1980;5(2):79-82. PubMed PMID: 7471318.

8: Clinical study of detorubicin. EORTC Clinical Screening Group. Recent Results Cancer Res. 1980;74:184-91. PubMed PMID: 7444139.

9: Maral R, Heusse D, Lavelle F, Cueille G, Marlard M, Jacquillat C, Maral J, Auclerc MF, Weil M, Auclerc G, Bernard J. Experimental and clinical activity of a new anthracycline derivative: detorubicin (14-diethoxyacetoxydaunorubicin). Recent Results Cancer Res. 1980;74:172-83. PubMed PMID: 7444138.

10: Preliminary results of a phase II trial on solid tumors of detorubicin, a new anthracyclin. Cancer Clin Trials. 1980 Summer;3(2):115-20. PubMed PMID: 7428135.