For research use only. Not for therapeutic Use.
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. Check for active clinical trials or closed clinical trials using this agent. (NCI Thesaurus).
| Catalog Number | I006441 |
| CAS Number | 66211-92-5 |
| Synonyms | Detorubicin; MCMC 4777; NSC 292652; RP 33921.;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 |
| Molecular Formula | C33H39NO14 |
| Purity | ≥95% |
| Solubility | Soluble in DMSO, not in water |
| Storage | 0 - 4°C for short term or -20 °C for long term |
| IUPAC Name | [2-[(2S,4S)-4-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-3,4-dihydro-1H-tetracen-2-yl]-2-oxoethyl] 2,2-diethoxyacetate |
| InChI | 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 |
| InChIKey | XZSRRNFBEIOBDA-CFNBKWCHSA-N |
| SMILES | CCOC(C(=O)OCC(=O)C1(CC(C2=C(C3=C(C(=C2C1)O)C(=O)C4=C(C3=O)C(=CC=C4)OC)O)OC5CC(C(C(O5)C)O)N)O)OCC |
| Reference | </br>1: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. Zijlstra JG, Meijer C, Timmer-Bosscha H, Le TK, de Vries EG, Mulder NH.Eur J Respir Dis Suppl. 1987;149:53-5. No abstract available. PMID: 3034649 </br>2:Detorubicin–an active anthracycline in untreated metastatic melanoma. Chawla SP, Legha SS, Benjamin RS.J Clin Oncol. 1985 Nov;3(11):1529-34. PMID: 4056844 </br>3:A prospective study of detorubicin in malignant mesothelioma. Colbert N, Vannetzel JM, Izrael V, Schlienger M, Milleron B, Blanchon F, Herman D, Akoun G, Roland J, Chatelet F, et al.Cancer. 1985 Nov 1;56(9):2170-4. PMID: 3902205 Free Article</br>4:Cellular pharmacology of detorubicin and doxorubicin in L1210 cells. Zenebergh A, Baurain R, Trouet A.Eur J Cancer Clin Oncol. 1984 Jan;20(1):115-21. PMID: 6537910 </br>5:[Chemotherapy in advanced malignant melanoma. Results of a controlled trial comparing a combination of dacarbazine (DTIC) and detorubicin with dacarbazine alone]. Chauvergne J, Bui NB, Cappelaere P, Gary-Bobo J, Guerrin J, Armand JP, Durand M.Sem Hop. 1982 Dec 16;58(46):2697-701. French. PMID: 6297068 </br>6:[Randomized trial of vincristin-methotrexate-bleomycin and cis-platin or detorubicin for advanced head and neck cancer (author/’s transl)]. Cappelaere P, Chauvergne J, Klein T, Gary-Bobo J, Guerrin J, Meeus L.Bull Cancer. 1981;68(5):422-7. French. PMID: 6174165 </br>7:Comparative toxicity of detorubicin and doxorubicin, free and DNA-bound, for hemopoietic stem cells. Huybrechts M, Trouet A.Cancer Chemother Pharmacol. 1980;5(2):79-82. PMID: 7471318 </br>8:Clinical study of detorubicin. EORTC Clinical Screening Group. [No authors listed]Recent Results Cancer Res. 1980;74:184-91. PMID: 7444139 </br>9:Experimental and clinical activity of a new anthracycline derivative: detorubicin (14-diethoxyacetoxydaunorubicin). Maral R, Heusse D, Lavelle F, Cueille G, Marlard M, Jacquillat C, Maral J, Auclerc MF, Weil M, Auclerc G, Bernard J.Recent Results Cancer Res. 1980;74:172-83. PMID: 7444138 </br>10:Preliminary results of a phase II trial on solid tumors of detorubicin, a new anthracyclin. [No authors listed]Cancer Clin Trials. 1980 Summer;3(2):115-20. PMID: 7428135 |
