Dacarbazine

Dacarbazine is a DNA alkylating prodrug that is activated by P450 enzymes in liver microsomes. Following activation, it is converted, through a series of reactions, into a methyldiazonium cation that alkylates DNA at all phases of the cell cycle and induces apoptosis. In vitro, dacarbazine inhibits the growth of B16/F1, A-875, and SK-MEL-5 melanoma and non-cancerous WI-38 lung fibroblast and L-02 hepatocyte cell lines (IC50s = 260, 287, 380, 526, and 367 µM, respectively). Dacarbazine toxicity to 518A2 and SK-MEL-28 melanoma cell lines increases in a time-dependent manner with IC50 values of 121 and >400 µM, respectively, following a 1 hour incubation and 2.5 and 50 µM, respectively, following a 96 hour incubation. In vivo, dacarbazine (70 mg/kg, once every 2 days) decreases tumor volume by 59.1% in a B16/F1 murine melanoma model in mice. Formulations containing dacarbazine have been used in the treatment of metastatic melanoma and for Hodgkin's lymphoma in combination with other antineoplastic agents.Formal Name: 5-(3,3-dimethyl-1-triazen-1-yl)-1H-imidazole-4-carboxamide. CAS Number: 4342-03-4. Synonyms: NCI C04717, NSC 45388. Molecular Formula: C6H10N6O. Formula Weight: 182.2. Purity: >98%. Formulation: (Request formulation change), A crystalline solid. Solubility: DMF: 0.3 mg/ml, DMSO: 0.5 mg/ml, Ethanol: 0.2 mg/ml, PBS (pH 7.2): 0.1 mg/ml. lambdamax: 236, 326 nm. SMILES: NC(C1=C(/N=N/N(C)C)N=CN1)=O. InChi Code: InChI=1S/C6H10N6O/c1-12(2)11-10-6-4(5(7)13)8-3-9-6/h3H,1-2H3,(H2,7,13)(H,8,9)/b11-10+. InChi Key: FDKXTQMXEQVLRF-ZHACJKMWSA-N.