Molecular structure of Dacarbazine, CAS Number: 4342-03-4
Dacarbazine (CAS 4342-03-4)
Alternate Names:
5-(3,3-Dimethyltriazeno)imidazole-4-carboxamide; DTIC
Application:
Dacarbazine is appears to exert cytotoxic effects
CAS Number:
4342-03-4
Molecular Weight:
182.18
Molecular Formula:
C6H10N6O
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.
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SDS & Certificate of Analysis
Dacarbazine exhibits cytotoxic effects through multiple mechanisms, including acting as an alkylating agent, inhibiting DNA synthesis as a purine analog, and inducing apoptosis and hepatotoxicity. As a DNA alkylating prodrug, dacarbazine is activated by P450 enzymes in liver microsomes. The activated form, a methyldiazonium cation, alkylates DNA throughout the cell cycle, leading to apoptosis. In vitro studies have demonstrated its growth inhibition properties against various cell lines, including B16/F1, A-875, SK-MEL-5 melanoma, WI-38 lung fibroblast, and L-02 hepatocyte (IC50s = 260, 287, 380, 526, and 367 μM, respectively). Dacarbazine also has the ability to cross the blood-brain barrier.
Dacarbazine (CAS 4342-03-4) References
- Metabolic activation of dacarbazine by human cytochromes P450: the role of CYP1A1, CYP1A2, and CYP2E1. | Reid, JM., et al. 1999. Clin Cancer Res. 5: 2192-7. PMID: 10473105
- In vivo administration of O(6)-benzylguanine does not influence apoptosis or mutation frequency following DNA damage in the murine intestine, but does inhibit P450-dependent activation of dacarbazine. | Toft, NJ., et al. 2000. Carcinogenesis. 21: 593-8. PMID: 10753191
- Validated high-performance liquid chromatographic assay for simultaneous determination of dacarbazine and the plasma metabolites 5-(3-hydroxymethyl-3-methyl-1-triazeno)imidazole-4-carboxamide and 5-(3-methyl-1-triazeno)imidazole-4-carboxamide. | Safgren, SL., et al. 2001. J Chromatogr B Biomed Sci Appl. 754: 91-6. PMID: 11318431
- Stability of dacarbazine in amber glass vials and polyvinyl chloride bags. | El Aatmani, M., et al. 2002. Am J Health Syst Pharm. 59: 1351-6. PMID: 12132562
- Causative agent of vascular pain among photodegradation products of dacarbazine. | Asahi, M., et al. 2002. J Pharm Pharmacol. 54: 1117-22. PMID: 12195827
- Mechanism of UVA-dependent DNA damage induced by an antitumor drug dacarbazine in relation to its photogenotoxicity. | Iwamoto, T., et al. 2008. Pharm Res. 25: 598-604. PMID: 17710513
- The 'old drug' dacarbazine as a second/third line chemotherapy in advanced soft tissue sarcomas. | Zucali, PA., et al. 2008. Invest New Drugs. 26: 175-81. PMID: 17898927
- A nanoemulsion formulation of dacarbazine reduces tumor size in a xenograft mouse epidermoid carcinoma model compared to dacarbazine suspension. | Kakumanu, S., et al. 2011. Nanomedicine. 7: 277-83. PMID: 21215333
- Synthesis of triazenoazaindoles: a new class of triazenes with antitumor activity. | Diana, P., et al. 2011. ChemMedChem. 6: 1291-9. PMID: 21523910
- The simulation of UV spectroscopy and electronic analysis of temozolomide and dacarbazine chemical decomposition to their metabolites. | Khalilian, MH., et al. 2016. J Mol Model. 22: 270. PMID: 27783227
- Photochemically stabilized formulation of dacarbazine with reduced production of algogenic photodegradants. | Uchida, A., et al. 2019. Int J Pharm. 564: 492-498. PMID: 31022505
- Caffeine improves the cytotoxic effect of dacarbazine on B16F10 murine melanoma cells. | Fagundes, TR., et al. 2022. Bioorg Chem. 120: 105576. PMID: 34979447
- Combined Therapy with Dacarbazine and Hyperthermia Induces Cytotoxicity in A375 and MNT-1 Melanoma Cells. | Salvador, D., et al. 2022. Int J Mol Sci. 23: PMID: 35408947
- MG-Pe: A Novel Galectin-3 Ligand with Antimelanoma Properties and Adjuvant Effects to Dacarbazine. | Biscaia, SMP., et al. 2022. Int J Mol Sci. 23: PMID: 35886983
Inhibitor of:
BAGE, Dendritic Cell marker, Histone cluster 2 H3C, Histone cluster 2 H3D, Histone cluster 2 H4B, and LLGL2.Activator of:
IFN-α10, and LOC645359.Ordering Information
| Product Name | Catalog # | UNIT | Price | Qty | FAVORITES | |
Dacarbazine, 1 g | sc-219954 | 1 g | $343.00 |