Dacarbazine

For research use only. Not for therapeutic Use.

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Dacarbazine(Cat No.:A000760)is an alkylating agent used primarily in cancer chemotherapy, particularly for treating melanoma and Hodgkin’s lymphoma. As a prodrug, it undergoes metabolic activation in the liver, forming methylating intermediates that damage DNA, leading to the inhibition of cell replication and tumor growth. Dacarbazine is known for its cytotoxic effects on rapidly dividing cancer cells, making it effective in disrupting tumor progression. It is an essential part of combination therapies and remains a cornerstone in the treatment of specific cancers due to its efficacy and broad therapeutic application.


Catalog Number A000760
CAS Number 4342-03-4
Synonyms

1H-imidazole-4-carboxamide, 5-(3,3-dimethyl-1-triazenyl)-dacarbazine (unspecified geometry).

Molecular Formula C6H10N6O
Purity ≥95%
Target DNA Synthesis
Solubility >2.3mg/mL in DMSO
Storage -20°C
IUPAC Name 4-(dimethylaminodiazenyl)-1H-imidazole-5-carboxamide
InChI 1S/C6H10N6O/c1-12(2)11-10-6-4(5(7)13)8-3-9-6/h3,11H,1-2H3,(H2,7,13)/b10-6+
InChIKey OMJKFYKNWZZKTK-UXBLZVDNSA-N
SMILES CN(C)NN=C1C(=NC=N1)C(=O)N
Reference

1: Grob JJ, Mortier L, D/&#39;Hondt L, Grange F, Baurain JF, Dr&eacute;no B, Lebbe C, Robert C, Dompmartin A, Neyns B, Gillet M, Louahed J, Jarnjak S, Lehmann FF. Safety and immunogenicity of MAGE-A3 cancer immunotherapeutic with dacarbazine in patients with MAGE-A3-positive metastatic cutaneous melanoma: an open phase I/II study with a first assessment of a predictive gene signature. ESMO Open. 2017 Nov 14;2(5):e000203. doi: 10.1136/esmoopen-2017-000203. eCollection 2017. PubMed PMID: 29177094; PubMed Central PMCID: PMC5687540.<br />
2: Ugurel S, Loquai C, Terheyden P, Schadendorf D, Richtig E, Utikal J, Gutzmer R, Rass K, Sunderk&ouml;tter C, Stein A, Fluck M, Kaatz M, Trefzer U, K&auml;hler K, Stadler R, Berking C, H&ouml;ller C, Kerschke L, Edler L, Kopp-Schneider A, Becker JC. Chemosensitivity-directed therapy compared to dacarbazine in chemo-naive advanced metastatic melanoma: a multicenter randomized phase-3 DeCOG trial. Oncotarget. 2017 Jun 27;8(44):76029-76043. doi: 10.18632/oncotarget.18635. eCollection 2017 Sep 29. PubMed PMID: 29100289; PubMed Central PMCID: PMC5652683.<br />
3: Schinzari G, Rossi E, Cassano A, Dadduzio V, Quirino M, Pagliara M, Blasi MA, Barone C. Cisplatin, dacarbazine and vinblastine as first line chemotherapy for liver metastatic uveal melanoma in the era of immunotherapy: a single institution phase II study. Melanoma Res. 2017 Dec;27(6):591-595. doi: 10.1097/CMR.0000000000000401. PubMed PMID: 29076951.<br />
4: Friedberg JW, Forero-Torres A, Bordoni RE, Cline VJM, Patel Donnelly D, Flynn PJ, Olsen G, Chen R, Fong A, Wang Y, Yasenchak CA. Frontline brentuximab vedotin in combination with dacarbazine or bendamustine in patients aged &ge;60 years with HL. Blood. 2017 Oct 16. pii: blood-2017-06-787200. doi: 10.1182/blood-2017-06-787200. [Epub ahead of print] PubMed PMID: 29038340.<br />
5: Tanaka R, Goshima F, Esaki S, Sato Y, Murata T, Nishiyama Y, Watanabe D, Kimura H. The efficacy of combination therapy with oncolytic herpes simplex virus HF10 and dacarbazine in a mouse melanoma model. Am J Cancer Res. 2017 Aug 1;7(8):1693-1703. eCollection 2017. PubMed PMID: 28861325; PubMed Central PMCID: PMC5574941.<br />
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