Dacarbazine

Base Information

• Chemical Name: Dacarbazine
• CAS No.: 4342-03-4
• Molecular Formula: C6H10N6O
• Molecular Weight: 182.185
• Hs Code.: 29349990
• European Community (EC) Number: 224-396-1
• DSSTox Substance ID: DTXSID0020369
• Nikkaji Number: J2.212H
• Wikipedia: Dacarbazine
• Wikidata: Q416975,Q27166417,Q63088173
• NCI Thesaurus Code: C411
• RXCUI: 3098
• ChEMBL ID: CHEMBL1574179
• Mol file: 4342-03-4.mol

Synonyms:5-(3,3-Dimethyl-1-triazeno)imidazole-4-carboxamide;Biocarbazine;Carboxamide, Dimethyl Imidazole;Dacarbazine;Decarbazine;Deticene;DIC;Dimethyl Imidazole Carboxamide;Dimethyl Triazeno Imidazole Carboxamide;DTIC;DTIC Dome;DTIC-Dome;DTICDome;ICDT;Imidazole Carboxamide, Dimethyl;NSC 45388;NSC-45388;NSC45388

Chemical Property of Dacarbazine

Chemical Property:

• Appearance/Colour: Off-white cryst.
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 199-205 °C
• Refractive Index: 1.678
• Boiling Point: 456.253 °C at 760 mmHg
• PKA: pKa 4.42 (Uncertain)
• Flash Point: 229.734 °C
• PSA: 99.73000
• Density: 1.486 g/cm³
• LogP: 0.76920
• Storage Temp.: 2-8°C
• Solubility.: Slightly soluble in water and in anhydrous ethanol, practically insoluble in methylene chloride.
• Water Solubility.: Slightly soluble in water, DMSO and ethanol /n
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 182.09160896
• Heavy Atom Count: 13
• Complexity: 215

Purity/Quality:

98%, ^*data from raw suppliers

Dacarbazine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T, Xi, Xn
• Hazard Codes: T,Xi,Xn
• Statements: 45-46-20/21/22-36/37/38
• Safety Statements: 53-36/37/39-45-37/39-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Drug Classes: Antineoplastic Agents, Alkylating Agents
• Canonical SMILES: CN(C)N=NC1=C(NC=N1)C(=O)N
• Recent ClinicalTrials: A Study to Compare Standard Therapy to Treat Hodgkin Lymphoma to the Use of Two Drugs, Brentuximab Vedotin and Nivolumab
• Recent EU Clinical Trials: A PHASE 2/3 STUDY TO EVALUATE THE EFFICACY AND SAFETY OF UNESBULIN IN UNRESECTABLE OR METASTATIC, RELAPSED OR REFRACTORY LEIOMYOSARCOMA
• Recent NIPH Clinical Trials: W-JHS HL01
• Uses: It belongs to antineoplastic agent. It is clinically used for the treatment of malignant melanoma with being effective in about 20-30% cases. Combination with vincristine and BCNU can further improve the efficacy. In addition, it also has certain efficacy in treating lung squamous cell carcinoma, sarcoma, leiomyosarcoma and fibrosarcoma but with poor efficacy in treating gastrointestinal cancer. Used as an antineoplastic. Used in the treatment of malignant melanoma and sarcomas. progestogen Dacarbazine is used as an antineoplastic for treatment of malignant melanoma and sarcomas.
• Production method: Take ethyl cyanoacetate as raw material, go through addition, amination, diazotization, coupling, reduction, formylation, cyclization, and, diazotization, condensation, through intermediate β-imino-β-ethoxy propionate hydrochloride, α-acetamide hydrochloride, α-amidino-α-phenylazo acetamide hydrochloride, 5-amino-imidazole-4-carboxamide hydrochloride to obtain it.
• Description: Dacarbazine is nevertheless considered the first representative of the series of triazene derivatives. It has been shown that it is an alkylating agent, and thus this drug inhibits RNA and protein synthesis to a greater degree than DNA. Dacarbazine is used intravenously for Hodgkin’s disease, soft-tissue sarcoma, and metastatic melanoma. A synonym of this drug is diticene.
• Indications: Dacarbazine (DTIC-Dome) is activated by photodecomposition and by enzymatic N-demethylation. Eventual formation of a methyl carbonium ion results in methylation of DNA and RNA and inhibition of nucleic acid and protein synthesis. As with other alkylating agents, cells in all phases of the cell cycle are susceptible to dacarbazine. The plasma half-life of dacarbazine is biphasic, with a distribution phase of 19 minutes and an elimination phase of 5 hours. The drug is not appreciably protein bound, and it does not enter the central nervous system (CNS). Urinary excretion of unchanged drug is by renal tubular secretion. Dacarbazine metabolism and decomposition is complex. Dacarbazine is the most active agent used in metastatic melanoma, producing a 20% remission rate. It is also combined with doxorubicin and other agents in the treatment of various sarcomas and Hodgkin’s disease. Dacarbazine may cause severe nausea and vomiting. Leukopenia and thrombocytopenia occur 2 weeks after treatment, with recovery by 3 to 4 weeks. Less common is a flulike syndrome of fever, myalgias, and malaise. Alopecia and transient abnormalities in renal and hepatic function also have been reported.
• Clinical Use: This DNA methylating agent is administered IV as a single agent in the treatment of malignant melanoma and in combination with other agents in the treatment of metastatic melanoma.
• Drug interactions: Potentially hazardous interactions with other drugs Aldesleukin: avoid concomitant use.Antipsychotics: avoid with clozapine, increased risk of agranulocytosis.

Technology Process of Dacarbazine

There total 3 articles about Dacarbazine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 76.2%

5-Aminoimidazole-4-carboxamide (360-97-4) + dimethyl amine (124-40-3) → 5-(3,3-dimethyl-1-triazeno)imidazone-4-carboxamide (4342-03-4)

Guidance literature:

5-Aminoimidazole-4-carboxamide; With hydrogenchloride; sodium nitrite; In water; for 0.5h; Cooling with ice;

dimethyl amine; In water; for 2h; Cooling with ice;

Reference yield:

→ 5-(3,3-dimethyl-1-triazeno)imidazone-4-carboxamide (4342-03-4)

Guidance literature:

Reference yield:

→ dacarbazine (4342-03-4)

Guidance literature:

DOI:10.1002/jps.2600570920

upstream raw materials:

5-Aminoimidazole-4-carboxamide

dimethyl amine

Downstream raw materials:

5-hydroxy-1H-imidazole-4-carboxamide

2-azahypoxanthine

Refernces

• 1、 -. "Cell". . . Retrieved 2007/10/05.
• 2、 -. "Anti-Claudin 3 Monoclonal Antibody and Treatment and Diagnosis of Cancer Using the Same". . . Retrieved 2010/05/13.