DACARBAZINE

Synonyms. Dacarbazine; 5-(3,3-Dimethyl-1-triazenyl)imidazole-4-carboxamide; DTIC; Dimethyltriazeno)imidazolecarboxamide; 4(5)-(3,3-Dimethyl-1-triazeno)imidazole-4-carboxamide; 4-(3,3-Dimethyl-1-triazeno)imidazole-5-carboxamide; 4-(5)-(3,3-Dimethyl-1-triazeno)imidazole -5(4)- carboxamide; 4-(Dimethyltriazeno)imidazole-5-carboxamide; 5-(3,3-Dimethyl-1-triazeno)imidazole- 4-carboxamide; 5-(3,3-Dimethyltriazeno)imidazole-4-carboxamide; 5-(Dimethyltriazeno)imidazole- 4-carboxamide; Biocarbazine; Dacarbazino; Dacarbazinum; Deticene; Di-me-triazenoimidazole carboxamide; ICDMT;

DACARBAZINE

Click for original image

 

PRODUCT IDENTIFICATION

CAS RN

4342-03-4

EINECS RN

224-396-1

FORMULA

 C6H10N6O

MOLE WEIGHT

182.18

H.S CODE

 2933.29.4500

SMILES

 c1(c(nc[nH]1)C(=O)N)/N=N/N(C)C

CLASSIFICATION

Alkylating agent, Antineoplastic, Triazine

EXTRA NOTES

 Dacarbazine has significant activity against melanomas. It is a synthetic analog of naturally occurring purine precursor 5-amino-1H-imidazole-4-carboxamide (AIC). Dacarbazine appears to exert cytotoxic effects by acting as an alkylating agent, by inhibiting DNA synthesis as a purine analog, and by inducing apoptosis. (SigmaAldrich)
Overall Carcinogenic Evaluation: Group 2B

 

PHYSICAL AND CHEMICAL PROPERTIES

PHYSICAL STATE.

yellow to reddish crystalline powder

MELTING POINT

205 C

BOILING POINT

 

DENSITY

 

SOLUBILITY IN WATER

Slightly soluble (4220 mg/l)

SOLVENT SOLUBILITY Slightly soluble in ethanol

VAPOR DENSITY

 

log P(octanol-water)

  

VAPOR PRESSURE

 2.20E-08 mm Hg

AUTOIGNITION TEMP

  
pH

 

REFRACTIVE INDEX

 

FLASH POINT

 

 
STABILITY AND REACTIVITY
STABILITY Stable under normal conditions.

INCOMPATIBLE MATERIALS

Strong oxidizing agents.

POLYMERIZATION

Has not been reported

NFPA RATINGS

Health: 2, Flammability: 0, Reactivity: 0

 

EXTERNAL LINKS & GENERAL DESCRIPTION

Wikipedia Linking - Dacarbazine

Google Scholar Search - Dacarbazine

Drug Information Portal (U.S. National Library of Medicine) - Dacarbazine

PubChem Compound Summary - Dacarbazine

Drug Bank -  Dacarbazine

KEGG (Kyoto Encyclopedia of Genes and Genomes) - Dacarbazine

http://www.ebi.ac.uk/ - Dacarbazine

http://www.ncbi.nlm.nih.gov/ - Dacarbazine

http://toxnet.nlm.nih.gov/
Hazardous Substances Data Bank - Dacarbazine

http://www.jbc.org/
Dacarbazine (DTIC) is the treatment of choice for metastatic melanoma, but its response in patients remains very poor. Ceramide has been shown to be a death effector and to play an important role in regulating cancer cell growth upon chemotherapy. Among ceramidases, the enzymes that catabolize ceramide, acid ceramidase (aCDase) has been implicated in cancer progression. Here we show that DTIC elicits a time- and dosedependent decrease of aCDase activity and an increase of intracellular ceramide levels in human A375 melanoma cells. The loss of enzyme activity occurred as a consequence of reactive oxygen species-dependent activation of cathepsin B-mediated degradation of aCDase.

 

SALES SPECIFICATION

APPEARANCE

yellow to reddish crystalline powder

IDENTIFICATION

positive (Test A,B)

CONTENT

98.0% ~ 101.0%
LOSS ON DRYING

0.5% max

HEAVY METALS

10ppm max
IMPURITY

2.0% max (Individual impurity: 1.0% max)

 

TRANSPORT & REGULATORY INFORMATION

UN NO.

Not regulated

HAZARD CLASS

  
PACKING GROUP  

 

SAFETY INFORMATION

HAZARD OVERVIEW

May be harmful if swallowed. Harmful in contact with skin or if inhaled. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation. May cause cancer. OSHA Hazards; Target Organ Effect, Irritant, Carcinogen. Target Organs:Blood, Liver. Other hazards: Photosensitizer.

GHS

  

SIGNAL WORD

Danger

PICTOGRAMS

HAZARD STATEMENTS

H312-H315-H319-H332-H335-H350

P STATEMENTS

P201-P261-P280-P305 + P351 + P338-P308 + P313

EC DIRECTIVES

 

HAZARD CODES

T

RISK PHRASES

45-46-20/21/22-36/37/38

SAFETY PHRASES

 53-36/37/39-45

 

PACKING