Dacarbazine

Title: Dacarbazine
CAS Registry Number: 4342-03-4
CAS Name: 5-(3,3-Dimethyl-1-triazenyl)-1H-imidazole-4-carboxamide
Additional Names: 5(or 4)-(dimethyltriazeno)imidazole-4(or 5)-carboxamide; DIC; DTIC
Manufacturers' Codes: NSC-45388
Trademarks: Dacatic (Lkefarmos); DTIC-Dome (Bayer); Deticene (Bellon)
Molecular Formula: C6H10N6O
Molecular Weight: 182.18
Percent Composition: C 39.56%, H 5.53%, N 46.13%, O 8.78%
Literature References: First synthesized in 1959 at the Southern Research Institute. Prepn: Shealy et al., J. Org. Chem. 27, 2150 (1962); Hano et al., Gann 59, 207 (1968), C.A. 69, 42527g (1968). Antitumor activity: Shealy et al., Biochem. Pharmacol. 11, 674 (1962); Hano et al., Gann 56, 417 (1965), C.A. 63, 18856g (1965). Mechanism of action studies: Saunders, Schultz, Biochem. Pharmacol. 19, 911 (1970). Metabolism: Skibba et al., ibid. 2043; Mizuno, Humphrey, Cancer Chemother. Rep. Part 1 56, 465 (1972). Review: Carter, Friedman, Eur. J. Cancer 8, 85-92 (1972), see also the series of articles on history, activity, mechanism of action and clinical studies: Cancer Treat. Rep. 60, 123-214 (1976).
Properties: Ivory microcrystalline substance; explosive decomp 250-255°. Also reported as mp 205°, Hano et al., loc. cit. (1965). uv max (0.1N HCl): 223 nm (7500); (pH 7): 237 nm (11200); both solns protected from light. Stable in neutral soln in absence of light.
Melting point: mp 205°, Hano et al., loc. cit. (1965)
Absorption maximum: uv max (0.1N HCl): 223 nm (7500); (pH 7): 237 nm (11200); both solns protected from light
CAUTION: This substance is reasonably anticipated to be a human carcinogen: Report on Carcinogens, Eleventh Edition (PB2005-104914, 2004) p III-76.
Therap-Cat: Antineoplastic.
Keywords: Antineoplastic; Alkylating Agents.
Daclizumab Dactinomycin Dalapon Dalbavancin Dalfopristin

Dacarbazine
Dacarbazine Formula V.1.svg
Dacarbazine ball-and-stick.png
Systematic (IUPAC) name
5-(3,3-Dimethyl-1-triazenyl)imidazole-4-carboxamide
Clinical data
Trade names Dtic-dome
AHFS/Drugs.com monograph
MedlinePlus a682750
Pregnancy cat. C
Legal status Prescription only
Routes IV
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half-life 5 hours
Excretion 40% renal (unchanged)
Identifiers
CAS number 4342-03-4 YesY
ATC code L01AX04
PubChem CID 2942
DrugBank DB00851
ChemSpider 10481959 YesY
UNII 7GR28W0FJI YesY
KEGG C06936 YesY
ChEBI CHEBI:4305 N
ChEMBL CHEMBL476 YesY
Chemical data
Formula C6H10N6O 
Mol. mass 182.18
 N (what is this?)  (verify)

Dacarbazine (da-KAR-ba-zeen) (brand names DTIC, DTIC-Dome; also known as DIC or Imidazole Carboxamide) is an antineoplastic chemotherapy drug used in the treatment of various cancers, among them malignant melanoma, Hodgkin lymphoma, sarcoma, and islet cell carcinoma of the pancreas.

Dacarbazine is a member of the class of alkylating agents, which destroy cancer cells by adding an alkyl group (CnH2n+1) to its DNA.

Dacarbazine is normally administered by intravenous infusion (IV) under the immediate supervision of a doctor or nurse. Dacarbazine is bioactivated in liver by demethylation to "MTIC" and then to diazomethane, which is an "alkylating agent".