D2390

Sigma-Aldrich

Dacarbazine

antineoplastic purine analog

Synonym(s):
DTIC, 5-(3,3-Dimethyl-1-triazenyl)imidazole-4-carboxamide
Empirical Formula (Hill Notation):
C6H10N6O
CAS Number:
Molecular Weight:
182.18
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.85

Quality Level

form

powder or crystals

solubility

1 M HCl: 50 mg/mL

Mode of action

DNA synthesis | interferes

antibiotic activity spectrum

neoplastics

storage temp.

2-8°C

SMILES string

CN(C)\N=N\c1[nH]cnc1C(N)=O

InChI

1S/C6H10N6O/c1-12(2)11-10-6-4(5(7)13)8-3-9-6/h3H,1-2H3,(H2,7,13)(H,8,9)/b11-10+

InChI key

FDKXTQMXEQVLRF-ZHACJKMWSA-N

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Application

Dacarbazine is a triazine antineoplastic agent that is used for DNA methylation via formation of methyl adducts. It is used to treat metastatic malignant melanomas and Hodgkin′s when used in combination with other antineoplastic agents.

Packaging

1 g in glass bottle
100 mg in glass bottle

Biochem/physiol Actions

Dacarbazine is a purine analog of naturally occurring purine precursor 5-amino-1H-imidazole-4-carboxamide (AIC). It is a synthetic triazine antineoplastic agent that exerts cytotoxic effects by acting as an alkylating agent and by inhibiting DNA synthesis and inducing apoptosis. It is known to induce hepatotoxicity in mice. Dacarbazine is not cell cycle-phase specific.

Other Notes

Keep container tightly closed in a dry and well-ventilated place.

Pictograms

Exclamation markHealth hazard

Signal Word

Danger

Target Organs

Respiratory system

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

Caroline Robert et al.
The Lancet. Oncology, 14(8), 733-740 (2013-06-06)
Patients with metastatic melanoma, 50% of whose tumours harbour a BRAF mutation, have a poor prognosis. Selumetinib, a MEK1/2 inhibitor, has shown antitumour activity in patients with BRAF-mutant melanoma and in preclinical models when combined with chemotherapy. This study was...
Masayuki Sanada et al.
Carcinogenesis, 28(12), 2657-2663 (2007-09-21)
O(6)-Methylguanine and O(6)-chloroethylguanine, which are the primary cytotoxic DNA lesions produced by 5-(3,3-dimethyl-1-triazeno)imidazole-4-carboxamide (dacarbazine) and 1-(4-amino-2-methyl-5-pyrimidinyl)methyl-3-(2-chloroethyl)-3-nitrosourea (ACNU), respectively, can be repaired by O(6)-methylguanine-DNA methyltransferase (MGMT), coded by the MGMT gene. However, the two types of drugs exhibit different effects on...
E M Hersh et al.
Annals of oncology : official journal of the European Society for Medical Oncology, 26(11), 2267-2274 (2015-09-28)
The efficacy and safety of nab-paclitaxel versus dacarbazine in patients with metastatic melanoma was evaluated in a phase III randomized, controlled trial. Chemotherapy-naïve patients with stage IV melanoma received nab-paclitaxel 150 mg/m(2) on days 1, 8, and 15 every 4...
Michiko Horiguchi et al.
The Journal of pharmacology and experimental therapeutics, 333(3), 782-787 (2010-03-24)
O(6)-methylguanine-DNA methyltransferase (MGMT) plays a crucial role in the defense against the alkylating agent-induced cytotoxic lesion O(6)-alkylguanine in DNA. Although a significant circadian variation in MGMT activity has been found in the liver of mice, the exact mechanism of the...
Annette E Hay et al.
Hematology/oncology clinics of North America, 28(1), 49-63 (2013-11-30)
Because long-term survival of patients with nonbulky stage IA to IIA Hodgkin lymphoma is dependent on disease control and avoidance of late toxic effects associated with the treatment received, the initial choice of treatment can be associated with trade-offs that...

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