D2390

Dacarbazine

Name: Dacarbazine
Brand: SIGMA

antineoplastic purine analog

Synonym(s):

5-(3,3-Dimethyl-1-triazenyl)imidazole-4-carboxamide, DTIC

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About This Item

Empirical Formula (Hill Notation):

C₆H₁₀N₆O

CAS Number:

4342-03-4

Molecular Weight:

182.18

EC Number:

224-396-1

MDL number:

MFCD00057167

UNSPSC Code:

51102829

PubChem Substance ID:

24893683

NACRES:

NA.85

Key Documents

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Quality Level

100

form

powder or crystals

solubility

1 M HCl: 50 mg/mL

antibiotic activity spectrum

neoplastics

mode of action

DNA synthesis | interferes

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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Show Differences

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This Item	PHR1924	SML1247	Y0000733
Sigma-Aldrich D2390 Dacarbazine	Supelco PHR1924 Dacarbazine	Sigma-Aldrich SML1247 NAB2	Y0000733 Dacarbazine
antibiotic activity spectrum neoplastics	antibiotic activity spectrum -	antibiotic activity spectrum -	antibiotic activity spectrum -
mode of action DNA synthesis \| interferes	mode of action -	mode of action -	mode of action -
Quality Level 100	Quality Level 300	Quality Level 100	Quality Level -
form powder or crystals	form powder	form powder	form -
solubility 1 M HCl: 50 mg/mL	solubility -	solubility DMSO: 5 mg/mL, clear (warmed)	solubility -
storage temp. 2-8°C	storage temp. 2-8°C	storage temp. 2-8°C	storage temp. 2-8°C

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.

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.[1] It is known to induce hepatotoxicity in mice.[2] Dacarbazine is not cell cycle-phase specific.

Other Notes

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

pictograms

GHS08,GHS07

signalword

Danger

hcodes

H302 + H312 + H332,H315,H319,H335,H340,H350

pcodes

P280 - P301 + P312 - P302 + P352 + P312 - P304 + P340 + P312 - P305 + P351 + P338 - P308 + P313

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Carc. 1B - Eye Irrit. 2 - Muta. 1B - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

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Selumetinib plus dacarbazine versus placebo plus dacarbazine as first-line treatment for BRAF-mutant metastatic melanoma: a phase 2 double-blind randomised study.

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

Modes of actions of two types of anti-neoplastic drugs, dacarbazine and ACNU, to induce apoptosis.

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

A randomized, controlled phase III trial of nab-Paclitaxel versus dacarbazine in chemotherapy-naïve patients with metastatic melanoma.

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

Glucocorticoid-dependent expression of O(6)-methylguanine-DNA methyltransferase gene modulates dacarbazine-induced hepatotoxicity in mice.

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

Re-evaluating the role of dacarbazine in metastatic melanoma: what have we learned in 30 years?

Alexander M M Eggermont et al.

European journal of cancer (Oxford, England : 1990), 40(12), 1825-1836 (2004-08-04)

Since dacarbazine was approved for treating metastatic melanoma in the 1970s, numerous studies have evaluated whether different schedules and dacarbazine-based combinations improve clinical outcomes. This evidence-based review shows that combining dacarbazine with other drugs having single-agent activity and/or hormonal or

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