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D2390

Sigma-Aldrich

Dacarbazine

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

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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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. 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

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Danger

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 Code

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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
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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