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| CAS No.: | 4342-03-4 |
|---|---|
| Name: | Dacarbazine |
| Molecular Structure: | |
|
|
|
| Formula: | C6H10N6O |
| Molecular Weight: | 182.185 |
| Synonyms: | Dimethyltriazenoimidazolecarboxamide;Di-me-triazenoimidazolecarboxamide;Biocarbazine R;Dtic-Dome (TN);DTIE;Dacarbazine (JAN/USP);Imidazole-4-carboxamide, 5- (3, 3-dimethyl-1-triazeno)-;4-(5)-(3, 3-Dimethyl-1-triazeno)imidazole-5(4)-carboxamide;Carboxamide, 5-(3,3-dimethyl-1-triazeno)imidazole-4-;5-(3,3-dimethyltriaz-1-en-1-yl)-1H-imidazole-4-carboxamide;1H-Imidazole-4-carboxamide, 5- (3,3-dimethyl-1-triazenyl)-;4-(5)-(3,3-Dimethyl-1-triazeno)imidazole-5(4)-carboxamide;5-(Dimethyltriazeno)imidazole-4-carboximide;4-(Dimethyltriazeno)imidazole-5-carboxamide;Carboxamide, 5-(3, 3-dimethyl-1-triazeno)imidazole-4-;Imidazole-4-carboxamide, 5-(3,3-dimethyl-1-triazenyl)-;(5Z)-5-(dimethylaminohydrazinylidene)imidazole-4-carboxamide;ICDT;DIC;4-(or 5)-(3, 3-Dimethyl-1-triazeno)imidazole-5(or 4)-carboxamide;Deticene;1H-Imidazole-4-carboxamide, 5-(3,3-dimethyl-1-triazenyl)-;4-[(1E)-3,3-Dimethyltriaz-1-en-1-yl]-1H-imidazole-5-carboxamide;4-(3, 3-Dimethyl-1-triazeno)imidazole-5-carboxamide;5-(Dimethyltriazeno)imidazole-4-carboxamide;1H-Imidazole-4-carboxamide,5-(3,3- dimethyl-1-triazenyl)-;DTIC;Imidazole-4(or 5)-carboxamide, 5(or 4)-(3, 3-dimethyl-1-triazeno)-;Darcarbazinum; |
| EINECS: | 224-396-1 |
| Density: | 1.486 g/cm3 |
| Melting Point: | 199-205 °C |
| Boiling Point: | 456.253 °C at 760 mmHg |
| Flash Point: | 229.734 °C |
| Solubility: | Insoluble in water |
| Appearance: | Off-white cryst. |
| Hazard Symbols: |
 T,  Xi,  Xn
|
| Risk Codes: | 45-46-20/21/22-36/37/38 |
| Safety: | 53-36/37/39-45-37/39-36-26 |
| PSA: | 99.73000 |
| LogP: | 0.76920 |
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5-Aminoimidazole-4-carboxamide
- 124-40-3
dimethyl amine
- 4342-03-4
5-(3,3-dimethyl-1-triazeno)imidazone-4-carboxamide
| Conditions | Yield |
|---|---|
| Stage #1: 5-Aminoimidazole-4-carboxamide With hydrogenchloride; sodium nitrite In water for 0.5h; Cooling with ice; Stage #2: dimethyl amine In water for 2h; Cooling with ice; | 76.2% |
- 4342-03-4
5-(3,3-dimethyl-1-triazeno)imidazone-4-carboxamide
| Conditions | Yield |
|---|---|
| In water at 38℃; for 24h; | 50% |
| Conditions | Yield |
|---|---|
| In water Irradiation; pH 1 or >/= 7.4; | |
| In ethanol at 37℃; Rate constant; buffer pH 1.2, ionic strength μ = 0.178; |
- 4342-03-4
5-(3,3-dimethyl-1-triazeno)imidazone-4-carboxamide
- 56973-26-3
5-hydroxy-1H-imidazole-4-carboxamide
| Conditions | Yield |
|---|---|
| In water at 20℃; Irradiation; pH 2-6; |
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Chemistry
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IUPAC Name: (5Z)-5-(Dimethylaminohydrazinylidene)imidazole-4-carboxamide
Molecular Formula: C6H10N6O
Molecular Weight: 182.22
EINECS: 224-396-1
Classification Code: Alkylating Agents; Antineoplastic; Antineoplastic Agents; Antineoplastic agents, alkylating; Drug / Therapeutic Agent; Human Data; Mutation data; Noxae; Reproductive Effect; Tumor data
Density:1.48 g/cm3
Melting Point:199-205 °C
Boiling Point: 456.3 °C at 760 mmHg
Flash Point: 229.7 °C
Storage temp.: 2-8 °C
Solubility:slightly soluble in ethanol and water
Index of Refraction: 1.677
Molar Refractivity: 46.21 cm3
Molar Volume: 122.6 cm3
Surface Tension: 60.6 dyne/cm
Enthalpy of Vaporization: 54.28 kJ/mol
Vapour Pressure of Dacarbazine (CAS NO.4342-03-4): 0.000981 mmHg at 25 °C
History
Dacarbazine gained FDA approval in May 1975 as DTIC-Dome. The drug was initially marketed by Bayer.
Uses
Dacarbazine (CAS NO.4342-03-4) is commonly used as a single agent in the treatment of metastatic melanoma, and as part of the ABVD chemotherapy regimen to treat Hodgkin lymphoma, and in the MAID regimen for sarcoma.
Toxicity Data With Reference
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| hamster | LD10 | parenteral | 250mg/kg (250mg/kg) | Journal of Surgical Oncology. Vol. 15, Pg. 355, 1980. | |
| human | TDLo | intravenous | 3500ug/kg (3.5mg/kg) | GASTROINTESTINAL: NAUSEA OR VOMITING BLOOD: LEUKOPENIA | Cancer Chemotherapy Reports, Part 1. Vol. 57, Pg. 83, 1973. |
| mouse | LD50 | intraperitoneal | 567mg/kg (567mg/kg) | Cancer Treatment Reports. Vol. 62, Pg. 721, 1978. | |
| mouse | LD50 | intravenous | 466mg/kg (466mg/kg) | BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) BEHAVIORAL: ANTIPSYCHOTIC | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 9, Pg. 3105, 1981. |
| mouse | LD50 | oral | 2032mg/kg (2032mg/kg) | BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) BEHAVIORAL: ANTIPSYCHOTIC | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 9, Pg. 3105, 1981. |
| rat | LD50 | intraperitoneal | 350mg/kg (350mg/kg) | Archiv fuer Geschwulstforschung. Vol. 50, Pg. 306, 1980. | |
| rat | LD50 | intravenous | 411mg/kg (411mg/kg) | BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) BEHAVIORAL: ANTIPSYCHOTIC | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 9, Pg. 3105, 1981. |
| rat | LD50 | oral | 2147mg/kg (2147mg/kg) | BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) BEHAVIORAL: ANTIPSYCHOTIC | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 9, Pg. 3105, 1981. |
Consensus Reports
NTP 10th Report on Carcinogens. IARC Cancer Review: Group 2B IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 (1987),p. 184.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Human Limited Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 26 (1981),p. 203.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Sufficient Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 26 (1981),p. 203.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . NCI Carcinogenesis Studies (ipr); Clear Evidence: mouse, rat RRCRBU Recent Results in Cancer Research. 52 (1975),1. . EPA Genetic Toxicology Program.
Safety Profile
Confirmed carcinogen with experimental carcinogenic and tumorigenic data. Poison by intraperitoneal and parenteral routes. Moderately toxic by ingestion and intravenous routes. Experimental teratogenic effects. Human systemic effects by intravenous route: nausea or vomiting, leukopenia (reduced white blood cell count), and changes in dehydrogenase enzymatic activity. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.
Hazard Codes: 
T,
Xi,
Xn
Risk Statements: 45-46-20/21/22-36/37/38
R45:May cause cancer.
R46:May cause heritable genetic damage.
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 53-36/37/39-45-37/39-36-26
S53:Avoid exposure - obtain special instructions before use.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S37/39:Wear suitable gloves and eye/face protection.
S36:Wear suitable protective clothing.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
WGK Germany: 3
RTECS: NI3950000
Specification
Dacarbazine (CAS NO.4342-03-4), its Synonyms are (Dimethyltriazeno)imidazolecarboxamide ; 1H-imidazole-4-carboxamide, 5-(3,3-dimethyl-1-triazenyl)- ; 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 ; 4-(or 5)-(3,3-Dimethyl-1-triazeno)imidazole-5(or 4)-carboxamide ; 5-(3,3-Dimethyl-1-triazeno)imidazole-4-carboxamide ; 5-(3,3-Dimethyltriazeno)imidazole-4-carboxamide ; 5-(Dimethyltriazeno)imidazole-4-carboxamide ; AI3-52825 ; Biocarbazine ; Biocarbazine R ; CCRIS 190 ; Carboxamide, 5-(3,3-dimethyl-1-triazeno)imidazole-4- ; DIC ; DTIC ; DTIC-Dome . It is white to ivory microcrystals or off-white crystalline solid.