Structure via PubChem · Public domain (PubChem)
dacarbazine
Sign in to saveAlso known as 4-(5)-(3,3-dimethyl-1-triazeno)imidazole-5(4)-carboxamide, 5-(3,3-dimethyl-1-triazeno)imidazole-4-carboxamide, 5-(dimethyltriazeno)imidazole-4-carboxamide, 4-(dimethyltriazeno)imidazole-5-carboxamide, 5-(3,3-dimethyltriazeno)imidazole-4-carboxamide, 4-(3,3-dimethyl-1-triazeno)imidazole-5-carboxamide, (E)-dacarbazine
Dacarbazine, also known as imidazole carboxamide and sold under the brand name DTIC-Dome, is a chemotherapy medication used in the treatment of melanoma and Hodgkin's lymphoma. For Hodgkin's lymphoma, it is often used together with vinblastine, bleomycin, and doxorubicin. It is given by injection into a vein.
Chemical data
- Formula
- C6H10N6O
- Molecular weight
- 182.18 g/mol
- IUPAC name
- 4-[(E)-dimethylaminodiazenyl]-1H-imidazole-5-carboxamide
- SMILES
- CN(C)/N=N/C1=C(NC=N1)C(=O)N
- InChIKey
- FDKXTQMXEQVLRF-ZHACJKMWSA-N
- XLogP
- -0.6
- Polar surface area
- 99.7 Ų
- H-bond donors
- 2
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1975
- Admin. routes
- parenteral
- Indications
- metastatic melanoma, melanoma, cutaneous melanoma, sarcoma
via ChEMBL · EBI
Research
12,343 papers- Dacarbazine.Profiles of drug substances, excipients, and related methodology · 2016
- [Dacarbazine].Annales de dermatologie et de venereologie · 2001
- Dacarbazine.International journal of dermatology · 1976
- Dacarbazine.Report on carcinogens : carcinogen profiles · 2004
- Dacarbazine.Report on carcinogens : carcinogen profiles · 2011
via PubMed
Wikidata facts
- Has part
- nitrogen
- Mass
- 182.0916
- Has use
- medication
Show 7 more facts
- Commons category
- Dacarbazine
- chemical formula
- C₆H₁₀N₆O
- medical condition treated
- rhabdomyosarcoma
- isomeric SMILES
- CN(C)/N=N/C1=C(N=CN1)C(=O)N
- canonical SMILES
- CN(C)N=NC1=C(N=CN1)C(=O)N
- World Health Organisation international non-proprietary name
- dacarbazine
- legal status (medicine)
- boxed warning
via Wikidata · CC0
~3 min read
Encyclopedic overview
7 sectionsContents
- Medical uses
- Side effects
- Mechanism of action
- Synthesis
- History
- Society and culture
- References
Dacarbazine, also known as imidazole carboxamide and sold under the brand name DTIC-Dome, is a chemotherapy medication used in the treatment of melanoma and Hodgkin's lymphoma. For Hodgkin's lymphoma, it is often used together with vinblastine, bleomycin, and doxorubicin. It is given by injection into a vein.
Common side effects include loss of appetite, vomiting, low white blood cell count, and low platelets. Other serious side effects include liver problems and allergic reactions. It is unclear if use in pregnancy is safe for the baby. Dacarbazine is in the alkylating agent and purine analog families of medication.
Excerpted from Wikipedia’s “dacarbazine” article, available under the CC BY-SA 4.0 licence.