Dacarbazine (CHEM003647)

Record Information
Version1.0
Creation Date2014-09-11 02:05:03 UTC
Update Date2026-05-14 16:50:44 UTC
Accession NumberCHEM003647
Identification
Common NameDacarbazine
ClassSmall Molecule
Description
Dacarbazine is only found in individuals that have used or taken this drug. It is an antineoplastic agent. It has significant activity against melanomas. The mechanism of action is not known, but appears to exert cytotoxic effects via its action as an alkylating agent. Other theories include DNA synthesis inhibition by its action as a purine analog, and interaction with SH groups. Dacarbazine is not cell cycle-phase specific.
Contaminant Sources
  • HMDB Contaminants - Urine
  • IARC Carcinogens Group 2B
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amide
  • Amine
  • Antineoplastic Agent, Alkylating
  • Drug
  • Human Neurotoxin
  • Metabolite
  • Organic Compound
  • Synthetic Compound
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
4-(3,3-Dimethyl-1-triazeno)imidazole-5-carboxamideChEBI
4-(5)-(3,3-Dimethyl-1-triazeno)imidazole-5(4)-carboxamideChEBI
4-(Dimethyltriazeno)imidazole-5-carboxamideChEBI
5-(3,3-Dimethyl-1-triazeno)imidazole-4-carboxamideChEBI
5-(3,3-Dimethyltriazeno)imidazole-4-carboxamideChEBI
5-(Dimethyltriazeno)imidazole-4-carboxamideChEBI
DacarbazinaChEBI
DacarbazinumChEBI
DeticeneChEBI
Di-me-triazenoimidazolecarboxamideChEBI
DICChEBI
DTICChEBI
Dtic-domeChEBI
HSDB 3219ChEBI
ICDMTChEBI
NCI-C04717ChEBI
NSC 45388ChEBI
NSC-45388ChEBI
DTCIHMDB
Biocarbazine RHMDB
DTIEHMDB
ICDTHMDB
Imidazole carboxamideHMDB
BiocarbazineMeSH
Carboxamide, dimethyl imidazoleMeSH
DTIC domeMeSH
DTICDomeMeSH
DecarbazineMeSH
Dimethyl imidazole carboxamideMeSH
Dimethyl triazeno imidazole carboxamideMeSH
Imidazole carboxamide, dimethylMeSH
Chemical FormulaC6H10N6O
Average Molecular Mass182.183 g/mol
Monoisotopic Mass182.092 g/mol
CAS Registry Number4342-03-4
IUPAC Name5-(dimethyltriaz-1-en-1-yl)-1H-imidazole-4-carboxamide
Traditional Namedacarbazine - dtic
SMILESCN(C)N=NC1=C(N=CN1)C(N)=O
InChI IdentifierInChI=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)
InChI KeyFDKXTQMXEQVLRF-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 2-heteroaryl carboxamides. 2-Heteroaryl carboxamides are compounds containing a heteroaromatic ring that carries a carboxamide group.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassCarboxylic acid derivatives
Direct Parent2-heteroaryl carboxamides
Alternative Parents
Substituents
  • 2-heteroaryl carboxamide
  • Imidazole-4-carbonyl group
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Vinylogous amide
  • Primary carboxylic acid amide
  • Propargyl-type 1,3-dipolar organic compound
  • Azacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point205°C
Boiling PointNot Available
Solubility4220 mg/L
Predicted Properties
PropertyValueSource
Water Solubility1.36 g/LALOGPS
logP-0.32ALOGPS
logP-0.43ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)5.89ChemAxon
pKa (Strongest Basic)1.72ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area99.73 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity49.71 m³·mol⁻¹ChemAxon
Polarizability17.78 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureErratic, slow and incomplete.
Mechanism of ToxicityThe mechanism of action is not known, but appears to exert cytotoxic effects via its action as an alkylating agent. Other theories include DNA synthesis inhibition by its action as a purine analog, and interaction with SH groups. Dacarbazine is not cell cycle-phase specific.
MetabolismHepatic. Route of Elimination: Dacarbazine is subject to renal tubular secretion rather than glomerular filtration. In man, dacarbazine is extensively degraded. Besides unchanged dacarbazine, 5-aminoimidazole -4 carboxamide (AIC) is a major metabolite of dacarbazine excreted in the urine. Half Life: 5 hours
Toxicity ValuesLD50=350mg/kg (orally in mice)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)2B, possibly carcinogenic to humans. (1)
Uses/SourcesDacarbazine is used in the treatment of various cancers, among them malignant melanoma, Hodgkin lymphoma, sarcoma, and islet cell carcinoma of the pancreas. As of mid-2006, dacarbazine 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. (Wikipedia)
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0014989
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkDacarbazine
Chemspider ID10437816
ChEBI ID4305
PubChem Compound ID2942
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10751609
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11318431
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=12195827
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=15010317
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=20082117
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=21471822
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=21654834
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=23029050
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=23318786
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=26940170
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=28096700
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=28250333
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=28387914
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=28419676
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=29076951
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=29184162
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=29287706
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=29296081
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=29305638
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=29344241
21. Psaroudi MC, Kyrtopoulos SA: Toxicity, mutation frequency and mutation spectrum induced by dacarbazine in CHO cells expressing different levels of O(6)-methylguanine-DNA methyltransferase. Mutat Res. 2000 Feb 14;447(2):257-65.
22. Safgren SL, Reid JM, Rios R, Ames MM: Validated high-performance liquid chromatographic assay for simultaneous determination of dacarbazine and the plasma metabolites 5-(3-hydroxymethyl-3-methyl-1-triazeno)imidazole-4-carboxamide and 5-(3-methyl-1-triazeno)imidazole-4-carboxamide. J Chromatogr B Biomed Sci Appl. 2001 Apr 15;754(1):91-6.
23. Sanada M, Takagi Y, Ito R, Sekiguchi M: Killing and mutagenic actions of dacarbazine, a chemotherapeutic alkylating agent, on human and mouse cells: effects of Mgmt and Mlh1 mutations. DNA Repair (Amst). 2004 Apr 1;3(4):413-20.
24. Hersh EM, O'Day SJ, Powderly J, Khan KD, Pavlick AC, Cranmer LD, Samlowski WE, Nichol GM, Yellin MJ, Weber JS: A phase II multicenter study of ipilimumab with or without dacarbazine in chemotherapy-naive patients with advanced melanoma. Invest New Drugs. 2011 Jun;29(3):489-98. doi: 10.1007/s10637-009-9376-8. Epub 2010 Jan 16.
25. Yi JH, Yi SY, Lee HR, Lee SI, Lim DH, Kim JH, Park KW, Lee J: Dacarbazine-based chemotherapy as first-line treatment in noncutaneous metastatic melanoma: multicenter, retrospective analysis in Asia. Melanoma Res. 2011 Jun;21(3):223-7. doi: 10.1097/CMR.0b013e3283457743.
26. Nardin A, Wong WC, Tow C, Molina TJ, Tissier F, Audebourg A, Garcette M, Caignard A, Avril MF, Abastado JP, Prevost-Blondel A: Dacarbazine promotes stromal remodeling and lymphocyte infiltration in cutaneous melanoma lesions. J Invest Dermatol. 2011 Sep;131(9):1896-905. doi: 10.1038/jid.2011.128. Epub 2011 Jun 9.
27. Engesaeter B, Engebraaten O, Florenes VA, Maelandsmo GM: Dacarbazine and the agonistic TRAIL receptor-2 antibody lexatumumab induce synergistic anticancer effects in melanoma. PLoS One. 2012;7(9):e45492. doi: 10.1371/journal.pone.0045492. Epub 2012 Sep 20.