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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:49 UTC

HMDB ID

HMDB0014989

Secondary Accession Numbers

HMDB14989

Metabolite Identification

Common Name

Dacarbazine

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. (from Martindale, The Extra Pharmacopoeia, 31st ed, p564)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.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 19-APR-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-12         0                                  
HETATM    1  C   UNK     0      -0.656   3.806   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       0.590   2.900   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0      -1.902   2.900   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -1.426   1.436   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.196   0.102   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.114   1.436   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       0.884   0.102   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       1.654  -1.232   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       3.964   0.102   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       3.194  -1.232   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       3.964  -2.565   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      -1.426  -1.232   0.000  0.00  0.00           N+0
HETATM   13  O   UNK     0      -3.736   0.102   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    6                                                       
CONECT    3    1    4                                                       
CONECT    4    6    3    5                                                  
CONECT    5    4   13   12                                                  
CONECT    6    2    4    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7   10                                                       
CONECT    9   10                                                            
CONECT   10    8    9   11                                                  
CONECT   11   10                                                            
CONECT   12    5                                                            
CONECT   13    5                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
4-(3,3-Dimethyl-1-triazeno)imidazole-5-carboxamide	ChEBI
4-(5)-(3,3-Dimethyl-1-triazeno)imidazole-5(4)-carboxamide	ChEBI
4-(Dimethyltriazeno)imidazole-5-carboxamide	ChEBI
5-(3,3-Dimethyl-1-triazeno)imidazole-4-carboxamide	ChEBI
5-(3,3-Dimethyltriazeno)imidazole-4-carboxamide	ChEBI
5-(Dimethyltriazeno)imidazole-4-carboxamide	ChEBI
Dacarbazina	ChEBI
Dacarbazinum	ChEBI
Deticene	ChEBI
Di-me-triazenoimidazolecarboxamide	ChEBI
DIC	ChEBI
DTIC	ChEBI
Dtic-dome	ChEBI
HSDB 3219	ChEBI
ICDMT	ChEBI
NCI-C04717	ChEBI
NSC 45388	ChEBI
NSC-45388	ChEBI
DTCI	HMDB
Biocarbazine R	HMDB
DTIE	HMDB
ICDT	HMDB
Imidazole carboxamide	HMDB
Biocarbazine	MeSH
Carboxamide, dimethyl imidazole	MeSH
DTIC dome	MeSH
DTICDome	MeSH
Decarbazine	MeSH
Dimethyl imidazole carboxamide	MeSH
Dimethyl triazeno imidazole carboxamide	MeSH
Imidazole carboxamide, dimethyl	MeSH

Chemical Formula

C₆H₁₀N₆O

Average Molecular Weight

182.1832

Monoisotopic Molecular Weight

182.091608972

IUPAC Name

5-(dimethyltriaz-1-en-1-yl)-1H-imidazole-4-carboxamide

Traditional Name

dacarbazine - dtic

CAS Registry Number

4342-03-4

SMILES

CN(C)N=NC1=C(N=CN1)C(N)=O

InChI Identifier

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)

InChI Key

FDKXTQMXEQVLRF-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Carboxylic acid derivatives

Direct Parent

2-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 Framework

Aromatic heteromonocyclic compounds

External Descriptors

monocarboxylic acid amide (CHEBI:4305 )
imidazoles (CHEBI:4305 )
triazene derivative (CHEBI:4305 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0014989)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	205 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1.36 g/L	Not Available
LogP	-1.6	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.36 g/L	ALOGPS
logP	-0.32	ALOGPS
logP	-0.43	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	5.89	ChemAxon
pKa (Strongest Basic)	1.72	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	99.73 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	49.71 m³·mol⁻¹	ChemAxon
Polarizability	17.78 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	141.903	31661259
DarkChem	[M-H]-	137.998	31661259
DeepCCS	[M+H]+	141.066	30932474
DeepCCS	[M-H]-	138.714	30932474
DeepCCS	[M-2H]-	174.509	30932474
DeepCCS	[M+Na]+	149.685	30932474
AllCCS	[M+H]+	140.6	32859911
AllCCS	[M+H-H2O]+	136.6	32859911
AllCCS	[M+NH4]+	144.3	32859911
AllCCS	[M+Na]+	145.4	32859911
AllCCS	[M-H]-	138.3	32859911
AllCCS	[M+Na-2H]-	139.3	32859911
AllCCS	[M+HCOO]-	140.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dacarbazine	CN(C)N=NC1=C(N=CN1)C(N)=O	2291.7	Standard polar	33892256
Dacarbazine	CN(C)N=NC1=C(N=CN1)C(N)=O	1818.0	Standard non polar	33892256
Dacarbazine	CN(C)N=NC1=C(N=CN1)C(N)=O	2159.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dacarbazine,1TMS,isomer #1	CN(C)N=NC1=C(C(=O)N[Si](C)(C)C)N=C[NH]1	1779.6	Semi standard non polar	33892256
Dacarbazine,1TMS,isomer #1	CN(C)N=NC1=C(C(=O)N[Si](C)(C)C)N=C[NH]1	1934.9	Standard non polar	33892256
Dacarbazine,1TMS,isomer #1	CN(C)N=NC1=C(C(=O)N[Si](C)(C)C)N=C[NH]1	3731.2	Standard polar	33892256
Dacarbazine,1TMS,isomer #2	CN(C)N=NC1=C(C(N)=O)N=CN1[Si](C)(C)C	1913.9	Semi standard non polar	33892256
Dacarbazine,1TMS,isomer #2	CN(C)N=NC1=C(C(N)=O)N=CN1[Si](C)(C)C	1956.1	Standard non polar	33892256
Dacarbazine,1TMS,isomer #2	CN(C)N=NC1=C(C(N)=O)N=CN1[Si](C)(C)C	3542.3	Standard polar	33892256
Dacarbazine,2TMS,isomer #1	CN(C)N=NC1=C(C(=O)N[Si](C)(C)C)N=CN1[Si](C)(C)C	1853.0	Semi standard non polar	33892256
Dacarbazine,2TMS,isomer #1	CN(C)N=NC1=C(C(=O)N[Si](C)(C)C)N=CN1[Si](C)(C)C	2052.2	Standard non polar	33892256
Dacarbazine,2TMS,isomer #1	CN(C)N=NC1=C(C(=O)N[Si](C)(C)C)N=CN1[Si](C)(C)C	3316.3	Standard polar	33892256
Dacarbazine,2TMS,isomer #2	CN(C)N=NC1=C(C(=O)N([Si](C)(C)C)[Si](C)(C)C)N=C[NH]1	1816.3	Semi standard non polar	33892256
Dacarbazine,2TMS,isomer #2	CN(C)N=NC1=C(C(=O)N([Si](C)(C)C)[Si](C)(C)C)N=C[NH]1	2063.8	Standard non polar	33892256
Dacarbazine,2TMS,isomer #2	CN(C)N=NC1=C(C(=O)N([Si](C)(C)C)[Si](C)(C)C)N=C[NH]1	3442.8	Standard polar	33892256
Dacarbazine,3TMS,isomer #1	CN(C)N=NC1=C(C(=O)N([Si](C)(C)C)[Si](C)(C)C)N=CN1[Si](C)(C)C	1955.2	Semi standard non polar	33892256
Dacarbazine,3TMS,isomer #1	CN(C)N=NC1=C(C(=O)N([Si](C)(C)C)[Si](C)(C)C)N=CN1[Si](C)(C)C	2117.8	Standard non polar	33892256
Dacarbazine,3TMS,isomer #1	CN(C)N=NC1=C(C(=O)N([Si](C)(C)C)[Si](C)(C)C)N=CN1[Si](C)(C)C	2997.6	Standard polar	33892256
Dacarbazine,1TBDMS,isomer #1	CN(C)N=NC1=C(C(=O)N[Si](C)(C)C(C)(C)C)N=C[NH]1	1987.2	Semi standard non polar	33892256
Dacarbazine,1TBDMS,isomer #1	CN(C)N=NC1=C(C(=O)N[Si](C)(C)C(C)(C)C)N=C[NH]1	2094.8	Standard non polar	33892256
Dacarbazine,1TBDMS,isomer #1	CN(C)N=NC1=C(C(=O)N[Si](C)(C)C(C)(C)C)N=C[NH]1	3732.5	Standard polar	33892256
Dacarbazine,1TBDMS,isomer #2	CN(C)N=NC1=C(C(N)=O)N=CN1[Si](C)(C)C(C)(C)C	2088.2	Semi standard non polar	33892256
Dacarbazine,1TBDMS,isomer #2	CN(C)N=NC1=C(C(N)=O)N=CN1[Si](C)(C)C(C)(C)C	2145.1	Standard non polar	33892256
Dacarbazine,1TBDMS,isomer #2	CN(C)N=NC1=C(C(N)=O)N=CN1[Si](C)(C)C(C)(C)C	3587.4	Standard polar	33892256
Dacarbazine,2TBDMS,isomer #1	CN(C)N=NC1=C(C(=O)N[Si](C)(C)C(C)(C)C)N=CN1[Si](C)(C)C(C)(C)C	2234.3	Semi standard non polar	33892256
Dacarbazine,2TBDMS,isomer #1	CN(C)N=NC1=C(C(=O)N[Si](C)(C)C(C)(C)C)N=CN1[Si](C)(C)C(C)(C)C	2372.5	Standard non polar	33892256
Dacarbazine,2TBDMS,isomer #1	CN(C)N=NC1=C(C(=O)N[Si](C)(C)C(C)(C)C)N=CN1[Si](C)(C)C(C)(C)C	3344.4	Standard polar	33892256
Dacarbazine,2TBDMS,isomer #2	CN(C)N=NC1=C(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C[NH]1	2195.5	Semi standard non polar	33892256
Dacarbazine,2TBDMS,isomer #2	CN(C)N=NC1=C(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C[NH]1	2429.5	Standard non polar	33892256
Dacarbazine,2TBDMS,isomer #2	CN(C)N=NC1=C(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C[NH]1	3442.3	Standard polar	33892256
Dacarbazine,3TBDMS,isomer #1	CN(C)N=NC1=C(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN1[Si](C)(C)C(C)(C)C	2492.3	Semi standard non polar	33892256
Dacarbazine,3TBDMS,isomer #1	CN(C)N=NC1=C(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN1[Si](C)(C)C(C)(C)C	2657.8	Standard non polar	33892256
Dacarbazine,3TBDMS,isomer #1	CN(C)N=NC1=C(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN1[Si](C)(C)C(C)(C)C	3058.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Dacarbazine GC-MS (Non-derivatized) - 70eV, Positive	splash10-002f-7900000000-1b20185f2f8cede43985	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dacarbazine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dacarbazine 10V, Positive-QTOF	splash10-001i-0900000000-19e145e04a29e85dbb78	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dacarbazine 20V, Positive-QTOF	splash10-0159-0900000000-46878b8c1d5ef1a88f40	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dacarbazine 40V, Positive-QTOF	splash10-0006-6900000000-7776976c8e2de261cdae	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dacarbazine 10V, Negative-QTOF	splash10-001i-1900000000-454c00afd7e71a2e94de	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dacarbazine 20V, Negative-QTOF	splash10-001c-2900000000-1247d4cc570997f56811	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dacarbazine 40V, Negative-QTOF	splash10-0006-9400000000-3bc8cd08fb9775dce145	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dacarbazine 10V, Positive-QTOF	splash10-00lr-0900000000-06f8b85fb44ca1de41ad	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dacarbazine 20V, Positive-QTOF	splash10-001v-5900000000-bb28672b3383c5c86fda	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dacarbazine 40V, Positive-QTOF	splash10-052b-9100000000-43b8467f20b35711585f	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dacarbazine 10V, Negative-QTOF	splash10-000x-7900000000-45eda8c3304bd65c690f	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dacarbazine 20V, Negative-QTOF	splash10-0006-9000000000-d22f5484d8086a357256	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dacarbazine 40V, Negative-QTOF	splash10-0006-9000000000-5a148f839c246fca824b	2021-10-11	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00851	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00851	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

10437816

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Dacarbazine

METLIN ID

Not Available

PubChem Compound

2942

PDB ID

Not Available

ChEBI ID

4305

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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. [PubMed:10751609 ]
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. [PubMed:11318431 ]
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. [PubMed:15010317 ]
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. [PubMed:20082117 ]
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. [PubMed:21471822 ]
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. [PubMed:21654834 ]
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. [PubMed:23029050 ]

Enzymes

Enzyme Details

1. DNA polymerase subunit alpha B

General function:: Not Available
Specific function:: May play an essential role at the early stage of chromosomal DNA replication by coupling the polymerase alpha/primase complex to the cellular replication machinery
Gene Name:: POLA2
Uniprot ID:: Q14181
Molecular weight:: 65948.0

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Lonn U, Lohn S: Prevention of dacarbazine damage of human neoplastic cell DNA by aphidicolin. Cancer Res. 1987 Jan 1;47(1):26-30. [PubMed:3098406 ]

Enzyme Details

2. 6-phosphogluconate dehydrogenase, decarboxylating

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the oxidative decarboxylation of 6-phosphogluconate to ribulose 5-phosphate and CO(2), with concomitant reduction of NADP to NADPH (By similarity).
Gene Name:: PGD
Uniprot ID:: P52209
Molecular weight:: 53139.56

References

Akkemik E, Budak H, Ciftci M: Effects of some drugs on human erythrocyte 6-phosphogluconate dehydrogenase: an in vitro study. J Enzyme Inhib Med Chem. 2010 Aug;25(4):476-9. doi: 10.3109/14756360903257900. [PubMed:20235752 ]
Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]

Enzyme Details

3. Cytochrome P450 2E1

General function:: Involved in monooxygenase activity
Specific function:: Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:: CYP2E1
Uniprot ID:: P05181
Molecular weight:: 56848.42

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

4. Cytochrome P450 1A1

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP1A1
Uniprot ID:: P04798
Molecular weight:: 58164.815

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

5. Cytochrome P450 1A2

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:: CYP1A2
Uniprot ID:: P05177
Molecular weight:: 58406.915

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Showing metabocard for Dacarbazine (HMDB0014989)

MOL for HMDB0014989 (Dacarbazine)

3D MOL for HMDB0014989 (Dacarbazine)

3D SDF for HMDB0014989 (Dacarbazine)

3D-SDF for HMDB0014989 (Dacarbazine)

PDB for HMDB0014989 (Dacarbazine)

3D PDB for HMDB0014989 (Dacarbazine)

SMILES for HMDB0014989 (Dacarbazine)

INCHI for HMDB0014989 (Dacarbazine)

Structure for HMDB0014989 (Dacarbazine)

3D Structure for HMDB0014989 (Dacarbazine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References

References

References

References

References