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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

2023-02-21 17:18:21 UTC

HMDB ID

HMDB0014991

Secondary Accession Numbers

HMDB14991

Metabolite Identification

Common Name

Temozolomide

Description

Temozolomide, also known as TMZ or temodal, belongs to the class of organic compounds known as imidazotetrazines. These are organic polycyclic compounds containing an imidazole ring fused to a tetrazine ring. Imidazole is 5-membered ring consisting of three carbon atoms, and two nitrogen centers at the 1- and 3-positions. Tetrazine is a six-membered aromatic heterocycle made up of four nitrogen atoms and a two carbon atoms. Based on a literature review a significant number of articles have been published on Temozolomide.

Structure

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

853
  Mrv0541 02231215032D          

 14 15  0  0  0  0            999 V2000
    3.0791    1.8772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2795   -1.8350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.6397    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.6397    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0556    0.2272    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.5978    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.1853    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6378   -1.3911    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.1853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5741   -0.4367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.0522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5741    0.8911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.0522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8305   -1.2209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 11  2  0  0  0  0
  2 14  2  0  0  0  0
  3  9  1  0  0  0  0
  3 11  1  0  0  0  0
  3 12  1  0  0  0  0
  4  7  1  0  0  0  0
  4 11  1  0  0  0  0
  4 13  1  0  0  0  0
  5 10  1  0  0  0  0
  5 12  2  0  0  0  0
  6  7  2  0  0  0  0
  6  9  1  0  0  0  0
  8 14  1  0  0  0  0
  9 10  2  0  0  0  0
 10 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014991

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1N=NC2=C(N=CN2C1=O)C(N)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H6N6O2/c1-11-6(14)12-2-8-3(4(7)13)5(12)9-10-11/h2H,1H3,(H2,7,13)

> <INCHI_KEY>
BPEGJWRSRHCHSN-UHFFFAOYSA-N

> <FORMULA>
C6H6N6O2

> <MOLECULAR_WEIGHT>
194.1508

> <EXACT_MASS>
194.055223466

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
16.875955761195286

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-methyl-4-oxo-3H,4H-imidazo[4,3-d][1,2,3,5]tetrazine-8-carboxamide

> <ALOGPS_LOGP>
-1.00

> <JCHEM_LOGP>
-0.2825381519999997

> <ALOGPS_LOGS>
-1.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.511549673808375

> <JCHEM_PKA_STRONGEST_BASIC>
-3.638478343476955

> <JCHEM_POLAR_SURFACE_AREA>
105.94

> <JCHEM_REFRACTIVITY>
47.8609

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.09e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
temozolomide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 853                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       5.748   3.504   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       7.988  -3.425   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       7.081   1.194   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       4.414   1.194   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       9.437   0.424   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       5.748  -1.116   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       4.414  -0.346   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0      10.524  -2.597   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       7.081  -0.346   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.538  -0.815   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.748   1.964   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.538   1.663   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.080   1.964   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.017  -2.279   0.000  0.00  0.00           C+0
CONECT    1   11                                                            
CONECT    2   14                                                            
CONECT    3    9   11   12                                                  
CONECT    4    7   11   13                                                  
CONECT    5   10   12                                                       
CONECT    6    7    9                                                       
CONECT    7    4    6                                                       
CONECT    8   14                                                            
CONECT    9    3    6   10                                                  
CONECT   10    5    9   14                                                  
CONECT   11    1    3    4                                                  
CONECT   12    3    5                                                       
CONECT   13    4                                                            
CONECT   14    2    8   10                                                  
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
3,4-Dihydro-3-methyl-4-oxoimidazo(5,1-D)-1,2,3,5-tetrazine-8-carboxamide	ChEBI
3,4-Dihydro-3-methyl-4-oxoimidazo(5,1-D)-as-tetrazine-8-carboxamide	ChEBI
3-Methyl-4-oxo-3,4-dihydroimidazo(5,1-D)(1,2,3,5)tetrazine-8-carboxamide	ChEBI
8-Carbamoyl-3-methylimidazo(5,1-D)-1,2,3,5-tetrazin-4(3H)-one	ChEBI
BRN 5547136	ChEBI
CCRG 81045	ChEBI
CCRG-81045	ChEBI
CCRIS 8996	ChEBI
m & b 39831	ChEBI
MB 39831	ChEBI
M&B 39831	ChEBI
Methazolastone	ChEBI
NSC 362856	ChEBI
SCH 52365	ChEBI
Temodal	ChEBI
Temodar	ChEBI
Temozolomida	ChEBI
Temozolomidum	ChEBI
TMZ	ChEBI
Temozolamide	HMDB
m And b 39831	HMDB
m And b-39831	HMDB
TMZ-Bioshuttle	HMDB
Temozolomide hexyl ester	HMDB
TMZA-he	HMDB
TMZ Bioshuttle	HMDB
m And b39831	HMDB

Chemical Formula

C₆H₆N₆O₂

Average Molecular Weight

194.1508

Monoisotopic Molecular Weight

194.055223466

IUPAC Name

3-methyl-4-oxo-3H,4H-imidazo[4,3-d][1,2,3,5]tetrazine-8-carboxamide

Traditional Name

temozolomide

CAS Registry Number

85622-93-1

SMILES

CN1N=NC2=C(N=CN2C1=O)C(N)=O

InChI Identifier

InChI=1S/C6H6N6O2/c1-11-6(14)12-2-8-3(4(7)13)5(12)9-10-11/h2H,1H3,(H2,7,13)

InChI Key

BPEGJWRSRHCHSN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as imidazotetrazines. These are organic polycyclic compounds containing an imidazole ring fused to a tetrazine ring. Imidazole is 5-membered ring consisting of three carbon atoms, and two nitrogen centers at the 1- and 3-positions. Tetrazine is a six-membered aromatic heterocycle made up of four nitrogen atoms and a two carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Imidazotetrazines

Sub Class

Not Available

Direct Parent

Imidazotetrazines

Alternative Parents

Substituents

Imidazotetrazine
2-heteroaryl carboxamide
Imidazole-4-carbonyl group
N-substituted imidazole
Tetrazine
Azole
Imidazole
Heteroaromatic compound
Vinylogous amide
Carboxamide group
Primary carboxylic acid amide
Carboxylic acid derivative
Azacycle
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monocarboxylic acid amide (CHEBI:72564 )
triazene derivative (CHEBI:72564 )
imidazotetrazine (CHEBI:72564 )

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

Cytoplasm (HMDB: HMDB0014991)
Membrane (HMDB: HMDB0014991)

Source

Exogenous

Exogenous (HMDB: HMDB0014991)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	212 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	5.09 g/L	Not Available
LogP	-2.8	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	5.09 g/L	ALOGPS
logP	-1	ALOGPS
logP	-0.28	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	10.51	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	105.94 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	47.86 m³·mol⁻¹	ChemAxon
Polarizability	16.88 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	142.475	31661259
DarkChem	[M-H]-	139.23	31661259
DeepCCS	[M+H]+	141.392	30932474
DeepCCS	[M-H]-	139.034	30932474
DeepCCS	[M-2H]-	174.322	30932474
DeepCCS	[M+Na]+	149.19	30932474
AllCCS	[M+H]+	141.0	32859911
AllCCS	[M+H-H2O]+	136.8	32859911
AllCCS	[M+NH4]+	144.9	32859911
AllCCS	[M+Na]+	146.0	32859911
AllCCS	[M-H]-	138.9	32859911
AllCCS	[M+Na-2H]-	139.2	32859911
AllCCS	[M+HCOO]-	139.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Temozolomide	CN1N=NC2=C(N=CN2C1=O)C(N)=O	2449.0	Standard polar	33892256
Temozolomide	CN1N=NC2=C(N=CN2C1=O)C(N)=O	1987.0	Standard non polar	33892256
Temozolomide	CN1N=NC2=C(N=CN2C1=O)C(N)=O	2254.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Temozolomide,1TMS,isomer #1	CN1N=NC2=C(C(=O)N[Si](C)(C)C)N=CN2C1=O	2133.6	Semi standard non polar	33892256
Temozolomide,1TMS,isomer #1	CN1N=NC2=C(C(=O)N[Si](C)(C)C)N=CN2C1=O	2214.3	Standard non polar	33892256
Temozolomide,1TMS,isomer #1	CN1N=NC2=C(C(=O)N[Si](C)(C)C)N=CN2C1=O	3691.8	Standard polar	33892256
Temozolomide,2TMS,isomer #1	CN1N=NC2=C(C(=O)N([Si](C)(C)C)[Si](C)(C)C)N=CN2C1=O	2150.6	Semi standard non polar	33892256
Temozolomide,2TMS,isomer #1	CN1N=NC2=C(C(=O)N([Si](C)(C)C)[Si](C)(C)C)N=CN2C1=O	2295.4	Standard non polar	33892256
Temozolomide,2TMS,isomer #1	CN1N=NC2=C(C(=O)N([Si](C)(C)C)[Si](C)(C)C)N=CN2C1=O	3251.5	Standard polar	33892256
Temozolomide,1TBDMS,isomer #1	CN1N=NC2=C(C(=O)N[Si](C)(C)C(C)(C)C)N=CN2C1=O	2398.2	Semi standard non polar	33892256
Temozolomide,1TBDMS,isomer #1	CN1N=NC2=C(C(=O)N[Si](C)(C)C(C)(C)C)N=CN2C1=O	2373.0	Standard non polar	33892256
Temozolomide,1TBDMS,isomer #1	CN1N=NC2=C(C(=O)N[Si](C)(C)C(C)(C)C)N=CN2C1=O	3657.7	Standard polar	33892256
Temozolomide,2TBDMS,isomer #1	CN1N=NC2=C(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN2C1=O	2651.6	Semi standard non polar	33892256
Temozolomide,2TBDMS,isomer #1	CN1N=NC2=C(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN2C1=O	2633.0	Standard non polar	33892256
Temozolomide,2TBDMS,isomer #1	CN1N=NC2=C(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN2C1=O	3202.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Temozolomide GC-MS (Non-derivatized) - 70eV, Positive	splash10-000f-5900000000-c57261fbff38ae5dbab0	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Temozolomide 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Temozolomide 35V, Positive-QTOF	splash10-0a4r-9300000000-49f7261125953a02508c	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Temozolomide 10V, Positive-QTOF	splash10-0002-0900000000-d9e1e206d7b06ccc479d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Temozolomide 20V, Positive-QTOF	splash10-0f6t-0900000000-34157e6c0ae2f946b796	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Temozolomide 40V, Positive-QTOF	splash10-004i-3900000000-39baca8459a2d7d69887	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Temozolomide 10V, Negative-QTOF	splash10-0006-0900000000-e01487cdb01c9cfbbca6	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Temozolomide 20V, Negative-QTOF	splash10-0f6x-2900000000-45ff34ca952c13e2e9e1	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Temozolomide 40V, Negative-QTOF	splash10-0006-9600000000-4719e8aa23ba0437bc9d	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Temozolomide 10V, Positive-QTOF	splash10-0002-0900000000-8368d930a3d0bfca1535	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Temozolomide 20V, Positive-QTOF	splash10-00ds-1900000000-01d724d7c70310752a11	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Temozolomide 40V, Positive-QTOF	splash10-0929-3900000000-05ec3267ff2f648a63d9	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Temozolomide 10V, Negative-QTOF	splash10-0006-0900000000-eece1187427402b6806b	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Temozolomide 20V, Negative-QTOF	splash10-0udi-0900000000-a10f3dd11710d4812249	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Temozolomide 40V, Negative-QTOF	splash10-022c-3900000000-bb2a07e9cfc644fa8c80	2021-10-11	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX 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 DB00853	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00853	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00853

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5201

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Temozolomide

METLIN ID

Not Available

PubChem Compound

5394

PDB ID

Not Available

ChEBI ID

72564

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

Yung WK: Temozolomide in malignant gliomas. Semin Oncol. 2000 Jun;27(3 Suppl 6):27-34. [PubMed:10866347 ]
Friedman HS, Kerby T, Calvert H: Temozolomide and treatment of malignant glioma. Clin Cancer Res. 2000 Jul;6(7):2585-97. [PubMed:10914698 ]
Mutter N, Stupp R: Temozolomide: a milestone in neuro-oncology and beyond? Expert Rev Anticancer Ther. 2006 Aug;6(8):1187-204. [PubMed:16925485 ]
Wick W, Platten M, Weller M: New (alternative) temozolomide regimens for the treatment of glioma. Neuro Oncol. 2009 Feb;11(1):69-79. doi: 10.1215/15228517-2008-078. Epub 2008 Sep 4. [PubMed:18772354 ]
Trinh VA, Patel SP, Hwu WJ: The safety of temozolomide in the treatment of malignancies. Expert Opin Drug Saf. 2009 Jul;8(4):493-9. doi: 10.1517/14740330902918281 . [PubMed:19435405 ]
Villano JL, Seery TE, Bressler LR: Temozolomide in malignant gliomas: current use and future targets. Cancer Chemother Pharmacol. 2009 Sep;64(4):647-55. doi: 10.1007/s00280-009-1050-5. Epub 2009 Jun 19. [PubMed:19543728 ]
Meije Y, Lizasoain M, Garcia-Reyne A, Martinez P, Rodriguez V, Lopez-Medrano F, Juan RS, Lalueza A, Aguado JM: Emergence of cytomegalovirus disease in patients receiving temozolomide: report of two cases and literature review. Clin Infect Dis. 2010 Jun 15;50(12):e73-6. doi: 10.1086/653011. [PubMed:20455691 ]
Neyns B, Tosoni A, Hwu WJ, Reardon DA: Dose-dense temozolomide regimens: antitumor activity, toxicity, and immunomodulatory effects. Cancer. 2010 Jun 15;116(12):2868-77. doi: 10.1002/cncr.25035. [PubMed:20564393 ]

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

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 performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

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 Temozolomide (HMDB0014991)

MOL for HMDB0014991 (Temozolomide)

3D MOL for HMDB0014991 (Temozolomide)

3D SDF for HMDB0014991 (Temozolomide)

3D-SDF for HMDB0014991 (Temozolomide)

PDB for HMDB0014991 (Temozolomide)

3D PDB for HMDB0014991 (Temozolomide)

SMILES for HMDB0014991 (Temozolomide)

INCHI for HMDB0014991 (Temozolomide)

Structure for HMDB0014991 (Temozolomide)

3D Structure for HMDB0014991 (Temozolomide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

References