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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2020-02-26 21:40:45 UTC
HMDB IDHMDB0014991
Secondary Accession Numbers
  • HMDB14991
Metabolite Identification
Common NameTemozolomide
DescriptionTemozolomide, 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
Data?1582753245
Synonyms
ValueSource
3,4-Dihydro-3-methyl-4-oxoimidazo(5,1-D)-1,2,3,5-tetrazine-8-carboxamideChEBI
3,4-Dihydro-3-methyl-4-oxoimidazo(5,1-D)-as-tetrazine-8-carboxamideChEBI
3-Methyl-4-oxo-3,4-dihydroimidazo(5,1-D)(1,2,3,5)tetrazine-8-carboxamideChEBI
8-Carbamoyl-3-methylimidazo(5,1-D)-1,2,3,5-tetrazin-4(3H)-oneChEBI
BRN 5547136ChEBI
CCRG 81045ChEBI
CCRG-81045ChEBI
CCRIS 8996ChEBI
m & b 39831ChEBI
MB 39831ChEBI
M&B 39831ChEBI
MethazolastoneChEBI
NSC 362856ChEBI
SCH 52365ChEBI
TemodalChEBI
TemodarChEBI
TemozolomidaChEBI
TemozolomidumChEBI
TMZChEBI
TemozolamideHMDB
m And b 39831HMDB
m And b-39831HMDB
TMZ-BioshuttleHMDB
Temozolomide hexyl esterHMDB
TMZA-heHMDB
TMZ BioshuttleHMDB
m And b39831HMDB
Chemical FormulaC6H6N6O2
Average Molecular Weight194.1508
Monoisotopic Molecular Weight194.055223466
IUPAC Name3-methyl-4-oxo-3H,4H-imidazo[4,3-d][1,2,3,5]tetrazine-8-carboxamide
Traditional Nametemozolomide
CAS Registry Number85622-93-1
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 KeyBPEGJWRSRHCHSN-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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazotetrazines
Sub ClassNot Available
Direct ParentImidazotetrazines
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 FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point212 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility5.09 g/LNot Available
LogP-2.8Not Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility5.09 g/LALOGPS
logP-1ALOGPS
logP-0.28ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)10.51ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area105.94 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity47.86 m³·mol⁻¹ChemAxon
Polarizability16.88 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available142.47531661259
DarkChem[M-H]-PredictedNot Available139.2331661259

Retention Indices

Underivatized

Not Available

Derivatized

Not Available
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000f-5900000000-c57261fbff38ae5dbab02017-09-01View Spectrum
MSMass Spectrum (Electron Ionization)splash10-000f-5900000000-c57261fbff38ae5dbab02021-09-05View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-d9e1e206d7b06ccc479d2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f6t-0900000000-34157e6c0ae2f946b7962016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-3900000000-39baca8459a2d7d698872016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-e01487cdb01c9cfbbca62016-08-04View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f6x-2900000000-45ff34ca952c13e2e9e12016-08-04View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9600000000-4719e8aa23ba0437bc9d2016-08-04View Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00853 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00853 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00853
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5201
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTemozolomide
METLIN IDNot Available
PubChem Compound5394
PDB IDNot Available
ChEBI ID72564
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Yung WK: Temozolomide in malignant gliomas. Semin Oncol. 2000 Jun;27(3 Suppl 6):27-34. [PubMed:10866347 ]
  2. Friedman HS, Kerby T, Calvert H: Temozolomide and treatment of malignant glioma. Clin Cancer Res. 2000 Jul;6(7):2585-97. [PubMed:10914698 ]
  3. Mutter N, Stupp R: Temozolomide: a milestone in neuro-oncology and beyond? Expert Rev Anticancer Ther. 2006 Aug;6(8):1187-204. [PubMed:16925485 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. 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

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
  1. 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 ]