Temozolomide (CHEM017846)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 04:41:23 UTC
Update Date2016-11-09 01:15:41 UTC
Accession NumberCHEM017846
Identification
Common NameTemozolomide
ClassSmall Molecule
DescriptionAn imidazotetrazine that is 3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine which is substituted at positions 3, 4, and 8 by methyl, oxo, and carboxamide groups, respectively. A prodrug for MTIC (5-(3-methyltriaz-1-en-1-yl)-1H-imidazole-4-carboxamide, formed by spontaneous hydrolysis of temozolomide in the body), it is used as an oral alkylating agent for the treatment of newly diagnosed malignant glioblastoma multiforme (concomitantly with radiotherapy) and malignant melanoma.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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 Mass194.151 g/mol
Monoisotopic Mass194.055 g/mol
CAS Registry Number85622-93-1
IUPAC Name3-methyl-4-oxo-3H,4H-imidazo[4,3-d][1,2,3,5]tetrazine-8-carboxamide
Traditional Nametemozolomide
SMILESCN1N=NC2=C(N=CN2C1=O)C(N)=O
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000f-5900000000-c57261fbff38ae5dbab0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0a4r-9300000000-49f7261125953a02508cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-d9e1e206d7b06ccc479dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f6t-0900000000-34157e6c0ae2f946b796Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-3900000000-39baca8459a2d7d69887Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-e01487cdb01c9cfbbca6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f6x-2900000000-45ff34ca952c13e2e9e1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9600000000-4719e8aa23ba0437bc9dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-8368d930a3d0bfca1535Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ds-1900000000-01d724d7c70310752a11Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0929-3900000000-05ec3267ff2f648a63d9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-eece1187427402b6806bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-a10f3dd11710d4812249Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-022c-3900000000-bb2a07e9cfc644fa8c80Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB00853
HMDB IDHMDB0014991
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkTemozolomide
Chemspider ID5201
ChEBI ID72564
PubChem Compound ID5394
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=22680781
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=22818211
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=23246370
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=23254891
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23293540
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=23335050
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=23362460
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=23377829
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=23385995
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=23389760
11. Yung WK: Temozolomide in malignant gliomas. Semin Oncol. 2000 Jun;27(3 Suppl 6):27-34.
12. Friedman HS, Kerby T, Calvert H: Temozolomide and treatment of malignant glioma. Clin Cancer Res. 2000 Jul;6(7):2585-97.
13. Mutter N, Stupp R: Temozolomide: a milestone in neuro-oncology and beyond? Expert Rev Anticancer Ther. 2006 Aug;6(8):1187-204.
14. 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.
15. 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 .
16. 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.
17. 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.
18. 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.