temozolomide   Click here for help

GtoPdb Ligand ID: 7301

Synonyms: CCRG-81045 | M-39831 | Temodal® | Temodar®
Approved drug
temozolomide is an approved drug (EMA and FDA (1999))
Compound class: Synthetic organic
Comment: Temozolomide is a DNA alkylating agent.
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2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 6
Hydrogen bond donors 1
Rotatable bonds 1
Topological polar surface area 108.17
Molecular weight 194.06
XLogP -1.26
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES NC(=O)c1ncn2c1nnn(c2=O)C
Isomeric SMILES NC(=O)c1ncn2c1nnn(c2=O)C
InChI 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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (EMA and FDA (1999))
Approved drug? Yes. FDA (1999)  |  EMA (1999)
IUPAC Name Click here for help
3-methyl-4-oxo-3H,4H-imidazo[4,3-d][1,2,3,5]tetrazine-8-carboxamide
International Nonproprietary Names Click here for help
INN number INN
6027 temozolomide
Synonyms Click here for help
CCRG-81045 | M-39831 | Temodal® | Temodar®
Database Links Click here for help
CAS Registry No. 85622-93-1
ChEMBL Ligand CHEMBL810
DrugBank Ligand DB00853
DrugCentral Ligand 2589
GtoPdb PubChem SID 178103874
PubChem CID 5394
Search Google for chemical match using the InChIKey BPEGJWRSRHCHSN-UHFFFAOYSA-N
Search Google for chemicals with the same backbone BPEGJWRSRHCHSN
Search PubMed clinical trials temozolomide
Search PubMed titles temozolomide
Search PubMed titles/abstracts temozolomide
UniChem Compound Search for chemical match using the InChIKey BPEGJWRSRHCHSN-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey BPEGJWRSRHCHSN-UHFFFAOYSA-N
Wikipedia Temozolomide

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MedChemExpress
Temozolomide (links to external site)
Cat. No. HY-17364