T2577

Temozolomide

≥98% (HPLC), powder, DNA methylating agent

• Synonym(s): 3,4-Dihydro-3-methyl-4-oxoimidazo[5,1-d]-1,2,3,5-tetrazine-8-carboxamide, 3-Methyl-4-oxo-8-imidazolo[5,1-d][1,2,3,5]tetrazinecarboxamide, 4-Methyl-5-oxo-2,3,4,6,8-pentazabicyclo[4.3.0]nona-2,7,9-triene-9-carboxamide, 8-Carbamoyl-3-methylimidazo[5,1-d]-1,2,3,5-tetrazin-4(3H)-one, NSC 362856
• Empirical Formula (Hill Notation): C₆H₆N₆O₂
• CAS Number: 85622-93-1
• Molecular Weight: 194.15
• MDL number: MFCD00866492
• UNSPSC Code: 12352200
• PubChem Substance ID: 329826714
• NACRES: NA.77

Properties

• Product Name: Temozolomide, ≥98% (HPLC)
• assay: ≥98% (HPLC)
• form: powder
• color: white to light brown
• solubility: DMSO: 10 mg/mL, clear; H₂O: insoluble
• originator: Schering Plough
• storage temp.: 2-8°C
• SMILES string: CN1N=Nc2c(ncn2C1=O)C(N)=O
• 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

Description

General description

Temozolomide is a small lipophilic alkylating agent. It interacts covalently with the nucleophile microenvironment within DNA (Guanine residues). Due to this property temozolomide is considered a cytotoxic agent. The mechanism of action of TMZ is dependent upon its ability to hydrolyze DNA, resulting in DNA degradation and destruction of tumor cells. Malignant Glioma cells respond primarily to TMZ by G2/ M cell cycle arrest or in rare cases by apoptosis. Temozolomide is a DNA methylating agent and drug resistance-modifying agent; anti-tumor and anti-angiogenic. Temozolomide induces G2/M arrest and apoptosis through adduction of a methyl group to O6 position of guanine in genomic DNA and functional inactivation of DNA repair protein O(6)-alkylguanine DNA alkyltransferase (AGT) in base excision repair (BER) pathway.

Application

Temozolomide has been used for analyzing drug resistance mechanisms in glioblastoma cell lines. Temozolomide has been used to induce cytotoxic effects on glioblastoma cells to study the outcome of protein disulfide isomerase (PDI) inhibition.

Biochem/physiol Actions

Temozolomide is a DNA methylating agent and drug resistance-modifying agent; anti-tumor and anti-angiogenic. Temozolomide induces G2/M arrest and apoptosis through adduction of a methyl group to O6 position of guanine in genomic DNA and functional inactivation of DNA repair protein O(6)-alkylguanine DNA alkyltransferase (AGT) in base excision repair (BER) pathway.

Features and Benefits

This compound is a featured product for Apoptosis research. Click here to discover more featured Apoptosis products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

This compound was developed by Schering Plough. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Preparation Note

Temozolomide is soluble in DMSO at a concentration that is greater than 20 mg/ml. It is insoluble in water.

Safety Information

• pictograms: GHS08,GHS07
• signalword: Danger
• hcodes: H302,H315,H319,H335,H340,H350,H360FD
• pcodes: P202 - P261 - P301 + P312 - P302 + P352 - P305 + P351 + P338 - P308 + P313
• Hazard Classifications: Acute Tox. 4 Oral - Carc. 1B - Eye Irrit. 2 - Muta. 1B - Repr. 1B - Skin Irrit. 2 - STOT SE 3
• target_organs: Respiratory system
• Storage Class: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• wgk_germany: WGK 3
• ppe: Eyeshields, Gloves, type P3 (EN 143) respirator cartridges