T2577

Temozolomide

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

• Synonim(y): 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
• Wzór empiryczny (zapis Hilla): C₆H₆N₆O₂
• Numer CAS: 85622-93-1
• Masa cząsteczkowa: 194.15
• Numer MDL: MFCD00866492
• Kod UNSPSC: 12352200
• Identyfikator substancji w PubChem: 329826714
• NACRES: NA.77

Właściwości

• Nazwa produktu: Temozolomide, ≥98% (HPLC)
• Poziom jakości: 100
• Próba: ≥98% (HPLC)
• Formularz: powder
• kolor: white to light brown
• rozpuszczalność: DMSO: 10 mg/mL, clear; H₂O: insoluble
• inicjator: Schering Plough
• temp. przechowywania: 2-8°C
• ciąg SMILES: 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)
• Klucz InChI: BPEGJWRSRHCHSN-UHFFFAOYSA-N

Opis

Opis ogólny

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.

Zastosowanie

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.

Działania biochem./fizjol.

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.

Cechy i korzyści

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.

Uwaga dotycząca przygotowania

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

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Informacja o środkach bezpieczeństwa

• Piktogramy: GHS08,GHS07
• Hasło ostrzegawcze: Danger
• Zwroty wskazujące rodzaj zagrożenia: H302,H315,H319,H335,H340,H350,H360FD
• Zwroty wskazujące środki ostrożności: P202 - P261 - P301 + P312 - P302 + P352 - P305 + P351 + P338 - P308 + P313
• Klasyfikacja zagrożeń: Acute Tox. 4 Oral - Carc. 1B - Eye Irrit. 2 - Muta. 1B - Repr. 1B - Skin Irrit. 2 - STOT SE 3
• Organy docelowe: Respiratory system
• Kod klasy składowania: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• Klasa zagrożenia wodnego (WGK): WGK 3
• Środki ochrony indywidualnej: Eyeshields, Gloves, type P3 (EN 143) respirator cartridges