5.00609

Temozolomide

• Sinonimo/i: Temozolomide, CCRG 81045, TMZ, 3,4-Dihydro-3-methyl-4-oxoimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide, NSC 362856, 3-Methyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide
• Formula empirica (notazione di Hill): C₆H₆N₆O₂
• Numero CAS: 85622-93-1
• Peso molecolare: 194.15
• Numero MDL: MFCD00866492
• Codice UNSPSC: 12352200

Proprietà

• Saggio: ≥99% (HPLC)
• Livello qualitativo: 100
• Forma fisica: solid
• Produttore/marchio commerciale: Calbiochem^®
• Condizioni di stoccaggio: OK to freeze; protect from light
• Colore: off-white
• Solubilità: DMSO: 25 mg/mL
• Temperatura di conservazione: 2-8°C
• InChI: 1S/C6H6N6O2/c1-11-6(14)12-2-8-3(4(7)13)5(12)9-10-11/h2H,1H3,(H2,7,13); BPEGJWRSRHCHSN-UHFFFAOYSA-N

Descrizione

Descrizione generale

A cell-permeable, orally bioavailable, blood-brain barrier-permeant MTIC [5-(3-methyltriazen-1-yl-)-imidazole-4-carboxamide] prodrug whose in vivo DNA alkylating activity is employed in anticancer therapy. MGMT (O⁶-methylguanine DNA methyl transferase) repairs TMZ-damaged DNA lesion by covalently transferring O⁶-methylation on guanine residues to a cysteine residue on the MGMT, forming the basis of TMZ-resistance in cancer treatment.

A cell-permeable, orally bioavailable, blood-brain barrier-permeant MTIC [5-(3-methyltriazen-1-yl-)-imidazole-4-carboxamide] prodrug whose in vivo DNA alkylating activity is employed in anticancer therapy. MGMT (O⁶-methylguanine DNA methyl transferase) repairs TMZ-damaged DNA lesion by covalently transferring O⁶-methylation on guanine residues to a cysteine residue on the MGMT, forming the basis of TMZ-resistance in cancer treatment.

Please note that the molecular weight for this compound is batch-specific due to variable water content. Please refer to the vial label or the certificate of analysis for the batch-specific molecular weight. The molecular weight provided represents the baseline molecular weight without water.

Azioni biochim/fisiol

Cell permeable: yes

Primary Target
DNA guanine residues

Reversible: no

Confezionamento

Packaged under inert gas

Attenzione

Toxicity: Harmful & Carcinogenic / Teratogenic (E)

Ricostituzione

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Altre note

Neyns, B., et al. 2010. Cancer116, 2868.
Marchesi, F., et al. 2007. Pharmacol. Res.56, 275.
Chakravarti, A., et al. 2006. Clin. Cancer Res.12, 4738.
Natsume, A., et al. 2005. Cancer Res.65, 7573.
Jen, J.F., et al. 2000. Pharm. Res.17, 1284.

Note legali

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Informazioni sulla sicurezza

• Pittogrammi: GHS07,GHS08
• Avvertenze: Danger
• Indicazioni di pericolo: H302 - H315 - H319 - H335 - H340 - H350 - H360FD
• Consigli di prudenza: P201 - P202 - P301 + P312 - P302 + P352 - P305 + P351 + P338 - P308 + P313
• Classi di pericolo: Acute Tox. 4 Oral - Carc. 1B - Eye Irrit. 2 - Muta. 1B - Repr. 1B - Skin Irrit. 2 - STOT SE 3
• Organi bersaglio: Respiratory system
• Codice della classe di stoccaggio: 6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• Classe di pericolosità dell'acqua (WGK): WGK 3