5.00609

Temozolomide

• Sinónimos: 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
• Fórmula empírica (notación de Hill): C₆H₆N₆O₂
• Número de CAS: 85622-93-1
• Peso molecular: 194.15
• Número MDL: MFCD00866492
• Código UNSPSC: 12352200
• NACRES: NA.77

Propiedades

• Ensayo: ≥99% (HPLC)
• Nivel de calidad: 100
• Formulario: solid
• fabricante / nombre comercial: Calbiochem^®
• condiciones de almacenamiento: OK to freeze; protect from light
• color: off-white
• solubilidad: DMSO: 25 mg/mL
• temp. de almacenamiento: 2-8°C
• cadena SMILES: [n]21c(nn[n]([c]2=O)C)c(nc1)C(=O)N
• InChI: 1S/C6H6N6O2/c1-11-6(14)12-2-8-3(4(7)13)5(12)9-10-11/h2H,1H3,(H2,7,13)
• Clave InChI: BPEGJWRSRHCHSN-UHFFFAOYSA-N

Descripción

Descripción general

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.

Acciones bioquímicas o fisiológicas

Cell permeable: yes

Primary Target
DNA guanine residues

Reversible: no

Envase

Packaged under inert gas

Advertencia

Toxicity: Harmful & Carcinogenic / Teratogenic (E)

Reconstitución

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

Otras notas

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.

Información legal

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

Información de seguridad

• Pictogramas: GHS07,GHS08
• Palabra de señalización: Danger
• Frases de peligro: H302 - H315 - H319 - H335 - H340 - H350 - H360FD
• Consejos de prudencia: P201 - P202 - P301 + P312 - P302 + P352 - P305 + P351 + P338 - P308 + P313
• Clasificaciones de peligro: Acute Tox. 4 Oral - Carc. 1B - Eye Irrit. 2 - Muta. 1B - Repr. 1B - Skin Irrit. 2 - STOT SE 3
• Órganos de actuación: Respiratory system
• Código de clase de almacenamiento: 6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• Clase de riesgo para el agua (WGK): WGK 3