5.00609

Temozolomide

• Sinônimo(s): 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 (Notação de Hill): C₆H₆N₆O₂
• Número CAS: 85622-93-1
• Peso molecular: 194.15
• Número MDL: MFCD00866492
• Código UNSPSC: 12352200
• NACRES: NA.77

Propriedades

• Ensaio: ≥99% (HPLC)
• Nível de qualidade: 100
• Formulário: solid
• fabricante/nome comercial: Calbiochem^®
• condição de armazenamento: OK to freeze; protect from light
• cor: off-white
• solubilidade: DMSO: 25 mg/mL
• temperatura de armazenamento: 2-8°C
• cadeia de caracteres 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)
• chave InChI: BPEGJWRSRHCHSN-UHFFFAOYSA-N

Descrição

Descrição geral

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.

Ações bioquímicas/fisiológicas

Cell permeable: yes

Primary Target
DNA guanine residues

Reversible: no

Embalagem

Packaged under inert gas

Advertência

Toxicity: Harmful & Carcinogenic / Teratogenic (E)

Reconstituição

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

Outras 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.

Informações legais

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

Informações de segurança

• Pictogramas: GHS07,GHS08
• Palavra indicadora: Danger
• Frases de perigo: H302 - H315 - H319 - H335 - H340 - H350 - H360FD
• Declarações de precaução: P201 - P202 - P301 + P312 - P302 + P352 - P305 + P351 + P338 - P308 + P313
• Classificações de perigo: Acute Tox. 4 Oral - Carc. 1B - Eye Irrit. 2 - Muta. 1B - Repr. 1B - Skin Irrit. 2 - STOT SE 3
• Órgãos-alvo: Respiratory system
• Código de classe de armazenamento: 6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• Classe de risco de água (WGK): WGK 3