5.00609

Temozolomide

• Synonym(e): 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
• Empirische Formel (Hill-System): C₆H₆N₆O₂
• CAS-Nummer: 85622-93-1
• Molekulargewicht: 194.15
• MDL-Nummer: MFCD00866492
• UNSPSC-Code: 12352200
• NACRES: NA.77

Eigenschaften

• Assay: ≥99% (HPLC)
• Qualitätsniveau: 100
• Form: solid
• Hersteller/Markenname: Calbiochem^®
• Lagerbedingungen: OK to freeze; protect from light
• Farbe: off-white
• Löslichkeit: DMSO: 25 mg/mL
• Lagertemp.: 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)
• InChIKey: BPEGJWRSRHCHSN-UHFFFAOYSA-N

Beschreibung

Allgemeine Beschreibung

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.

Biochem./physiol. Wirkung

Cell permeable: yes

Primary Target
DNA guanine residues

Reversible: no

Verpackung

Packaged under inert gas

Warnhinweis

Toxicity: Harmful & Carcinogenic / Teratogenic (E)

Rekonstituierung

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

Sonstige Hinweise

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.

Rechtliche Hinweise

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

Sicherheitshinweise

• Piktogramme: GHS07,GHS08
• Signalwort: Danger
• H-Sätze: H302 - H315 - H319 - H335 - H340 - H350 - H360FD
• P-Sätze: P201 - P202 - P301 + P312 - P302 + P352 - P305 + P351 + P338 - P308 + P313
• Gefahreneinstufungen: Acute Tox. 4 Oral - Carc. 1B - Eye Irrit. 2 - Muta. 1B - Repr. 1B - Skin Irrit. 2 - STOT SE 3
• Zielorgane: Respiratory system
• Lagerklassenschlüssel: 6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• WGK: WGK 3