5.00609

Temozolomide

• Synonym(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
• Empirical Formula (Hill Notation): C₆H₆N₆O₂
• CAS Number: 85622-93-1
• Molecular Weight: 194.15
• MDL number: MFCD00866492
• UNSPSC Code: 12352200
• NACRES: NA.77

Properties

• assay: ≥99% (HPLC)
• Quality Level: 100
• form: solid
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze; protect from light
• color: off-white
• solubility: DMSO: 25 mg/mL
• storage temp.: 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)
• InChI key: BPEGJWRSRHCHSN-UHFFFAOYSA-N

Description

General description

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 Actions

Cell permeable: yes

Primary Target
DNA guanine residues

Reversible: no

Packaging

Packaged under inert gas

Warning

Toxicity: Harmful & Carcinogenic / Teratogenic (E)

Reconstitution

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

Other Notes

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.

Legal Information

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

Safety Information

• pictograms: GHS07,GHS08
• signalword: Danger
• hcodes: H302 - H315 - H319 - H335 - H340 - H350 - H360FD
• pcodes: P201 - P202 - P301 + P312 - P302 + P352 - P305 + P351 + P338 - P308 + P313
• Hazard Classifications: Acute Tox. 4 Oral - Carc. 1B - Eye Irrit. 2 - Muta. 1B - Repr. 1B - Skin Irrit. 2 - STOT SE 3
• target_organs: Respiratory system
• Storage Class: 6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• wgk_germany: WGK 3