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Merck

T2577

Temozolomide

≥98% (HPLC), powder, DNA methylating agent

Synonym(s):

3,4-Dihydro-3-methyl-4-oxoimidazo[5,1-d]-1,2,3,5-tetrazine-8-carboxamide, 3-Methyl-4-oxo-8-imidazolo[5,1-d][1,2,3,5]tetrazinecarboxamide, 4-Methyl-5-oxo-2,3,4,6,8-pentazabicyclo[4.3.0]nona-2,7,9-triene-9-carboxamide, 8-Carbamoyl-3-methylimidazo[5,1-d]-1,2,3,5-tetrazin-4(3H)-one, NSC 362856

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About This Item

Empirical Formula (Hill Notation):
C6H6N6O2
CAS Number:
85622-93-1
Molecular Weight:
194.15
UNSPSC Code:
12352200
PubChem Substance ID:
329826714
NACRES:
NA.77
MDL number:
MFCD00866492

Key Documents

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Product Name

Temozolomide, ≥98% (HPLC)

SMILES string

CN1N=Nc2c(ncn2C1=O)C(N)=O

InChI key

BPEGJWRSRHCHSN-UHFFFAOYSA-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)

assay

≥98% (HPLC)

form

powder

color

white to light brown

solubility

DMSO: 10 mg/mL, clear, H2O: insoluble

originator

Schering Plough

storage temp.

2-8°C

Quality Level

100

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General description

Temozolomide is a small lipophilic alkylating agent. It interacts covalently with the nucleophile microenvironment within DNA (Guanine residues). Due to this property temozolomide is considered a cytotoxic agent. The mechanism of action of TMZ is dependent upon its ability to hydrolyze DNA, resulting in DNA degradation and destruction of tumor cells. Malignant Glioma cells respond primarily to TMZ by G2/ M cell cycle arrest or in rare cases by apoptosis. Temozolomide is a DNA methylating agent and drug resistance-modifying agent; anti-tumor and anti-angiogenic. Temozolomide induces G2/M arrest and apoptosis through adduction of a methyl group to O6 position of guanine in genomic DNA and functional inactivation of DNA repair protein O(6)-alkylguanine DNA alkyltransferase (AGT) in base excision repair (BER) pathway.

Application

Temozolomide has been used for analyzing drug resistance mechanisms in glioblastoma cell lines. Temozolomide has been used to induce cytotoxic effects on glioblastoma cells to study the outcome of protein disulfide isomerase (PDI) inhibition.

Biochem/physiol Actions

Temozolomide is a DNA methylating agent and drug resistance-modifying agent; anti-tumor and anti-angiogenic. Temozolomide induces G2/M arrest and apoptosis through adduction of a methyl group to O6 position of guanine in genomic DNA and functional inactivation of DNA repair protein O(6)-alkylguanine DNA alkyltransferase (AGT) in base excision repair (BER) pathway.

Features and Benefits

This compound is a featured product for Apoptosis research. Click here to discover more featured Apoptosis products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound was developed by Schering Plough. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Preparation Note

Temozolomide is soluble in DMSO at a concentration that is greater than 20 mg/ml. It is insoluble in water.

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Danger

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

WGK 3

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

T2577-VAR: + T2577-100MG: + T2577-25MG: + T2577-BULK:

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Certificates of Analysis (COA)

Lot/Batch Number
0000521689
0000521690
0000521689
0000294621
0000294622

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Antonin Dréan et al.
Journal of neuro-oncology, 138(3), 479-486 (2018-03-10)
ATP-binding cassette transporters (ABC transporters) regulate traffic of multiple compounds, including chemotherapeutic agents, through biological membranes. They are expressed by multiple cell types and have been implicated in the drug resistance of some cancer cells. Despite significant research in ABC
Michael Weller et al.
International journal of cancer, 134(10), 2437-2447 (2014-03-13)
The epidermal growth factor receptor vIII mutant (EGFRvIII) is found in ~50% of all EGFR-amplified glioblastomas and constitutes a tumor-specific therapeutic target. To assess molecular testing approaches and the prognostic role of EGFRvIII in patients treated according to current standards
Leon D Ortiz et al.
Clinics (Sao Paulo, Brazil), 67 Suppl 1, 119-123 (2012-05-25)
Temozolomide is an alkylating agent used in the treatment of gliomas and, more recently, aggressive pituitary adenomas and carcinomas. Temozolomide methylates DNA and, thereby, has antitumor effects. O6-methylguanine-DNA methyltransferase, a DNA repair enzyme, removes the alkylating adducts that are induced
Mark R Gilbert et al.
The New England journal of medicine, 370(8), 699-708 (2014-02-21)
Concurrent treatment with temozolomide and radiotherapy followed by maintenance temozolomide is the standard of care for patients with newly diagnosed glioblastoma. Bevacizumab, a humanized monoclonal antibody against vascular endothelial growth factor A, is currently approved for recurrent glioblastoma. Whether the
Herwig M Strik et al.
Current neurology and neuroscience reports, 12(3), 286-293 (2012-03-23)
Even in modern times of high-precision brain surgery and irradiation, malignant gliomas belong to the deadliest types of cancer. Due to a marked primary and presumably also acquired resistance, the beneficial effects of cytotoxic chemotherapy are limited. Only one randomized
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