This product is stable at ambient temperatures for relatively short periods of time. The item is shipped at ambient temperature. A transit time of up to 2 weeks or a brief temperature excursion will not impact the quality of this material. Upon delivery, this product should be stored at refrigerated at 2 - 8°C.
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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€147.00
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25 MG
€147.00
100 MG
€416.00
About This Item
Empirical Formula (Hill Notation):
C6H6N6O2
CAS Number:
Molecular Weight:
194.15
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
Recommended Products
Product Name
Temozolomide, ≥98% (HPLC)
Quality Level
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
SMILES string
CN1N=Nc2c(ncn2C1=O)C(N)=O
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
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General description
Temozolomide is a small lipophilic alkylating agent.[1] 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.[1] 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.[2]
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.
Signal Word
Danger
Hazard Statements
Precautionary Statements
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 Code
6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
WGK
WGK 3
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Customers Also Viewed
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
Mark R Gilbert et al.
Journal of clinical oncology : official journal of the American Society of Clinical Oncology, 31(32), 4085-4091 (2013-10-09)
Radiotherapy with concomitant and adjuvant temozolomide is the standard of care for newly diagnosed glioblastoma (GBM). O(6)-methylguanine-DNA methyltransferase (MGMT) methylation status may be an important determinant of treatment response. Dose-dense (DD) temozolomide results in prolonged depletion of MGMT in blood
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
Julien Hadoux et al.
International journal of cancer, 135(11), 2711-2720 (2014-04-23)
Cyclophosphamide-dacarbazine-vincristine regimen is recommended for the treatment of malignant pheochromocytoma and paraganglioma (MPP); however, dacarbazine is the only recognized active drug in neuroendocrine tumours. We investigated the therapeutic benefit of temozolomide (TMZ), an oral alternative to dacarbazine, in patients with
Olivier L Chinot et al.
The New England journal of medicine, 370(8), 709-722 (2014-02-21)
Standard therapy for newly diagnosed glioblastoma is radiotherapy plus temozolomide. In this phase 3 study, we evaluated the effect of the addition of bevacizumab to radiotherapy-temozolomide for the treatment of newly diagnosed glioblastoma. We randomly assigned patients with supratentorial glioblastoma
Articles
We presents an article on Autophagy in Cancer Promotes Therapeutic Resistance
Cell cycle phases (G1, S, G2, M) regulate cell growth, DNA replication, and division in proliferating cells.
Apoptosis regulation involves multiple pathways and molecules for cellular homeostasis.
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Is undissolved Temozolomide still stable if it was stored at RT for 3 days upon arrival?
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How long is this stable for between 2-8 degrees celsius?
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This product is not assigned an expiration date. Products that are robust in nature and extremely stable, in the original unopened container, are not assigned an expiration date or retest schedule. These products will have no dating reported on either the label or the Certificate of Analysis.
Products that are not assigned an expiration or retest date are covered by a warranty period of 1 year from the date of product shipment.
Full Product Dating Information may be reviewed at the link below: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/190/408/product-dating-information-ms.pdfHelpful?
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How long is Temozolomide stable for when dissolved as recommended, in DMSO at 10 mg/mL and storaged at 2-8C? Also, can the solution only be stored at 2-8C or can it be stored at -20C or -80C for long term storage
1 answer-
Wherever possible, solutions should be prepared fresh and used on the same day. However, should stock solutions need to be prepared in advance, store in aliquots at -20°C for up to 1 month. Allow aliquots to equilibrate to room temperature prior to opening. The long term storage at other temperatures is not determined. However, the published reference below may prove helpful:
Link: https://onlinelibrary.wiley.com/doi/abs/10.1002/j.2055-2335.2012.tb00145.xHelpful?
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Is Temozolomide (Product No. T2577) an active drug or a prodrug?
1 answer-
Temozolomide is considered a prodrug. It is hydrolyzed in vivo to MTIC (monomethyl triazeno imidazole carboxamide). See: Kim, H. et al., High-performance liquid chromatographic analysis and stability of anti-tumor agent temozolomide in human plasma. Journal of Pharmaceutical and Biomedical Analysis, 24(3), 461-468 (2001).
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What is the Department of Transportation shipping information for this product?
1 answer-
Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.
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Do you have a reference for the analysis of Temozolomide (Product No. T2577) in serum?
1 answer-
We have not confirmed the method in our labs here at Sigma, but see: Kim, H. et al., High-performance liquid chromatographic analysis and stability of anti-tumor agent temozolomide in human plasma. Journal of Pharmaceutical and Biomedical Analysis, 24(3), 461-468 (2001).
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