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T2577

Temozolomide

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

Synonim(y):

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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Gabaryty przesyłkiSKUDostępnośćCena netto
25 mg
Skontaktuj się z Obsługą Klienta, aby uzyskać informacje na temat dostępności
811,00 zł
100 mg
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2230,00 zł

Informacje o tej pozycji

Wzór empiryczny (zapis Hilla):
C6H6N6O2
Numer CAS:
Masa cząsteczkowa:
194.15
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
MDL number:
Assay:
≥98% (HPLC)
Form:
powder

811,00 zł


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Nazwa produktu

Temozolomide, ≥98% (HPLC)

Quality Segment

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

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.[1]

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.
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Ta pozycja
76899Y0001827SML2528
form

powder

form

-

form

powder

form

powder

assay

≥98% (HPLC)

assay

≥99.0% (HPLC)

assay

-

assay

≥98% (HPLC)

Quality Level

100

Quality Level

100

Quality Level

-

Quality Level

100

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

solubility

DMSO: 10 mg/mL, clear, H2O: insoluble

solubility

-

solubility

-

solubility

DMSO: 2 mg/mL, clear

color

white to light brown

color

-

color

-

color

white to beige


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pictograms

Health hazardExclamation mark

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

Klasa składowania

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



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Produkty

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.

Powiązane treści






Numer pozycji handlu globalnego

SKUNUMER GTIN
T2577-100MG04061835559268
T2577-25MG04061835559275

Questions

1–6 of 6 Questions  
  1. Is undissolved Temozolomide still stable if it was stored at RT for 3 days upon arrival?

    1 answer
    1. 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.

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  2. How long is this stable for between 2-8 degrees celsius?

    1 answer
    1. 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.pdf

      Helpful?

  3. 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
    1. 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.x

      Helpful?

  4. Do you have a reference for the analysis of Temozolomide (Product No. T2577) in serum?

    1 answer
    1. 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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  5. Is Temozolomide (Product No. T2577) an active drug or a prodrug?

    1 answer
    1. 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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  6. What is the Department of Transportation shipping information for this product?

    1 answer
    1. 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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