Molecular structure of Temozolomide, CAS Number: 85622-93-1
Temozolomide (CAS 85622-93-1)
See product citations (32)
Alternate Names:
8-Carbamoyl-3-methylimidazo[5,1-d]-1,2,3,5-tetrazin-4(3H)-one; 8-Carbamoyl-3-methylimidazo[5,1-d]-1,2,3,5-tetrazin-4(3H)-one; Methazolastone; Temodar; Temodal; Temozolomidum; Temozolodida; TMZ-Bioshuttle; 1-d)(1,2,3,5)tetrazine-8-carboxamide,3,4-dihydro-3-methyl-4-oxo-imidazo(; 3,4-dihydro-3-methyl-4-oxoimidazo(5,1-d)-1,2,3,5-tetrazine-8-carboxamide; 3-methyl-4-oxo-3,4-dihydroimidazo(5,1-d)(1,2,3,5)tetrazine-8-carboxamide; 8-carbamoyl-3-methylimidazo(5,1-d)-1,2,3,5-tetrazin-4(3h)-one; ccrg81045; m&b39831; mb39831; methazolastone
Application:
Temozolomide is an apoptosis inducer which causes arrest at the G2/M cell cycle checkpoint
CAS Number:
85622-93-1
Purity:
≥99%
Molecular Weight:
194.2
Molecular Formula:
C6H6N6O2
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.
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SDS & Certificate of Analysis
Temozolomide is an antitumor, antiangiogenic compound in vitro that may act to work by alkylating DNA, typically through addition of a methyl group to guanine in genomic DNA. The efficacy of Temozolomide is dependent on its ability to methylate the DNA, thus triggering apoptosis however, some cells are able to repair this damage via the enzymes O-6-methylguanine-DNA methyltransferase (MGMT). As a consequence, temozolomide is far more efficacious in tumor cells that have silenced this repair enzyme. Research has also been conducted to determine whether MGMT inhibitors such as O-6-benzylguanine might help to increase the efficacy of temozolomide. Furthermore, it has been implicated in causing arrest at the G2/M cell cycle checkpoint, which might also play a role in its cytotoxicity.
Temozolomide (CAS 85622-93-1) References
- p53 effects both the duration of G2/M arrest and the fate of temozolomide-treated human glioblastoma cells. | Hirose, Y., et al. 2001. Cancer Res. 61: 1957-63. PMID: 11280752
- Antitumor Imidazotetrazines. 35. New Synthetic Routes to the Antitumor Drug Temozolomide. | Wang, Y., et al. 1997. J Org Chem. 62: 7288-7294. PMID: 11671842
- Combined treatment with temozolomide and poly(ADP-ribose) polymerase inhibitor enhances survival of mice bearing hematologic malignancy at the central nervous system site. | Tentori, L., et al. 2002. Blood. 99: 2241-4. PMID: 11877304
- Current and future developments in the use of temozolomide for the treatment of brain tumours. | Stupp, R., et al. 2001. Lancet Oncol. 2: 552-60. PMID: 11905710
- Temozolomide induces apoptosis and senescence in glioma cells cultured as multicellular spheroids. | Günther, W., et al. 2003. Br J Cancer. 88: 463-9. PMID: 12569392
- Inhibition of angiogenesis by non-toxic doses of temozolomide. | Kurzen, H., et al. 2003. Anticancer Drugs. 14: 515-22. PMID: 12960735
- Temozolomide: a novel treatment for pituitary carcinoma. | Lim, S., et al. 2006. Lancet Oncol. 7: 518-20. PMID: 16750503
- Temozolomide-mediated radiation enhancement in glioblastoma: a report on underlying mechanisms. | Chakravarti, A., et al. 2006. Clin Cancer Res. 12: 4738-46. PMID: 16899625
- Temozolomide preferentially depletes cancer stem cells in glioblastoma. | Beier, D., et al. 2008. Cancer Res. 68: 5706-15. PMID: 18632623
- Phase II trial of temozolomide plus o6-benzylguanine in adults with recurrent, temozolomide-resistant malignant glioma. | Quinn, JA., et al. 2009. J Clin Oncol. 27: 1262-7. PMID: 19204199
- MSH6 mutations arise in glioblastomas during temozolomide therapy and mediate temozolomide resistance. | Yip, S., et al. 2009. Clin Cancer Res. 15: 4622-9. PMID: 19584161
- The neuropharmacokinetics of temozolomide in patients with resectable brain tumors: potential implications for the current approach to chemoradiation. | Portnow, J., et al. 2009. Clin Cancer Res. 15: 7092-8. PMID: 19861433
- Antitumor imidazotetrazines. 1. Synthesis and chemistry of 8-carbamoyl-3-(2-chloroethyl)imidazo[5,1-d]-1,2,3,5-tetrazin-4(3 H)-one , a novel broad-spectrum antitumor agent. | Stevens, MF., et al. 1984. J Med Chem. 27: 196-201. PMID: 6694168
- Temozolomide: a review of its discovery, chemical properties, pre-clinical development and clinical trials. | Newlands, ES., et al. 1997. Cancer Treat Rev. 23: 35-61. PMID: 9189180
Inhibitor of:
82-FIP, ADAR3, ATXN2L, BAGE, BHLHB4, Bhlhb9, C1QBP, C9orf25, CHL1, COL4A6, CTAGE3, DCAR, DCAR1, EHZF, Endomucin, FOXB1, FRMD7, GluR-1, Gm8994, GSC, HoxC9, ISCA2, ITBA1, KIAA1822L, KIR3DL1, LHX4, LOC100039815, LOC100040158, LOC100041319, LOC100041436, MATH-1, Mex3a, MGMT, NBPF24, NBPF7, Nestin, NG2, Olfr1053, Olfr628, Olr1199, Olr690, Olr724, Olr744, Olr766, PCDHGA4, PHAX, phostensin, Placental GH, PLP-H, Ruvbl2, Shank 1, SLC38A8, Slfn11, SSTR3, Thrombospondin 4, USP44, WARP, WCRF, XRRA1, and ZNF703.Activator of:
γ Enolase, APLF, AQP4, BRAF35, BRCA2, C17orf112, CT45, cyclin 3a, DDI1, DNA pol ζ, FKBP51, GADD 45α, GAGE10, granzyme H, Histone cluster 1 H2AE, Histone cluster 1 H2BG, KIAA0247, LRRC3B, MAGE, MAGE-A1, MAGE-A3, MAGE-A5, MAGE-E1, Melanoma Marker, melusin, MPHOSPH8, Mucin 16, NBPF15, pADPr, PARP-10, PRAMEF18, PRAMEF20, PRAMEF3, RBBP9, Ref-1, SSX2-IP, Varicella Zoster Virus gpI, and Wip1.Ordering Information
| Product Name | Catalog # | UNIT | Price | Qty | FAVORITES | |
Temozolomide, 25 mg | sc-203292 | 25 mg | $89.00 | |||
Temozolomide, 100 mg | sc-203292A | 100 mg | $250.00 |