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MedKoo Cat#: 100810 | Name: Temozolomide
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Temozolomide, also known as SCH 52365 , MB39831, and RP46161, is a triazene analog of dacarbazine with antineoplastic activity. As a cytotoxic alkylating agent, temozolomide is converted at physiologic pH to the short-lived active compound, monomethyl triazeno imidazole carboxamide (MTIC). The cytotoxicity of MTIC is due primarily to methylation of DNA at the O6 and N7 positions of guanine, resulting in inhibition of DNA replication. Unlike dacarbazine, which is metabolized to MITC only in the liver, temozolomide is metabolized to MITC at all sites. Temozolomide is administered orally and penetrates well into the central nervous system.

Chemical Structure

Temozolomide
Temozolomide
CAS#85622-93-1

Theoretical Analysis

MedKoo Cat#: 100810

Name: Temozolomide

CAS#: 85622-93-1

Chemical Formula: C6H6N6O2

Exact Mass: 194.0552

Molecular Weight: 194.15

Elemental Analysis: C, 37.12; H, 3.11; N, 43.29; O, 16.48

Price and Availability

Size Price Availability Quantity
100mg USD 150.00 Ready to ship
500mg USD 250.00 Ready to ship
1g USD 450.00 Ready to ship
5g USD 950.00 Ready to ship
10g USD 1,450.00 Ready to ship
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No Data
Synonym
SCH-52365; SCH52365; SCH 52365; MB39831; MB-39831; MB 39831; RP46161; RP 46161; R-P46161; CCRG81045; TMZ. US brand names: Methazolastone; Temodar. Foreign brand name: Temodal
IUPAC/Chemical Name
3-methyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide.
InChi Key
BPEGJWRSRHCHSN-UHFFFAOYSA-N
InChi Code
InChI=1S/C6H6N6O2/c1-11-6(14)12-2-8-3(4(7)13)5(12)9-10-11/h2H,1H3,(H2,7,13)
SMILES Code
O=C(C1=C(N2C=N1)N=NN(C)C2=O)N
Appearance
white solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
  According to http://en.wikipedia.org/wiki/Temozolomide, Temozolomide (brand names Temodar and Temodal Schering-Plough Corporation) is an oral alkylating agent which can be used for the treatment of Grade IV astrocytoma -- an aggressive brain tumor, also known as glioblastoma multiforme as well as Melanoma, a form of skin cancer. It is also indicated for Grade III Anaplastic Astrocytoma and not indicated for, but now used to treat oligodendroglioma brain tumors in some countries, replacing the older (and less well-tolerated) PCV (Procarbazine-Lomustine-Vincristine) regimen. The agent was developed by Malcolm Stevens and his team at Aston University in Birmingham, A derivative of imidazotetrazine, temozolomide is the prodrug of MTIC (3-methyl-(triazen-1-yl)imidazole-4-carboxamide). It has been available in the US since August 1999, and in other countries since the early 2000s.   TEMODAR contains temozolomide, an imidazotetrazine derivative. The chemical name of temozolomide is 3,4-dihydro-3-methyl-4-oxoimidazo[5,1-d]-as-tetrazine-8-carboxamide. The material is a white to light tan/light pink powder with a molecular formula of C6H6N6O2 and a molecular weight of 194.15. The molecule is stable at acidic pH ( < 5) and labile at pH > 7; hence TEMODAR can be administered orally and intravenously. The prodrug, temozolomide, is rapidly hydrolyzed to the active 5-(3-methyltriazen-1-yl) imidazole-4-carboxamide (MTIC) at neutral and alkaline pH values, with hydrolysis taking place even faster at alkaline pH.   Temozolomide is available in the United States in 5 mg, 20 mg, 100 mg, 140 mg, 180 mg & 250 mg capsules. Now also available in an IV form for people who can not swallow capsules or who have insurance that does not cover oral cancer agents!        
Biological target:
: Temozolomide is a monofunctional SN-1 alkylating agent that can modify nitrogen atoms in the DNA ring and the extracyclic oxygen group, chemically converted to MTIC and degrades to methyldiazonium cation, which transfers methyl groups to DNA at physiologic pH. A DNA damage inducer in L-1210 and L-1210/BCNU cells. Temozolomide induces apoptosis and exhibits antitumor and antiangiogenic activity.
In vitro activity:
In vitro IC50 inhibitory growth values for TMZ after 3 days of culture were 472 ± 14 µM for U87, 118 ± 3 µM for U373, 634 ± 23 µM for T98G, and 719 ± 12 µM for Hs683 GBM cells.Temozolomide decreased the expression levels of HIF-1α, ID-1, ID-2, and cMyc in the glioma models investigated, all of which playing major roles in angiogenesis and the switch to hypoxic metabolism. These changes could be, at least partly, responsible for the impairment of angiogenesis observed in vitro. Reference: Neoplasia. 2008 Dec; 10(12): 1383–1392. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2586689/
In vivo activity:
Toxicologic studies showed that no drug-related death occurred in mice treated with Temozolomide (100 or 200 mg/kg) or with NU1025 ± Temozolomide and that the maximal weight loss was 12%. All mice recovered initial body weight 1 week after treatment. Histologic studies were carried out to analyze tumor growth in the brain of untreated animals. Results indicated that lymphoma cells were microscopically evident 2 days after challenge (Figure1A) and that tumor infiltration in brain parenchyma progressively increased during the following days (Figure 1B-C). Moreover, intracranial injection of L5178Y cells was fatal in 12 to 21 days, and macroscopic evidence of tumor was observed in additional mice killed when moribund. Reference: Blood. 2002 Mar 15;99(6):2241-4. https://www.sciencedirect.com/science/article/pii/S0006497120381179?via%3Dihub
Solvent mg/mL mM
Solubility
Soluble in DMSO, not in water 20.8 107.29
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 194.15 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Perazzoli G, Prados J, Ortiz R, Caba O, Cabeza L, Berdasco M, Gónzalez B, Melguizo C. Temozolomide Resistance in Glioblastoma Cell Lines: Implication of MGMT, MMR, P-Glycoprotein and CD133 Expression. PLoS One. 2015 Oct 8;10(10):e0140131. doi: 10.1371/journal.pone.0140131. PMID: 26447477; PMCID: PMC4598115. 2. Mathieu V, De Nève N, Le Mercier M, Dewelle J, Gaussin JF, Dehoux M, Kiss R, Lefranc F. Combining bevacizumab with temozolomide increases the antitumor efficacy of temozolomide in a human glioblastoma orthotopic xenograft model. Neoplasia. 2008 Dec;10(12):1383-92. doi: 10.1593/neo.08928. PMID: 19048117; PMCID: PMC2586689. 3. Tentori L, Leonetti C, Scarsella M, d'Amati G, Portarena I, Zupi G, Bonmassar E, Graziani G. Combined treatment with temozolomide and poly(ADP-ribose) polymerase inhibitor enhances survival of mice bearing hematologic malignancy at the central nervous system site. Blood. 2002 Mar 15;99(6):2241-4. doi: 10.1182/blood.v99.6.2241. PMID: 11877304. 4. Catapano CV, Broggini M, Erba E, Ponti M, Mariani L, Citti L, D'Incalci M. In vitro and in vivo methazolastone-induced DNA damage and repair in L-1210 leukemia sensitive and resistant to chloroethylnitrosoureas. Cancer Res. 1987 Sep 15;47(18):4884-9. PMID: 3621181.
In vitro protocol:
1. Perazzoli G, Prados J, Ortiz R, Caba O, Cabeza L, Berdasco M, Gónzalez B, Melguizo C. Temozolomide Resistance in Glioblastoma Cell Lines: Implication of MGMT, MMR, P-Glycoprotein and CD133 Expression. PLoS One. 2015 Oct 8;10(10):e0140131. doi: 10.1371/journal.pone.0140131. PMID: 26447477; PMCID: PMC4598115. 2. Mathieu V, De Nève N, Le Mercier M, Dewelle J, Gaussin JF, Dehoux M, Kiss R, Lefranc F. Combining bevacizumab with temozolomide increases the antitumor efficacy of temozolomide in a human glioblastoma orthotopic xenograft model. Neoplasia. 2008 Dec;10(12):1383-92. doi: 10.1593/neo.08928. PMID: 19048117; PMCID: PMC2586689.
In vivo protocol:
1. Tentori L, Leonetti C, Scarsella M, d'Amati G, Portarena I, Zupi G, Bonmassar E, Graziani G. Combined treatment with temozolomide and poly(ADP-ribose) polymerase inhibitor enhances survival of mice bearing hematologic malignancy at the central nervous system site. Blood. 2002 Mar 15;99(6):2241-4. doi: 10.1182/blood.v99.6.2241. PMID: 11877304. 2. Catapano CV, Broggini M, Erba E, Ponti M, Mariani L, Citti L, D'Incalci M. In vitro and in vivo methazolastone-induced DNA damage and repair in L-1210 leukemia sensitive and resistant to chloroethylnitrosoureas. Cancer Res. 1987 Sep 15;47(18):4884-9. PMID: 3621181.
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Postoperative NEOadjuvant TEMozolomide followed by chemoradiotherapy versus upfront chemoradiotherapy for glioblastoma multiforme (NEOTEM) trial: Interim results. Neurooncol Adv. 2024 Nov 14;6(1):vdae195. doi: 10.1093/noajnl/vdae195. PMID: 39664679; PMCID: PMC11632829. 4: Babič D, Jovčevska I, Zottel A. B7-H3 in glioblastoma and beyond: significance and therapeutic strategies. Front Immunol. 2024 Nov 25;15:1495283. doi: 10.3389/fimmu.2024.1495283. PMID: 39664380; PMCID: PMC11632391. 5: Lee G, Kim SJ, Choi Y, Park J, Park JK. Bioprinting of a multi-composition array to mimic intra-tumor heterogeneity of glioblastoma for drug evaluation. Microsyst Nanoeng. 2024 Dec 11;10(1):186. doi: 10.1038/s41378-024-00843-w. PMID: 39663377; PMCID: PMC11634888. 6: Delahousse J, Wagner AD, Borchmann S, Adjei AA, Haanen J, Burgers F, Letsch A, Quaas A, Oertelt-Prigione S, Oezdemir BC, Verhoeven RHA, Della Pasqua O, Paci A, Mir O. 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Surg Neurol Int. 2024 Nov 22;15:428. doi: 10.25259/SNI_588_2024. PMID: 39640319; PMCID: PMC11618790. 13: Nomura N, Nagasaka S, Suzuki K, Yamamoto J. Imaging-tracked progression of primary leptomeningeal gliomatosis: A case report. Surg Neurol Int. 2024 Nov 8;15:411. doi: 10.25259/SNI_759_2024. PMID: 39640309; PMCID: PMC11618755. 14: Ercelik M, Tekin C, Gurbuz M, Tuncbilekli Y, Dogan HY, Mutlu B, Eser P, Tezcan G, Parın FN, Yildirim K, Sarihan M, Akpinar G, Kasap M, Bekar A, Kocaeli H, Taskapilioglu MO, Aksoy SA, Ozpar R, Hakyemez B, Tunca B. A new nano approach to prevent tumor growth in the local treatment of glioblastoma: Temozolomide and rutin-loaded hybrid layered composite nanofiber. Asian J Pharm Sci. 2024 Dec;19(6):100971. doi: 10.1016/j.ajps.2024.100971. Epub 2024 Oct 23. 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