Temozolomide (CCRG 81045)

For research use only.

Catalog No.S1237 Synonyms: NSC 362856,TMZ

123 publications

Temozolomide (CCRG 81045) Chemical Structure

CAS No. 85622-93-1

Temozolomide (CCRG81045, NSC 362856, TMZ) 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 activity.

Selleck's Temozolomide (CCRG 81045) has been cited by 123 publications

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Biological Activity

Description Temozolomide (CCRG81045, NSC 362856, TMZ) 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 activity.
Features Methazolastone is a second-generation alkylating agent.
Targets
DNA replication [1]
(L-1210, L-1210/BCNU cells)
In vitro

Methazolastone causes formation of DNA alkali-labile sites which are present in similar amounts and repaired at a similar rate in L-1210 and L-1210/BCNU cell lines. In L-1210 but not in L-1210/BCNU methazolastone induces an arrest of cells in SL-G2-M phases.[1] Methazolastone sensitivity of both chemo-sensitive and resistant cells (D54-R and U87-R) is enhanced significantly under hyperoxia. Both Methazolastone and hyperoxia are associated with increased phosphorylation of ERK p44/42 MAPK (Erk1/2), but to a lesser extent in D54-R cells, suggesting that Erk1/2 activity may be involved in regulation of hyperoxia and Methazolastone-mediated cell death. Hyperoxia enhances Methazolastone toxicity in GBM cells by induction of apoptosis, possibly via MAPK-related pathways. [2] Methazolastone induces in monocytes the DNA damage response pathways ATM-Chk2 and ATR-Chk1 resulting in p53 activation. [3] Chronic Methazolastone exposure results in acquired Methazolastone-resistance and elevates miR-21 expression. [4] Methazolastone treatment triggers endoplasmic reticula (ER) stress with increased expression of GADD153 and GRP78 proteins, and deceases pro-caspase 12 protein. Methazolastone induces autophagy through mitochondrial damage- and ER stress-dependent mechanisms to protect glioma cells. [5]

Cell Data
Cell Lines Assay Type Concentration Incubation Time Formulation Activity Description PMID
Kelly NX7GSpF4T3Kxd4ToJGlvcGmkaYTpc44hSXO|YYm= M4\6S|Q5KGh? MXLJR|UxRTF|OT6yNQKBkcLz4pEJOU46PSEQvF2= MWS8ZUB1[XKpZYS9K39jdGGwazegbJJm\j1paIT0dJM7Ny:ydXLt[YQvdmOkaT7ucI0vdmmqLnfvek8zPTl4MEK4Nkc,OjV7NkCyPFI9N2F-
KellyCis83 M{LKb2dzd3e2aDDJcohq[mm2aX;uJGF{e2G7 NHnFTmo1QCCq NVLXUWJFUUN3ME2yOVEvODEkgJpCtgKBkTF3Lke1JO69VQ>? NXTFSGNSRGFidHHy[4V1RSehYnzhcosoKGi{ZX[9K4h1fHC|Oj:vdJVjdWWmLn7jZokvdmyvLn7pbE5od3ZxMkW5OlAzQDJpPkK1PVYxOjh{PD;hQi=>
SK-N-AS NEfnWGdIem:5dHigTY5pcWKrdHnvckBCe3OjeR?= NH:1N5g1QCCq MUPJR|UxRTJ{Nz63NQKBkcLz4pEJNlIvOTVizszN MVe8ZUB1[XKpZYS9K39jdGGwazegbJJm\j1paIT0dJM7Ny:ydXLt[YQvdmOkaT7ucI0vdmmqLnfvek8zPTl4MEK4Nkc,OjV7NkCyPFI9N2F-
SK-N-ASCis24 NYPsOmF4T3Kxd4ToJGlvcGmkaYTpc44hSXO|YYm= MnXhOFghcA>? NF\ufXBKSzVyPUS4NE43OOLCidMx5qCKOTBzLkG1JO69VQ>? M2DMW|xiKHSjcnfleF0oZ2KuYX7rK{BpemWoPTfoeJRxezpxL4D1Zo1m\C6wY3LpMo5tdS6waXiu[493NzJ3OU[wNlgzLz5{NUm2NFI5OjxxYU6=
CHP-212 M4ToWGdzd3e2aDDJcohq[mm2aX;uJGF{e2G7 NILrVZg1QCCq NGfn[XFKSzVyPUeuPVfjiIoEsfMAjVAvPjlizszN MVi8ZUB1[XKpZYS9K39jdGGwazegbJJm\j1paIT0dJM7Ny:ydXLt[YQvdmOkaT7ucI0vdmmqLnfvek8zPTl4MEK4Nkc,OjV7NkCyPFI9N2F-
CHP-212Cis100 NVTUSVNsT3Kxd4ToJGlvcGmkaYTpc44hSXO|YYm= NGnFbZQ1QCCq MXfJR|UxRTlwNUZihKnDueLCiUCuPFgh|ryP NHfxeJQ9[SC2YYLn[ZQ:L1:kbHHub{chcHKnZk2nbJR1eHN8Lz;weYJu\WRwbnPibU5vdG1wbnnoModwfi9{NUm2NFI5Oid-MkW5OlAzQDJ:L3G+
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U87MG MlL2RY51cXS3bX;yJIF{e2G7 M4LJcGFvfGm2dX3vdkBi[3Srdnn0fUBi\2GrboP0JIh2dWGwIGW4O21IKGOnbHzzJI9zfGixdH;wbYNidGy7IIjlco9oemGodHXkJIlvKEijcnzhckBvfWSnIH3veZNmKGK{YXnuJIF{e2W|c3XkJIF{KGmwY4LlZZNmKGmwIH3veZNmKHO3co\peoFtKGG2IEWwJJVud2xxa3esJIl3KGGmbXnubZN1\XKnZDDvcoNmKGSjaXz5JIZweiB3IHThfZM> NE\LTlQ9[SC2YYLn[ZQ:L1:kbHHub{chcHKnZk2nbJR1eHN8Lz;weYJu\WRwbnPibU5vdG1wbnnoModwfi9{N{[xOFQyPCd-Mke2NVQ1OTR:L3G+
MDCK MlvDR5l1d3SxeHnjbZR6KGG|c3H5 NGnvWVMzPCCqcoO= NEjtdpVEgXSxdH;4bYNqfHliYXfhbY5{fCCPRFPLJINmdGy|IHX4dJJme3OrbnegZ4Fz[m:waXOgZY5pgWS{YYPlJFkh[XO|ZYPz[YQh[XNicnXkeYN1cW:wIHnuJINmdGxidnnhZoltcXS7IHnuZ5Vj[XSnZDDmc5IhOjRiaILzJI1m[XO3cnXkJIFnfGW{IEeg[IF6eyC3bnTldkBvd3Kvb4jpZ{Bkd26maYTpc44h[nlibXX0bJlt\W6nIHLseYUhe3SjaX7pcoch[mG|ZXSgZ4xwdm:pZX7pZ{B{fXK4aY\hcEBie3OjeR?= MYS8ZUB1[XKpZYS9K39jdGGwazegbJJm\j1paIT0dJM7Ny:ydXLt[YQvdmOkaT7ucI0vdmmqLnfvek8zPzh{M{i3PUc,Ojd6MkO4O|k9N2F-
MDCK MUDDfZRwfG:6aXPpeJkh[XO|YYm= NUfKWFRYOjRiaILz NGT4OHZEgXSxdH;4bYNqfHliYXfhbY5{fCCPRFPLJINmdGy|IHX4dJJme3OrbnegZ4Fz[m:waXOgZY5pgWS{YYPlJFkh[XO|ZYPz[YQh[XNicnXkeYN1cW:wIHnuJINmdGxidnnhZoltcXS7IHnuZ5Vj[XSnZDDmc5IhOjRiaILzJI1m[XO3cnXkJIFnfGW{IEeg[IF6eyC3bnTldkBpgXCxeHnjJINwdmSrdHnvckBjgSCvZYTofYxmdmViYnz1[UB{fGGrbnnu[{Bj[XOnZDDjcI9vd2enbnnjJJN2en[rdnHsJIF{e2G7 MV68ZUB1[XKpZYS9K39jdGGwazegbJJm\j1paIT0dJM7Ny:ydXLt[YQvdmOkaT7ucI0vdmmqLnfvek8zPzh{M{i3PUc,Ojd6MkO4O|k9N2F-
NB-EBc1 M{LNfpFJXFNiYYPzZZk> NFzJTWJyUFSVIH;mJJBm\GmjdILpZ{Bk[W6lZYKgZ4VtdCCuaX7ld{B1dyCrZHXueIlngSCvdXz0bZBt\SCxcIDvdpR2dmm2aXXzJIZweiCmcoXnJJJmeHW{cH;zbY5oQiCScnntZZJ6KHOlcnXlckBnd3JiTlKtSWJkOSClZXzsdy=> NYPWSm5mRGFidHHy[4V1RSehYnzhcosoKGi{ZX[9K4h1fHC|Oj:vdJVjdWWmLn7jZokvdmyvLn7pbE5od3ZxMkm0N|UyOzlpPkK5OFM2OTN7PD;hQi=>
C6 NYDzeoxQS3m2b4TvfIlkcXS7IHHzd4F6 M3nieVQh\GG7cx?= MkLMSWM2OCB;IEG2MlUh|ryP M4PieFxiKHSjcnfleF0oZ2KuYX7rK{BpemWoPTfoeJRxezpxL4f3e{5m[mlwYXOueYsw[2inbXLsM4NwdXCxdX7kY5JmeG:{dG;jZZJlN0OKRV3CUFgyOC9pPlPoSW1DVDxxYU6=
U87 NEHO[|dEgXSxdH;4bYNqfHliYYPzZZk> NHv4W244OiCqcoO= MXvJR|UxKD1iMUmuN|gh|ryP NYDWbGdQRGFidHHy[4V1RSehYnzhcosoKGi{ZX[9K4h1fHC|Oj:ve5d4NmWkaT7hZ{52cy:laHXtZoww[2:vcH;1coRgemWyb4L0Y4NiemRxQ1jFUWJNQDFyLze+R4hGVUKOPD;hQi=>
SNB19 NV;MO5lUT3Kxd4ToJIlvcGmkaYTpc44h[XO|YYm= M4HyS|ch\GG7cx?= Mnv4S2k2OCB;IEO1Mlch|ryP MmS3QIEhfGG{Z3X0QUdg[myjbnunJIhz\WZ;J3j0eJB{Qi9xd4f3MoVjcS6jYz71b{9kcGWvYnyvZ49ueG:3bnTfdoVxd3K2X3PhdoQwS0iHTVLMPFExNyd-Q3jFUWJNRC:jPh?=
SNB19 M1Prdmdzd3e2aDDpcohq[mm2aX;uJIF{e2G7 Mln4O{Bl[Xm| M1O2N2dKPTBiPTC0OU43KM7:TR?= NFfpZ2M9[SC2YYLn[ZQ:L1:kbHHub{chcHKnZk2nbJR1eHN8Lz;3e5cv\WKrLnHjMpVsN2OqZX3icE9kd22yb4Xu[H9z\XCxcoTfZ4Fz\C:FSFXNRmw5OTBxJ{7DbGVOSkx:L3G+
U373 M37hZWZ2dmO2aX;uJIF{e2G7 MWSxNFAhfU1? MX[3NkBpenN? MoXwTY5lfWO2aX;uJI9nKGSxdXLs[UB{fHKjbnTl[EBFVkFiYoLlZYshcW5iZX3weJkhfmWldH;yJJRz[W6|ZnXjeIVlKGi3bXHuJHU{PzNiY3XscJMh[XO|ZYPz[YQh[XNiaX7jdoVie2ViaX6g[4FudWFvSELBXEBt\X[nbDDheEAyODBidV2gZYZ1\XJiN{KgbJJ{KGK7IH\sc5ch[3m2b33leJJ6 MUO8ZUB1[XKpZYS9K39jdGGwazegbJJm\j1paIT0dJM7Ny:5d4eu[YJqNmGlLoXrM4Np\W2kbD;jc41xd3WwZG;y[ZBwenShY3Hy[E9EUEWPQly4NVAwLz6FaFXNRmw9N2F-
Glioma M2[yNWFvfGm2dX3vdkBie3OjeR?= NULGT2Q3SW62aYT1cY9zKGGldHn2bZR6KGGpYXnud5QhUG:vbzDzZZBq\W6|IDjoeY1idiliR3zpc41iKGOnbHzzJJhmdm:pcnHmeIVlKGmwIITyZY5{\2WwaXOgcY92e2ViYYPz[ZN{\WRiYYOgcY92e2Vic4Xyeol3[Wx? MlzwQIEhfGG{Z3X0QUdg[myjbnunJIhz\WZ;J3j0eJB{Qi9xd4f3MoVjcS6jYz71b{9kcGWvYnyvZ49ueG:3bnTfdoVxd3K2X3PhdoQwS0iHTVLMPFExNyd-Q3jFUWJNRC:jPh?=

... Click to View More Cell Line Experimental Data

Assay
Methods Test Index PMID
Western blot
pERK / ERK / p-p38 / p38; 

PubMed: 24436439     


Cells were treated with TMZ (0.5 mM) time dependently, and Western blotting was used to analyze for phosphorylated ERK and p38 MAPK expression.

DR5 / c-FLIP / Survivin / XIAP; 

PubMed: 24436439     


Western blot analysis showing expressions in DR5 and antiapoptotic proteins (c-FLIP, survivin, and XIAP) in glioma cells treated with increasing doses of TMZ (0–2 mM) for 24 hours. 

24436439
Growth inhibition assay
Cell viability; 

PubMed: 25751281     


Distinct temozolomide-resistance for MGMT-expressing (SF767) and MGMT-negative (U87) GBM cells was assessed.

25751281
Immunofluorescence
Phalloidin / Phospho-H2A.X; 

PubMed: 27375225     


Immunofluorescence analysis of the level of phospho-H2A.X in nucleus which can reflect DNA damage response increased significantly at day 6, peaked during days 7-10 and decreased significantly at day 12 after treatment temozolomide (200 μM). 

cleaved caspase-3; 

PubMed: 25663820     


Representative Photomicrographs of cleaved caspase-3 immunoreactivity in control (DMSO treated) and treated group of U87 cells. Base line immunofluorescence was detected in control group. Significant Increase in immunofluorescence is detected in all treated groups with the highest observed intensity in combination treatment group (NA-2 + TMZ).

27375225 25663820
In vivo After a daily i.p. dose of 40 mg/kg for 5 consecutive days (days 1-5 after tumor transplant), methazolastone increases life-span by 86% in L-1210 and 22% in L-1210/BCNU. In L-1210/BCNU no effect is seen after 100 μM or 200 μM treatment; only 400 μM methazolastone produced an accumulation of cells in premitotic phase but much less than in L-1210. In L-1210/BCNU the maximum accumulation of cells in SL-G2-M is, after 48 hours-72 hours, approximately 30% as compared to 23% in untreated cells. Cells accumulates in SL-G2-M occurred too when L- 1210 leukemia-bearing mice are treated i.v. with methazola stone (40 mg/kg). No such effect is seen on L-1210/BCNU cells from mice given the same drug dose. [1]

Protocol

Cell Research:

[1]

- Collapse
  • Cell lines: L-1210 and L-1210/BCNU cells
  • Concentrations: 0 μM -100 μM
  • Incubation Time: l hours
  • Method:

    L-1210 and L-1210/BCNU cells are seeded at 0.2 × 104 cells/mL and incubated for 24 hours. The cultures are treated with Methazolastone for l hours at 37oC, then washed twice in PBS by centrifugation and resuspended in fresh medium. Controls and treated samples are diluted in fresh medium 1:4 at 48 hours and 1:2 at 96 hours. Using these dilutions cell concentrations throughout the experiments are between 3 × 105 and 8 × 105/mL. Control growth is logarithmic in this range.


    (Only for Reference)
Animal Research:

[1]

- Collapse
  • Animal Models: DBA/2 mice with L-1210 and L-1210/BCNU cells
  • Dosages: 40 mg/kg
  • Administration: Administered via i.v.
    (Only for Reference)

Solubility (25°C)

In vitro DMSO 38 mg/mL warmed (195.72 mM)
Water Insoluble
Ethanol Insoluble
In vivo Add solvents to the product individually and in order(Data is from Selleck tests instead of citations):
5% DMSO+30% PEG 300+ddH2O
For best results, use promptly after mixing.
2mg/mL

* Please note that Selleck tests the solubility of all compounds in-house, and the actual solubility may differ slightly from published values. This is normal and is due to slight batch-to-batch variations.

Chemical Information

Molecular Weight 194.15
Formula

C6H6N6O2

CAS No. 85622-93-1
Storage powder
in solvent
Synonyms NSC 362856,TMZ
Smiles CN1C(=O)N2C=NC(=C2N=N1)C(=O)N

In vivo Formulation Calculator (Clear solution)

Step 1: Enter information below (Recommended: An additional animal making an allowance for loss during the experiment)
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Step 2: Enter the in vivo formulation ()
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Bio Calculators

Molarity Calculator

Molarity Calculator

Calculate the mass, volume or concentration required for a solution. The Selleck molarity calculator is based on the following equation:

Mass (mg) = Concentration (mM) × Volume (mL) × Molecular Weight (g/mol)

  • Mass
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*When preparing stock solutions, please always use the batch-specific molecular weight of the product found on the via label and SDS / COA (available on product pages).

Dilution Calculator

Dilution Calculator

Calculate the dilution required to prepare a stock solution. The Selleck dilution calculator is based on the following equation:

Concentration (start) x Volume (start) = Concentration (final) x Volume (final)

This equation is commonly abbreviated as: C1V1 = C2V2 ( Input Output )

  • C1
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    C2
    V2

* When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / COA (available online).

The Serial Dilution Calculator Equation

  • Serial Dilutions

  • Computed Result

  • C1=C0/X C1: LOG(C1):
    C2=C1/X C2: LOG(C2):
    C3=C2/X C3: LOG(C3):
    C4=C3/X C4: LOG(C4):
    C5=C4/X C5: LOG(C5):
    C6=C5/X C6: LOG(C6):
    C7=C6/X C7: LOG(C7):
    C8=C7/X C8: LOG(C8):
Molecular Weight Calculator

Molecular Weight Calculator

Enter the chemical formula of a compound to calculate its molar mass and elemental composition:

Total Molecular Weight: g/mol

Tip: Chemical formula is case sensitive. C10H16N2O2 c10h16n2o2

Instructions to calculate molar mass (molecular weight) of a chemical compound:

To calculate molar mass of a chemical compound, please enter its chemical formula and click 'Calculate'.

Definitions of molecular mass, molecular weight, molar mass and molar weight:

Molecular mass (molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.

Molarity Calculator

Mass Concentration Volume Molecular Weight

Clinical Trial Information

NCT Number Recruitment interventions Conditions Sponsor/Collaborators Start Date Phases
NCT03796507 Withdrawn Drug: Temozolomide Glioma of Brain University of Rochester|National Institutes of Health (NIH) September 1 2021 Early Phase 1
NCT04901702 Recruiting Drug: Onivyde|Drug: Talazoparib|Drug: Temozolomide Recurrent Solid Tumor|Recurrent Ewing Sarcoma|Recurrent Hepatoblastoma|Recurrent Malignant Germ Cell Tumor|Recurrent Malignant Solid Neoplasm|Recurrent Neuroblastoma|Recurrent Osteosarcoma|Recurrent Peripheral Primitive Neuroectodermal Tumor|Recurrent Rhabdoid Tumor|Recurrent Rhabdomyosarcoma|Recurrent Soft Tissue Sarcoma|Recurrent Wilms Tumor|Refractory Ewing Sarcoma|Refractory Hepatoblastoma|Refractory Malignant Germ Cell Tumor|Refractory Malignant Solid Neoplasm|Refractory Neuroblastoma|Refractory Osteosarcoma|Refractory Peripheral Primitive Neuroectodermal Tumor|Refractory Rhabdoid Tumor|Refractory Rhabdomyosarcoma|Refractory Soft Tissue Sarcoma St. Jude Children''s Research Hospital|Pfizer|Ipsen June 9 2021 Phase 1|Phase 2
NCT04893785 Not yet recruiting Drug: Cabozantinib and Temozolomide Lung Neuroendocrine Neoplasm|GEP Neuroendocrine Tumor National Cancer Institute Naples June 2021 Phase 2
NCT04200066 Not yet recruiting Drug: Temozolomide Tamoxifen Maprotiline Glioblastoma|Brain Tumor University of Rochester May 1 2021 Phase 1
NCT04610736 Recruiting Drug: Temozolomide Oral Suspension Pediatric Cancer Orphelia Pharma|ClinSearch March 2021 Phase 1

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Answers to questions you may have can be found in the inhibitor handling instructions. Topics include how to prepare stock solutions, how to store inhibitors, and issues that need special attention for cell-based assays and animal experiments.

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Cell Lines Assay Type Concentration Incubation Time Formulation Activity Description PMID