Temozolomide (CCRG 81045)

Catalog No.S1237 Synonyms: NSC 362856,TMZ

For research use only.

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.

Temozolomide (CCRG 81045) Chemical Structure

CAS No. 85622-93-1

Selleck's Temozolomide (CCRG 81045) has been cited by 142 publications

Purity & Quality Control

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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 MVjHdo94fGhiSX7obYJqfGmxbjDBd5NigQ>? MkjnOFghcA>? NI\GOoxKSzVyPUGzPU4zOOLCidMx5qCKPS57NTFOwG0> MWi8ZUB1[XKpZYS9K39jdGGwazegbJJm\j1paIT0dJM7Ny:ydXLt[YQvdmOkaT7ucI0vdmmqLnfvek8zPTl4MEK4Nkc,OjV7NkCyPFI9N2F-
KellyCis83 M3S5W2dzd3e2aDDJcohq[mm2aX;uJGF{e2G7 MmC4OFghcA>? NVzib21MUUN3ME2yOVEvODEkgJpCtgKBkTF3Lke1JO69VQ>? MVW8ZUB1[XKpZYS9K39jdGGwazegbJJm\j1paIT0dJM7Ny:ydXLt[YQvdmOkaT7ucI0vdmmqLnfvek8zPTl4MEK4Nkc,OjV7NkCyPFI9N2F-
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SK-N-ASCis24 M3uyc2dzd3e2aDDJcohq[mm2aX;uJGF{e2G7 NFHnd4E1QCCq MXrJR|UxRTR6MD62NQKBkcLz4pEJNVAyNjF3IN88US=> MkfLQIEhfGG{Z3X0QUdg[myjbnunJIhz\WZ;J3j0eJB{Qi9xcIXicYVlNm6lYnmucoxuNm6raD7nc5YwOjV7NkCyPFIoRjJ3OU[wNlgzRC:jPh?=
CHP-212 NYLjNVM2T3Kxd4ToJGlvcGmkaYTpc44hSXO|YYm= MnrmOFghcA>? NGH1OIZKSzVyPUeuPVfjiIoEsfMAjVAvPjlizszN NYHyZ44zRGFidHHy[4V1RSehYnzhcosoKGi{ZX[9K4h1fHC|Oj:vdJVjdWWmLn7jZokvdmyvLn7pbE5od3ZxMkW5OlAzQDJpPkK1PVYxOjh{PD;hQi=>
CHP-212Cis100 M2Gwc2dzd3e2aDDJcohq[mm2aX;uJGF{e2G7 NU\n[nA{PDhiaB?= M4i2UGlEPTB;OT61OgKBkcLz4pEJNE45QCEQvF2= NGnxfGc9[SC2YYLn[ZQ:L1:kbHHub{chcHKnZk2nbJR1eHN8Lz;weYJu\WRwbnPibU5vdG1wbnnoModwfi9{NUm2NFI5Oid-MkW5OlAzQDJ:L3G+
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U87MG MonNRY51cXS3bX;yJIF{e2G7 MkeyRY51cXS3bX;yJIFkfGm4aYT5JIFo[Wmwc4SgbJVu[W5iVUi3UWch[2WubIOgc5J1cG:2b4DpZ4FtdHlieHXuc4dz[W[2ZXSgbY4hUGG{bHHuJI52\GVibX;1d4Uh[nKjaX6gZZN{\XO|ZXSgZZMhcW6lcnXhd4UhcW5ibX;1d4Uhe3W{dnn2ZYwh[XRiNUCgeY1wdC:tZzygbZYh[WSvaX7pd5RmemWmIH;uZ4Uh\GGrbImg[o9zKDViZHH5dy=> NHXiSmQ9[SC2YYLn[ZQ:L1:kbHHub{chcHKnZk2nbJR1eHN8Lz;weYJu\WRwbnPibU5vdG1wbnnoModwfi9{N{[xOFQyPCd-Mke2NVQ1OTR:L3G+
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MDCK MWfDfZRwfG:6aXPpeJkh[XO|YYm= M2LR[VI1KGi{cx?= MljmR5l1d3SxeHnjbZR6KGGpYXnud5QhVUSFSzDj[YxteyCneIDy[ZN{cW6pIHPhdoJwdmmlIHHubJllemG|ZTC5JIF{e2W|c3XkJIF{KHKnZIXjeIlwdiCrbjDj[YxtKH[rYXLpcIl1gSCrbnP1ZoF1\WRiZn;yJFI1KGi{czDt[YF{fXKnZDDh[pRmeiB5IHThfZMhfW6mZYKgbJlxd3irYzDjc45lcXSrb36gZpkhdWW2aIns[Y5mKGKudXWgd5RicW6rbnegZoF{\WRiY3zvco9o\W6rYzDzeZJ3cX[jbDDhd5NigQ>? NGfn[Jc9[SC2YYLn[ZQ:L1:kbHHub{chcHKnZk2nbJR1eHN8Lz;weYJu\WRwbnPibU5vdG1wbnnoModwfi9{N{iyN|g4QSd-Mke4NlM5Pzl:L3G+
NB-EBc1 NGTwem9yUFSVIHHzd4F6 MWnxTHRUKG:oIIDl[IlifHKrYzDjZY5k\XJiY3XscEBtcW6nczD0c{Bq\GWwdHnmfUBufWy2aYDs[UBweHCxcoT1col1cWW|IH\vdkBlenWpIILldJVzeG:|aX7nPkBRemmvYYL5JJNkemWnbjDmc5IhVkJvRVLjNUBk\Wyucx?= M3fLUVxiKHSjcnfleF0oZ2KuYX7rK{BpemWoPTfoeJRxezpxL4D1Zo1m\C6wY3LpMo5tdS6waXiu[493NzJ7NEO1NVM6Lz5{OUSzOVE{QTxxYU6=
C6 NIjYN29EgXSxdH;4bYNqfHliYYPzZZk> MVq0JIRigXN? M1XYWmVEPTBiPTCxOk42KM7:TR?= NXvIS4lORGFidHHy[4V1RSehYnzhcosoKGi{ZX[9K4h1fHC|Oj:ve5d4NmWkaT7hZ{52cy:laHXtZoww[2:vcH;1coRgemWyb4L0Y4NiemRxQ1jFUWJNQDFyLze+R4hGVUKOPD;hQi=>
U87 NHHFWVBEgXSxdH;4bYNqfHliYYPzZZk> NV\CfGMzPzJiaILz MWjJR|UxKD1iMUmuN|gh|ryP NWr3T2N5RGFidHHy[4V1RSehYnzhcosoKGi{ZX[9K4h1fHC|Oj:ve5d4NmWkaT7hZ{52cy:laHXtZoww[2:vcH;1coRgemWyb4L0Y4NiemRxQ1jFUWJNQDFyLze+R4hGVUKOPD;hQi=>
SNB19 MYTHdo94fGhiaX7obYJqfGmxbjDhd5NigQ>? M4m4cVch\GG7cx?= NX73dWhlT0l3MDC9JFM2NjdizszN NYPk[GhxRGFidHHy[4V1RSehYnzhcosoKGi{ZX[9K4h1fHC|Oj:ve5d4NmWkaT7hZ{52cy:laHXtZoww[2:vcH;1coRgemWyb4L0Y4NiemRxQ1jFUWJNQDFyLze+R4hGVUKOPD;hQi=>
SNB19 MUjHdo94fGhiaX7obYJqfGmxbjDhd5NigQ>? NGTOSGM4KGSjeYO= NGjUXHhIUTVyIE2gOFUvPiEQvF2= Mo\hQIEhfGG{Z3X0QUdg[myjbnunJIhz\WZ;J3j0eJB{Qi9xd4f3MoVjcS6jYz71b{9kcGWvYnyvZ49ueG:3bnTfdoVxd3K2X3PhdoQwS0iHTVLMPFExNyd-Q3jFUWJNRC:jPh?=
U373 Mo\OSpVv[3Srb36gZZN{[Xl? NETGZ4UyODBidV2= MmrRO|IhcHK| MXTJcoR2[3Srb36gc4Yh\G:3YnzlJJN1emGwZHXkJGRPSSCkcnXhb{BqdiCnbYD0fUB3\WO2b4KgeJJidnOoZXP0[YQhcHWvYX6gWVM4OyClZXzsd{Bie3Onc4Pl[EBieyCrbnPy[YF{\SCrbjDnZY1u[S2KMlHYJIxmfmWuIHH0JFExOCC3TTDh[pRmeiB5MjDodpMh[nliZnzve{BkgXSxbXX0dpk> NEfzeWc9[SC2YYLn[ZQ:L1:kbHHub{chcHKnZk2nbJR1eHN8Lz;3e5cv\WKrLnHjMpVsN2OqZX3icE9kd22yb4Xu[H9z\XCxcoTfZ4Fz\C:FSFXNRmw5OTBxJ{7DbGVOSkx:L3G+
Glioma MlLHRY51cXS3bX;yJIF{e2G7 M1PMcGFvfGm2dX3vdkBi[3Srdnn0fUBi\2GrboP0JGhwdW9ic3HwbYVveyBqaIXtZY4qKEeuaX;tZUBk\WyuczD4[Y5w\3KjZoTl[EBqdiC2cnHud4dmdmmlIH3veZNmKGG|c3Xzd4VlKGG|IH3veZNmKHO3co\peoFt M2LTTFxiKHSjcnfleF0oZ2KuYX7rK{BpemWoPTfoeJRxezpxL4f3e{5m[mlwYXOueYsw[2inbXLsM4NwdXCxdX7kY5JmeG:{dG;jZZJlN0OKRV3CUFgyOC9pPlPoSW1DVDxxYU6=
Assay
Methods Test Index PMID
Western blot pERK / ERK / p-p38 / p38 ; DR5 / c-FLIP / Survivin / XIAP 24436439
Growth inhibition assay Cell viability 25751281
Immunofluorescence Phalloidin / Phospho-H2A.X ; cleaved caspase-3 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 (from reference)

Cell Research:

[1]

  • 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.

Animal Research:

[1]

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

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

Chemical Information

Molecular Weight 194.15
Formula

C6H6N6O2

CAS No. 85622-93-1
Storage 3 years -20°C powder
2 years -80°C in solvent
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)

mg/kg g μL

Step 2: Enter the in vivo formulation (This is only the calculator, not formulation. Please contact us first if there is no in vivo formulation at the solubility Section.)

% DMSO % % Tween 80 % ddH2O
%DMSO %

Calculation results:

Working concentration: mg/ml;

Method for preparing DMSO master liquid: mg drug pre-dissolved in μL DMSO ( Master liquid concentration mg/mL, Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug. )

Method for preparing in vivo formulation: Take μL DMSO master liquid, next addμL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O, mix and clarify.

Method for preparing in vivo formulation: Take μL DMSO master liquid, next add μL Corn oil, mix and clarify.

Note: 1. Please make sure the liquid is clear before adding the next solvent.
2. Be sure to add the solvent(s) in order. You must ensure that the solution obtained, in the previous addition, is a clear solution before proceeding to add the next solvent. Physical methods such
as vortex, ultrasound or hot water bath can be used to aid dissolving.

Molarity Calculator

Mass Concentration Volume Molecular Weight

Clinical Trial Information

NCT Number Recruitment Interventions Conditions Sponsor/Collaborators Start Date Phases
NCT05128734 Not yet recruiting Drug: Temozolomide|Drug: Olaparib Breast Cancer Triple Negative AHS Cancer Control Alberta April 1 2022 Phase 2
NCT04200066 Not yet recruiting Drug: Temozolomide Tamoxifen Maprotiline Glioblastoma|Brain Tumor University of Rochester December 1 2021 Phase 1
NCT03796507 Withdrawn Drug: Temozolomide Glioma of Brain University of Rochester|National Institutes of Health (NIH) September 1 2021 Early Phase 1
NCT04901702 Active not 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

(data from https://clinicaltrials.gov, updated on 2022-01-17)

Tech Support

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.

Handling Instructions

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