| Size | Price | Stock | Qty |
|---|---|---|---|
| 250mg |
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| 500mg | |||
| Other Sizes |
| Targets |
Temozolomide acid targets DNA, specifically through methylation at the O6 and N7 positions of guanine residues. The compound is a DNA alkylating agent that transfers a methyl group to DNA bases. The O6-methylguanine adduct is the most cytotoxic lesion, as it mispairs with thymine during DNA replication, leading to DNA mismatch repair and ultimately apoptosis. The compound's activity is dependent on the DNA repair protein MGMT.
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|---|---|
| ln Vitro |
In vitro, temozolomide acid is the active metabolite of temozolomide responsible for its cytotoxic activity. It alkylates DNA at the O6 and N7 positions of guanine, leading to DNA damage and apoptosis. The compound's activity is assessed by measuring DNA alkylation, cell viability, and apoptosis in cancer cell lines. Its cytotoxicity is dependent on MGMT expression levels.
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| ln Vivo |
In vivo, temozolomide acid is formed by the spontaneous hydrolysis of temozolomide in the bloodstream and tissues. The compound is responsible for the antitumor activity of temozolomide in patients with glioblastoma and other malignant gliomas. Its DNA-alkylating activity leads to tumor cell death. The compound's efficacy is influenced by MGMT promoter methylation status in tumors.
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| Enzyme Assay |
In vitro enzyme/receptor binding assays are not applicable for temozolomide acid as it is a DNA alkylating agent rather than an enzyme inhibitor. The compound's mechanism is based on DNA alkylation rather than receptor binding. Its DNA alkylation activity is assessed by measuring O6-methylguanine adduct formation using HPLC or mass spectrometry.
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| Cell Assay |
In vitro cell-based assays for temozolomide acid use various cancer cell lines, including glioma cells. Cells are treated with serial dilutions of the compound, and cell viability is measured using MTT or other assays. DNA damage is assessed by measuring γ-H2AX foci formation or comet assays. Apoptosis is assessed by annexin V staining or caspase activity assays. The compound's cytotoxicity is correlated with MGMT expression levels.
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| Animal Protocol |
In vivo animal models for temozolomide acid include mouse xenograft models of glioblastoma. The compound is administered orally or intravenously, and its effects on tumor growth and survival are evaluated. Pharmacodynamic studies measure DNA alkylation and MGMT expression in tumor tissues. Dose-response studies establish the effective dose for antitumor activity.
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| ADME/Pharmacokinetics |
Temozolomide acid has a molecular formula of C6H6N4O3 and a molecular weight of 182.14. It is the active hydrolysis product of temozolomide formed at physiological pH. The compound is soluble in water and DMSO. It is stored at -20°C. Pharmacokinetic parameters of temozolomide and its metabolites are documented in clinical studies. The compound is eliminated primarily via the kidneys.
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| Toxicity/Toxicokinetics |
The toxicity profile of temozolomide acid is similar to that of temozolomide. Common adverse effects include myelosuppression (neutropenia, thrombocytopenia), nausea, vomiting, and fatigue. The compound is contraindicated in patients with severe bone marrow suppression. The compound is for research use only and not for human use. Appropriate safety precautions should be taken during handling.
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| References |
:J Pharm Pharmacol. 2007 Jun;59(6):787-94.
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| Additional Infomation |
Temozolomide acid is the active hydrolysis product and metabolite of temozolomide, a DNA alkylating agent used for the treatment of glioblastoma and other malignant gliomas. The compound is formed by spontaneous hydrolysis of temozolomide at physiological pH and is responsible for its cytotoxic activity. Temozolomide acid alkylates DNA at O6 and N7 positions of guanine, leading to DNA damage and apoptosis. It is used for research purposes.
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| Molecular Formula |
C6H5N5O3
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|---|---|
| Molecular Weight |
195.1356
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| Exact Mass |
195.039
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| CAS # |
113942-30-6
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| PubChem CID |
11830328
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| Appearance |
White to off-white solid powder
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| Density |
2.0±0.1 g/cm3
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| Boiling Point |
487.7±37.0 °C at 760 mmHg
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| Melting Point |
177 ºC (decomp)
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| Flash Point |
248.7±26.5 °C
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| Vapour Pressure |
0.0±1.3 mmHg at 25°C
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| Index of Refraction |
1.860
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| LogP |
-1.46
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
6
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
14
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| Complexity |
317
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
VVTMIOYTNALQAW-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C6H5N5O3/c1-10-6(14)11-2-7-3(5(12)13)4(11)8-9-10/h2H,1H3,(H,12,13)
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| Chemical Name |
3-methyl-4-oxoimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxylic acid
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~512.45 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (12.81 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (12.81 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (12.81 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.1245 mL | 25.6226 mL | 51.2453 mL | |
| 5 mM | 1.0249 mL | 5.1245 mL | 10.2491 mL | |
| 10 mM | 0.5125 mL | 2.5623 mL | 5.1245 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution 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 stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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