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| Targets |
1-Benzylimidazole targets cytochrome P-450 isozymes, which it induces, and thromboxane A2 synthase, which it inhibits. Cytochrome P-450 enzymes are a family of heme-containing monooxygenases involved in drug metabolism and steroid biosynthesis. Thromboxane A2 synthase is an enzyme that produces thromboxane A2, a potent vasoconstrictor and platelet aggregator. The compound is also a potential aromatase inhibitor. Aromatase is an enzyme that converts androgens to estrogens, and its inhibition is a therapeutic strategy for estrogen-dependent cancers. The imidazole nitrogen coordinates to the heme iron of cytochrome P-450 enzymes.
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| ln Vitro |
Benzylimidazole is a stimulator of UDP-glucosyltransferase and a selective inhibitor of thromboxane synthase. One cytochrome P450 enzyme is thromboxane synthase. Numerous reactions in drug metabolism and the synthesis of cholesterol, steroids, and other lipids are catalyzed by cytochrome P450 proteins. Hemostasis, heart disease, and stroke are just a few of the pathophysiological processes in which this enzyme is crucial. There are two transcript variants expressed by this gene. 1. Benzimidazole specifically prevents thromboxane synthase from functioning. Benzimidazole decreases TXB2 levels and improves blood flow in rats that have suffered a cerebral ischemia-reperfusion injury. In dose-dependent hepatitis in male Wistar rats, 1-benzimidazole (25, 75, and 100 mg/kg/day) was administered gastrically. 1. Benzimidazole 60–70% lowers plasma triglyceride levels. 1. Three distinct forms of UDP-glucuronyltransferase are stimulated by benzomidazole. 1-Benzimidazole exhibited a significant increase in activity against monoterpenoid alcohols such as nopol, 1-naphthol, morphine, and 4-methylthrinone. In a concentration-dependent manner, benamidazole raises hepatocyte CYP1A catalytic activity and CYP1A mRNA.
In vitro, 1-benzylimidazole acts as an inducer of various cytochrome P-450 isozymes and an inhibitor of thromboxane A2 synthase. It is also a potential aromatase inhibitor. These activities make it a useful tool compound for studying cytochrome P-450 induction, thromboxane biosynthesis, and aromatase inhibition. In cell-based assays, the compound would be expected to modulate these enzyme activities and affect downstream signaling pathways. Typical concentrations for enzyme inhibition studies range from 1-100 µM. The compound's imidazole ring is a key pharmacophore for coordinating to heme iron in cytochrome P-450 enzymes. |
| ln Vivo |
In vivo, 1-benzylimidazole would be expected to modulate cytochrome P-450 enzyme activities, thromboxane biosynthesis, and aromatase activity based on its in vitro activities. However, systematic in vivo pharmacological studies including efficacy in animal models have not been well documented for this compound. The compound is primarily used as a research reagent and tool compound for studying enzyme induction and inhibition. Any in vivo effects would depend on the dose, route of administration, and the specific biological system being studied. The compound is not approved for therapeutic use.
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| Enzyme Assay |
In vitro enzyme assays for 1-benzylimidazole typically involve cytochrome P-450 induction studies or thromboxane A2 synthase inhibition studies. A standard protocol for P-450 induction involves treating hepatocytes or liver microsomes with the compound at concentrations ranging from 1-100 µM for 24-48 hours, followed by measurement of P-450 enzyme activity using specific substrates (e.g., ethoxyresorufin for CYP1A). For thromboxane A2 synthase inhibition, the enzyme is incubated with the substrate prostaglandin H₂ and varying concentrations of the test compound, and product formation is measured by ELISA or radioimmunoassay.
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| Cell Assay |
In vitro cell culture experiments with 1-benzylimidazole typically involve hepatocytes or other cell lines expressing cytochrome P-450 enzymes. Cells are cultured in appropriate media and treated with the compound at concentrations ranging from 1-100 µM for 24-48 hours. P-450 enzyme activity is measured using fluorogenic or luminescent substrates. Cell viability is assessed using MTT assays to ensure that observed effects are not due to cytotoxicity. For aromatase inhibition studies, cells expressing aromatase (e.g., JEG-3 cells) are treated with the compound and testosterone, and estradiol production is measured by ELISA.
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| Animal Protocol |
In vivo animal studies with 1-benzylimidazole are not well documented, as the compound is primarily used as a research reagent. If conducted, typical protocols would involve oral or intraperitoneal administration in rodents at doses ranging from 1-50 mg/kg. Blood and tissue samples would be collected for measurement of P-450 enzyme activities, thromboxane levels, or estradiol levels. Animals would be monitored for clinical signs and body weight changes. However, such studies are not standard for this compound as it is not a drug candidate.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of 1-benzylimidazole are not well characterized as it is not a drug substance. Based on its physicochemical properties (molecular weight 158.20, logP approximately 2.0-2.5), the compound would be expected to have good oral bioavailability if administered. It would likely undergo metabolism via cytochrome P-450-mediated oxidation at the imidazole ring or the benzyl group. However, the compound is not intended for human exposure and has not been evaluated in formal pharmacokinetic studies. For research applications, the compound is typically used in vitro.
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| Toxicity/Toxicokinetics |
Toxicological data for 1-benzylimidazole are limited as it is a research reagent. Standard laboratory safety precautions should be followed when handling this compound, including the use of gloves, safety glasses, and working in a fume hood. The compound should be stored in a cool, dry place away from light and moisture. No acute toxicity data are available. The compound is not intended for drug, household, or other uses.
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| References |
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| Additional Infomation |
1-Benzylimidazole is an N-imidazole derivative that has been shown to have strong cardiotonic activity.
1-Benzylimidazole is a biochemical reagent that acts as an inducer of various cytochrome P-450 isozymes and an inhibitor of thromboxane A2 synthase. It is also a potential aromatase inhibitor. The compound is also known as N-benzylimidazole. It has not undergone clinical trials and is not approved as a pharmaceutical. Its mechanism of action involves coordination of the imidazole nitrogen to heme iron in cytochrome P-450 enzymes, leading to enzyme induction or inhibition depending on the specific isozyme. |
| Molecular Formula |
C10H10N2
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| Molecular Weight |
158.20
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| Exact Mass |
158.084
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| CAS # |
4238-71-5
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| PubChem CID |
77918
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| Appearance |
White to off-white solid powder
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| Density |
1.0±0.1 g/cm3
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| Boiling Point |
310.0±11.0 °C at 760 mmHg
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| Melting Point |
68-70 °C
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| Flash Point |
141.3±19.3 °C
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| Vapour Pressure |
0.0±0.6 mmHg at 25°C
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| Index of Refraction |
1.580
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| LogP |
1.46
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
1
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
12
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| Complexity |
130
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C1=CC=C(C=C1)CN2C=CN=C2
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| InChi Key |
KKKDZZRICRFGSD-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C10H10N2/c1-2-4-10(5-3-1)8-12-7-6-11-9-12/h1-7,9H,8H2
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| Chemical Name |
1-benzylimidazole
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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 (632.11 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (15.80 mM) (saturation unknown) in 10% DMSO + 40% PEG300 +5% Tween-80 + 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. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 6.3211 mL | 31.6056 mL | 63.2111 mL | |
| 5 mM | 1.2642 mL | 6.3211 mL | 12.6422 mL | |
| 10 mM | 0.6321 mL | 3.1606 mL | 6.3211 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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