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| Other Sizes |
| Targets |
Diclofenac methyl ester targets the same enzymes as diclofenac: cyclooxygenase‑1 (COX‑1) and cyclooxygenase‑2 (COX‑2). By inhibiting these enzymes, it reduces the production of pro‑inflammatory prostaglandins. The methyl ester group enhances membrane permeability and lipophilicity compared to diclofenac, potentially improving passive diffusion across biological membranes. The compound is also classified as an endogenous metabolite that participates in Phase II metabolic pathways.
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| ln Vitro |
Diclofenac methyl ester exhibits acute cytotoxicity with an LC₅0 of 0.5 mg/L in the aquatic crustacean Hyalella azteca. In vitro, the compound retains COX‑1 and COX‑2 inhibitory activity, although the esterified form is less potent than the parent diclofenac due to the requirement for esterase‑mediated hydrolysis to release the active free carboxylic acid. The compound has been used to study the environmental fate of diclofenac in aquatic ecosystems, where it is formed through biotransformation processes involving an S‑adenosylmethionine‑dependent carboxylic acid methyltransferase.
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| ln Vivo |
In animal studies, when administered orally or intravenously, diclofenac methyl ester is rapidly hydrolyzed by plasma and tissue esterases to release diclofenac, which then exerts its anti‑inflammatory and analgesic effects. The esterification to the methyl ester represents a prodrug strategy to improve bioavailability or alter the pharmacokinetic profile of diclofenac. The compound has been used in studies of inflammation, pain management, and drug delivery research, particularly for improving drug absorption and targeting.
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| Enzyme Assay |
The inhibition of COX‑1 and COX‑2 by diclofenac methyl ester can be assessed using an enzyme immunoassay (EIA) kit. Purified ovine COX‑1 or human recombinant COX‑2 is incubated with arachidonic acid (10 uM) as substrate in 100 mM Tris‑HCl buffer (pH 8.0) containing 5 uM hematin and 2 mM phenol for 2 minutes at 37degC. Diclofenac methyl ester is added at concentrations ranging from 0.01-100 uM. The reaction is stopped by adding 1 M HCl, and the amount of prostaglandin E2 (PGE2) produced is measured using a competitive EIA kit. The half‑maximal inhibitory concentration (IC₅0) is calculated from the dose‑response curve.
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| Cell Assay |
Cell viability in response to diclofenac methyl ester can be assessed using the MTT assay. Human hepatocytes (e.g., HepG2 cells) or other relevant cell lines are seeded in 96‑well plates and treated with the compound at concentrations ranging from 1-500 uM for 24-72 hours. After treatment, MTT reagent is added and incubated for 4 hours at 37degC, followed by DMSO solubilization. Absorbance is measured at 570 nm to calculate the half‑maximal inhibitory concentration (IC₅0). The LC₅0 of 0.5 mg/L in H. azteca was determined using aquatic invertebrate toxicity testing protocols (OECD Guideline 202).
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| Animal Protocol |
The acute toxicity of diclofenac methyl ester to aquatic organisms can be assessed using a Daphnia magna immobilization test according to OECD Guideline 202. Young daphnids (<24 hours old) are exposed to diclofenac methyl ester at concentrations ranging from 0.1-10 mg/L in reconstituted water for 48 hours at 20degC. Immobilization (lack of swimming ability) is recorded at 24 and 48 hours. The median effective concentration (EC₅0) is calculated using probit analysis or the Trimmed Spearman‑Karber method. The LC₅0 of 0.5 mg/L in H. azteca was determined using a similar protocol.
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| ADME/Pharmacokinetics |
After absorption, the methyl ester group of diclofenac methyl ester is rapidly cleaved by plasma and tissue esterases (primarily carboxylesterases) to release the active parent drug diclofenac. This conversion results in diclofenac pharmacokinetics: approximately 99% plasma protein binding, a volume of distribution of 0.12-0.17 L/kg, hepatic metabolism via CYP2C9 and CYP3A4 to 4′‑hydroxy‑ and 5‑hydroxydiclofenac, and elimination via both biliary excretion (60-80%) and renal excretion (20-40%). The methyl ester itself has a very short half‑life due to rapid hydrolysis.
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| Toxicity/Toxicokinetics |
The LD₅0 of diclofenac methyl ester has not been directly determined, but toxicity is expected to be similar to or lower than that of diclofenac (oral LD₅0 approximately 50-100 mg/kg in rodents). The compound may cause gastrointestinal ulceration, hepatotoxicity, and nephrotoxicity similar to other NSAIDs, particularly with chronic use. In aquatic organisms, the compound exhibits acute cytotoxicity with an LC₅0 of 0.5 mg/L in H. azteca, indicating moderate toxicity to aquatic invertebrates. The compound should be handled with appropriate personal protective equipment.
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| References | |
| Additional Infomation |
Diclofenac methyl ester is not a drug and is not approved for human therapeutic use. It is a research chemical and analytical reference standard used to study diclofenac metabolism, ester prodrug strategies, and the environmental fate of diclofenac in aquatic ecosystems. The esterified form enhances membrane permeability and bioavailability, making it useful in prodrug development and pharmacokinetic studies. Diclofenac methyl ester is a valuable tool for drug absorption and targeting research, particularly for improving the delivery of carboxylic acid‑containing drugs. Its CAS number is 15307‑78‑5, and its molecular formula is C1₅H13Cl2NO2.
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| Molecular Formula |
C15H13CL2NO2
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|---|---|
| Molecular Weight |
310.18
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| Exact Mass |
309.032
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| CAS # |
15307-78-5
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| PubChem CID |
519102
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| Appearance |
Solid powder
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| Density |
1.335g/cm3
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| Boiling Point |
373.8ºC at 760 mmHg
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| Melting Point |
102 °C
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| Flash Point |
179.9ºC
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| Vapour Pressure |
8.72E-06mmHg at 25°C
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| Index of Refraction |
1.618
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| LogP |
4.525
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
5
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| Heavy Atom Count |
20
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| Complexity |
317
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| Defined Atom Stereocenter Count |
0
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| SMILES |
ClC1C([H])=C([H])C([H])=C(C=1N([H])C1=C([H])C([H])=C([H])C([H])=C1C([H])([H])C(=O)OC([H])([H])[H])Cl
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| InChi Key |
VETACGBDFVVKGZ-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C15H13Cl2NO2/c1-20-14(19)9-10-5-2-3-8-13(10)18-15-11(16)6-4-7-12(15)17/h2-8,18H,9H2,1H3
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| Chemical Name |
methyl 2-[2-(2,6-dichloroanilino)phenyl]acetate
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| Synonyms |
Methyl dichlorophenate
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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 : 12.5 mg/mL (40.30 mM; with sonication (<60°C))
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|---|---|
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.2239 mL | 16.1197 mL | 32.2393 mL | |
| 5 mM | 0.6448 mL | 3.2239 mL | 6.4479 mL | |
| 10 mM | 0.3224 mL | 1.6120 mL | 3.2239 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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