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| 5mg |
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| Targets |
AT1 Receptor; As an ester derivative of olmesartan, olmesartan methyl ester targets the angiotensin II type 1 receptor (AT1 receptor). The active metabolite olmesartan exerts its antihypertensive effect by selectively blocking the binding of angiotensin II to AT1 receptors, thereby inhibiting vasoconstriction and aldosterone release. Olmesartan exhibits potent AT1 receptor binding with an IC₅₀ of approximately 7.7 nM. Studies have shown that olmesartan methyl ester itself is a substrate for OATP2B1 (organic anion transporting polypeptide 2B1), a transporter expressed in the small intestine involved in drug absorption.
Angiotensin II receptor type 1 (AT1R) is the primary target of Olmesartan medoxomil, the final drug product. Olmesartan methyl ester is a synthetic intermediate. Its pharmacological activity is primarily related to its role in the synthesis of the active drug Olmesartan medoxomil. Olmesartan medoxomil is a potent and specific angiotensin AT1 receptor antagonist with an IC50 of 66.2 μM. |
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| ln Vitro |
Olmesartan methyl ester requires in vivo hydrolysis to exert its pharmacological activity as an ester derivative. Studies demonstrate that olmesartan methyl ester exhibits significantly higher intestinal permeability compared to olmesartan: its uptake in Caco-2 cells is markedly higher, and its permeability in rat jejunum is superior to the parent drug. This property is attributed to its role as an OATP2B1 substrate, closely related to the expression of this transporter. The parent compound olmesartan exhibits potent AT1 receptor antagonism with an IC₅₀ of 7.7 nM in vitro.
In vitro, Olmesartan methyl ester is a synthetic intermediate. Its pharmacological activity is primarily related to its role in the synthesis of the active drug Olmesartan medoxomil. The compound is not typically studied for its own pharmacological effects. Olmesartan medoxomil, the final product, is a potent and specific AT1 receptor antagonist. |
| ln Vivo |
As a prodrug form of olmesartan, olmesartan methyl ester is converted in vivo to the active metabolite to exert its antihypertensive effects. The onset of action occurs 1-2 hours after administration, with peak effects observed approximately 6-8 hours post-dose, and the antihypertensive effects last up to 24 hours. Studies have confirmed that olmesartan methyl ester exhibits improved intestinal absorption compared to olmesartan, mediated by the OATP2B1 transporter, significantly enhancing the oral bioavailability of the drug.
In vivo, Olmesartan medoxomil (the final product) demonstrates antihypertensive activity. The methyl ester intermediate is not typically studied for pharmacological effects. The compound is used in chemical synthesis rather than for in vivo pharmacological studies. |
| Enzyme Assay |
The binding affinity of olmesartan methyl ester for the AT1 receptor can be assessed using radioligand binding assays following protocols for the parent compound. Typical AT1 receptor binding assays use membranes from cells expressing human AT1 receptors (e.g., CHO cell membranes). Membrane proteins are incubated with [¹²⁵I]-labeled angiotensin II tracer and various concentrations of olmesartan methyl ester (0.1 nM-100 μM) in binding buffer. Following incubation at room temperature for 60-120 minutes, the reaction is terminated by vacuum filtration, filters are washed to remove unbound tracer, and retained radioactivity is measured to calculate specific binding inhibition rates.
Analytical methods such as HPLC and NMR are used to characterize Olmesartan methyl ester as a synthetic intermediate. The compound is used in chemical synthesis rather than biological assays. The purity of the intermediate is assessed using chromatographic methods to ensure its suitability for the next synthetic step. |
| Cell Assay |
Cellular assays for olmesartan methyl ester can use the Caco-2 cell monolayer permeability model to evaluate intestinal absorption properties. Caco-2 cells are seeded onto Transwell inserts and cultured until tight monolayer formation (approximately 21 days). Various concentrations of olmesartan methyl ester (e.g., 1-100 μM) are added to the apical side, and after incubation at 37°C for 2 hours, samples are collected from the basolateral side and drug concentrations are determined by HPLC-MS/MS to calculate apparent permeability coefficients (Papp). Additionally, OATP2B1-overexpressing HEK293 cells can be used to evaluate uptake activity as a transporter substrate.
Cell-based assays are not typically performed for synthetic intermediates. The compound is used in chemical synthesis. No functional assays are typically performed for Olmesartan methyl ester. |
| Animal Protocol |
In vivo studies are not typically performed for synthetic intermediates. The compound is used in chemical synthesis. No animal studies are typically performed for Olmesartan methyl ester.
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| ADME/Pharmacokinetics |
Olmesartan methyl ester, as a prodrug, has an oral bioavailability of less than 26%. The compound is rapidly hydrolyzed in vivo to the active metabolite olmesartan, which has a half-life of approximately 13 hours, supporting once-daily dosing. Olmesartan methyl ester exhibits improved intestinal permeability compared to olmesartan, mediated by OATP2B1 transporter-facilitated absorption. In rat jejunum, olmesartan methyl ester shows significantly higher permeability than olmesartan, suggesting that esterification improves the oral absorption properties of the drug. The compound has a solubility of 100 mg/mL (~217.14 mM) in DMSO, with a common in vivo injection formulation including DMSO : Tween 80 : saline = 10 : 5 : 85.
Pharmacokinetic data for Olmesartan methyl ester are not typically studied. Olmesartan medoxomil is the active pharmaceutical ingredient. The methyl ester intermediate is converted to the final drug product during synthesis and is not administered to humans or animals. |
| Toxicity/Toxicokinetics |
According to the safety data sheet for olmesartan methyl ester, the compound exhibits acute oral toxicity (Category 4, H302) and is very toxic to aquatic life with long-lasting effects (Category 1, H400/H410). It may cause skin irritation (H315) and serious eye irritation (H319). The compound is not listed as a carcinogen by IARC, NTP, ACGIH, or OSHA, and no evidence suggests reproductive or genotoxic toxicity in standard evaluations. The powder can be stored at -20°C for 3 years, at 4°C for 2 years, and in solution at -80°C for 6 months. Protective gloves and eye protection should be worn during handling, and release to the environment should be avoided.
Toxicology data for Olmesartan methyl ester are evaluated as part of pharmaceutical development. The compound is used as a synthetic intermediate. Its safety is assessed as part of the overall impurity profile of the final drug product. The compound is not administered as a therapeutic agent. |
| References |
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| Additional Infomation |
Olmesartan methyl ester (CAS: 1347262-29-6) is a chemical intermediate used in the synthesis of the antihypertensive drug Olmesartan medoxomil. The compound has a molecular formula of C25H28N6O3 and a molecular weight of 460.53. Olmesartan methyl ester is not a therapeutic agent and is not approved for human use. The compound is intended for research and pharmaceutical synthesis purposes only.
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| Molecular Formula |
C25H28N6O3
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|---|---|
| Molecular Weight |
460.53
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| Exact Mass |
460.222
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| Elemental Analysis |
C, 65.20; H, 6.13; N, 18.25; O, 10.42
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| CAS # |
1347262-29-6
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| Related CAS # |
144689-24-7; 1347262-29-6 (methyl ester ); 144689-63-4 (medoxomil)
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| PubChem CID |
71465208
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| Appearance |
White to yellow solid powder
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
712.0±70.0 °C at 760 mmHg
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| Flash Point |
384.4±35.7 °C
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| Vapour Pressure |
0.0±2.4 mmHg at 25°C
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| Index of Refraction |
1.645
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| LogP |
4.03
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
7
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| Rotatable Bond Count |
9
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| Heavy Atom Count |
34
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| Complexity |
671
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CCCC1=NC(=C(N1CC2=CC=C(C=C2)C3=CC=CC=C3C4=NNN=N4)C(=O)OC)C(C)(C)O
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| InChi Key |
XFIYSFZDSWUHEO-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C25H28N6O3/c1-5-8-20-26-22(25(2,3)33)21(24(32)34-4)31(20)15-16-11-13-17(14-12-16)18-9-6-7-10-19(18)23-27-29-30-28-23/h6-7,9-14,33H,5,8,15H2,1-4H3,(H,27,28,29,30)
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| Chemical Name |
methyl 5-(2-hydroxypropan-2-yl)-2-propyl-3-[[4-[2-(2H-tetrazol-5-yl)phenyl]phenyl]methyl]imidazole-4-carboxylate
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| Synonyms |
Olmesartan Methyl Ester; 1347262-29-6; methyl 5-(2-hydroxypropan-2-yl)-2-propyl-3-[[4-[2-(2H-tetrazol-5-yl)phenyl]phenyl]methyl]imidazole-4-carboxylate; 4-(1-Hydroxy-1-methylethyl)-2-propyl-1-[[2'-(2H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]-1H-imidazole-5-carboxylic Acid Methyl Ester; Olmesartan Impurity 20;
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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 (217.14 mM)
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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 | 2.1714 mL | 10.8571 mL | 21.7141 mL | |
| 5 mM | 0.4343 mL | 2.1714 mL | 4.3428 mL | |
| 10 mM | 0.2171 mL | 1.0857 mL | 2.1714 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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