| Size | Price | Stock | Qty |
|---|---|---|---|
| 5mg |
|
||
| 25mg |
|
| Targets |
Levolansoprazole targets the H+/K+-stimulated ATPase enzyme system, commonly known as the gastric proton pump, located in the parietal cells of the stomach. This enzyme is the final common step in the pathway of gastric acid secretion. Levolansoprazole binds irreversibly to the proton pump, forming a covalent disulfide bond with cysteine residues on the enzyme. This irreversible inhibition results in a prolonged suppression of gastric acid production that lasts beyond the compound's presence in the plasma. The compound's mechanism is specific to the parietal cell proton pump, making it a highly effective anti-secretory agent.
|
|---|---|
| ln Vitro |
IC50 of 0.76 μM indicates that lansoprazole suppresses the generation of stomach acid in a concentration-dependent manner around 0.3 to 3 μM [4]. Concentration-dependent, reversible, and repeatable arterial ischemia is caused by lansoprazole (30–300 μM) fatigue [5].
Levolansoprazole demonstrates potent in vitro activity by irreversibly inhibiting H+/K+-stimulated ATPase pumps in parietal cells, with an IC50 of 5.2 μM. It also inhibits acid formation in isolated canine parietal cells with an IC50 of 82 μM. This in vitro activity confirms its direct inhibition of the gastric proton pump. Furthermore, levolansoprazole has been shown to inhibit SARS-CoV-2-induced cytotoxicity in various cell lines, suggesting additional, non-PPI related activities that may be of interest for antiviral research. |
| ln Vivo |
Treatment with lansoprazole (20–40 mg/kg) has been shown to dramatically lessen memory impairments as well as biochemical and histological alterations brought on by STZ and HFD [3]. AChE activity increases caused by STZ and HFD were considerably attenuated by lansoprazole (20 mg/kg and 40 mg/kg, next door) [3]. The increase in brain MPO levels brought on both STZ and HFD can be considerably reduced by lansoprazole (20 mg/kg and 40 mg/kg, facial) [3]. In addition, compared to control animals, HFD mice treated with lansoprazole (20 mg/kg and 40 mg/kg, face) exhibited a substantial drop in body weight [3].
Levolansoprazole is an orally active proton pump inhibitor used in vivo to prevent the stomach from producing acid. By irreversibly inhibiting the gastric proton pump, it effectively reduces basal and stimulated gastric acid secretion. Its in vivo activity is well-established in the treatment of acid-related disorders such as gastroesophageal reflux disease (GERD) and peptic ulcers. The (S)-enantiomer is expected to provide the therapeutic benefits of lansoprazole with potentially different pharmacokinetic or pharmacodynamic properties. |
| Enzyme Assay |
In vitro enzyme assays for levolansoprazole typically involve the measurement of H+/K+-ATPase activity in gastric membrane preparations. The enzyme is incubated with ATP and a proton gradient-generating system. Levolansoprazole is added at various concentrations, and the release of inorganic phosphate from ATP hydrolysis is measured colorimetrically or using a coupled enzyme assay. The compound's ability to inhibit the ATPase activity is quantified, and an IC50 value is determined from a dose-response curve.
|
| Cell Assay |
In vitro cellular assays for levolansoprazole are performed using isolated canine parietal cells, a well-established model for studying gastric acid secretion. The cells are cultured and treated with levolansoprazole at various concentrations. Acid formation is stimulated with a secretagogue such as histamine, and the acid production is measured by the accumulation of the weak base 14C-aminopyrine. The compound's ability to inhibit acid formation is quantified, and an IC50 value is determined.
|
| Animal Protocol |
In vivo animal models for PPIs like levolansoprazole typically involve the use of rats or dogs. Animals are administered the compound orally, and gastric acid secretion is stimulated. The gastric contents are collected and titrated to measure acid output. The compound's efficacy is determined by its ability to reduce acid secretion compared to a control group. These studies are used to establish the in vivo potency, duration of action, and dose-response relationship of the compound.
|
| ADME/Pharmacokinetics |
Levolansoprazole has a molecular weight of 369.362 g/mol and a molecular formula of C16H14F3N3O2S. It is an orally active compound that is well-absorbed from the gastrointestinal tract. As a PPI, it is a prodrug that requires an acidic environment to be converted to its active form, which then binds covalently to the proton pump. The compound is soluble in DMSO and has a purity of ≥95%. It is typically stored in a dry, dark place at room temperature for short-term storage and at -20°C for long-term storage.
|
| Toxicity/Toxicokinetics |
As a proton pump inhibitor, levolansoprazole is generally well-tolerated. However, like other PPIs, long-term use may be associated with an increased risk of certain adverse effects, including vitamin B12 deficiency, osteoporosis-related fractures, and an increased risk of gastrointestinal infections. The compound is intended for research use only and is not for human consumption. Detailed toxicological data are not provided in the search results.
|
| References |
|
| Additional Infomation |
See also: Lansoprazole (note moved to).
Levolansoprazole is the (S)-enantiomer of lansoprazole, which is an orally active proton pump inhibitor. It is a proton pump inhibitor that irreversibly inhibits H+/K+-stimulated ATPase pumps in parietal cells. The compound has also shown activity against SARS-CoV-2-induced cytotoxicity, hinting at broader biological activities. It is also known as S-Lansoprazole and is used for research purposes to study gastric acid secretion and the pharmacology of PPIs. |
| Molecular Formula |
C16H14F3N3O2S
|
|---|---|
| Molecular Weight |
369.36
|
| Exact Mass |
369.075
|
| CAS # |
138530-95-7
|
| Related CAS # |
Lansoprazole;103577-45-3;(R)-Lansoprazole;138530-94-6;Lansoprazole-d4;934294-22-1
|
| PubChem CID |
9578006
|
| Appearance |
Off-white to light yellow solid powder
|
| Density |
1.5±0.1 g/cm3
|
| Boiling Point |
555.8±60.0 °C at 760 mmHg
|
| Flash Point |
289.9±32.9 °C
|
| Vapour Pressure |
0.0±1.5 mmHg at 25°C
|
| Index of Refraction |
1.635
|
| LogP |
2.76
|
| Hydrogen Bond Donor Count |
1
|
| Hydrogen Bond Acceptor Count |
8
|
| Rotatable Bond Count |
5
|
| Heavy Atom Count |
25
|
| Complexity |
480
|
| Defined Atom Stereocenter Count |
1
|
| SMILES |
CC1=C(C=CN=C1C[S@](=O)C2=NC3=CC=CC=C3N2)OCC(F)(F)F
|
| InChi Key |
MJIHNNLFOKEZEW-VWLOTQADSA-N
|
| InChi Code |
InChI=1S/C16H14F3N3O2S/c1-10-13(20-7-6-14(10)24-9-16(17,18)19)8-25(23)15-21-11-4-2-3-5-12(11)22-15/h2-7H,8-9H2,1H3,(H,21,22)/t25-/m0/s1
|
| Chemical Name |
2-[(S)-[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methylsulfinyl]-1H-benzimidazole
|
| Synonyms |
(-)-Lansoprazole (S)-Lansoprazole Levolansoprazole
|
| HS Tariff Code |
2934.99.9001
|
| 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)
|
| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
|
|---|---|
| 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 | 2.7074 mL | 13.5369 mL | 27.0739 mL | |
| 5 mM | 0.5415 mL | 2.7074 mL | 5.4148 mL | |
| 10 mM | 0.2707 mL | 1.3537 mL | 2.7074 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.
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
