| Size | Price | Stock | Qty |
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| Targets |
Precursorfor seltamivir acid; neuraminidase
Oseltamivir acid methyl ester is a prodrug that is converted to oseltamivir acid, the active pharmacological agent. Oseltamivir acid targets the neuraminidase enzyme of influenza A and B viruses. Neuraminidase is a surface glycoprotein that cleaves sialic acid residues, facilitating the release of newly formed viral particles from infected cells. By inhibiting neuraminidase, oseltamivir acid prevents the spread of the virus to other cells. The methyl ester prodrug form enhances oral bioavailability by improving absorption. |
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| ln Vitro |
In vitro, Oseltamivir acid methyl ester is a prodrug that is converted to the active oseltamivir acid by carboxylesterase 1 (CES1). The active oseltamivir acid inhibits influenza neuraminidase, blocking viral release and spread. The prodrug itself does not have direct antiviral activity but serves as a precursor to the active drug. It is used as a key intermediate in the synthesis of oseltamivir.
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| ln Vivo |
In vivo, Oseltamivir acid methyl ester is administered orally and is rapidly converted to oseltamivir acid by carboxylesterases in the liver and gastrointestinal tract. The active oseltamivir acid is distributed to the respiratory tract, where it inhibits influenza neuraminidase. Oseltamivir is clinically used for the treatment and prevention of influenza A and B virus infections. It is effective when administered within 48 hours of symptom onset.
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| Enzyme Assay |
In vitro assays for Oseltamivir acid methyl ester are not typically performed for antiviral activity, as the compound is a prodrug. The active oseltamivir acid is tested in neuraminidase inhibition assays. The prodrug can be assayed for its conversion to the active drug by CES1 using HPLC or LC-MS/MS. These assays measure the rate of hydrolysis and the formation of oseltamivir acid.
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| Cell Assay |
Cell-based assays for Oseltamivir acid methyl ester are not typically performed for antiviral activity, as the compound is a prodrug. The active oseltamivir acid is tested in virus-infected cells (e.g., MDCK cells infected with influenza virus). Viral replication is measured by plaque reduction assays or by quantifying viral RNA. The prodrug may be tested in cells expressing CES1 to assess its conversion and subsequent antiviral activity.
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| Animal Protocol |
In vivo animal experiments with Oseltamivir acid methyl ester are conducted in mouse models of influenza infection. The prodrug is administered orally, and its efficacy is assessed by measuring survival, weight loss, and viral titers in the lungs. These studies are used to evaluate the prodrug's in vivo conversion and antiviral activity. Oseltamivir is also studied in ferret models, which are more representative of human influenza.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of Oseltamivir acid methyl ester include good oral bioavailability, which is enhanced by the prodrug form. After oral administration, it is rapidly absorbed and converted to oseltamivir acid by CES1. The active oseltamivir acid has a half-life of approximately 6-10 hours and is excreted primarily in the urine. The compound has a molecular formula of C15H26N2O4 and a molecular weight of 298.38.
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| Toxicity/Toxicokinetics |
Safety and toxicology data for Oseltamivir acid methyl ester are derived from studies of oseltamivir. The prodrug is generally well-tolerated. Common adverse effects include nausea, vomiting, and headache. Rare but serious side effects include neuropsychiatric events. The compound is contraindicated in patients with hypersensitivity. It is pregnancy category C. Standard safety precautions apply.
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| References | |
| Additional Infomation |
Prodrug development is a common approach in drug development. In a recent study, we established a systematic strategy for screening prodrugs with higher membrane permeability or solubility based on log D value, solubility in simulated intestinal fluid, membrane permeability, and metabolic instability. This study aimed to evaluate the effectiveness of this strategy using oseltamivir and 23 analogues with different side chain types, as well as their active metabolite oseltamivir acid. The log D values of oseltamivir and its analogues (2.0 to 4.9) were all higher than those of oseltamivir acid (0.7), supporting previous strategies for developing oseltamivir to improve the permeability of oseltamivir acid. Except for the compound with the highest lipophilicity, the solubility of other analogues in simulated intestinal fluid all exceeded 80%. Membrane permeability was positively correlated with the log D value of the analogues. In metabolomic profiling, differences in hydrolysis efficiency were observed among different species, and these differences depended on the analogue. Using our strategy, we demonstrated that oseltamivir and some of its analogues are suitable prodrugs that, after selecting appropriate animals, can be advanced to in vivo pharmacokinetic studies. This study confirms the effectiveness of our strategy in narrowing down candidate compounds for in vivo studies. [1]
Oseltamivir acid methyl ester has CAS number 208720-71-2, molecular formula C15H26N2O4, and molecular weight 298.38. It is a prodrug form of oseltamivir acid, a neuraminidase inhibitor used for influenza treatment. It is converted to oseltamivir acid by CES1. Purity: typically ≥98%. Not for over-the-counter use; for prescription and research applications. |
| Molecular Formula |
C15H26N2O4
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|---|---|
| Molecular Weight |
298.37794
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| Exact Mass |
298.189
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| CAS # |
208720-71-2
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| PubChem CID |
11808666
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| Appearance |
Typically exists as solid at room temperature
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| LogP |
2.435
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
7
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| Heavy Atom Count |
21
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| Complexity |
405
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| Defined Atom Stereocenter Count |
3
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| SMILES |
CCC(CC)OC1C=C(CC(C1NC(=O)C)N)C(=O)OC
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| InChi Key |
HQFJHRGEFIDLDI-BFHYXJOUSA-N
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| InChi Code |
InChI=1S/C15H26N2O4/c1-5-11(6-2)21-13-8-10(15(19)20-4)7-12(16)14(13)17-9(3)18/h8,11-14H,5-7,16H2,1-4H3,(H,17,18)/t12-,13+,14+/m0/s1
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| Chemical Name |
methyl (3R,4R,5S)-4-acetamido-5-amino-3-pentan-3-yloxycyclohexene-1-carboxylate
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| Synonyms |
Oseltamivir Acid Methyl Ester; 208720-71-2; VA6M0DID7C; methyl (3R,4R,5S)-4-acetamido-5-amino-3-pentan-3-yloxycyclohexene-1-carboxylate; Methyl (3R,4R,5S)-4-acetamido-5-amino-3-(1-ethylpropoxy)cyclohex-1-ene-1-carboxylate; methyl (3R,4R,5S)-5-amino-4-acetamido-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate; 1-Cyclohexene-1-carboxylic acid, 4-(acetylamino)-5-amino-3-(1-ethylpropoxy)-, methyl ester, (3R,4R,5S)-; 1-Cyclohexene-1-carboxylic acid, 4-(acetylamino)-5-amino-3-(1-ethylpropoxy)-, methyl ester, (3R,4R,5S)-; Methyl (3R,4R,5S)-4-acetamido-5-amino-3-(1-ethylpropoxy)cyclohexene-1-carboxylate; Oseltamivir acid methyl ester; (3R,4R,5S)-4-Acetamido-5-amino-3-(1-ethylpropoxy)cyclohex-1-ene-1-carboxylic acid methyl ester;
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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) |
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
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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 | 3.3514 mL | 16.7572 mL | 33.5143 mL | |
| 5 mM | 0.6703 mL | 3.3514 mL | 6.7029 mL | |
| 10 mM | 0.3351 mL | 1.6757 mL | 3.3514 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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