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| Targets |
Laninamivir Octanoate targets the influenza virus neuraminidase (NA) enzyme. Neuraminidase is a surface glycoprotein that plays a critical role in the viral life cycle by cleaving sialic acid residues, facilitating the release of newly formed virions from infected host cells and preventing viral aggregation. As a prodrug, Laninamivir Octanoate itself is inactive and requires conversion to its active metabolite, laninamivir, which is a potent and selective inhibitor of both influenza A and B neuraminidases. By inhibiting this enzyme, the active metabolite prevents the release and spread of the virus, thereby limiting infection.
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| ln Vitro |
Laninamivir Octanoate (CS-8958) demonstrates inhibitory action against the H1N1 strain, H3N2 strain and H2N2 (A/Singapore/1/57) virus with IC50 of 631-1170 nM, 39.2-221 nM and 128 nM respectively. [1].
In vitro, Laninamivir Octanoate is a potent inhibitor of influenza neuraminidase. The active metabolite, laninamivir, demonstrates significant inhibitory activity against various influenza strains. It inhibits avian H12N5 NA (N5), pH1N1 N1 NA (p09N1), and A/RI/5+/1957 H2N2 N2 (p57N2) with IC₅₀ values of 0.90 nM, 1.83 nM, and 3.12 nM, respectively. Against the H1N1, H3N2, and H2N2 (A/Singapore/1/57) viruses, the prodrug itself shows IC₅₀ values of 631-1170 nM, 39.2-221 nM, and 128 nM, respectively. These data confirm its potent and broad-spectrum in vitro antiviral activity. |
| ln Vivo |
Infection models demonstrated notable life-prolonging benefits when lanamivir octanoate (CS-8958; 95 μg/kg; intranasally; 3 doses; 4 hours before infection, 4 hours, and 17 hours after infection) was administered [1].
In vivo, Laninamivir Octanoate has demonstrated notable efficacy in influenza infection models. In a study on female BALB/c mice infected with influenza A virus A/PR/8/34, intranasal administration of 0.2 μmol/kg (95 μg/kg) of the compound, given in three doses (4 hours before infection, and 4 and 17 hours after infection), resulted in significant life-prolonging benefits. Its long-acting nature is a key feature, as a single inhaled dose provides a complete treatment course, distinguishing it from other neuraminidase inhibitors that require more frequent dosing. |
| Enzyme Assay |
Non-cell-based in vitro assays for Laninamivir Octanoate typically involve neuraminidase inhibition assays. In these assays, the compound (or its active metabolite) is incubated with the neuraminidase enzyme from various influenza strains. The enzymatic activity is measured using a fluorogenic substrate, and the concentration required to inhibit 50% of the enzyme activity (IC₅₀) is determined. These assays are essential for characterizing the compound's potency against different viral strains and for monitoring resistance.
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| Cell Assay |
Cellular assays are used to assess the antiviral activity of Laninamivir Octanoate in infected cell cultures. In these assays, cells are infected with influenza virus and treated with varying concentrations of the compound. Viral replication is then quantified by measuring the viral titer, plaque formation, or the expression of viral proteins. The half-maximal effective concentration (EC₅₀) is determined, providing a measure of the compound's antiviral efficacy in a cellular context.
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| Animal Protocol |
Animal/Disease Models: Female balb/c (Bagg ALBino) mouse (5-6 weeks old) infected with influenza A virus A/PR/8/34 [1]
Doses: 0.2 μmol/kg (95 μg/kg) Route of Administration: intranasal Administration; Three doses; 4 hrs (hrs (hours)) before infection, 4 hrs (hrs (hours)) and 17 hrs (hrs (hours)) after infection Experimental Results: demonstrated life-prolonging effect in infection model. In vivo animal models for Laninamivir Octanoate typically involve influenza virus infection in mice, such as the female BALB/c model infected with A/PR/8/34 virus. The compound is administered intranasally, and its efficacy is assessed by measuring survival rates, body weight changes, and lung viral titers. These studies are critical for evaluating the compound's in vivo efficacy, pharmacokinetics, and optimal dosing regimens. The prolonged retention of the active metabolite in the lungs is a key endpoint in these studies. |
| ADME/Pharmacokinetics |
Laninamivir Octanoate has a molecular weight of 472.53 g/mol and a molecular formula of C₂₁H₃₆N₄O₈. It is a solid powder soluble in DMSO. The compound is administered via inhalation as a dry powder formulation (Inavir®). Following a single inhaled dose, only about 15% of the drug is systemically absorbed, with the majority retained in the lungs. The active metabolite, laninamivir, persists in the epithelial lining fluid at concentrations exceeding viral NA IC₅₀ values for at least 240 hours (10 days) post-dose.
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| Toxicity/Toxicokinetics |
Laninamivir Octanoate is generally well-tolerated. Common adverse effects associated with its use as an inhaled antiviral are typically mild and may include bronchospasm, cough, or gastrointestinal symptoms. It is approved for clinical use in Japan. The compound is intended for research use in non-clinical settings. As with all research chemicals, standard safety precautions should be followed.
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| References |
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| Additional Infomation |
Laninamivir octanoate hydrate is a fatty acid ester. Laninamivir octanoate has been used in clinical trials for the treatment of asthma. See also: Laninamivir octanoate monohydrate (note moved to).
Laninamivir Octanoate is also known as CS-8958, Inavir, and R-125489. It is a novel, long-acting prodrug of the neuraminidase inhibitor laninamivir, approved in Japan since 2010 for the treatment and prophylaxis of influenza. Its defining pharmacological feature is its prolonged intrapulmonary retention, allowing for a single-dose treatment regimen. It has also been used in clinical trials for the treatment of asthma. Its CAS number is 203120-46-1. |
| Molecular Formula |
C21H36N4O8
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| Molecular Weight |
472.5325
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| Exact Mass |
472.253
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| Elemental Analysis |
C, 53.38; H, 7.68; N, 11.86; O, 27.09
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| CAS # |
203120-46-1
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| Related CAS # |
Laninamivir;203120-17-6;Laninamivir octanoate hydrate;1233643-88-3
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| PubChem CID |
9847629
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| Appearance |
White to off-white solid powder
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| Density |
1.4±0.1 g/cm3
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| Index of Refraction |
1.572
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| LogP |
1.54
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| Hydrogen Bond Donor Count |
5
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| Hydrogen Bond Acceptor Count |
9
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| Rotatable Bond Count |
15
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| Heavy Atom Count |
33
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| Complexity |
723
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| Defined Atom Stereocenter Count |
5
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| SMILES |
O1C(C(=O)O[H])=C([H])[C@@]([H])([C@]([H])([C@]1([H])[C@@]([H])([C@@]([H])(C([H])([H])OC(C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])=O)O[H])OC([H])([H])[H])N([H])C(C([H])([H])[H])=O)/N=C(\N([H])[H])/N([H])[H]
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| InChi Key |
UKTIJASCFRNWCB-RMIBSVFLSA-N
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| InChi Code |
InChI=1S/C21H36N4O8/c1-4-5-6-7-8-9-16(28)32-11-14(27)18(31-3)19-17(24-12(2)26)13(25-21(22)23)10-15(33-19)20(29)30/h10,13-14,17-19,27H,4-9,11H2,1-3H3,(H,24,26)(H,29,30)(H4,22,23,25)/t13-,14+,17+,18+,19+/m0/s1
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| Chemical Name |
(2R,3R,4S)-3-acetamido-4-(diaminomethylideneamino)-2-[(1R,2R)-2-hydroxy-1-methoxy-3-octanoyloxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid
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| Synonyms |
Laninamivir Octanoate; CS-8958; CS 8958; CS8958; R-125489; R 125489; R125489;
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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 (~211.63 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (5.29 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in 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 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (5.29 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (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 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.1163 mL | 10.5813 mL | 21.1627 mL | |
| 5 mM | 0.4233 mL | 2.1163 mL | 4.2325 mL | |
| 10 mM | 0.2116 mL | 1.0581 mL | 2.1163 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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