Laninamivir (Inavir, CS8958, R125489)

Alias: CS8958; CS-8958; CS 8958;R-125489; R 125489; R125489;

Cat No.:V5767 Purity: ≥98%

COA Product Data Instructions for use SDS

Laninamivir (Inavir, CS-8958,R-125489) is a novel and potent neuraminidase inhibitor with antiviral activities.

Laninamivir (Inavir, CS8958, R125489) Chemical Structure CAS No.: 203120-17-6
Product category: Influenza Virus

This product is for research use only, not for human use. We do not sell to patients.

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1-708-310-1919 sales@invivochem.com

Other Forms of Laninamivir (Inavir, CS8958, R125489):

Official Supplier of:

Top Publications Citing lnvivochem Products

Nature 2021, 597(7874):119-125.

Cell 2020,183:1202-1218.e25.

Science Adv 2022: 8, eabm9427.

Nature 597, 119–125 (2021)

Cell Stem Cell 2020,26(6):845-861.e12.

Science Trans Med 2023,15(701):eadd7872.

STTT 2023,8(1):91.

Cell Reports 2023,42(4):112313

Science Trans Med 2023, 15: eadd7872.

Cancer Cell 2021,39(4):529-547.e7.

Cancer Discov 2022,12(4):1106-1127.

Immunity 2023,56(3):620-634.e11.

J Am Chem Soc 2022,144:21831-21836.

Cell 2020,183:1202-1218.e25.

Science Adv 2022:8,eabm9427.

Nature 2021,597(7874):119-125.

Cell 2020,183:1202-1218.e25.

PNAS Nexus 2022,1(3):pgac063.

ACS Nano 2023,17(10):9110-9125.

Biomaterial 2023 Sep16:302:122333.

Purity & Quality Control Documentation

Current batch：

Purity: ≥98%

COA

MSDS

Instructions

Product Description
Bioactivity & Protocols
Physicochemical Properties
Solubility Data
Calculators
Clinical Trial Information
Biological Data

Product Description

Laninamivir (Inavir, CS-8958, R-125489) is a novel and potent neuraminidase inhibitor with antiviral activities. It inhibits avian H12N5 NA (N5), pH1N1 N1 NA (p09N1) and A/RI/5+/1957 H2N2 N2 (p57N2) strains with IC50s of 0.90 nM, 1.83 nM and 3.12 nM, respectively. Laninamivir exhibits clinical efficacy for both treatment and prophylaxis of influenza virus infection, resulting from hydrolytic bioactivation into its pharmacologically active metabolite laninamivir in the pulmonary tissue.

Biological Activity I Assay Protocols (From Reference)

Targets	N5(IC50= 0.90 nM);p09N1(IC50= 1.83 nM);p57N2(IC50= 3.12 nM)
ln Vitro	Common oseltamivir-resistant viruses, including those with the common His274Tyr substitution, are effectively inhibited by laninamivir (R 125489)[1]. Like Zanamivir, laninamivir (R 125489) has a similar binding mechanism and is effective against p57N2, p09N1, and N5[1].
References	[1]. Structural and functional analysis of laninamivir and its octanoate prodrug reveals group specific mechanisms for influenza NA inhibition. PLoS Pathog. 2011 Oct;7(10):e1002249.
Additional Infomation	Laninamivir is a member of acetamides. Laninamivir has been used in trials studying the treatment of Influenza.

These protocols are for reference only. InvivoChem does not independently validate these methods.

Physicochemical Properties

Molecular Formula	C13H22N4O6
Molecular Weight	346.33638
Exact Mass	346.148
Elemental Analysis	C, 45.08; H, 6.40; N, 16.18; O, 32.34
CAS #	203120-17-6
Related CAS #	Laninamivir octanoate;203120-46-1;Laninamivir octanoate hydrate;1233643-88-3
PubChem CID	502272
Appearance	White to off-white solid powder
Density	1.6±0.1 g/cm3
Index of Refraction	1.634
LogP	-3.06
Hydrogen Bond Donor Count	6
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	7
Heavy Atom Count	24
Complexity	532
Defined Atom Stereocenter Count	5
SMILES	CC(N[C@@H]1[C@@H](NC(N)=N)C=C(O[C@H]1[C@H](OC)[C@H](O)CO)C(O)=O)=O
InChi Key	LANWZBLPTYVJPY-PKIKSRDPSA-N
InChi Code	InChI=1S/C13H22N4O6/c1-6(19)16-11-8(17-13(14)15)4-10(12(20)21)23-9(11)3-7(5-18)22-2/h4,7-9,11,18H,3,5H2,1-2H3,(H,16,19)(H,20,21)(H4,14,15,17)/t7-,8+,9-,11-/m1/s1
Chemical Name	(2R,3R,4S)-3-acetamido-4-guanidino-2-((R)-3-hydroxy-2-methoxypropyl)-3,4-dihydro-2H-pyran-6-carboxylic acid
Synonyms	CS8958; CS-8958; CS 8958;R-125489; R 125489; R125489;
HS Tariff Code	2934.99.03.00
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 Data

Solubility (In Vitro)	H2O : ~5 mg/mL (~14.44 mM )
Solubility (In Vivo)	Solubility in Formulation 1: 3.12 mg/mL (9.01 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication (<60°C). (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	2.8873 mL	14.4367 mL	28.8734 mL
	5 mM	0.5775 mL	2.8873 mL	5.7747 mL
	10 mM	0.2887 mL	1.4437 mL	2.8873 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.

Calculator

Mass

Concentration

Volume

Molecular Weight*

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

Calculate the Mass of a compound required to prepare a solution of known volume and concentration
Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume

See Example

An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?

Enter 350.26 in the Molecular Weight (MW) box
Enter 10 in the Concentration box and choose the correct unit (mM)
Enter 5 in the Volume box and choose the correct unit (mL)
Click the “Calculate” button
The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Concentration (Start)

Volume (Start)

Concentration (End)

Volume (End)

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:

Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
Enter 25 into the Concentration (End) box and select the correct unit (mM)
Enter 25 into the Volume (End) box and choose the correct unit (mL)
Click the “Calculate” button
The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box

Molecular formula

Total molecular weight

g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4 c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:

To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.

Definitions of molecular mass, molecular weight, molar mass and molar weight:

Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.

Volume (to add to vial)

Mass (in vial)

Desired Reconstitution Concentration

Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
Click the “Calculate” button
The answer appears in the Volume (to add to vial) box

In vivo Formulation Calculator (Clear solution)

Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)

Dosage mg/kg

Average weight of animals g

Dosing volume per animal μL

Number of animals

Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)

% DMSO

% Tween 80

% ddH₂O

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.

Note： (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.

Clinical Trial Information

NCT Number	Recruitment	interventions	Conditions	Sponsor/Collaborators	Start Date	Phases
NCT02022761	COMPLETED	Drug: Laninamivir octanoate	Asthma	Biota Scientific Management Pty Ltd	2013-10	Phase 1
NCT01793883	COMPLETEDWITH RESULTS	Drug: 40 mg Laninamivir Octanoate Drug: 80 mg Laninamivir Octanoate Drug: Placebo	Influenza	Biota Scientific Management Pty Ltd	2013-05	Phase 2
NCT02014649	TERMINATED	Drug: 20 mg laninamivir octanoate Drug: Placebo Drug: 40 mg laninamivir octanoate	Influenza	Biota Scientific Management Pty Ltd	2013-11	Phase 1 Phase 2
NCT00995826	COMPLETED	Drug: CS-8958 Other: Placebo	Influenza	Biota Scientific Management Pty Ltd	2009-04	Phase 1
NCT05648448	RECRUITING	Drug: Oseltamivir Drug: Zanamivir	Influenza Influenza, Human	University of Oxford	2023-02-22	Phase 2

Biological Data

The chemical structures of influenza NA inhibitors used in this study. 1, Neu5Ac2en (NA transition state analogue); 2, zanamivir; 3, laninamivir; 4, laninamivir octanoate (CS-8958); and 5, oseltamivir.Structural and functional analysis of laninamivir and its octanoate prodrug reveals group specific mechanisms for influenza NA inhibition. PLoS Pathog. 2011 Oct;7(10):e1002249.

Comparison of the active sites of p57N2, p09N1 and N5. Group 2 p57N2 has a 150-cavity deficient active site with a salt bridge between Asp147 and His150 which stabilizes the closed conformation of its 150-loop (upper left - green). p09N1 is an atypical group 1 structure and also has a 150-cavity deficient active site similar to many group 2 structures (upper right - magenta). N5 is a typical group 1 NA and displays a 150-cavity in its uncomplexed structure (lower left - yellow) that closes upon inhibitor binding (lower right - yellow: N5-laninamivir complex).Structural and functional analysis of laninamivir and its octanoate prodrug reveals group specific mechanisms for influenza NA inhibition. PLoS Pathog. 2011 Oct;7(10):e1002249.

Binding of laninamivir and zanamivir to p57N2, p09N1 and N5. In each panel, zanamivir appears as the same color as the respective NA active site and laninamivir appears as turquoise. Acidic and basic side chains of key residues are colored red and blue, respectively. The 4-guanidino group of laninamivir and zanamivir is buried deep beneath the 150-loop where it engages many key interactions with NA residues (Table 2). Although the binding modes of laninamivir and zanamivir are highly similar, the accessibility of the 4-guanidino to its binding site is lowest in p57N2, with a 147–150 salt bridge in its closed 150-loop (A - green) and highest in group 1 N5, which contains a 150-cavity in its uncomplexed structure (C - yellow). Inhibition by zanamivir and laninamivir are highest for N5, and lowest for p57N2. p09N1, with its unique 150-loop characteristics (B - magenta), has intermediate laninamivir inhibition.Structural and functional analysis of laninamivir and its octanoate prodrug reveals group specific mechanisms for influenza NA inhibition. PLoS Pathog. 2011 Oct;7(10):e1002249.