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.

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)

Biological Activity

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.

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.