SML3534

Laninamivir octanoate

≥98% (HPLC)

• Synonym(s): 3-(O)-octanoyl R 125489, 3-(O)-octanoyl R-125489, 3-(O)-octanoyl R125489, 4S,5R,6R)-5-Acetamido-4-guanidino-6-((1R,2R)-2-hydroxy-1-methoxy-3-(octanoyloxy)propyl)-5,6-dihydro-4H-pyran-2-carboxylic acid, 5-(Acetylamino)-4-[(aminoiminomethyl)amino]-2,6-anhydro-3,4,5-trideoxy-7-O-methyl-D-glycero-D-galacto-non-2-enonic acid 9-octanoate, CS 8958, CS-8958, CS8958, LNO, Laninamivir prodrug
• Empirical Formula (Hill Notation): C₂₁H₃₆N₄O₈
• CAS Number: 203120-46-1
• Molecular Weight: 472.53
• MDL number: MFCD28138619
• UNSPSC Code: 12352200
• NACRES: NA.77

Properties

• Quality Level: 100
• Assay: ≥98% (HPLC)
• form: powder
• color: white to beige
• solubility: DMSO: 2 mg/mL, clear (Warmed)
• storage temp.: 2-8°C
• SMILES string: CCCCCCCC(OC[C@@H](O)[C@@H](OC)[C@@]1([H])[C@H](NC(C)=O)[C@@H](NC(N)=N)C=C(C(O)=O)O1)=O
• 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
• InChI key: UKTIJASCFRNWCB-RMIBSVFLSA-N

Description

Biochem/physiol Actions

Laninamivir (R-125489) prodrug with improved in vivo efficacy than R-125489 and Zanamivir in a mouse influenza virus A (IAV) infection model.

Laninamivir octanoate (CS-8958) is the prodrug form of Laninamivir (R-125489), a potent inhibitor agianst the neuraminidase (NA) activities of various type A and B influenza viruses, including subtypes N1 to N9 and Oseltamivir-resistant strains. When administered intranasally (3X 0.2 μmol/kg; 4 h before, 4 h & 18 h post infection), CS-8958 shows improved in vivo efficacy (100% survival rate on day 20 post infecfion) than R-125489 (100/30/20% survival rate on day 7/10/20 post infecfion) and Zanamivir (100%/0% death on day 7/10) in a mouse influenza virus A/Puerto Rico/8/34 infection model, with prolonged survival effect post a single dosage given even 7 days before infection. Note: Laninamivir octanoate is mainly used for in vivo studies, it exhibits only weak to little antiviral potency before it is converted to the active drug form.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable