Laninamivir

Base Information

• Chemical Name: Laninamivir
• CAS No.: 203120-17-6
• Deprecated CAS: 857906-77-5
• Molecular Formula: C₁₃H₂₂N₄O₇
• Molecular Weight: 346.34
• UNII: B408IW3GL5
• DSSTox Substance ID: DTXSID60942457
• Nikkaji Number: J1.767.223A
• Wikipedia: Laninamivir
• Wikidata: Q6487096
• NCI Thesaurus Code: C174629
• Metabolomics Workbench ID: 144542
• ChEMBL ID: CHEMBL466246
• Mol file: 203120-17-6.mol

Synonyms:5-(acetylamino)-4-((aminoiminomethyl)amino)-2,6-anhydro-3,4,5-trideoxy-7-O-methyl-D-glycero-D-galacto-non-2-enonic acid;laninamivir;laninamivir octanoate;laninamivir octanoate hydrate;laninamivir octanoate monohydrate;laninamivir trifluoroacetate;R 125489;R-125489;R125489

Chemical Property of Laninamivir

Chemical Property:

• Refractive Index: 1.633
• PKA: 3.81±0.70(Predicted)
• PSA: 190.71000
• Density: 1.61 g/cm³
• LogP: -0.89050
• Storage Temp.: -20°C Freezer
• Solubility.: Water (Slightly)
• XLogP3: -3.2
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 7
• Exact Mass: 346.14884905
• Heavy Atom Count: 24
• Complexity: 532

Purity/Quality:

99% ^*data from raw suppliers

Laninamivir ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC1C(C=C(OC1C(C(CO)O)OC)C(=O)O)N=C(N)N
• Isomeric SMILES: CC(=O)N[C@@H]1[C@H](C=C(O[C@H]1[C@@H]([C@@H](CO)O)OC)C(=O)O)N=C(N)N
• Recent NIPH Clinical Trials: The special drug use surveillance of INAVIR for inhalation suspension set (Safety evaluation in pediatric patients under five years old)
• Description: Laninamivir octanoate (CS-8958), an ester prodrug form of the neuraminidase (NA) inhibitor laninamivir (R-125489), was approved in Japan in 2010 for treatment of influenza virus infections. Laninamivir octanoate is given by intranasal administration at a 20 mg or 40 mg dose. It has a long half-life in humans such that efficacy can be achieved after only a single dose. In addition to vaccines for immunoprophylaxis, antiviral drugs play an essential role in the treatment of influenza virus infections. Two viral proteins have been targeted for therapeutic intervention: the M2 ion channel and NA.
• Uses: A new potent neuraminidase (NA) inhibitor, shows long-acting anti-influenza virus activity. A new potent labelled neuraminidase A new potent neuraminidase

Technology Process of Laninamivir

There total 24 articles about Laninamivir which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.0%

(2R,3R,4S)-3-acetamido-6-carboxy-2-((1R,2R)-2,3-dihydroxy-1-methoxypropyl)-3,4-dihydro-2H-pyran-4-aminium hydrochloride + 1H-pyrazole-1-carboximidamide hydrochloride (4023-02-3) → Laninamivir (203120-17-6)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 50 ℃; for 72h; Inert atmosphere;

DOI:10.1002/anie.201408138

Reference yield: 63.3%

methyl (4S,5R,6R)-5-acetamido-4-guanidino-6-[(S)-methoxy-((R)-2-oxo-[1,3]dioxolan-4-yl)-methyl]-5,6-dihydro-4H-pyran-2-carboxylate (1072449-92-3) → Laninamivir (203120-17-6)

Guidance literature:

With methanol; potassium carbonate; at 20 ℃; for 23h; Product distribution / selectivity;

Reference yield: 62.3%

(2R,3R,4S)-3-acetamide-4-[2,3-bis(tert-butoxycarbonyl)guanidino]-2-[(1R,2R)-2,3-dihydroxy-1-methoxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid → Laninamivir (203120-17-6)

Guidance literature:

With water; at 80 ℃; for 3.7h; Product distribution / selectivity;

upstream raw materials:

methyl (4S,5R,6R)-5-acetamido-4-amino-6-[(1S,2R)-2,3-diacetoxy-1-methoxy-propyl]-5,6-dihydro-4H-pyran-2-carboxylate

(4S,5R,6R,1'S,2'R)-5-acetylamino-4-azido-6-(2',3'-diacetoxy-1'-methoxy)propyl-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester

(4S,5R,6R,1'S,2'R)-5-acetylamino-4-(bis-N,N'-tert-butyloxycarbonyl)guanidino-6-(2',3'-diacetoxy-1'-methyloxy)propyl-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester

(2R,3R,4S)-3-acetamide-4-amino-2-[(1R,2R)-2,3-dihydroxy-1-methoxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid

Refernces

• 1、 -. "METHOD FOR PRODUCING NEURAMINIC ACID DERIVATIVE". Paragraph 0141. . Retrieved 2014/10/29.
• 2、 -. "DRUG FOR TREATMENT OF INFLUENZA". Page/Page column 9. . Retrieved 2009/12/07.