Peramivir

Base Information

• Chemical Name: Peramivir
• CAS No.: 330600-85-6
• Deprecated CAS: 229614-55-5
• Molecular Formula: C15H28N4O4
• Molecular Weight: 328.40722
• UNII: IDL9Q29886,9ZS94HQO3B
• DSSTox Substance ID: DTXSID10904727
• Nikkaji Number: J1.350.588H
• Wikipedia: Peramivir
• Wikidata: Q412734
• NCI Thesaurus Code: C175841
• RXCUI: 1598096
• Metabolomics Workbench ID: 144531
• ChEMBL ID: CHEMBL139367
• Mol file: 330600-85-6.mol

Synonyms:(1S,2S,3R,4R)-3-((1S)-1-acetamido-2-ethylbutyl)-4-((amino(imino)methyl)amino)-2-hydroxycyclopentanecarboxylic acid trihydrate;3-(1'-acetylamino-2'-ethyl)butyl-4-((aminoimino)methyl)amino-2-hydroxycyclopentane-1-carboxylic acid;BCX 1812;BCX-1812;BCX1812;peramivir;peramivir trihydrate;Rapivab;RWJ 270201;RWJ-270201;RWJ270201

Chemical Property of Peramivir

Chemical Property:

• Refractive Index: 1.613
• PKA: 4.08±0.70(Predicted)
• PSA: 151.03000
• Density: 1.39 g/cm³
• LogP: 1.44240
• Storage Temp.: 2-8°C
• Solubility.: Methanol (Slightly, Heated), Water (Slightly)
• XLogP3: 0
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 328.21105539
• Heavy Atom Count: 23
• Complexity: 460

Purity/Quality:

99% ^*data from raw suppliers

Peramivir ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antiviral Agents
• Canonical SMILES: CCC(CC)C(C1C(CC(C1O)C(=O)O)N=C(N)N)NC(=O)C
• Isomeric SMILES: CCC(CC)[C@@H]([C@H]1[C@@H](C[C@@H]([C@H]1O)C(=O)O)N=C(N)N)NC(=O)C
• Recent ClinicalTrials: Safety, PK and Effectiveness of IV Peramivir Versus Oseltamivir in Pediatric Subjects With Uncomplicated Influenza
• Recent EU Clinical Trials: A Phase 3, Multicenter, Randomized, Double-Blind, Controlled Study to Evaluate the Efficacy and Safety of Peramivir Administered Intravenously in Addition to Standard of Care Compared to Standard of Care Alone in Adults and Adolescents who are Hospitalized due to Serious Influenza.
• Recent NIPH Clinical Trials: Effect of peramivir on respiratory symptom improvement in patients with respiratory disease
• Description: Peramivir is a neuraminidase (NA) inhibitor that was approved in Japan in 2010 for treatment of patients with influenza. It is the only NA inhibitor available for IV use and is the first of two NA inhibitors approved in 2010, the second being the inhaled drug laninamivir octanoate . Peramivir is the only NA inhibitor approved for IV use,which gives it a unique place in influenza treatment for seriously ill patients. Peramivir was discovered using structure-based drug design and is synthesized in six steps from Boc-protected methyl (1S,4R)-4-amino-cyclopent-2-enecarboxylate, which is prepared from 2-azabicyclo[2.2.1]hept-5-en-3-one. Cycloaddition of the cyclopentene olefin with a nitrile oxide provided an intermediate fused cyclopentane-dihydroisoxazole. Hydrogenolysis and acetylation set up a fully functionalized cyclopentane with all four stereocenters established. Deprotection of the amine and acid groups was followed by installation of the guanidine moiety to provide peramivir. Like zanamivir and oseltamivir, peramivir is a potent inhibitor of influenza virus A and B NA [strain A(H1N1) IC50= 0.34 nM; strain A(H3N2) IC50= 0.60 nM; strain B IC50= 1.36 nM]. However, peramivir is less potent against oseltamivirresistant viruses that have the H275Y NA mutation. These viruses remain sensitive to zanamivir. Peramivir is active against influenza A and B viruses and has a lowenzymatic off-rate, suggesting that it could inhibitNAactivity for a prolonged period and allow lower frequency of dosing. Peramivir has proven efficacious in preclinical animal models of influenza infection. Peramivir is an inhibitor of influenza neuraminidase (IC50s = 0.09 and 11 nM for influenza A and B neuraminidases, respectively). It is selective for influenza neuraminidase over bacterial, mammalian, and other viral neuraminidases (IC50s = >300 μM). Peramivir inhibits neuraminidase activity in H1N1, H2N2, H3N2, and H6N2 influenza strains (IC50s = 0.09-1.1 nM) and reduces lysis of MDCK cells infected with influenza (EC50s = <0.01-21 nM). Pretreatment with peramivir (10-100 mg/kg) protects mice against lethal influenza infections. It also increases survival in ferrets infected intranasally with avian influenza type A H5N1 when injected intramuscularly after infection. Formulations containing peramivir have been used to treat influenza.
• Uses: A new antiviral agent for influenza treatment; it can be used as neuraminidase inhibitor for treating human and avian influenza.