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Details

Stereochemistry ABSOLUTE
Molecular Formula C15H28N4O4
Molecular Weight 328.4072
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PERAMIVIR ANHYDROUS

SMILES

[H][C@@]1([C@@H](NC(C)=O)C(CC)CC)[C@H](O)[C@H](C[C@H]1NC(N)=N)C(O)=O

InChI

InChIKey=XRQDFNLINLXZLB-CKIKVBCHSA-N
InChI=1S/C15H28N4O4/c1-4-8(5-2)12(18-7(3)20)11-10(19-15(16)17)6-9(13(11)21)14(22)23/h8-13,21H,4-6H2,1-3H3,(H,18,20)(H,22,23)(H4,16,17,19)/t9-,10+,11+,12-,13+/m0/s1

HIDE SMILES / InChI

Description

Peramivir is a transition-state analogue and a potent, specific influenza viral neuraminidase inhibitor. Rapivab (peramivir injection) is indicated for the treatment of acute uncomplicated influenza in patients 18 years and older who have been symptomatic for no more than 2 days. Efficacy of Rapivab is based on clinical trials in which the predominant influenza virus type was influenza A and a limited number of subjects infected with influenza B virus were enrolled. Since influenza viruses change over time emergence of resistance substitutions could decrease drug effectiveness. Other factors such as changes in viral virulence might also diminish clinical benefit of antiviral drug. Efficacy could not be established in patients with serious influenza requiring hospitalization.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
0.08 nM [IC50]
0.22 nM [EC50]
0.045 nM [EC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
RAPIVAB

Cmax

ValueDoseCo-administeredAnalytePopulation
46800 ng/mL
600 mg single, intravenous
PERAMIVIR ANHYDROUS serum
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
102700 ng × h/mL
600 mg single, intravenous
PERAMIVIR ANHYDROUS serum
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
20 h
600 mg single, intravenous
PERAMIVIR ANHYDROUS serum
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
70%
600 mg single, intravenous
PERAMIVIR ANHYDROUS serum
Homo sapiens

Doses

AEs

PubMed

Sample Use Guides

In Vivo Use Guide
The recommended dose of RAPIVAB in adult patients 18 years of age or older with acute uncomplicated influenza is a single 600 mg dose, administered via intravenous infusion for 15 to 30 minutes. The dose should be reduced for patients with baseline creatinine clearance below 50 mL/min to 200 mg dose (at 30-49 mL/min creatinine clearance), and 100 mg dose (at 10-29 mL/min creatinine clearance).
Route of Administration: Intravenous
In Vitro Use Guide
The concentrations of peramivir required for inhibition of influenza virus in cell culture varied with the virus strain tested. The effect of antiviral compounds on the replication of influenza viruses in MDCK cells was determined by flow cytometric analysis of virus-infected cells. The mean 50% effective concentrations (EC50 values) of peramivir were in the range of 0.045-0.071 nM), 0.065-0.07 nM and 0.215-33.58 nM for influenza A/H1N1 virus, A/H3N2 virus, and B virus strains, respectively.