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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

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

CNS Activity

Approval Year

PMID

PMID

TitleDatePMID
BCX-1812 (RWJ-270201): discovery of a novel, highly potent, orally active, and selective influenza neuraminidase inhibitor through structure-based drug design.
2000 Sep 21
Comparison of the anti-influenza virus activity of RWJ-270201 with those of oseltamivir and zanamivir.
2001 Apr
Comparison of the activities of zanamivir, oseltamivir, and RWJ-270201 against clinical isolates of influenza virus and neuraminidase inhibitor-resistant variants.
2001 Dec
Characterization of an influenza A (H3N2) virus resistant to the cyclopentane neuraminidase inhibitor RWJ-270201.
2001 Dec
Systematic structure-based design and stereoselective synthesis of novel multisubstituted cyclopentane derivatives with potent antiinfluenza activity.
2001 Dec 6
Primary immune system effects of the orally administered cyclopentane neuraminidase inhibitor RWJ-270201 in influenza virus-infected mice.
2001 Jun
In vivo influenza virus-inhibitory effects of the cyclopentane neuraminidase inhibitor RJW-270201.
2001 Mar
Cyclopentane neuraminidase inhibitors with potent in vitro anti-influenza virus activities.
2001 Mar
Comparison of efficacies of RWJ-270201, zanamivir, and oseltamivir against H5N1, H9N2, and other avian influenza viruses.
2001 Oct
Influence of virus strain, challenge dose, and time of therapy initiation on the in vivo influenza inhibitory effects of RWJ-270201.
2001 Sep
In vitro characterization of A-315675, a highly potent inhibitor of A and B strain influenza virus neuraminidases and influenza virus replication.
2002 Apr
Peramivir (BCX-1812, RWJ-270201): potential new therapy for influenza.
2002 Jun
Combination treatment of influenza A virus infections in cell culture and in mice with the cyclopentane neuraminidase inhibitor RWJ-270201 and ribavirin.
2002 May
Structural studies of the resistance of influenza virus neuramindase to inhibitors.
2002 May 23
Comparison of colorimetric, fluorometric, and visual methods for determining anti-influenza (H1N1 and H3N2) virus activities and toxicities of compounds.
2002 Oct
Inhibition of influenza virus infections in immunosuppressed mice with orally administered peramivir (BCX-1812).
2003 Sep
A QSAR study on influenza neuraminidase inhibitors.
2006 Feb 15
Patent

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.
Name Type Language
PERAMIVIR ANHYDROUS
Common Name English
RWJ-270201
Code English
(1S,2S,3R,4R)-3-((1S)-1-ACETYLAMINO-2-ETHYLBUTYL)-4-((AMINOIMINOMETHYL)AMINO)-2-HYDROXYCYCLOPENTANECARBOXYLIC ACID
Systematic Name English
PERAMIVIR [INN]
Common Name English
PERAMIVIR [MI]
Common Name English
Code System Code Type Description
EVMPD
SUB32136
Created by admin on Tue Mar 06 10:58:12 UTC 2018 , Edited by admin on Tue Mar 06 10:58:12 UTC 2018
PRIMARY
LactMed
330600-85-6
Created by admin on Tue Mar 06 10:58:12 UTC 2018 , Edited by admin on Tue Mar 06 10:58:12 UTC 2018
PRIMARY
PUBCHEM
154234
Created by admin on Tue Mar 06 10:58:12 UTC 2018 , Edited by admin on Tue Mar 06 10:58:12 UTC 2018
PRIMARY SWITZERF
CAS
330600-85-6
Created by admin on Tue Mar 06 10:58:12 UTC 2018 , Edited by admin on Tue Mar 06 10:58:12 UTC 2018
PRIMARY
MERCK INDEX
M8534
Created by admin on Tue Mar 06 10:58:12 UTC 2018 , Edited by admin on Tue Mar 06 10:58:12 UTC 2018
PRIMARY Merck Index
INN
8184
Created by admin on Tue Mar 06 10:58:12 UTC 2018 , Edited by admin on Tue Mar 06 10:58:12 UTC 2018
PRIMARY
WIKIPEDIA
PERAMIVIR
Created by admin on Tue Mar 06 10:58:12 UTC 2018 , Edited by admin on Tue Mar 06 10:58:12 UTC 2018
PRIMARY
RXCUI
1598096
Created by admin on Tue Mar 06 10:58:12 UTC 2018 , Edited by admin on Tue Mar 06 10:58:12 UTC 2018
PRIMARY RxNorm