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Peramivir

Peramivir structure

CAS No:
330600-85-6
Formula:
C15H28N4O4
Chemical Name:
Peramivir
Synonyms:
Cyclopentanecarboxylic acid,3-[(1S)-1-(acetylamino)-2-ethylbutyl]-4-[(aminoiminomethyl)amino]-2-hydroxy-,(1S,2S,3R,4R)-;(1S,2S,3R,4R)-3-[(1S)-1-(Acetylamino)-2-ethylbutyl]-4-[(aminoiminomethyl)amino]-2-hydroxycyclopentanecarboxylic acid;RWJ 270201;BCX 1812;Peramivir;Rapiacta;(1S,2S,3R,4R)-3-((1S)-1-Acetamido-2-ethylbutyl)-4-(diaminomethylideneamino)-2-hydroxycyclopentane-1-carboxylic acid;(1S,2S,3S,4R)-3-((1S)-1-Acetamido-2-ethylbutyl)-4-(diaminomethylideneamino)-2-hydroxycyclopentane-1-carboxylic acid;Rapivab;Alpivab;229614-55-5
Categories:
Pharmaceutical Intermediates > Bulk Drug Intermediates

Description

Peramivir is a member of the class of guanidines that is used (as its trihydrate) for the treatment of acute uncomplicated influenza in patients 18 years and older who have been symptomatic for no more than two days. It has a role as an antiviral drug and an EC 3.2.1.18 (exo-alpha-sialidase) inhibitor. It is a member of cyclopentanols, a member of acetamides, a member of guanidines and a 3-hydroxy monocarboxylic acid. It contains a peramivir hydrate.|Peramivir is an antiviral agent developed by Biocryst Pharmaceuticals to treat influenza A/B. The development of peramivir has been supported by the US Department of Health and Human Services as part of the government's effort to prepare for a flu pandemic. Being an influenza virus neuraminidase inhibitor, peramivir works by preventing new viruses from emerging from infected cells. Due to the poor oral bioavailability, the oral formulation of the drug was previously abandoned by Johnson and Johnson Company. The injectable intravenous formulation of peramivir was approved by the FDA in September 2017 for the treatment of acute uncomplicated influenza to pediatric patients 2 years and older who have been symptomatic for no more than two days.|Peramivir is an inhibitor of the influenza neuraminidase enzyme and is used as therapy of acute symptomatic influenza A and B. Peramivir has not been associated with serum enzyme elevations during therapy or with clinically apparent liver injury.

Peramivir Basic Attributes

Molecular Weight：

328.41 g/mol

Exact Mass：

328.41

UNII：

9ZS94HQO3B

DSSTox ID：

DTXSID60146317

ATC Code：

J05AH03|J - Antiinfectives for systemic use

Characteristics

PSA：

151 Å²

Toxicity

Hepatotoxicity：

Despite widespread use, there is little evidence that peramivir, when given as recommended as a single intravenous infusion, is associated with liver injury, either in the form of serum enzyme elevations or clinically apparent liver disease. A proportion of patients with influenza may have minor serum enzyme elevations during the acute illness, but these appear to be independent of therapy and are not exacerbated by peramivir.

Drug Information

Drug Indication：

Indicated for the treatment of acute uncomplicated influenza in patients 18 years and older who have been symptomatic for no more than two days.|FDA Label|Alpivab is indicated for the treatment of uncomplicated influenza in adults and children from the age of 2 years.|Treatment of influenza

LiverTox Summary：

Peramivir is an inhibitor of the influenza neuraminidase enzyme and is used as therapy of acute symptomatic influenza A and B. Peramivir has not been associated with serum enzyme elevations during therapy or with clinically apparent liver injury.

Drug Classes：

Antiviral Agents

MeSH：

Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly. (See all compounds classified as Antiviral Agents.)|Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)

Mechanism of Action：

Peramivir is an inhibitor of influenza neuraminidase, preventing new virus particles from leaving infected cells.

MeSH Entry Terms：

(1S,2S,3R,4R)-3-((1S)-1-acetamido-2-ethylbutyl)-4-((amino(imino)methyl)amino)-2-hydroxycyclopentanecarboxylic acid trihydrate

Peramivir Use and Manufacturing

Use Classification：

Human drugs -> Alpivab -> EMA Drug Category|Antivirals for systemic use -> Human pharmacotherapeutic group|Human Drugs -> EU pediatric investigation plans|Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:328.41
Hydrogen Bond Donor Count:5
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:7
Exact Mass:328.21105539
Monoisotopic Mass:328.21105539
Topological Polar Surface Area:151
Heavy Atom Count:23
Complexity:460
Defined Atom Stereocenter Count:5
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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