Peramivir

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Cat Number

API0232272

CAS Number

330600-85-6

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Product Detail Description Scientific Support Advanced Innovations Customer Q&A

CAS Number

330600-85-6

Storage

Store at 2-8°C

Synonyms

BCX-1812; Rapiacta; RWJ-270201; Peramivir anhydrous; RAPIVAB

Molecular Formula

C15H28N4O4

Molecular Weight

328.41

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

Appearance

White to off-white solid powder

Melting Point

170-172°C

Relative Density

1.39

General Description

Peramivir is a synthetic cyclopentane carboxylate derivative, a neuraminidase inhibitor with a guanidino group and a carboxylic acid group. Its chemical structure is (1S,2S,3S,4R)-3-[(1S)-1-acetamido-2-ethylbutyl]-4-[(diaminomethylidene)amino]-2-hydroxycyclopentane-1-carboxylic acid.

Mechanism of Action

Peramivir inhibits the neuraminidase enzyme of influenza viruses, preventing the cleavage of sialic acid residues from the host cell surface, which is essential for the release of new virions. This blocks the spread of the virus within the respiratory tract. The drug has a high affinity for the viral neuraminidase and is effective against both influenza A and B viruses.

Application

Peramivir is indicated for the treatment of acute uncomplicated influenza in adults and pediatric patients who have been symptomatic for no more than 48 hours. It is also used for the treatment of influenza in patients who are unable to take oral therapy. The drug is effective in reducing the duration and severity of influenza symptoms.

Peramivir, an intravenous neuraminidase inhibitor for influenza, is effective against human influenza A and B and emerging strains. Single‑dose administration is well tolerated, with mild‑to‑moderate gastrointestinal effects and self‑limiting neutropenia. It is approved for adults and has pediatric data in Japan. Peramivir provides a valuable alternative for critically ill patients or those unable to take oral antivirals.

Fig. 1 Peramivir bound to influenza A/H7N9 neuraminidase. (Alame MM, et al., 2016)

References

Alame MM, et al. Peramivir: A Novel Intravenous Neuraminidase Inhibitor for Treatment of Acute Influenza Infections. Front Microbiol. 2016;7:450.

In a randomized trial of 92 high-risk patients with seasonal influenza, a single intravenous dose of peramivir (600 mg) was compared to 5 days of oral oseltamivir (75 mg BID). Median times to clinical stability were 40.0 hours (peramivir) and 37.8 hours (oseltamivir), with no significant difference. Adverse events occurred in 2.2% (peramivir) vs 13.0% (oseltamivir). Peramivir is a useful option for influenza-infected high-risk patients.

Fig. 2 Time course of virus titers in peramivir and oseltamivir dose groups. (Nakamura S, et al., 2017)

References

Nakamura S, et al. Efficacy and Safety of Intravenous Peramivir Compared With Oseltamivir in High-Risk Patients Infected With Influenza A and B Viruses: A Multicenter Randomized Controlled Study. Open Forum Infect Dis. 2017;4(3):ofx129.

Does Peramivir require refrigerated storage as a neuraminidase inhibitor?

Yes, it must be stored at 2-8°C. At room temperature, degradation via hydrolysis of the guanidine and cyclopentane ring occurs.

Is Peramivir sensitive to light and moisture during storage?

Yes, it is photosensitive and hygroscopic. Store in original, tightly sealed, light-resistant containers with desiccant under refrigeration.

What is the stability of Peramivir after reconstitution for intravenous infusion?

Reconstituted solutions are stable for up to 24 hours under refrigeration.

How is the impurity peramivir guanidine (a hydrolysis product) monitored?

This degradation product is specifically quantified using a stability-indicating HPLC method, ensuring it remains within ICH limits.