Peramivir

Aeuraminidase inhibitor;antiviral drug CAS# 330600-85-6

Peramivir

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Quality Control of Peramivir

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Chemical structure

Peramivir

3D structure

Chemical Properties of Peramivir

Cas No. 330600-85-6 SDF Download SDF
PubChem ID 154234 Appearance Powder
Formula C15H28N4O4 M.Wt 328.41
Type of Compound N/A Storage Desiccate at -20°C
Synonyms RWJ-270201; BCX-1812
Solubility Soluble in DMSO
Chemical Name (1S,2S,3S,4R)-3-[(1S)-1-acetamido-2-ethylbutyl]-4-(diaminomethylideneamino)-2-hydroxycyclopentane-1-carboxylic acid
SMILES CCC(CC)C(C1C(CC(C1O)C(=O)O)N=C(N)N)NC(=O)C
Standard InChIKey XRQDFNLINLXZLB-CKIKVBCHSA-N
Standard InChI 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
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Peramivir

DescriptionPeramivir (RWJ 270201; Rapiacta; BCX 1812) is a transition-state analogue and a potent, specific influenza viral neuraminidase inhibitor with an IC50 of median 0.09 nM. IC50 Value: 0.09 nM Target: Neuraminidase Peramivir is an experimental antiviral drug developed by BioCryst Pharmaceuticals for the treatment of influenza. It has been authorized for the emergency use of treatment of certain hospitalized patients with known or suspected 2009 H1N1 influenza. Peramivir is a neuraminidase inhibitor, acting as a transition-state analogue inhibitor of influenza neuraminidase and thereby preventing new viruses from emerging from infected cells. From Wikipedia

References:
[1]. Efficacy, safety, and pharmacokinetics of intravenous peramivir in children with 2009 pandemic H1N1 influenza A virus infection By Sugaya, Norio; Kohno, Shigeru; Ishibashi, Toru; Wajima, Toshihiro; Takahashi, Takao From Antimicrobial Agents and Chemothera [2]. Louie JK, Yang S, Yen C, Acosta M, Schechter R, Uyeki TM. Use of Intravenous Peramivir for Treatment of Severe Influenza A(H1N1)pdm09. PLoS One. 2012;7(6):e40261. [3]. Sakata H. Clinical efficiency in children treated with intravenous drip infusion of peramivir.Jpn J Antibiot. 2011 Dec;64(6):383-7. [4]. Abed Y, Pizzorno A, Boivin G. Therapeutic Activity of Intramuscular Peramivir in Mice Infected with a Recombinant Influenza A/WSN/33 (H1N1) Virus Containing the H275Y Neuraminidase Mutation. Antimicrob Agents Chemother. 2012 Aug;56(8):4375-80. [5]. Hikita T, Hikita H, Hikita F, Hikita N, Hikita S. Clinical effectiveness of peramivir in comparison with other neuraminidase inhibitors in pediatric influenza patients.Int J Pediatr. 2012;2012:834181.

Peramivir Dilution Calculator

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Peramivir Molarity Calculator

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Preparing Stock Solutions of Peramivir

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.045 mL 15.2249 mL 30.4497 mL 60.8995 mL 76.1244 mL
5 mM 0.609 mL 3.045 mL 6.0899 mL 12.1799 mL 15.2249 mL
10 mM 0.3045 mL 1.5225 mL 3.045 mL 6.0899 mL 7.6124 mL
50 mM 0.0609 mL 0.3045 mL 0.609 mL 1.218 mL 1.5225 mL
100 mM 0.0304 mL 0.1522 mL 0.3045 mL 0.609 mL 0.7612 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Peramivir

Peramivir is an experimental antiviral drug developed by BioCryst Pharmaceuticals for the treatment of influenza. It has been authorized for the emergency use of treatment of certain hospitalized patients with known or suspected 2009 H1N1 influenza. Peramivir is a neuraminidase inhibitor, acting as a transition-state analogue inhibitor of influenza neuraminidase and thereby preventing new viruses from emerging from infected cells. From Wikipedia

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References on Peramivir

In Vitro Evaluation of Absorption Characteristics of Peramivir for Oral Delivery.[Pubmed:28000173]

Eur J Drug Metab Pharmacokinet. 2017 Oct;42(5):757-765.

BACKGROUND AND OBJECTIVE: Peramivir is a novel antiviral agent approved for the treatment of severe influenza. However, the development of oral formulation of Peramivir has been severely hurdled by poor bioavailability (human, Peramivir. METHODS: In vitro gastrointestinal stability, metabolic stability in human intestinal S9 fraction and Caco-2 permeability were performed. The liquid chromatography with tandem mass spectrometric (LC-MS/MS) was used to quantify Peramivir in buffer and biological sample. Using GastroPlus software, intestinal effective permeability coefficient (P eff) of Peramivir was estimated. RESULTS: Our results indicated that Peramivir maintained stability in pH 5.5 and 7.4 buffers, fasted state simulated gastric fluid and fasted state simulated intestinal fluid, and human intestinal S9 fractions. The apparent permeability coefficient (P app) values of Peramivir (10 muM) were 3.29 +/- 0.73 x 10(-7) cm/s in a Caco-2 cell model. In vivo intestinal effective permeability coefficient (P eff) was estimated to be 0.06 x 10(-4) cm/s. Furthermore, co-incubating with cyclosporine, mitoxantrone, rifampicin, or paroxetine, the apical (AP) to basolateral (BL) flux of Peramivir decreased (p < 0.05). The efflux and influx of Peramivir was not significantly affected with co-incubation with verapamil, MK-571, or diclofenac (p > 0.05). CONCLUSIONS: These results revealed that carrier-mediated transports, including OATP1B (organic anion transport 1B) and OCT1 (organic cation transport 1), might be involved in the absorption of Peramivir. In conclusion, our results provide insight into the poor oral bioavailability of Peramivir. Peramivir can be classified as a BCS-III (high solubility/low permeability) and BDDCS-III high solubility/poor metabolism) drug. The oral bioavailability of Peramivir primarily depends on its permeability across cell membranes. Both of passive and active transports are involved in the permeability of Peramivir.

Therapeutic efficacy of peramivir against H5N1 highly pathogenic avian influenza viruses harboring the neuraminidase H275Y mutation.[Pubmed:28012921]

Antiviral Res. 2017 Mar;139:41-48.

High morbidity and mortality associated with human cases of highly pathogenic avian influenza (HPAI) viruses, including H5N1 influenza virus, have been reported. The purpose of the present study was to evaluate the antiviral effects of Peramivir against HPAI viruses. In neuraminidase (NA) inhibition and virus replication inhibition assays, Peramivir showed strong inhibitory activity against H5N1, H7N1 and H7N7 HPAI viruses with sub-nanomolar activity in enzyme assays. In H5N1 viruses containing the NA H275Y mutation, the antiviral activity of Peramivir against the variant was lower than that against the wild-type. Evaluation of the in vivo antiviral activity showed that a single intravenous treatment of Peramivir (10 mg/kg) prevented lethality in mice infected with wild-type H5N1 virus and also following infection with H5N1 virus with the H275Y mutation after a 5 day administration of Peramivir (30 mg/kg). Furthermore, mice injected with Peramivir showed low viral titers and low levels of proinflammatory cytokines in the lungs. These results suggest that Peramivir has therapeutic activity against HPAI viruses even if the virus harbors the NA H275Y mutation.

Pharmacokinetics and safety of intravenous peramivir, neuraminidase inhibitor of influenza virus, in healthy Japanese subjects.[Pubmed:27805571]

Antivir Ther. 2017;22(4):313-323.

BACKGROUND: Intravenous Peramivir is a potent neuraminidase (NA) inhibitor with activity against influenza A and B viruses. The early use of NA inhibitors has been shown to reduce mortality in influenza patients. METHODS: To evaluate the pharmacokinetics of Peramivir and confirm the safety and tolerability of multiple infusions of Peramivir in healthy Japanese subjects, two Phase I, single-centre, randomized, double-blind and placebo-controlled studies consisting of a multiple-dose study and a high-dose study were conducted. RESULTS: Multiple intravenous infusions of Peramivir were well tolerated up to 800 mg once a day and 400 mg twice daily for 6 days. Dose proportionalities for maximum plasma concentration (Cmax) and area under the plasma concentration-time curve (AUC) were established up to the 800 mg dose. Approximately 90% of unchanged Peramivir was excreted into urine within 12 h after treatment with 800 mg of Peramivir. The Peramivir plasma and upper respiratory tract fluid levels were significantly higher than the 50% inhibition concentrations for NA enzyme activity (IC50) of epidemic influenza viruses, including those harbouring the H274Y mutation. CONCLUSIONS: The pharmacokinetic properties obtained here for intravenous Peramivir are consistent with the previously reported clinical efficacy and safety of this antiviral.

Pharmacokinetics of Peramivir in an Adolescent Patient Receiving Continuous Venovenous Hemodiafiltration.[Pubmed:28337082]

J Pediatr Pharmacol Ther. 2017 Jan-Feb;22(1):60-64.

Critically ill patients requiring renal replacement therapy commonly experience pharmacokinetic alterations. This case report describes the pharmacokinetics of Peramivir (Rapivab, BioCryst Pharmaceuticals, Inc, Durham, NC), the first US Food and Drug Administration-approved intravenous neuraminidase inhibitor for the treatment of influenza, in an adolescent patient receiving continuous renal replacement therapy (CRRT). A 49.5-kg, 17-year-old Caucasian female presented with fever, cough, and persistent hypoxia. She quickly progressed to acute respiratory and renal failure in the setting of viral septic shock as a result of a severe influenza H1N1 infection. On hospital day 3, therapy was switched from oseltamivir (Tamiflu, Roche Laboratories Inc, Nutley, NJ) to Peramivir owing to the concern for inadequate enteral absorption. On the third day of Peramivir treatment, at a dose of 200 mg daily, Peramivir serum concentrations revealed a smaller peak concentration, larger volumes of distribution, similar 24-hour area under the curve, and a shorter half-life as compared to adult patients with normal renal function. This illustrated the significant differences in pharmacokinetics when administered in the setting of CRRT. The patient had resolution of viral infection as evidenced by negative respiratory viral panel polymerase chain reaction at hospital day 14 and was eventually discharged at her baseline.

Description

Peramivir (RWJ-270201;BCX-1812) is a highly potent, selective and orally active influenza virus neuraminidase (NA) inhibitor, with IC50 values ranging form 0.9 to 4.3 nM for nine NA subtypes.

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