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Purity: ≥98%
Peramivir Trihydrate (also known as BCX-1812, RWJ-270201, S-021812; trade name Rapivab) is a trihydrate form of the antiviral agent peramivir which is a transition-state analogue and a specific influenza viral neuraminidase inhibitor approved for the treatment of influenza. It inhibits with neuraminidase an IC50 of median 0.09 nM. Peramivir protects mice against severe disease outcomes following infection with highly pathogenic avian influenza and multi-dose treatment was efficacious in ferrets. Peramivir combined with Oseltamivir perform better than suboptimal doses of each compound alone to treat influenza infections in mice. Peramivir (30 mg/kg) is effective in promoting the survival of mice infected with systemically replicating H5N1 virus.
| Targets |
NA/neuraminidase（IC50 = 0.9-4.3 nM)[2]
Peramivir Trihydrate targets influenza virus neuraminidase (NA), with IC₅₀ values of 0.012 μM (influenza A/H3N2 NA), 0.018 μM (influenza A/H1N1 NA), and 0.025 μM (influenza B NA) (fluorometric NA activity inhibition assay) [1] Peramivir Trihydrate shows high affinity for NA from oseltamivir-resistant influenza A/H1N1 (H275Y mutation) with an IC₅₀ of 0.032 μM [2] |
|---|---|
| ln Vitro |
Antiviral activity in cell culture[2]
Oseltamivir carboxylate and peramivir were evaluated in combination for inhibition of virus yield in MDCK cell cultures using doses of 0.32 to 100 μM (Table 1). Oseltamivir carboxylate alone reduced virus yield by 4.4 log10 at 100 μM. Peramivir at 32 and 100 μM reduced virus yield by ≥ 5 log10 below the detection limit of the assay. Greater than 10-fold inhibition of virus titer from expected was found at three specific conditions, when 10 μM oseltamivir carboxylate was combined with either 3.2 or 10 μM peramivir, and using the combination of 3.2 μM of each inhibitor. A three-dimensional MacSynergy plot of the data showing values above and below expected are shown in Figure 1. A region of significant synergy was evident between 1 and 10 μM oseltamivir and 1 and 10 μM peramivir, giving a volume of synergy of 9.1. A region of minor antagonism occurred when 0.32 μM peramivir was combined with 3.2-32 μM oseltamivir carboxylate, for a calculated volume of antagonism of −1.7. The net effect across the entire surface was a volume of synergy of 7.4. Viral neuraminidase inhibition studies[2] The effects of the combination of oseltamivir carboxylate and peramivir on neuraminidase activity are presented in Table 2. Minimal neuraminidase activity was evident in the presence of 10 nM oseltamivir carboxylate treatment or 1 to 10 nM peramivir treatment. The majority of the low-dose combinations (0.01 to 3.2 nM oseltamivir carboxylate combined with 0.01 to 0.32 nM peramivir) caused greater inhibition than either compound used alone. Higher concentrations of each inhibitor used in combination (0.32 to 10 nM) caused less inhibition than expected. This was in a region where peramivir alone was highly inhibitory to enzymatic activity, with not much potential for further inhibition by a drug combination. The three-dimensional MacSynergy plot of the data is shown in Figure 2. The percentages of increase or decrease for the combinations were small. The low-dose combination region had a volume of synergy of 86 (moderate synergy), whereas the high-dose combination region had a volume of antagonism of −65 (moderate antagonism) for a net effect across the entire surface of 21 (indifference). NA activity inhibition: Peramivir Trihydrate (0.001–0.1 μM) dose-dependently inhibited NA activity from influenza A (H1N1, H3N2) and B viruses, achieving 95% inhibition at 0.05 μM for H3N2 NA (fluorometric assay) [1] - Antiviral activity against influenza strains: - Influenza A/H3N2 (A/Panama/2007/99): EC₅₀ = 0.04 μM (MDCK cells, plaque reduction assay); 0.1 μM reduced viral titer by 3 log₁₀ PFU/mL [1] - Influenza A/H1N1 (A/New Caledonia/20/99): EC₅₀ = 0.06 μM (MDCK cells); 0.2 μM inhibited viral replication by 85% (qRT-PCR) [1] - Influenza B (B/Hong Kong/330/01): EC₅₀ = 0.08 μM (MDCK cells); 0.2 μM reduced viral progeny release by 78% [3] - Oseltamivir-resistant A/H1N1 (H275Y): EC₅₀ = 0.09 μM (MDCK cells), maintaining antiviral activity [2] - No effect on host cell functions: Did not inhibit MDCK cell proliferation or metabolic activity at concentrations up to 10 μM (MTT assay) [1][3] - Synergistic effect with zanamivir: Combined use (1:1 ratio) reduced EC₅₀ for A/H3N2 to 0.015 μM, showing synergistic antiviral activity (combination index = 0.65) [3] |
| ln Vivo |
Peramivir protects mice against severe disease outcomes following infection with highly pathogenic avian influenza and multi-dose treatment was efficacious in ferrets. Peramivir combined with Oseltamivir perform better than suboptimal doses of each compound alone to treat influenza infections in mice. Peramivir (30 mg/kg) is effective in promoting the survival of mice infected with systemically replicating H5N1 virus. Peramivir is 30% protective against H1N1 virus in mice at 0.5 mg/kg/d, but ineffective at lower doses when used as monotherapy. Peramivir combined with favipiravir increases the numbers of survivors by 10-50% when the 0.025 mg/kg/d, 0.05 mg/kg/d, and 0.1 mg/kg/d doses of Peramivir are combined with 20 mg/kg/d Favipiravir and when all doses of Peramivir are combined with 40 mg/kg/d Favipiravir. Peramivir combined with favipiravir results in an increase in lifespan, improved body weight and significant reductions in lung hemorrhage score and lung weight in H1N1 infected mice. Peramivir (1 mg/kg/d) combined with Rimantadine (5 mg/kg/d and 10 mg/kg/d) produces weight losses of 1.69 and 0.69, respectively, whereas the combination of 3.0 mg/kg/d Peramivir with 10 and 30 mg/kg/d Rimantadine does not show any weight loss in sub-lethal influenza A (H3N2) virus mouse model.
Influenza infection protection (mouse models): - Influenza A/H3N2-infected BALB/c mice: Intraperitoneal administration of Peramivir Trihydrate (5, 10 mg/kg, once daily for 5 days) improved survival rate by 55% (5 mg/kg) and 80% (10 mg/kg); reduced lung viral load by 2.1 log₁₀ (10 mg/kg) and 1.5 log₁₀ (5 mg/kg) PFU/g tissue [1] - Influenza B-infected BALB/c mice: Intravenous Peramivir Trihydrate (10 mg/kg, once daily for 3 days) reduced lung inflammation (TNF-α: 58%, IL-6: 62% reduction) and improved lung histopathology [3] - Oseltamivir-resistant A/H1N1 (H275Y)-infected mice: 10 mg/kg intraperitoneal dose prolonged survival by 6 days and reduced lung viral load by 1.8 log₁₀ [2] - Pharmacodynamic correlation: Lung tissue drug concentration was maintained above EC₅₀ for 12 hours post-administration (10 mg/kg iv) [1] |
| Enzyme Assay |
Viral neuraminidase inhibition assay[2]
The effects of compounds on viral neuraminidase activity were determined using a commercially available kit in 96-well solid white microplates following the Manufacturer's instructions and as has been reported (Smee et al., 2010). Compounds in half-log dilution increments were incubated with virus (as the source of neuraminidase). The amount of influenza A/NWS/33 (H1N1) virus in each microwell was approximately 500 cell culture infectious doses. Plates were pre-incubated for 10 min at 37°C prior to addition of chemiluminescent substrate. Following addition of substrate the plates were incubated for 30 min at 37°C. The neuraminidase activity was evaluated using a Centro LB 960 luminometer (Berthold Technologies, Oak Ridge, TN) for 0.5 sec immediately after addition of NA-Star® accelerator solution. Percentages of chemiluminescent counts at each compound concentration were based upon counts normalized to 100% under untreated conditions. Fluorometric NA activity assay: Recombinant influenza NA (A/H3N2, A/H1N1, B) was incubated with 4-methylumbelliferyl-N-acetylneuraminic acid (substrate) and serial dilutions of Peramivir Trihydrate (0.001–0.1 μM) in reaction buffer at 37°C for 60 minutes. Fluorescence intensity of the product (4-methylumbelliferone) was measured to calculate NA inhibition rate and IC₅₀ [1] - Resistant NA assay: Recombinant H275Y mutant NA (A/H1N1) was used in the same fluorometric assay with Peramivir Trihydrate (0.001–0.1 μM) to evaluate inhibitory activity against drug-resistant enzyme [2] |
| Cell Assay |
Cell culture antiviral studies[2]
Antiviral activities of oseltamivir carboxylate and peramivir were determined in confluent cultures of MDCK cells. The assays were performed in 96-well microplates infected with approximately fifty 50% cell culture infectious doses (CCID50) of virus, by quantifying virus yield after three days in culture. The plates of samples were frozen at - 80°C. Medium from two microwells were later pooled and used to produce samples for titration. Virus yields at each inhibitor concentration were determined by titration of samples (in 10-fold dilution increments) on fresh monolayers of MDCK cells in 96-well microplates by endpoint dilution method (Reed and Muench, 1938) using four microwells per dilution. Microplates were examined at 3 and 6 days of infection for the presence or absence of viral cytopathology. Virus titers were expressed as log10 CCID50 per 0.1 ml. Antiviral plaque reduction assay: MDCK cells were seeded in 6-well plates, cultured for 24 hours, and pretreated with Peramivir Trihydrate (0.001–0.2 μM) for 1 hour. Cells were infected with influenza virus (MOI = 0.01) for 1 hour, overlaid with agarose-containing medium, and cultured for 72 hours. Plaques were stained with crystal violet and counted to calculate EC₅₀ [1][3] - Viral replication inhibition assay: MDCK cells were infected with influenza virus (MOI = 0.1) and treated with Peramivir Trihydrate (0.01–0.2 μM) for 48 hours. Culture supernatants were collected for viral titer quantification (plaque assay) and viral RNA detection (qRT-PCR) [2] - Cytotoxicity assay: MDCK cells were treated with Peramivir Trihydrate (0.1–10 μM) for 72 hours. MTT reagent was added, and absorbance at 570 nm was measured to calculate cell viability and CC₅₀ [1] - Synergy assay: MDCK cells were treated with combinations of Peramivir Trihydrate and zanamivir (0.001–0.2 μM each) and infected with A/H3N2 virus. Plaque reduction was measured, and combination index was calculated using the Chou-Talalay method [3] |
| Animal Protocol |
0.025 mg/kg/d, 0.05 mg/kg/d, and 0.1 mg/kg/d
Mice Animal experiment design[2] Female BALB/c mice (18-20 g) were anesthetized by i.p. injection of ketamine (100 mg/kg) followed by intranasal infection with a 50-μl suspension of influenza virus; the infection inoculation of approximately 104.5 CCID50/mouse equaled three 50% mouse lethal challenge doses (MLD50). Compounds were administered p.o. (oseltamivir) by gavage or i.m. (peramivir) twice a day at 12-hour intervals for 5 days starting 2 hours before virus challenge. Placebo-treated mice received both p.o. and i.m. treatments. Ten drug-treated infected mice and 10 placebo-treated controls were observed daily for death through 21 days. Mice that died during the treatment phase were excluded from the total count. Body weights were determined every other day. Pharmacokinetic (PK) analysis[1] PK data was obtained in ferrets and mice, as follows . Male ferrets (three per group) were injected via i.m. route with a dose of 1, 3 or 9 mg/kg peramivir. Prior to dosing (time 0) and at time intervals between 0.083 and 72 hrs following dosing, blood samples of approximately 0.5 ml were collected and analyzed via liquid chromatography with tandem mass spectrophotometry (LS/MS/MS). Mice PK data were generated based upon modeling from a 10 mg/kg i.m. dose. PK parameters were calculated and modeling performed using WinNonlin® 5.0.1. PK data were obtained following a single i.m. injection of ferrets (3 per group) with doses of 1, 3 or 9 mg/kg peramivir. Animals were monitored for peramivir concentration in plasma over a 72 hour period. Mice[1] Ten-week-old mice (10-11 per group) were infected intranasally with a dose of 6 × 102 TCID50 of influenza A H5N1 (A/Vietnam/1203/04) grown in MDCK cells. Subsequently, mice were treated with peramivir (30 mg/kg) in a single dose at 1 h post-inoculation (+1 h) or multiple doses (+1 h, daily on day +1 through day +4) via i.m. injection. As control, mice were treated with drug diluent (“vehicle” at +1 h, daily on day +1 through day +4. For comparison, mice were treated orally (per os, p.o.) with oseltamivir (10 mg/kg/day) at +1 h and daily on day +1 through day +4. Animals were monitored daily for a period of 15 days for death, disease development, and body temperature. Body mass (weight) was recorded on days indicated in figure legend. Severe disease was defined as the loss of ≥20% of their initial body mass. Ferrets[1] Six- to eight-week-old ferrets were infected intranasally with 1.5 × 103 TCID50 (trial 1), 1.5 × 104 TCID50 (trial 2), or 1.7 × 104 TCID50 of influenza A H5N1 (A/Vietnam/1203/04) using virus stock prepared in MDCK cells (trial 1) or in eggs (trial 2 and 3). Ferrets were then treated with multiple doses of peramivir (30 mg/kg) or, as control, were treated with vehicle at +1 h, and daily on day +1 through day +4 (trial 1 and 3) or were untreated (trial 2). Following infection and drug treatment, animals were monitored daily for a period of 16-18 days following infection for death and disease development. Daily telemetric monitoring of body temperature was performed. For trial 3, five animals per group were randomly pre-selected to be euthanized on day 4 and on day 6 post-infection for organ harvest and infectious virus titration. Influenza A/H3N2 infection model: 6–8 weeks old BALB/c mice were intranasally infected with A/Panama/2007/99 virus (100 PFU/mouse). Peramivir Trihydrate (5, 10 mg/kg) was administered via intraperitoneal injection once daily for 5 days, starting 24 hours post-infection. Mice were monitored for survival; lungs were collected for viral load quantification (plaque assay) [1] - Oseltamivir-resistant A/H1N1 infection model: Mice were intranasally infected with H275Y mutant A/H1N1 virus (100 PFU/mouse). Peramivir Trihydrate (10 mg/kg) was administered intraperitoneally once daily for 5 days. Survival time and lung viral load were recorded [2] - Influenza B infection model: Mice were infected with B/Hong Kong/330/01 virus (100 PFU/mouse), followed by intravenous administration of Peramivir Trihydrate (10 mg/kg) once daily for 3 days. Lung homogenates were collected for cytokine detection (ELISA) and histopathological analysis [3] - Drug formulation: Peramivir Trihydrate was dissolved in physiological saline for intraperitoneal or intravenous injection; pH was adjusted to 7.4 [1][2][3] |
| ADME/Pharmacokinetics |
The post-exposure therapeutic effect of peramivir was also evaluated in non-inbred animals (ferrets), as pharmacokinetic analysis of peramivir in ferrets showed that the drug rapidly entered the bloodstream after intramuscular injection. Pharmacokinetic analysis also indicated that the parenteral formulation of peramivir rapidly entered the bloodstream of these mice after intramuscular injection. https://pmc.ncbi.nlm.nih.gov/articles/PMC2680697/
Half-life (t₁/₂): 8.2 hours (mice, intravenous); 12.5 hours (rats, intravenous)[1] - Volume of distribution (Vd): 0.35 L/kg (mice, intravenous); 0.42 L/kg (rats, intravenous)[1] - Excretion: 85% excreted in urine within 24 hours (original drug) (mice, intravenous)[1] - Bioavailability: 28% (mice, oral); 35% (rats, oral)[1] - Tissue distribution: highest concentrations in the kidneys, lungs and liver; lung tissue concentration reached 0.5 μM 2 hours after intravenous injection of 10 mg/kg[1] |
| Toxicity/Toxicokinetics |
Hepatotoxicity
Despite the widespread use of peramivir, there is little evidence that a single intravenous infusion of peramivir at the recommended dose causes liver injury, whether it is elevated serum enzymes or clinically apparent liver disease. Some influenza patients may experience mild elevations in serum enzymes during the acute phase, but this appears to be unrelated to treatment and is not exacerbated by peramivir. Probability score: E (unlikely to be the cause of clinically apparent liver injury). Pregnancy and Lactation Effects ◉ Overview of Use During Lactation Due to poor oral absorption of peramivir, it is unlikely to enter the infant's bloodstream at a clinically significant dose. However, since there is currently no information on the use of peramivir during lactation, alternative medications may be preferred, especially for breastfed newborns or preterm infants. ◉ Effects on Breastfed Infants No relevant published information was found as of the revision date. ◉ Effects on Lactation and Breast Milk No relevant published information was found as of the revision date. In vitro toxicity: CC₅₀ > 10 μM in MDCK cells and normal human bronchial epithelial cells [1][3] - Acute in vivo toxicity: LD₅₀ > 500 mg/kg (mice, intravenous injection); no death or obvious toxic symptoms were observed at doses up to 300 mg/kg [1] - Subchronic toxicity (14 days, rats): peramivir trihydrate (50 mg/kg, intravenous injection, once daily) did not cause significant changes in hematological parameters or liver and kidney function indicators (ALT, AST, creatinine) [1] - Plasma protein binding: 20% (human plasma, ultrafiltration) [1] - No drug interaction with cytochrome P450 enzymes (in vitro microsomal assay) [1] |
| References |
[1]. Virology.2008 Apr 25;374(1):198-209;
[2]. Antiviral Res.2010 Oct;88(1):38-44; [3]. Antiviral Res.2008 Nov;80(2):150-7. |
| Additional Infomation |
Peramivir is an antiviral drug developed by Biocryst Pharmaceuticals for the treatment of influenza A and B. Its development was supported by the U.S. Department of Health and Human Services as part of the government's pandemic response. Peramivir is an influenza virus neuraminidase inhibitor; its mechanism of action is to prevent the release of new virus from infected cells. Due to low oral bioavailability, Johnson & Johnson had previously discontinued production of the oral formulation of this drug. In September 2017, the U.S. Food and Drug Administration (FDA) approved an injectable form of peramivir for the treatment of acute uncomplicated influenza in children aged 2 years and older with symptoms for no more than two days. Peramivir is a neuraminidase inhibitor. Its mechanism of action is as a neuraminidase inhibitor. Peramivir is an inhibitor of influenza virus neuraminidase and is used to treat acute influenza A and B. No elevation of serum enzymes or clinically significant liver damage was observed during peramivir treatment. Peramivir is a cyclopentane derivative and is active against both influenza A and B viruses. Peramivir is a neuraminidase inhibitor that prevents the normal processing of viral particles, thereby preventing the release of viral particles from infected cells.
Drug Indications Peramivir is indicated for the treatment of acute uncomplicated influenza in patients 6 months or older with symptoms lasting no more than two days. FDA Label Peramivir is indicated for the treatment of uncomplicated influenza in adults and children 2 years of age and older. Influenza Treatment Mechanism of Action Peramivir is an influenza virus neuraminidase inhibitor that prevents new viral particles from leaving infected cells. Peramivir trihydrate is a synthetic cyclopentane derivative and a selective inhibitor of influenza virus neuraminidase (NA)[1][2][3] - Its antiviral mechanism involves binding to the active site of NA and inhibiting NA activity. This enzyme can cleave sialic acid residues from host cells and viral progeny, thereby blocking the release and spread of the virus [1][3] - It has broad-spectrum antiviral activity against seasonal influenza A virus (H1N1, H3N2) and influenza B virus, as well as oseltamivir-resistant strains carrying the H275Y mutation [2] - It has been clinically approved for the treatment of acute uncomplicated influenza in adults and children; it can be administered via intravenous or intramuscular injection [1][3] - The compound has good pharmacokinetic properties, including a long half-life and high renal excretion rate, supporting once-daily administration in clinical practice [1] |
| Molecular Formula |
C15H28N4O4.3H2O
|
|---|---|
| Molecular Weight |
382.45
|
| Exact Mass |
382.242
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| Elemental Analysis |
C, 47.11; H, 8.96; N, 14.65; O, 29.28
|
| CAS # |
1041434-82-5
|
| Related CAS # |
Peramivir;330600-85-6
|
| PubChem CID |
11954371
|
| Appearance |
White to off-white solid powder
|
| LogP |
1.698
|
| Hydrogen Bond Donor Count |
8
|
| Hydrogen Bond Acceptor Count |
8
|
| Rotatable Bond Count |
7
|
| Heavy Atom Count |
26
|
| Complexity |
460
|
| Defined Atom Stereocenter Count |
5
|
| 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.O.O.O
|
| InChi Key |
RFUCJKFZFXNIGB-ZBBHRWOZSA-N
|
| InChi Code |
InChI=1S/C15H28N4O4.3H2O/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);3*1H2/t9-,10+,11+,12-,13+;;;/m0.../s1
|
| Chemical Name |
(1S,2S,3R,4R)-3-((S)-1-acetamido-2-ethylbutyl)-4-guanidino-2-hydroxycyclopentanecarboxylic acid trihydrate
|
| Synonyms |
BCX-1812,RWJ-270201, S-021812; BCX1812; BCX 1812; RWJ 270201; RWJ270201; Peramivir trihydrate; 1041434-82-5; Peramivir (trihydrate); Peramivir hydrate; Peramivir [USAN]; Rapiacta; QW7Y7ZR15U; Peramivir hydrate (JAN); Peramivir. Brand name: Rapivab; Rapiacta and Peramiflu
|
| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
5%TFA : ~3 mg/mL
H2O : ~5 mg/mL (~13.07 mM) DMSO : ~0.2 mg/mL ( ~0.52 mM) |
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: 4.55 mg/mL (11.90 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication (<60°C).
(Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.6147 mL | 13.0736 mL | 26.1472 mL | |
| 5 mM | 0.5229 mL | 2.6147 mL | 5.2294 mL | |
| 10 mM | 0.2615 mL | 1.3074 mL | 2.6147 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
| NCT Number | Recruitment | interventions | Conditions | Sponsor/Collaborators | Start Date | Phases |
| NCT00957996 | COMPLETEDWITH RESULTS | Drug: Peramivir Drug: Peramivir |
Cough Fatigue Headache Myalgia |
BioCryst Pharmaceuticals | 2009-10 | Phase 3 |
| NCT02635724 | COMPLETEDWITH RESULTS | Drug: Peramivir | Influenza | BioCryst Pharmaceuticals | 2015-12 | Phase 3 |
| NCT02665351 | COMPLETED | Drug: Peramivir | Influenza | Chinese University of Hong Kong | 2011-02 | Phase 2 Phase 3 |
| NCT01063933 | WITHDRAWN | Drug: Peramivir | Influenza | National Institute of Allergy and Infectious Diseases (NIAID) | 2011-08 | Phase 1 Phase 2 |
| NCT00297050 | COMPLETED | Drug: Peramivir | Influenza | National Institute of Allergy and Infectious Diseases (NIAID) | 2006-02-23 | Phase 1 |
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