Identification

Summary

Peramivir is an intravenous antiviral agent used to treat acute uncomplicated influenza in patients aged 2 years and older who are shown to be symptomatic for no more than two days.

Brand Names
Rapivab
Generic Name
Peramivir
DrugBank Accession Number
DB06614
Background

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.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Thumb
Weight
Average: 328.4072
Monoisotopic: 328.211055404
Chemical Formula
C15H28N4O4
Synonyms
  • Peramivir
  • Peramivir anhydrous
External IDs
  • RWJ 270201
  • RWJ-270201
  • RWJ270201

Pharmacology

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.Label

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action

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

TargetActionsOrganism
UNeuraminidaseNot AvailableInfluenza A virus (strain A/Tern/Australia/G70C/1975 H11N9)
UNeuraminidaseNot AvailableInfluenza A virus (strain A/Bangkok/1/1979 H3N2)
UNeuraminidaseNot AvailableInfluenza B virus (strain B/Beijing/1/1987)
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
Adverseeffects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
Adenovirus type 7 vaccine liveThe therapeutic efficacy of Adenovirus type 7 vaccine live can be decreased when used in combination with Peramivir.
Anthrax vaccineThe therapeutic efficacy of Anthrax vaccine can be decreased when used in combination with Peramivir.
Bacillus calmette-guerin substrain connaught live antigenThe therapeutic efficacy of Bacillus calmette-guerin substrain connaught live antigen can be decreased when used in combination with Peramivir.
Bacillus calmette-guerin substrain russian BCG-I live antigenThe therapeutic efficacy of Bacillus calmette-guerin substrain russian BCG-I live antigen can be decreased when used in combination with Peramivir.
Bacillus calmette-guerin substrain tice live antigenThe therapeutic efficacy of Bacillus calmette-guerin substrain tice live antigen can be decreased when used in combination with Peramivir.
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Peramivir.
Human adenovirus e serotype 4 strain cl-68578 antigenThe therapeutic efficacy of Human adenovirus e serotype 4 strain cl-68578 antigen can be decreased when used in combination with Peramivir.
Rubella virus vaccineThe therapeutic efficacy of Rubella virus vaccine can be decreased when used in combination with Peramivir.
Typhoid Vaccine LiveThe therapeutic efficacy of Typhoid Vaccine Live can be decreased when used in combination with Peramivir.
Varicella zoster vaccine (live/attenuated)The therapeutic efficacy of Varicella zoster vaccine (live/attenuated) can be decreased when used in combination with Peramivir.
Interactions
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Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Peramivir hydrateQW7Y7ZR15U1041434-82-5RFUCJKFZFXNIGB-ZBBHRWOZSA-N
International/Other Brands
Peramiflu / Rapiacta / Rapivab
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AlpivabInjection, solution, concentrate200 mgIntravenousBiocryst2021-01-122020-12-09EU flag
RapivabSolution10 mg / mLIntravenousBiocryst Pharmaceuticals IncNot applicableNot applicableCanada flag
RapivabSolution600 mg/60mLIntravenousBioCryst Pharmaceuticals, Inc.2014-12-20Not applicableUS flag
RapivabSolution600 mg/60mLIntravenousSeqirus USA Inc.2014-12-20Not applicableUS flag

Categories

ATC Codes
J05AH03 — Peramivir
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma carbon atom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Gamma amino acids and derivatives
Alternative Parents
Beta hydroxy acids and derivatives / Cyclopentanols / Acetamides / Secondary carboxylic acid amides / Guanidines / Cyclic alcohols and derivatives / Propargyl-type 1,3-dipolar organic compounds / Monocarboxylic acids and derivatives / Carboxylic acids / Carboximidamides
show 4 more
Substituents
Acetamide / Alcohol / Aliphatic homomonocyclic compound / Beta-hydroxy acid / Carbonyl group / Carboxamide group / Carboximidamide / Carboxylic acid / Cyclic alcohol / Cyclopentanol
show 15 more
Molecular Framework
Aliphatic homomonocyclic compounds
External Descriptors
guanidines, acetamides, 3-hydroxy monocarboxylic acid, cyclopentanols (CHEBI:85202)
Affected organisms
  • Influenza A virus
  • Influenza B virus

Chemical Identifiers

UNII
9ZS94HQO3B
CAS number
330600-85-6
InChI Key
XRQDFNLINLXZLB-CKIKVBCHSA-N
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
IUPAC Name
(1S,2S,3R,4R)-4-carbamimidamido-3-[(1S)-1-acetamido-2-ethylbutyl]-2-hydroxycyclopentane-1-carboxylic acid
SMILES
[H][C@@]1([C@@H](NC(C)=O)C(CC)CC)[C@H](O)[C@H](C[C@H]1NC(N)=N)C(O)=O

References

General References
  1. Bantia S, Arnold CS, Parker CD, Upshaw R, Chand P: Anti-influenza virus activity of peramivir in mice with single intramuscular injection. Antiviral Res. 2006 Jan;69(1):39-45. Epub 2005 Nov 21. [Article]
  2. FDA Approved Drug Products: RAPIVAB (peramivir) intravenous [Link]
PubChem Compound
154234
PubChem Substance
175427078
ChemSpider
135903
BindingDB
5024
RxNav
619693
ChEBI
85202
ChEMBL
CHEMBL139367
ZINC
ZINC000003981610
PDBe Ligand
BCZ
Wikipedia
Peramivir
PDB Entries
1l7f / 1l7g / 1l7h / 2f10 / 2htu / 3k37 / 3k39 / 4mwv / 4mx0
FDA label
Download (197 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentFlu caused by Influenza1
3CompletedTreatmentCough / Fatigue / Headache / Myalgia / Nasal Congestion / Seasonal Influenza / Sore Throat1
3CompletedTreatmentFlu caused by Influenza2
3TerminatedTreatmentCough / Fever / Headache / Nasal Congestion / Seasonal Influenza / Sore Throat1
3TerminatedTreatmentFlu caused by Influenza2
3WithdrawnNot AvailableFlu caused by Influenza1
2CompletedTreatmentAcute, Uncomplicated Human Influenza1
2CompletedTreatmentFlu caused by Influenza2
2, 3CompletedTreatmentFlu caused by Influenza1
1CompletedTreatmentFlu caused by Influenza1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Injection, solution, concentrateIntravenous200 MG
SolutionIntravenous10 mg / mL
SolutionIntravenous600 mg/60mL
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US8778997No2014-07-152027-05-07US flag
US6562861No2003-05-132018-12-17US flag
US6503745No2003-01-072019-11-05US flag
US10391075No2019-08-272027-02-12US flag

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.38 mg/mLALOGPS
logP-0.27ALOGPS
logP-2.1ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)4.09ChemAxon
pKa (Strongest Basic)12.46ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area148.53 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity94.46 m3·mol-1ChemAxon
Polarizability34.85 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.6611
Blood Brain Barrier+0.623
Caco-2 permeable-0.6852
P-glycoprotein substrateNon-substrate0.6498
P-glycoprotein inhibitor INon-inhibitor0.9244
P-glycoprotein inhibitor IINon-inhibitor0.852
Renal organic cation transporterNon-inhibitor0.884
CYP450 2C9 substrateNon-substrate0.7276
CYP450 2D6 substrateNon-substrate0.8204
CYP450 3A4 substrateNon-substrate0.6063
CYP450 1A2 substrateNon-inhibitor0.797
CYP450 2C9 inhibitorNon-inhibitor0.8469
CYP450 2D6 inhibitorNon-inhibitor0.9138
CYP450 2C19 inhibitorNon-inhibitor0.8338
CYP450 3A4 inhibitorNon-inhibitor0.8732
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9711
Ames testNon AMES toxic0.6544
CarcinogenicityNon-carcinogens0.8109
BiodegradationNot ready biodegradable0.6663
Rat acute toxicity2.5219 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9958
hERG inhibition (predictor II)Non-inhibitor0.9672
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets2
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Kind
Protein
Organism
Influenza A virus (strain A/Tern/Australia/G70C/1975 H11N9)
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Catalyzes the removal of terminal sialic acid residues from viral and cellular glycoconjugates. Cleaves off the terminal sialic acids on the glycosylated HA during virus budding to facilitate virus...
Gene Name
NA
Uniprot ID
P03472
Uniprot Name
Neuraminidase
Molecular Weight
52468.405 Da
References
  1. Woods CJ, Malaisree M, Long B, McIntosh-Smith S, Mulholland AJ: Computational assay of H7N9 influenza neuraminidase reveals R292K mutation reduces drug binding affinity. Sci Rep. 2013 Dec 20;3:3561. doi: 10.1038/srep03561. [Article]
  2. Kodama M, Yoshida R, Hasegawa T, Izawa M, Kitano M, Baba K, Noshi T, Seki T, Okazaki K, Tsuji M, Kanazu T, Kamimori H, Homma T, Kobayashi M, Sakoda Y, Kida H, Sato A, Yamano Y: The relationship between in vivo antiviral activity and pharmacokinetic parameters of peramivir in influenza virus infection model in mice. Antiviral Res. 2014 Sep;109:110-5. doi: 10.1016/j.antiviral.2014.06.016. Epub 2014 Jul 2. [Article]
  3. Wu Y, Bi Y, Vavricka CJ, Sun X, Zhang Y, Gao F, Zhao M, Xiao H, Qin C, He J, Liu W, Yan J, Qi J, Gao GF: Characterization of two distinct neuraminidases from avian-origin human-infecting H7N9 influenza viruses. Cell Res. 2013 Dec;23(12):1347-55. doi: 10.1038/cr.2013.144. Epub 2013 Oct 29. [Article]
Kind
Protein
Organism
Influenza A virus (strain A/Bangkok/1/1979 H3N2)
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Catalyzes the removal of terminal sialic acid residues from viral and cellular glycoconjugates. Cleaves off the terminal sialic acids on the glycosylated HA during virus budding to facilitate virus...
Gene Name
NA
Uniprot ID
P06818
Uniprot Name
Neuraminidase
Molecular Weight
52140.54 Da
References
  1. Bantia S, Arnold CS, Parker CD, Upshaw R, Chand P: Anti-influenza virus activity of peramivir in mice with single intramuscular injection. Antiviral Res. 2006 Jan;69(1):39-45. Epub 2005 Nov 21. [Article]
Kind
Protein
Organism
Influenza B virus (strain B/Beijing/1/1987)
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Catalyzes the removal of terminal sialic acid residues from viral and cellular glycoconjugates. Cleaves off the terminal sialic acids on the glycosylated HA during virus budding to facilitate virus...
Gene Name
NA
Uniprot ID
P27907
Uniprot Name
Neuraminidase
Molecular Weight
51429.21 Da
References
  1. Bantia S, Arnold CS, Parker CD, Upshaw R, Chand P: Anti-influenza virus activity of peramivir in mice with single intramuscular injection. Antiviral Res. 2006 Jan;69(1):39-45. Epub 2005 Nov 21. [Article]

Drug created at March 19, 2008 16:41 / Updated at December 08, 2021 01:57