Peramivir
Identification
- Name
- Peramivir
- Accession Number
- DB06614
- Description
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
Structure for Peramivir (DB06614)
- Weight
- Average: 328.4072
Monoisotopic: 328.211055404 - Chemical Formula
- C15H28N4O4
- Synonyms
- Peramivir
- Peramivir anhydrous
- External IDs
- RWJ 270201
- RWJ-270201
- RWJ270201
Pharmacology
Accelerate your drug discovery research with the industry’s only fully connected ADMET dataset, ideal for:Accelerate your drug discovery research with our fully connected ADMET dataset- 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
- Associated Conditions
- Contraindications & Blackbox Warnings
Contraindications & Blackbox WarningsWith our commercial data, access important information on dangerous risks, contraindications, and adverse effects.Our Blackbox Warnings cover Risks, Contraindications, and Adverse Effects- Pharmacodynamics
- Not Available
- Mechanism of action
Peramivir is an inhibitor of influenza neuraminidase, preventing new virus particles from leaving infected cells.
Target Actions Organism UNeuraminidase Not Available Influenza A virus (strain A/Tern/Australia/G70C/1975 H11N9) UNeuraminidase Not Available Influenza A virus (strain A/Bangkok/1/1979 H3N2) UNeuraminidase Not Available Influenza 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
Reduce medical errorsand improve treatment outcomes with our comprehensive & structured data on drug adverse effects.Reduce medical errors & improve treatment outcomes with our adverse effects data- Toxicity
- Not Available
- Affected organisms
- Influenza A virus
- Influenza B virus
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAdenovirus type 7 vaccine live The therapeutic efficacy of Adenovirus type 7 vaccine live can be decreased when used in combination with Peramivir. Anthrax vaccine The therapeutic efficacy of Anthrax vaccine can be decreased when used in combination with Peramivir. Bacillus calmette-guerin substrain connaught live antigen The therapeutic efficacy of Bacillus calmette-guerin substrain connaught live antigen can be decreased when used in combination with Peramivir. Bacillus calmette-guerin substrain tice live antigen The therapeutic efficacy of Bacillus calmette-guerin substrain tice live antigen can be decreased when used in combination with Peramivir. BCG vaccine The therapeutic efficacy of BCG vaccine can be decreased when used in combination with Peramivir. Human adenovirus e serotype 4 strain cl-68578 antigen The therapeutic efficacy of Human adenovirus e serotype 4 strain cl-68578 antigen can be decreased when used in combination with Peramivir. Rubella virus vaccine The therapeutic efficacy of Rubella virus vaccine can be decreased when used in combination with Peramivir. Typhoid Vaccine Live The 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. Vibrio cholerae CVD 103-HgR strain live antigen The therapeutic efficacy of Vibrio cholerae CVD 103-HgR strain live antigen can be decreased when used in combination with Peramivir. 
Improve patient outcomesBuild effective decision support tools with the industry’s most comprehensive drug-drug interaction checker.Learn more - Food Interactions
- No interactions found.
Products
Comprehensive & structured drug product infoFrom application numbers to product codes, connect different identifiers through our commercial datasets.Easily connect various identifiers back to our datasets- Product Ingredients
Ingredient UNII CAS InChI Key Peramivir hydrate QW7Y7ZR15U 1041434-82-5 RFUCJKFZFXNIGB-ZBBHRWOZSA-N - International/Other Brands
- Peramiflu / Rapiacta / Rapivab
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Alpivab Injection, solution, concentrate 200 mg Intravenous Biocryst 2021-01-12 2020-12-09 EU 
Rapivab Solution 600 mg/60mL Intravenous BioCryst Pharmaceuticals, Inc. 2014-12-20 Not applicable US 
Rapivab Solution 10 mg Intravenous Biocryst Pharmaceuticals Inc Not applicable Not applicable Canada 
Rapivab Solution 600 mg/60mL Intravenous Seqirus USA Inc. 2014-12-20 Not applicable US
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)
Chemical Identifiers
- UNII
- IDL9Q29886
- 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
- 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. [PubMed:16325932]
- External Links
- PubChem Compound
- 154234
- PubChem Substance
- 175427078
- ChemSpider
- 135903
- BindingDB
- 5024
- 619693
- ChEBI
- 85202
- ChEMBL
- CHEMBL139367
- ZINC
- ZINC000003981610
- PDBe Ligand
- BCZ
- Wikipedia
- Peramivir
- AHFS Codes
- 08:18.28 — Neuraminidase Inhibitors
- PDB Entries
- 1l7f / 1l7g / 1l7h / 2f10 / 2htu / 3k37 / 3k39 / 4mwv / 4mx0
- FDA label
- Download (197 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Treatment Flu caused by Influenza 1 3 Completed Treatment Coughing / Fatigue / Headache / Nasal Congestion / Seasonal Influenza / Sore Throat / Soreness, Muscle 1 3 Completed Treatment Flu caused by Influenza 2 3 Terminated Treatment Coughing / Fever / Headache / Nasal Congestion / Seasonal Influenza / Sore Throat 1 3 Terminated Treatment Flu caused by Influenza 2 3 Withdrawn Not Available Flu caused by Influenza 1 2 Completed Treatment Acute, Uncomplicated Human Influenza 1 2 Completed Treatment Flu caused by Influenza 2 2, 3 Completed Treatment Flu caused by Influenza 1 1 Completed Treatment Flu caused by Influenza 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Injection, solution, concentrate Intravenous 200 MG Solution Intravenous 10 mg Solution Intravenous 600 mg/60mL - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US8778997 No 2014-07-15 2027-05-07 US US6562861 No 2003-05-13 2018-12-17 US US6503745 No 2003-01-07 2019-11-05 US US10391075 No 2019-08-27 2027-02-12 US
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.38 mg/mL ALOGPS logP -0.27 ALOGPS logP -2.1 ChemAxon logS -2.9 ALOGPS pKa (Strongest Acidic) 4.09 ChemAxon pKa (Strongest Basic) 12.46 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 7 ChemAxon Hydrogen Donor Count 6 ChemAxon Polar Surface Area 148.53 Å2 ChemAxon Rotatable Bond Count 7 ChemAxon Refractivity 94.46 m3·mol-1 ChemAxon Polarizability 34.85 Å3 ChemAxon Number of Rings 1 ChemAxon Bioavailability 1 ChemAxon Rule of Five No ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.6611 Blood Brain Barrier + 0.623 Caco-2 permeable - 0.6852 P-glycoprotein substrate Non-substrate 0.6498 P-glycoprotein inhibitor I Non-inhibitor 0.9244 P-glycoprotein inhibitor II Non-inhibitor 0.852 Renal organic cation transporter Non-inhibitor 0.884 CYP450 2C9 substrate Non-substrate 0.7276 CYP450 2D6 substrate Non-substrate 0.8204 CYP450 3A4 substrate Non-substrate 0.6063 CYP450 1A2 substrate Non-inhibitor 0.797 CYP450 2C9 inhibitor Non-inhibitor 0.8469 CYP450 2D6 inhibitor Non-inhibitor 0.9138 CYP450 2C19 inhibitor Non-inhibitor 0.8338 CYP450 3A4 inhibitor Non-inhibitor 0.8732 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9711 Ames test Non AMES toxic 0.6544 Carcinogenicity Non-carcinogens 0.8109 Biodegradation Not ready biodegradable 0.6663 Rat acute toxicity 2.5219 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9958 hERG inhibition (predictor II) Non-inhibitor 0.9672
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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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
- 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. [PubMed:24356381]
- 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. [PubMed:24997412]
- 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. [PubMed:24165891]
- 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
- 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. [PubMed:16325932]
- 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
- 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. [PubMed:16325932]
Drug created on March 19, 2008 16:41 / Updated on March 04, 2021 11:01