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Identification
NamePeramivir
Accession NumberDB06614
TypeSmall Molecule
GroupsApproved, Investigational
Description

Peramivir is an experimental antiviral drug being developed by Biocryst Pharmaceuticals to treat influenza A/B. The development of peramivir is supported by the US Department of Health and Human Services as part of the government’s effort to prepare for a flu pandemic. The drug has had a long history. An oral formulation was abandoned by Johnson and Johnson due to poor bioavailability. BioCryst is now developing a injectable version, in partnership with Green Cross Pharmaceuticals in South Korea and with Shionogi Pharmaceuticals in Japan. The drug is in Phase II studies.

Structure
Thumb
SynonymsNot Available
External Identifiers
  • RWJ 270201
  • RWJ-270201
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Rapivabsolution600 mg/60mLintravenousBio Cryst Pharmaceuticals, Inc.2015-01-02Not applicableUs
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Peramivir hydrate
1041434-82-5
Thumb
  • InChI Key: RFUCJKFZFXNIGB-ZBBHRWOZSA-N
  • Monoisotopic Mass: 382.242749451
  • Average Mass: 382.458
DBSALT001847
CategoriesNot Available
UNII9ZS94HQO3B
CAS number330600-85-6
WeightAverage: 328.4072
Monoisotopic: 328.211055404
Chemical FormulaC15H28N4O4
InChI KeyXRQDFNLINLXZLB-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)-2-ethyl-1-[(1-hydroxyethylidene)amino]butyl]-2-hydroxycyclopentane-1-carboxylic acid
SMILES
[H][C@](N=C(C)O)(C(CC)CC)[C@]1([H])[C@]([H])(O)[C@]([H])(C[C@@]1([H])NC(N)=N)C(O)=O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as delta amino acids and derivatives. These are compounds containing a carboxylic acid group and an amino group at the C5 carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentDelta amino acids and derivatives
Alternative Parents
Substituents
  • Delta amino acid or derivatives
  • Gamma amino acid or derivatives
  • Beta-hydroxy acid
  • Hydroxy acid
  • Cyclopentanol
  • Cyclic alcohol
  • Secondary alcohol
  • Guanidine
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboximidic acid derivative
  • Carboximidic acid
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Imine
  • Carbonyl group
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationInvestigated for use/treatment in influenza.
PharmacodynamicsNot Available
Mechanism of actionPeramivir is a neuraminidase inhibitor, acting as a transition-state analogue inhibitor of influenza neuraminidase and thereby preventing new viruses from emerging from infected cells.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Influenza A virus
  • Influenza B virus
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
Solutionintravenous600 mg/60mL
PricesNot Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US6503745 No1999-11-052019-11-05Us
US6562861 No1998-12-172018-12-17Us
US8778997 No2007-05-072027-05-07Us
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.171 mg/mLALOGPS
logP-0.14ALOGPS
logP-1.3ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)3.99ChemAxon
pKa (Strongest Basic)12.48ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area152.02 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity94.98 m3·mol-1ChemAxon
Polarizability34.94 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
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. [PubMed:16325932 ]
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

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 release. Additionally helps virus spread through the circulation by further removing sialic acids from the cell surface. These cleavages prevent self-aggregation and ensure the efficient spread of th...
Gene Name:
NA
Uniprot ID:
P06818
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. [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 release. Additionally helps virus spread through the circulation by further removing sialic acids from the cell surface. These cleavages prevent self-aggregation and ensure the efficient spread of th...
Gene Name:
NA
Uniprot ID:
P27907
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. [PubMed:16325932 ]
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Drug created on March 19, 2008 10:41 / Updated on May 25, 2016 02:17