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Identification
NamePerflutren
Accession NumberDB00556  (APRD01177)
Typesmall molecule
Groupsapproved
Description

Perflutren, a diagnostic drug that is intended to be used for contrast enhancement during the indicated echocardiographic procedures, is comprised of lipid-coated microspheres filled with octafluoropropane(OFP) gas. When exposed to ultrasound waves, the microspheres resonate and “echo” strong signals back to the ultrasound machine. The difference in density between the gas-filled bubbles and the blood around them creates an increased level of contrast visible in the resulting ultrasound image. During echocardiography, activated Perflutren enhances images of the inner edges or borders of the heart, producing an improved image that may enable physicians to better diagnose patients.

Structure
Thumb
Synonyms
SynonymLanguageCode
OctafluoropropaneNot AvailableNot Available
OctafluorpropanNot AvailableNot Available
PerfluoropropaneNot AvailableNot Available
SaltsNot Available
Brand names
NameCompany
DefinityLantheus Medical Imaging
Brand mixturesNot Available
Categories
CAS number76-19-7
WeightAverage: 188.0193
Monoisotopic: 187.98722564
Chemical FormulaC3F8
InChI KeyQYSGYZVSCZSLHT-UHFFFAOYSA-N
InChI
InChI=1S/C3F8/c4-1(5,2(6,7)8)3(9,10)11
IUPAC Name
octafluoropropane
SMILES
FC(F)(F)C(F)(F)C(F)(F)F
Mass Specshow(7.49 KB)
Taxonomy
KingdomOrganic Compounds
SuperclassOrganonitrogen Compounds
ClassAmines
SubclassPolyamines
Direct parentPolyamines
Alternative parentsOrganofluorides; Alkyl Fluorides
Substituentsorganofluoride; organohalogen; alkyl halide; alkyl fluoride
Classification descriptionThis compound belongs to the polyamines. These are compounds containing more than one amine group.
Pharmacology
IndicationUsed as an ultrasound contrast imaging in cardiology and radiology.
PharmacodynamicsPerflutren, a diagnostic drug that is intended to be used for contrast enhancement during the indicated echocardiographic procedures, comprised of lipid-coated microspheres filled with octafluoropropane(OFP) gas. It provide contrast enhancement of the endocardial borders during echocardiography. The perflutren lipid microspheres exhibit lower acoustic impedance than blood and enhance the intrinsic backscatter of blood.
Mechanism of actionPerflutren is comprised of gas-filled microspheres that are injected or infused into the body. When exposed to ultrasound waves, the microspheres resonate and "echo" strong signals back to the ultrasound machine. The difference in density between the gas-filled bubbles and the blood around them creates an increased level of contrast visible in the resulting ultrasound image. During echocardiography, activated Perflutren enhances images of the inner edges or borders of the heart, producing an improved image that may enable physicians to better diagnose patients.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

OFP is not metabolized. The phospholipid components of the microspheres are thought to be metabolized to free fatty acids.

Route of eliminationNot Available
Half lifeThe mean half-life of OFP in blood 1.9 minutes
ClearanceNot Available
ToxicityThere is new temporal evidence that perflutren may be associated with new-onset seizure activity following perflutren microbubble contrast injection during dobutamine-atropine stress echocardiography. [PMID: 23432576]
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9954
Blood Brain Barrier + 0.9907
Caco-2 permeable + 0.6518
P-glycoprotein substrate Non-substrate 0.8894
P-glycoprotein inhibitor I Non-inhibitor 0.9583
P-glycoprotein inhibitor II Non-inhibitor 0.9396
Renal organic cation transporter Non-inhibitor 0.9256
CYP450 2C9 substrate Non-substrate 0.865
CYP450 2D6 substrate Substrate 0.5549
CYP450 3A4 substrate Non-substrate 0.7591
CYP450 1A2 substrate Non-inhibitor 0.6831
CYP450 2C9 substrate Non-inhibitor 0.8595
CYP450 2D6 substrate Non-inhibitor 0.9581
CYP450 2C19 substrate Non-inhibitor 0.8397
CYP450 3A4 substrate Non-inhibitor 0.9509
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9136
Ames test Non AMES toxic 0.9656
Carcinogenicity Carcinogens 0.6661
Biodegradation Not ready biodegradable 0.944
Rat acute toxicity 1.6879 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9796
hERG inhibition (predictor II) Non-inhibitor 0.9174
Pharmacoeconomics
Manufacturers
  • Lantheus medical imaging inc
Packagers
Dosage forms
FormRouteStrength
SuspensionIntravenous
Prices
Unit descriptionCostUnit
Optison vial56.16USDml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
CountryPatent NumberApprovedExpires (estimated)
United States60336451996-06-192016-06-19
United States61466571992-12-222009-12-22
Canada22565922010-06-012017-06-16
Canada21074662001-07-032012-03-18
Properties
Stateliquid
Experimental Properties
PropertyValueSource
melting point-147.6 °CPhysProp
boiling point-36.6 °CPhysProp
water solubility5.7 mg/L (at 15 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP3Not Available
Predicted Properties
PropertyValueSource
water solubility1.46e-01 g/lALOGPS
logP2.96ALOGPS
logP2.78ChemAxon
logS-3.1ALOGPS
physiological charge0ChemAxon
hydrogen acceptor count0ChemAxon
hydrogen donor count0ChemAxon
polar surface area0ChemAxon
rotatable bond count2ChemAxon
refractivity17.54ChemAxon
polarizability7.1ChemAxon
number of rings0ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterNoChemAxon
Veber's ruleYesChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

James L. Webster, Steven H. Swearingen, Douglas W. Bruhnke, Leo E. Manzer, Elrey L. McCann, “Synthesis of perfluoropropane.” U.S. Patent US5220083, issued August, 1967.

US5220083
General Reference
  1. Quinones A, Benenstein R, Saric M: New-Onset Seizure after Perflutren Microbubble Injection during Dobutamine Stress Echocardiography. Echocardiography. 2013 Feb 22. doi: 10.1111/echo.12149. Pubmed
External Links
ResourceLink
KEGG DrugD01738
ChEBI31980
ChEMBLCHEMBL1663
PharmGKBPA164781354
Drug Product Database2243173
RxListhttp://www.rxlist.com/cgi/generic3/definity.htm
Drugs.comhttp://www.drugs.com/cdi/perflutren-lipid-microspheres.html
WikipediaOctafluoropropane
ATC CodesNot Available
AHFS Codes
  • 92:00.00
PDB EntriesNot Available
FDA labelshow(584 KB)
MSDSshow(64 KB)
Interactions
Drug Interactions
Drug
ArtemetherAdditive QTc-prolongation may occur. Concomitant therapy should be avoided.
LumefantrineAdditive QTc-prolongation may occur. Concomitant therapy should be avoided.
TacrolimusAdditive QTc-prolongation may occur increasing the risk of serious ventricular arrhythmias. Concomitant therapy should be used with caution.
ThiothixeneMay cause additive QTc-prolonging effects. Increased risk of ventricular arrhythmias. Consider alternate therapy. Thorough risk:benefit assessment is required prior to co-administration.
ToremifeneAdditive QTc-prolongation may occur, increasing the risk of serious ventricular arrhythmias. Consider alternate therapy. A thorough risk:benefit assessment is required prior to co-administration.
TrimipramineAdditive QTc-prolongation may occur, increasing the risk of serious ventricular arrhythmias. Concomitant therapy should be used with caution.
VoriconazoleAdditive QTc prolongation may occur. Consider alternate therapy or monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).
VorinostatAdditive QTc prolongation may occur. Consider alternate therapy or monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).
ZiprasidoneAdditive QTc-prolonging effects may increase the risk of severe arrhythmias. Concomitant therapy is contraindicated.
ZuclopenthixolAdditive QTc prolongation may occur. Consider alternate therapy or use caution and monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).
Zuclopenthixol acetateAdditive QTc prolongation may occur. Consider alternate therapy or use caution and monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).
Zuclopenthixol decanoateAdditive QTc prolongation may occur. Consider alternate therapy or use caution and monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).
Food InteractionsNot Available
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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:11