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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
1,1,1,2,2,3,3,3-OctafluoropropaneNot AvailableNot Available
DefinityNot AvailableNot Available
FC 218Not AvailableNot Available
Freon 218Not AvailableNot Available
OctafluoropropaneNot AvailableNot Available
OctafluorpropanNot AvailableNot Available
OktafluorpropanNot AvailableNot Available
PerfluoropropaneNot AvailableNot Available
PerflutrenNot AvailableNot Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Definityinjection, suspension6.52 mg/mLintravenousLantheus Medical Imaging, Inc.2001-07-31Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Definitysuspension150 µlintravenousLantheus Mi Canada IncNot AvailableNot AvailableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot 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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as organofluorides. These are compounds containing a chemical bond between a carbon atom and a fluorine atom.
KingdomOrganic compounds
Super ClassOrganohalogen compounds
ClassOrganofluorides
Sub ClassNot Available
Direct ParentOrganofluorides
Alternative Parents
Substituents
  • Hydrocarbon derivative
  • Organofluoride
  • Alkyl halide
  • Alkyl fluoride
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
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
PropertyValueProbability
Human Intestinal Absorption+0.9954
Blood Brain Barrier+0.9907
Caco-2 permeable+0.6518
P-glycoprotein substrateNon-substrate0.8894
P-glycoprotein inhibitor INon-inhibitor0.9583
P-glycoprotein inhibitor IINon-inhibitor0.9396
Renal organic cation transporterNon-inhibitor0.9256
CYP450 2C9 substrateNon-substrate0.865
CYP450 2D6 substrateSubstrate0.5549
CYP450 3A4 substrateNon-substrate0.7591
CYP450 1A2 substrateNon-inhibitor0.6831
CYP450 2C9 substrateNon-inhibitor0.8595
CYP450 2D6 substrateNon-inhibitor0.9581
CYP450 2C19 substrateNon-inhibitor0.8397
CYP450 3A4 substrateNon-inhibitor0.9509
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9136
Ames testNon AMES toxic0.9656
CarcinogenicityCarcinogens 0.6661
BiodegradationNot ready biodegradable0.944
Rat acute toxicity1.6879 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9796
hERG inhibition (predictor II)Non-inhibitor0.9174
Pharmacoeconomics
Manufacturers
  • Lantheus medical imaging inc
Packagers
Dosage forms
FormRouteStrength
Injection, suspensionintravenous6.52 mg/mL
Suspensionintravenous150 µl
Prices
Unit descriptionCostUnit
Optison vial56.16USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
CountryPatent NumberApprovedExpires (estimated)
Canada21074662001-07-032012-03-18
Canada22565922010-06-012017-06-16
United States60336451996-06-192016-06-19
United States61466571992-12-222009-12-22
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 Solubility0.146 mg/mLALOGPS
logP2.96ALOGPS
logP2.78ChemAxon
logS-3.1ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity17.54 m3·mol-1ChemAxon
Polarizability7.1 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (7.49 KB)
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
ATC CodesNot Available
AHFS Codes
  • 92:00.00
PDB EntriesNot Available
FDA labelDownload (584 KB)
MSDSDownload (64 KB)
Interactions
Drug Interactions
Drug
MifepristoneMay enhance the QTc-prolonging effect of Moderate Risk QTc-Prolonging Agents.
Food InteractionsNot Available
Comments
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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:11