Perflutren

Identification

Summary

Perflutren is a diagnostic medication to improve contrast during echocardiograms.

Brand Names
Definity, Luminity, Optison
Generic Name
Perflutren
DrugBank Accession Number
DB00556
Background

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.

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 188.0193
Monoisotopic: 187.98722564
Chemical Formula
C3F8
Synonyms
  • 1,1,1,2,2,3,3,3-octafluoropropane
  • Freon 218
  • Octafluoropropane
  • Octafluorpropan
  • Oktafluorpropan
  • Perfluoropropane
  • Perflutren
  • Perflutreno
External IDs
  • DMP 115
  • DMP-115
  • FC 218
  • FS-069
  • FS069
  • MRX-115

Pharmacology

Indication

Used as an ultrasound contrast imaging in cardiology and radiology.

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Perflutren, 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 action

Perflutren 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.

Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

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

Route of elimination

Not Available

Half-life

The mean half-life of OFP in blood 1.9 minutes

Clearance

Not Available

Adverse Effects
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Toxicity

There 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]

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
AcrivastineThe risk or severity of QTc prolongation can be increased when Acrivastine is combined with Perflutren.
AdenosineThe risk or severity of QTc prolongation can be increased when Perflutren is combined with Adenosine.
AjmalineThe risk or severity of QTc prolongation can be increased when Ajmaline is combined with Perflutren.
AlfuzosinThe risk or severity of QTc prolongation can be increased when Alfuzosin is combined with Perflutren.
AlimemazineThe risk or severity of QTc prolongation can be increased when Alimemazine is combined with Perflutren.
AmantadineThe risk or severity of QTc prolongation can be increased when Amantadine is combined with Perflutren.
AmifampridineThe risk or severity of QTc prolongation can be increased when Perflutren is combined with Amifampridine.
AmiodaroneThe risk or severity of QTc prolongation can be increased when Perflutren is combined with Amiodarone.
AmisulprideThe risk or severity of QTc prolongation can be increased when Amisulpride is combined with Perflutren.
AmitriptylineThe risk or severity of QTc prolongation can be increased when Amitriptyline is combined with Perflutren.
Interactions
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Food Interactions
No interactions found.

Products

Products
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International/Other Brands
Optison
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
DefinitySuspension150 mcL / mLIntravenousLantheus Mi Canada Inc2002-02-16Not applicableCanada flag
DefinityInjection, suspension6.52 mg/1mLIntravenousLantheus Medical Imaging, Inc.2001-07-31Not applicableUS flag
Definity RTInjection, suspension6.52 mg/1mLIntravenousLantheus Medical Imaging, Inc.2020-10-01Not applicableUS flag
LuminityInjection, solution150 μl/mlIntravenousLantheus Eu Limited2016-09-08Not applicableEU flag
LuminityInjection, solution150 μl/mlIntravenousLantheus Eu Limited2016-09-08Not applicableEU flag
Optison0.19 mg/mlIntravenousGe Healthcare As2020-12-21Not applicableEU flag
Optison0.19 mg/mlIntravenousGe Healthcare As2020-12-21Not applicableEU flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Optison Perflutren Protein-Type A MicrospheresPerflutren (0.22 mg/1mL) + Human albumin microspheres (10 mg/1mL)Injection, solutionIntravenousGE Healthcare Inc.2002-01-02Not applicableUS flag

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This 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.
Kingdom
Organic compounds
Super Class
Organohalogen compounds
Class
Organofluorides
Sub Class
Not Available
Direct Parent
Organofluorides
Alternative Parents
Hydrocarbon derivatives / Alkyl fluorides
Substituents
Aliphatic acyclic compound / Alkyl fluoride / Alkyl halide / Hydrocarbon derivative / Organofluoride
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
fluorocarbon (CHEBI:31980)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
CK0N3WH0SR
CAS number
76-19-7
InChI Key
QYSGYZVSCZSLHT-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

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 References
  1. Quinones A, Benenstein R, Saric M: New-onset seizure after perflutren microbubble injection during dobutamine stress echocardiography. Echocardiography. 2013 Apr;30(4):E95-7. doi: 10.1111/echo.12149. Epub 2013 Feb 22. [Article]
  2. FDA Approved Drug Products: Optison (perflutren protein-t ype A microspheres) suspension for intravenous injection [Link]
Human Metabolome Database
HMDB0014696
KEGG Drug
D01738
PubChem Compound
6432
PubChem Substance
46506030
ChemSpider
6192
RxNav
283753
ChEBI
31980
ChEMBL
CHEMBL1663
ZINC
ZINC000008214651
PharmGKB
PA164781354
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Octafluoropropane
FDA label
Download (584 KB)
MSDS
Download (64 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedNot AvailableEchocardiography1
4CompletedDiagnosticAtrial Fibrillation1
4CompletedDiagnosticBreast Cancer1
4CompletedDiagnosticCardiac Allograft Vasculopathy1
4CompletedDiagnosticCardiovascular Disease (CVD) / Coronary Artery Disease (CAD)1
4CompletedDiagnosticKidney Transplantation1
4CompletedDiagnosticPulmonary Heart Disease1
4CompletedDiagnosticPulmonary Hypertension (PH)1
4CompletedDiagnosticVentricular Ejection Fraction1
4CompletedOtherCardiovascular Disease (CVD)1

Pharmacoeconomics

Manufacturers
  • Lantheus medical imaging inc
Packagers
  • Bristol-Myers Squibb Co.
  • Concorde Specialty Gases Inc.
  • GE Healthcare Inc.
  • Lantheus Medical Imaging Inc.
Dosage Forms
FormRouteStrength
Tablet, coatedOral500 mg
Injection, suspensionIntravenous6.52 mg/1mL
SuspensionIntravenous150 mcL / mL
Gas; injection, suspensionIntravenous
Injection, solutionIntravenous150 μl/ml
Injection, suspensionIntravenous
Injection, solutionIntravenous
Prices
Unit descriptionCostUnit
Optison vial56.16USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US6146657No2000-11-142009-12-22US flag
CA2256592No2010-06-012017-06-16Canada flag
CA2107466No2001-07-032012-03-18Canada flag
US6723303No2004-04-202021-04-20US flag
US6033645No2000-03-072016-06-19US flag
US8685441No2014-04-012019-01-13US flag
US8658205No2014-02-252019-04-20US flag
US9545457No2017-01-172019-01-13US flag
US9789210No2017-10-172037-03-16US flag
US10588988No2017-05-042037-05-04US flag
US10583207No2015-12-282035-12-28US flag
US10583208No2017-03-162037-03-16US flag
US10022460No2015-12-282035-12-28US flag

Properties

State
Liquid
Experimental Properties
PropertyValueSource
melting point (°C)-147.6 °CPhysProp
boiling point (°C)-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 FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
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 inhibitorNon-inhibitor0.8595
CYP450 2D6 inhibitorNon-inhibitor0.9581
CYP450 2C19 inhibitorNon-inhibitor0.8397
CYP450 3A4 inhibitorNon-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
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (7.49 KB)
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

Drug created on June 13, 2005 13:24 / Updated on July 24, 2021 14:58