Perflutren

Identification

Name
Perflutren
Accession Number
DB00556  (APRD01177)
Type
Small Molecule
Groups
Approved
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
  • 1,1,1,2,2,3,3,3-Octafluoropropane
  • FC 218
  • Freon 218
  • Octafluoropropane
  • Octafluorpropan
  • Oktafluorpropan
  • Perfluoropropane
  • Perflutren
External IDs
DMP 115 / DMP-115 / FS069 / MRX-115
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
DefinityInjection, suspension6.52 mg/1mLIntravenousLantheus Medical Imaging2001-07-31Not applicableUs
DefinitySuspension150 mclIntravenousLantheus Mi Canada Inc2002-02-16Not applicableCanada
LuminityInjection, solution150 μl/mlIntravenousLantheus Mi Canada Inc2006-09-20Not applicableEu
LuminityInjection, solution150 μl/mlIntravenousLantheus Mi Canada Inc2006-09-20Not applicableEu
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Optison Perflutren Protein-Type A MicrospheresPerflutren (0.22 mg/1mL) + Human albumin microspheres (10 mg/1mL)Injection, solutionIntravenousGe Healthcare2002-01-02Not applicableUs
International/Other Brands
Definity
Categories
UNII
CK0N3WH0SR
CAS number
76-19-7
Weight
Average: 188.0193
Monoisotopic: 187.98722564
Chemical Formula
C3F8
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

Pharmacology

Indication

Used as an ultrasound contrast imaging in cardiology and radiology.

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
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]

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
AbexinostatThe risk or severity of QTc prolongation can be increased when Perflutren is combined with Abexinostat.
AcebutololThe risk or severity of QTc prolongation can be increased when Perflutren is combined with Acebutolol.
AceprometazineThe risk or severity of QTc prolongation can be increased when Perflutren is combined with Aceprometazine.
AcetyldigoxinThe risk or severity of QTc prolongation can be increased when Acetyldigoxin is combined with Perflutren.
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.
AlcaftadineThe risk or severity of QTc prolongation can be increased when Alcaftadine 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.
Food Interactions
Not 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 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. [PubMed:23432576]
External Links
Human Metabolome Database
HMDB0014696
KEGG Drug
D01738
PubChem Compound
6432
PubChem Substance
46506030
ChemSpider
6192
ChEBI
31980
ChEMBL
CHEMBL1663
PharmGKB
PA164781354
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Octafluoropropane
AHFS Codes
  • 36:89.00* — Other Diagnostics
FDA label
Download (584 KB)
MSDS
Download (64 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0Active Not RecruitingDiagnosticAdult Soft Tissue Sarcoma / Retroperitoneal Sarcoma / Sarcoma, Bone1
0CompletedDiagnosticRenal Cancers1
0Not Yet RecruitingDiagnosticAsbestosis / Asthma Bronchial / Bronchiectasis / Chronic Obstructive Pulmonary Disease (COPD) / Cold Virus / Cystic Fibrosis (CF) / Emphysema / Interstitial Lung Disease (ILD) / Lung Cancers / Lung Infection / Lung Resection / Lung Transplant / Mesothelioma / Obstructive Sleep Apnea (OSA) / Pulmonary Dysplasia / Pulmonary Embolism (PE) / Pulmonary Fibrosis / Pulmonary Hypertension (PH) / Seasonal Allergies1
0RecruitingDiagnosticAdnexal Masses1
1CompletedDiagnosticHepatocellular,Carcinoma1
1RecruitingDiagnosticCancer, Breast1
1TerminatedDiagnosticNeoplasms, Hepatic1
1, 2RecruitingDiagnosticHealthy Volunteers / Physiology1
1, 2TerminatedTreatmentAcute Ischemic Stroke (AIS)1
2Active Not RecruitingDiagnosticChronic Kidney Disease (CKD) / Cystic Kidney Disease1
2Active Not RecruitingDiagnosticProstatic Neoplasms1
2CompletedDiagnosticRenal Cell Adenocarcinoma1
2RecruitingDiagnosticBlood Pressures / Cardiac Catheterizations / Echocardiography / Heart Failure, Unspecified / Heart Ventricles1
2RecruitingDiagnosticChronic Kidney Disease (CKD) / Cystic Kidney Disease1
2RecruitingTreatmentST Segment Elevation Myocardial Infarction (STEMI)1
2, 3RecruitingTreatmentExudative Macular Degeneration / Retinal Hemorrhage1
3CompletedTreatmentRetinal Detachment / Vitreoretinopathy, Proliferative1
3Not Yet RecruitingDiagnosticCardiac Diseases1
3RecruitingDiagnosticChemoembolization, Therapeutic / Hepatocellular,Carcinoma1
4Active Not RecruitingDiagnosticCancer, Breast1
4CompletedNot AvailableCardiovascular Disease (CVD)1
4CompletedDiagnosticCardiac Allograft Vasculopathy1
4CompletedDiagnosticCoronary Artery Disease / Heart Diseases1
4CompletedDiagnosticHigh Blood Pressure (Hypertension)1
4CompletedDiagnosticPulmonary Heart Disease1
4Enrolling by InvitationDiagnosticMyocardial Perfusion Imaging1
4RecruitingDiagnosticHigh Blood Pressure (Hypertension)1
Not AvailableActive Not RecruitingDiagnosticIschaemic Cardiomyopathy / Ventricular Tachycardia (VT)1
Not AvailableCompletedNot AvailableCancer, Breast1
Not AvailableCompletedNot AvailableCoronary Artery Disease / Type 2 Diabetes Mellitus1
Not AvailableCompletedNot AvailableDiabetes, Diabetes Mellitus Type 11
Not AvailableCompletedNot AvailableEndoleaks1
Not AvailableCompletedDiagnosticCerebrovascular Accidents / Intracranial Pressure Increase1
Not AvailableCompletedDiagnosticCoronary Artery Disease / Myocardial Perfusion Abnormalities1
Not AvailableCompletedDiagnosticNeoplasms, Hepatic1
Not AvailableCompletedDiagnosticRenal Cancers1
Not AvailableNot Yet RecruitingDiagnosticHepatocellular,Carcinoma1
Not AvailableRecruitingBasic ScienceExposure to Man-made Visible Light1
Not AvailableRecruitingBasic ScienceIntermittent Claudication / Peripheral Artery Disease (PAD) / Vasodilation1
Not AvailableRecruitingDiagnosticCancer, Breast1
Not AvailableTerminatedDiagnosticDuctal Carcinoma In-situ1
Not AvailableUnknown StatusDiagnosticContrast Induced Acute Kidney Injury1
Not AvailableUnknown StatusDiagnosticKidney1
Not AvailableWithdrawnDiagnosticCarotid Stenosis / Coronary Stenosis / Myocardial Reperfusion1
Not AvailableWithdrawnDiagnosticPancreatic Tumors1

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
Injection, suspensionIntravenous6.52 mg/1mL
SuspensionIntravenous150 mcl
Injection, solutionIntravenous150 μl/ml
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)
US6146657No1992-12-222009-12-22Us
CA2256592No2010-06-012017-06-16Canada
CA2107466No2001-07-032012-03-18Canada
US6723303No2001-04-202021-04-20Us
US6033645No1996-06-192016-06-19Us
US8685441No1999-01-132019-01-13Us
US8658205No1999-04-202019-04-20Us
US9545457No1999-01-132019-01-13Us
US9789210No2017-03-162037-03-16Us

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

Taxonomy

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
Hydrocarbon derivative / Organofluoride / Alkyl halide / Alkyl fluoride / Aliphatic acyclic compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
fluorocarbon (CHEBI:31980)

Drug created on June 13, 2005 07:24 / Updated on September 23, 2018 19:37