PERFLENAPENT

Details

Stereochemistry	ACHIRAL
Molecular Formula	C5F12
Molecular Weight	288.0343
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F

InChI

InChIKey=NJCBUSHGCBERSK-UHFFFAOYSA-N

InChI=1S/C5F12/c6-1(7,2(8,9)4(12,13)14)3(10,11)5(15,16)17

HIDE SMILES / InChI

Description
Sources: http://ec.europa.eu/health/documents/community-register/1998/199807173235/anx_3235_en.pdf
Curator's Comment: Description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/9383597 and http://www.thepharmaletter.com/article/first-approval-for-sonus-echogen

Perflenapent (EchoGen, Sonus Pharmaceuticals, Bothel, WA, USA) is a transpulmonary echocardiographic contrast agent for use in patients with suspected or established cardiovascular disease to provide opacification of cardiac chambers, enhance left ventricular border delineation with resulting improvement in wall motion visualisation. EchoGen comprises liquid droplets of dodecafluoropentane stabilised by polyfluoroalkyl(polyoxyethylene) ethanol and dispersed in an aqueous formulation containing sucrose. Dodecafluoropentane is the chemical name used to reflect the perflenapent/perflisopent mixture. Following activation and administration of EchoGen, dodecafluoropentane microbubbles are formed. EchoGen should only be used in patients where the study without contrast enhancement is inconclusive. The European Commission has approved SONUS Pharmaceuticals' EchoGen (perflenapent emulsion) in all 15 countries of the European Union. EchoGen is a fluorocarbon-based ultrasound contrast agent which has been approved as a transpulmonary echocardiographic contrast agent for use in patients with suspected or established cardiovascular disease who have had previous inconclusive non-contrast studies. Additional approved labeling in the EU states that the use of EchoGen in spectral and color Doppler studies was shown to enhance the visualization of blood flow across mitral, aortic and tricuspid valves in a subset of patients. In 2000 SONUS Pharmaceuticals withdrew the NDA for EchoGen in the USA.

Originator

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cardiovascular diseases 71 Sources: http://ec.europa.eu/health/documents/community-register/1998/199807173235/anx_3235_en.pdf	Diagnostic		Approved 8429	EchoGen Approved Use EchoGen is a transpulmonary echocardiographic contrast agent for use in patients with suspected or established cardiovascular disease to provide opacification of cardiac chambers, enhance left ventricular border delineation with resulting improvement in wall motion visualisation. EchoGen should only be used in patients where the study without contrast enhancement is inconclusive. Launch Date 1994

PubMed

Title	Date	PubMed
Human pharmacokinetics of a perfluorocarbon ultrasound contrast agent evaluated with gas chromatography.	2001 Apr	11368867
[Safety and efficiency of Echogen. Transthoracic echocardiography study].	2001 May-Jun	11432089
Radiosensitization of hypoxic tumor cells by dodecafluoropentane: a gas-phase perfluorochemical emulsion.	2002 Jul 1	12097264
In vivo droplet vaporization for occlusion therapy and phase aberration correction.	2002 Jun	12075966
Lithotripter shock waves with cavitation nucleation agents produce tumor growth reduction and gene transfer in vivo.	2002 Oct	12467861
HPFP, a model propellant for pMDIs.	2003 Jan	12602491
Combination of contrast with stress echocardiography: a practical guide to methods and interpretation.	2004 Aug 26	15331015
On the acoustic vaporization of micrometer-sized droplets.	2004 Jul	15295987
The theory and application of intravascular microbubbles as an ultra-effective means of transporting oxygen and other gases.	2004 Spring	15233165
Explaining the phase behaviour of the pharmaceutically relevant polymers poly(ethylene glycol) and poly(vinyl pyrrolidone) in semi-fluorinated liquids.	2005 Aug	16102252
Tissue nitrogen elimination in oxygen-breathing pigs is enhanced by fluorocarbon-derived intravascular micro-bubbles.	2005 Jul-Aug	16238071
A respiration-metabolism chamber system and a GC-MS method developed for studying exhalation of perfluorobutane in rats after intravenous injection of the ultrasound contrast agent Sonazoid.	2005 Sep 15	15964732
High-pressure aerosol suspensions--a novel laser diffraction particle sizing system for hydrofluoroalkane pressurised metered dose inhalers.	2005 Sep 30	16102928
Intravascular fluorocarbon-stabilized microbubbles protect against fatal anemia in rats.	2006	16893811
Spatial control of gas bubbles and their effects on acoustic fields.	2006 Jan	16364801
Surfactant design for the 1,1,1,2-tetrafluoroethane-water interface: ab initio calculations and in situ high-pressure tensiometry.	2006 Oct 10	17014104
A study of the formulation design of acoustically active lipospheres as carriers for drug delivery.	2007 Aug	17320362
Multifunctional nanoparticles for combining ultrasonic tumor imaging and targeted chemotherapy.	2007 Jul 18	17623798
Determination of reference ultrasound parameters for model and hydrofluoroalkane propellants using high-resolution ultrasonic spectroscopy.	2008	18459053
Ultrasound enhanced prehospital thrombolysis using microbubbles infusion in patients with acute ST elevation myocardial infarction: rationale and design of the Sonolysis study.	2008 Dec 10	19068143
Towards aberration correction of transcranial ultrasound using acoustic droplet vaporization.	2008 Mar	17935872
Effect of molecular weight and end-group nature on the solubility of ethylene oxide oligomers in 2H, 3H-decafluoropentane and its fully fluorinated analogue, perfluoropentane.	2008 May	18416935
Environmental hazards and health risk of common liquid perfluoro-n-alkanes, potent greenhouse gases.	2009 Feb	18845341
Comparative studies of pentacene and perfluoropentacene grown on a Bi(0001) surface.	2009 Mar 4	19417500
Development and evaluation of perfluorocarbon nanobubbles for apomorphine delivery.	2009 Oct	19156914
Comparison of surfactants used to prepare aqueous perfluoropentane emulsions for pharmaceutical applications.	2010 Apr 6	20218695
Delivery of chlorambucil using an acoustically-triggered perfluoropentane emulsion.	2010 Aug	20691925
Delivery of water-soluble drugs using acoustically triggered perfluorocarbon double emulsions.	2010 Dec	20872050
Fluid adsorption in ordered mesoporous solids determined by in situ small-angle X-ray scattering.	2010 Jul 14	20490405
Adsorption in periodically ordered mesoporous organosilica materials studied by in situ small-angle X-ray scattering and small-angle neutron scattering.	2010 May 4	20201568
An in vitro study of a phase-shift nanoemulsion: a potential nucleation agent for bubble-enhanced HIFU tumor ablation.	2010 Nov	20888685
Initial investigation of acoustic droplet vaporization for occlusion in canine kidney.	2010 Oct	20800939
In vitro characterization of perfluorocarbon droplets for focused ultrasound therapy.	2010 Sep 7	20693614

Patents

Sample Use Guides

In Vivo Use Guide

Adults and the Elderly Administer perflenapent (EchoGen) as an intravenous bolus at a dose of 0.05 ml/kg and at a rate of 1 ml/sec.

Route of Administration: Intravenous

In Vitro Use Guide

Perflenapent (EchoGen) was negative in the in vitro structural aberration assay in human lymphocytes at the clinical dose but gave a positive result at a dose of 5,000 ug/ml (100 times the human dose).

Name

Type

Language

PERFLENAPENT

Official Name

English

DODECAFLUOROPENTANE [EMA EPAR]

Common Name

English

PERFLENAPENT [USAN]

Common Name

English

PERFLENAPENT [MART.]

Common Name

English

NVX-108

Code

English

Dodecafluoropentane

Systematic Name

English

PERFLUOROPENTANE

Systematic Name

English

PENTANE, DODECAFLUORO-

Systematic Name

English

ECHOGEN

Brand Name

English

Perflenapent [WHO-DD]

Common Name

English

perflenapent [INN]

Common Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

507515