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

Molecular Formula	C5F12
Molecular Weight	288.0343
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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 72 Sources: http://ec.europa.eu/health/documents/community-register/1998/199807173235/anx_3235_en.pdf	Diagnostic		Approved 8583	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

AUC

Value	Dose	Analyte	Population
8.3 mg × min/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11368867/	0.01 mL/kg single, intravenous dose: 0.01 mL/kg route of administration: Intravenous experiment type: SINGLE co-administered:	PERFLENAPENT blood	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status:
10 mg × min/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11368867/	0.02 mL/kg single, intravenous dose: 0.02 mL/kg route of administration: Intravenous experiment type: SINGLE co-administered:	PERFLENAPENT blood	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
21.8 mg × min/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11368867/	0.05 mL/kg single, intravenous dose: 0.05 mL/kg route of administration: Intravenous experiment type: SINGLE co-administered:	PERFLENAPENT blood	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
42.6 mg × min/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11368867/	0.1 mL/kg single, intravenous dose: 0.1 mL/kg route of administration: Intravenous experiment type: SINGLE co-administered:	PERFLENAPENT blood	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
2.5 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11368867/	0.01 mL/kg single, intravenous dose: 0.01 mL/kg route of administration: Intravenous experiment type: SINGLE co-administered:	PERFLENAPENT blood	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status:
2.1 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11368867/	0.02 mL/kg single, intravenous dose: 0.02 mL/kg route of administration: Intravenous experiment type: SINGLE co-administered:	PERFLENAPENT blood	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1.8 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11368867/	0.05 mL/kg single, intravenous dose: 0.05 mL/kg route of administration: Intravenous experiment type: SINGLE co-administered:	PERFLENAPENT blood	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
2.3 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11368867/	0.1 mL/kg single, intravenous dose: 0.1 mL/kg route of administration: Intravenous experiment type: SINGLE co-administered:	PERFLENAPENT blood	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
0.05 mL/kg single, intravenous Studied dose Dose: 0.05 mL/kg Route: intravenous Route: single Dose: 0.05 mL/kg Sources: https://pubmed.ncbi.nlm.nih.gov/9609895/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/9609895/	Sources: https://pubmed.ncbi.nlm.nih.gov/9609895/

PubMed

Title	Date	PubMed
Delivery of water-soluble drugs using acoustically triggered perfluorocarbon double emulsions.	2010-12	20872050
An in vitro study of a phase-shift nanoemulsion: a potential nucleation agent for bubble-enhanced HIFU tumor ablation.	2010-11	20888685
Initial investigation of acoustic droplet vaporization for occlusion in canine kidney.	2010-10	20800939
In vitro characterization of perfluorocarbon droplets for focused ultrasound therapy.	2010-09-07	20693614
Delivery of chlorambucil using an acoustically-triggered perfluoropentane emulsion.	2010-08	20691925
Fluid adsorption in ordered mesoporous solids determined by in situ small-angle X-ray scattering.	2010-07-14	20490405
Adsorption in periodically ordered mesoporous organosilica materials studied by in situ small-angle X-ray scattering and small-angle neutron scattering.	2010-05-04	20201568
Comparison of surfactants used to prepare aqueous perfluoropentane emulsions for pharmaceutical applications.	2010-04-06	20218695
Hypoxia due to shunts in pig lung treated with O2 and fluorocarbon-derived intravascular microbubbles.	2010-04	20196682
Partitioning and phase equilibria of PEGylated excipients in fluorinated liquids.	2010-03-15	19995596
Helical C(2) structure of perfluoropentane and the C(2v) structure of perfluoropropane.	2010-01-21	20014813
Preparation and characterization of dextran nanobubbles for oxygen delivery.	2009-11-03	19616610
Development and evaluation of perfluorocarbon nanobubbles for apomorphine delivery.	2009-10	19156914
Comparative studies of pentacene and perfluoropentacene grown on a Bi(0001) surface.	2009-03-04	19417500
Environmental hazards and health risk of common liquid perfluoro-n-alkanes, potent greenhouse gases.	2009-02	18845341
In vitro comparison of dodecafluoropentane (DDFP), perfluorodecalin (PFD), and perfluoroctylbromide (PFOB) in the facilitation of oxygen exchange.	2009	19548131
Ultrasound enhanced prehospital thrombolysis using microbubbles infusion in patients with acute ST elevation myocardial infarction: rationale and design of the Sonolysis study.	2008-12-10	19068143
Elaborating the phase behaviour of ethylene oxide oligomers and analogues in 2H, 3H-perfluoropentane.	2008-10-01	18601989
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.	2008-05	18416935
Towards aberration correction of transcranial ultrasound using acoustic droplet vaporization.	2008-03	17935872
Determination of reference ultrasound parameters for model and hydrofluoroalkane propellants using high-resolution ultrasonic spectroscopy.	2008	18459053
A study of the formulation design of acoustically active lipospheres as carriers for drug delivery.	2007-08	17320362
Multifunctional nanoparticles for combining ultrasonic tumor imaging and targeted chemotherapy.	2007-07-18	17623798
Surfactant design for the 1,1,1,2-tetrafluoroethane-water interface: ab initio calculations and in situ high-pressure tensiometry.	2006-10-10	17014104
Value of adenosine infusion for infarct size determination using real-time myocardial contrast echocardiography.	2006-02-08	16466579
Spatial control of gas bubbles and their effects on acoustic fields.	2006-01	16364801
Intravascular fluorocarbon-stabilized microbubbles protect against fatal anemia in rats.	2006	16893811
Towards an understanding of adsorption behaviour in non-aqueous systems: adsorption of poly(vinyl pyrrolidone) and poly(ethylene glycol) onto silica from 2H, 3H-perfluoropentane.	2005-11	16259769
Tissue nitrogen elimination in oxygen-breathing pigs is enhanced by fluorocarbon-derived intravascular micro-bubbles.	2005-10-22	16238071
High-pressure aerosol suspensions--a novel laser diffraction particle sizing system for hydrofluoroalkane pressurised metered dose inhalers.	2005-09-30	16102928
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.	2005-09-15	15964732
Explaining the phase behaviour of the pharmaceutically relevant polymers poly(ethylene glycol) and poly(vinyl pyrrolidone) in semi-fluorinated liquids.	2005-08	16102252
Surface energy and interparticle forces correlations in model pMDI formulations.	2005-05	15906178
Sound speed estimation using automatic ultrasound image registration.	2004-09	15478971
Combination of contrast with stress echocardiography: a practical guide to methods and interpretation.	2004-08-26	15331015
On the acoustic vaporization of micrometer-sized droplets.	2004-07	15295987
The theory and application of intravascular microbubbles as an ultra-effective means of transporting oxygen and other gases.	2004	15233165
HPFP, a model propellant for pMDIs.	2003-01	12602491
Lithotripter shock waves with cavitation nucleation agents produce tumor growth reduction and gene transfer in vivo.	2002-10	12467861
Radiosensitization of hypoxic tumor cells by dodecafluoropentane: a gas-phase perfluorochemical emulsion.	2002-07-01	12097264
In vivo droplet vaporization for occlusion therapy and phase aberration correction.	2002-06	12075966
[Safety and efficiency of Echogen. Transthoracic echocardiography study].	2001-07-04	11432089
Human pharmacokinetics of a perfluorocarbon ultrasound contrast agent evaluated with gas chromatography.	2001-04	11368867

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).

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:01:47 GMT 2025` Edited by `admin` on `Mon Mar 31 18:01:47 GMT 2025`
Record UNII	483AU1Y5CZ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

Dodecafluoropentane

Preferred Name

English

PERFLENAPENT

Official Name

English

DODECAFLUOROPENTANE [EMA EPAR]

Common Name

English

PERFLENAPENT [USAN]

Common Name

English

PERFLENAPENT [MART.]

Common Name

English

NVX-108

Code

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