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Perflutren

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Chemistry

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Also known as: Perfluoropropane, Octafluoropropane, Definity, 76-19-7, Propane, octafluoro-, 1,1,1,2,2,3,3,3-octafluoropropane

Molecular Formula

C₃F₈

Molecular Weight

188.02 g/mol

InChI Key

QYSGYZVSCZSLHT-UHFFFAOYSA-N

FDA UNII

CK0N3WH0SR

Perflutren Lipid Microspheres is an injectable suspension of liposome-encapsuled microspheres containing the fluorocarbon gas perflutren for contrast enhancement in ultrasound procedures. Because the acoustic impedance of perflutren lipid microspheres is much lower than that of blood, impinging ultrasound waves are scattered and reflected at the microsphere-blood interface and may be visualized with ultrasound imaging.

Perflutren is a Contrast Agent for Ultrasound Imaging. The mechanism of action of perflutren is as an Ultrasound Contrast Activity.

1 2D Structure

Perflutren

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

1,1,1,2,2,3,3,3-octafluoropropane

2.1.2 InChI

InChI=1S/C3F8/c4-1(5,2(6,7)8)3(9,10)11

2.1.3 InChI Key

QYSGYZVSCZSLHT-UHFFFAOYSA-N

2.1.4 Canonical SMILES

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

2.2 Other Identifiers

2.2.1 UNII

CK0N3WH0SR

2.3 Synonyms

2.3.1 MeSH Synonyms

1. C3f8-gas

2. Definity

3. Mrx-115

4. Octafluoropropane

5. Perfluoropropane

2.3.2 Depositor-Supplied Synonyms

1. Perfluoropropane

2. Octafluoropropane

3. Definity

4. 76-19-7

5. Propane, Octafluoro-

6. 1,1,1,2,2,3,3,3-octafluoropropane

7. Freon 218

8. Optison

9. Oktafluorpropan

10. Genetron 218

11. Dmp 115

12. Mrx-115

13. Octafluorpropan

14. 9048-46-8

15. Fc 218

16. Fc 218 (refrigerant)

17. Bovine Serum Albumin

18. Fs069

19. Hfc 218

20. Pfc 218

21. Un 2424

22. Dmp-115

23. R 218

24. Fs-069

25. Ck0n3wh0sr

26. Luminity

27. Chebi:31980

28. Perflutren [usan]

29. Propane, 1,1,1,2,2,3,3,3-octafluoro-

30. C3f8-gas

31. Perflutren Lipid Microsphere

32. Einecs 200-941-9

33. Unii-ck0n3wh0sr

34. Un2424

35. Perflutren Lipid Microspheres

36. Bovine Albumin

37. Perflutren [usan:inn:ban]

38. C3f8

39. Hsdb 8074

40. Octafluoro-propane

41. Definity (tn)

42. Mfcd00039239

43. Optison (salt/mix)

44. Perflutren [ii]

45. Perflutren [inn]

46. Perflutren [jan]

47. Perflutren [vandf]

48. Ec 200-941-9

49. Perflutren-lipid Microsphere

50. Perflutren [mart.]

51. Perflutren Protein-type A Microspheres Injection

52. Chembl1663

53. Perflutren [who-dd]

54. Perfluoropropane [mi]

55. Perflutren (jan/usan/inn)

56. Perflutren [ema Epar]

57. Perfluoropropane [inci]

58. Dtxsid9052503

59. Perflutren [orange Book]

60. Octafluoropropane [vandf]

61. Oxtafluoropropane [vandf]

62. Amy6865

63. Mrx 115

64. Octafluoropropane-lipid Microsphere

65. Ym454

66. Zinc8214651

67. Akos006228213

68. Db00556

69. Fs-6566

70. Octafluoropropaneor Refrigerant Gas R 218

71. Db-056033

72. Ft-0621948

73. Ft-0631321

74. Liposome-encapsulated Perfluoropane Microsphere

75. 1,1,1,2,2,3,3,3-octakis(fluoranyl)propane

76. D01738

77. A838638

78. Q412659

79. Octafluoropropaneor Refrigerant Gas R 218 [un2424] [nonflammable Gas]

2.4 Create Date

2005-03-27

3 Chemical and Physical Properties

Molecular Formula	C₃F₈
Molecular Weight	188.02 g/mol
XLogP3	3.1
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	0
Exact Mass	187.98722530 g/mol
Monoisotopic Mass	187.98722530 g/mol
Topological Polar Surface Area	0 Å²
Heavy Atom Count	11
Formal Charge	0
Complexity	120
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 4
Drug Name	Definity
PubMed Health	Perflutren Lipid Microsphere (Injection)
Drug Classes	Radiological Non-Ionic Contrast Media
Active Ingredient	Perflutren
Dosage Form	Injectable
Route	Intravenous
Strength	6.52mg/ml
Market Status	Prescription
Company	Lantheus Medcl

2 of 4
Drug Name	Optison
PubMed Health	Perflutren Protein Type A Microsphere (Injection)
Drug Classes	Diagnostic Agent, Cardiac Function
Active Ingredient	Albumin human
Dosage Form	Injectable
Route	Injection
Strength	10mg/ml
Market Status	Prescription
Company	Ge Healthcare

3 of 4
Drug Name	Definity
PubMed Health	Perflutren Lipid Microsphere (Injection)
Drug Classes	Radiological Non-Ionic Contrast Media
Active Ingredient	Perflutren
Dosage Form	Injectable
Route	Intravenous
Strength	6.52mg/ml
Market Status	Prescription
Company	Lantheus Medcl

4 of 4
Drug Name	Optison
PubMed Health	Perflutren Protein Type A Microsphere (Injection)
Drug Classes	Diagnostic Agent, Cardiac Function
Active Ingredient	Albumin human
Dosage Form	Injectable
Route	Injection
Strength	10mg/ml
Market Status	Prescription
Company	Ge Healthcare

4.2 Therapeutic Uses

Contrast Media; Fluorocarbons

National Library of Medicine's Medical Subject Headings online file (MeSH, 2009)

THERAPEUTIC CATEGORY: Diagnostic aid (ultrasound contrast agent). Adjunct in repair of retinal detachment

O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 1236

Activated Perflutren Lipid Microsphere Injectable Suspension is indicated for use in patients with suboptimal echocardiograms to opacify the left ventricular chamber and to improve the delineation of the left ventricular endocardial border. /Included in US product label/

US Natl Inst Health; DailyMed. Current Medication Information for DEFINITY (perflutren) injection, suspension (October 2011). Available from, as of June 1, 2012: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=8ab9c79c-1b5c-4e86-899c-cc74686f070a

4.3 Drug Warning

/BOXED WARNING/ Serious cardiopulmonary reactions, including fatalities, have occurred uncommonly during or following perflutren-containing microsphere administration. Most serious reactions occur within 30 minutes of administration. Assess all patients for the presence of any condition that precludes perflutren-containing microsphere administration. Always have resuscitation equipment and trained personnel readily available.

Do not administer Perflutren to patients with known or suspected: right-to-left, bi-directional, or transient right-to-left cardiac shunts; hpersensitivity to perflutren. Do not administer Perflutren by intra-arterial injection.

Serious cardiopulmonary reactions including fatalities have occurred uncommonly during or shortly following perflutren-containing microsphere administration, typically within 30 minutes of administration. The risk for these reactions may be increased among patients with unstable cardiopulmonary conditions (acute myocardial infarction, acute coronary artery syndromes, worsening or unstable congestive heart failure, or serious ventricular arrhythmias). Always have cardiopulmonary resuscitation personnel and equipment readily available prior to Perflutren administration and monitor all patients for acute reactions. The reported reactions include: fatal cardiac or respiratory arrest, shock, syncope, symptomatic arrhythmias (atrial fibrillation, tachycardia, bradycardia, supraventricular tachycardia, ventricular fibrillation, ventricular tachycardia), hypertension, hypotension, dyspnea, hypoxia, chest pain, respiratory distress, stridor, wheezing, loss of consciousness, and convulsions.

In postmarketing use, uncommon but serious anaphylactoid reactions were observed during or shortly following perflutren-containing microsphere administration including: Shock, hypersensitivity, bronchospasm, throat tightness, angioedema, edema (pharyngeal, palatal, mouth, peripheral, localized), swelling (face, eye, lip, tongue, upper airway), facial hypoesthesia, rash, urticaria, pruritus, flushing, and erythema have occurred in patients with no prior exposure to perflutren-containing microsphere products.

For more Drug Warnings (Complete) data for Octafluoropropane (17 total), please visit the HSDB record page.

4.4 Drug Indication

Used as an ultrasound contrast imaging in cardiology and radiology.

FDA Label

This medicinal product is for diagnostic use only.

Luminity is an ultrasound contrast-enhancing agent for use in patients in whom non-contrast echocardiography was suboptimal (suboptimal is considered to indicate that at least two of six segments in the 4- or 2-chamber view of the ventricular border were not evaluable) and who have suspected or established coronary artery disease, to provide opacification of cardiac chambers and improvement of left ventricular endocardial border delineation at both rest and stress.

This medicinal product is for diagnostic use only.

Optison 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-endocardial-border delineation with resulting improvement in wall-motion visualisation.

Optison should only be used in patients where the study without contrast enhancement is inconclusive.

5 Pharmacology and Biochemistry

5.1 Pharmacology

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.

5.2 MeSH Pharmacological Classification

Contrast Media

Substances used to allow enhanced visualization of tissues. (See all compounds classified as Contrast Media.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

PERFLUTREN

5.3.2 FDA UNII

CK0N3WH0SR

5.3.3 Pharmacological Classes

Ultrasound Contrast Activity [MoA]; Contrast Agent for Ultrasound Imaging [EPC]

5.4 ATC Code

V08DA04

V08DA01

5.5 Absorption, Distribution and Excretion

Human pharmacokinetics information is not available for the intact or degassed lipid microspheres. The pharmacokinetics of octafluoropropane gas (OFP) was evaluated in healthy subjects (n=8) after the IV administration of activated perflutren-containing microspheres at a 50 uL/kg dose. ... OFP was not detectable after 10 minutes in most subjects either in the blood or in expired air.

OFP gas binding to plasma proteins or partitioning into blood cells has not been studied. However, OFP protein binding is expected to be minimal due to its low partition coefficient into whole blood.

It is not known whether perflutren-containing microspheres are excreted in human milk.

A physiologically based pharmacokinetic model was developed to evaluate the kinetics of one of the newest sonographic contrast agents available, FS069 or Optison. This material consists of octafluoropropane gas encapsulated in proteinaceous microspheres, injected intravenously for use as a myocardial contrast agent in humans. This model has six compartments: two lung compartments (alveolar and dead volume), and compartments for the heart, slowly perfused tissue, richly perfused tissue, and gastrointestinal tract. The model was developed to determine the distribution and excretion of the octafluoropropane in the body. Despite the high affinity of octafluoropropane for tissue, the model predicted that nearly 100% of the material would be exhaled from the lungs within 6 min. The model verified the results of a phase I clinical trial with 10 healthy subjects. Ventilation rate was found to play a critical role in the complete excretion of this contrast agent. ...

PMID:9952073 Hutter JC et al; J Ultrasound Med 18 (1): 1-11 (1999)

5.6 Metabolism/Metabolites

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

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

5.7 Biological Half-Life

The mean half-life of OFP in blood 1.9 minutes

OFP concentrations in blood were shown to decline in a mono-exponential fashion with a mean half-life of 1.3 minutes in healthy subjects.

The pharmacokinetics of octafluoropropane gas (OFP) was evaluated in subjects (n=11) with chronic obstructive pulmonary disease (COPD). The mean half-life of OFP in blood was 1.9 minutes. The total lung clearance of OFP was similar to that in healthy subjects.

5.8 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.

Perflutren lipid microspheres exhibit lower acoustic impedance than blood and enhance the intrinsic backscatter of blood. These physical acoustic properties of activated perflutren-containing microspheres provide contrast enhancement of the left ventricular chamber and aid delineation of the left ventricular endocardial border during echocardiography.

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