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5EXCIPIENTS BY APPLICATIONS

Chemistry

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Also known as: 63-89-8, Dppc, Dipalmitoylphosphatidylcholine, 1,2-dipalmitoyl-l-lecithin, 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine, Pc(16:0/16:0)

Molecular Formula

C₄₀H₈₀NO₈P

Molecular Weight

734.0 g/mol

InChI Key

KILNVBDSWZSGLL-KXQOOQHDSA-N

FDA UNII

319X2NFW0A

PC(16:0/16:0) is a metabolite found in or produced by Saccharomyces cerevisiae.

1 2D Structure

DPPC

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[(2R)-2,3-di(hexadecanoyloxy)propyl] 2-(trimethylazaniumyl)ethyl phosphate

2.1.2 InChI

InChI=1S/C40H80NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-39(42)46-36-38(37-48-50(44,45)47-35-34-41(3,4)5)49-40(43)33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h38H,6-37H2,1-5H3/t38-/m1/s1

2.1.3 InChI Key

KILNVBDSWZSGLL-KXQOOQHDSA-N

2.1.4 Canonical SMILES

CCCCCCCCCCCCCCCC(=O)OCC(COP(=O)([O-])OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCC

2.1.5 Isomeric SMILES

CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCC

2.2 Other Identifiers

2.2.1 UNII

319X2NFW0A

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. 63-89-8

2. Dppc

3. Dipalmitoylphosphatidylcholine

4. 1,2-dipalmitoyl-l-lecithin

5. 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine

6. Pc(16:0/16:0)

7. Colfoscerili Palmitas

8. L-dppc

9. Palmitate De Colfosceril

10. Palmitato De Colfoscerilo

11. (r)-2,3-bis(palmitoyloxy)propyl (2-(trimethylammonio)ethyl) Phosphate

12. Dppc, L-

13. Dppc, R-

14. Dipalmitoyl Lecithin, L-

15. 1,2-dipalmitoyl-sn-glycero-3-phosphorylcholine

16. Dipalmitoyl Phosphatidylcholine

17. 1,2-dihexadecanoyl-sn-glycero-3-phosphorylcholine

18. Phosphatidylcholine(32:0)

19. 1,2-dipalmitoyl-3-sn-phosphatidylcholine

20. Dipalmitoyl-phosphatidylcholine

21. 319x2nfw0a

22. Dipalmitoyl Glycerophosphocholine

23. Chebi:72999

24. 129y83

25. Phosphatidylcholine(16:0/16:0)

26. 1-16:0-2-16:0-phosphatidylcholine

27. L-a-dipalmitoyl Lecithin

28. 16:0-16:0-pc

29. Choline Hydroxide, Dihydrogen Phosphate, Inner Salt, Ester With L-1,2-dipalmitin

30. 129-y-83

31. Mfcd00036903

32. Pc 32:0

33. (2-{[(2r)-2,3-bis(hexadecanoyloxy)propyl Phosphonato]oxy}ethyl)trimethylazanium

34. 3,5,9-trioxa-4-phosphapentacosan-1-aminium, 4-hydroxy-n,n,n-trimethyl-10-oxo-7-((1-oxohexadecyl)oxy)-, Hydroxide, Inner Salt, 4-oxide, (r)-

35. L-dipalmitoyl Lecithin

36. 1,2-diacyl-sn-glycero-3-phoshocholine

37. Unii-319x2nfw0a

38. 1,2-dipalmitoyl-sn-glycero-3-phosphatidylcholine

39. 1,2-dipalmitoyl-phosphatidylcholine

40. Dipalmitoyl-gpc

41. Colfoscerilpalmitat

42. Colfoscerili Palmitas [inn-latin]

43. Colfoscerilpalmitate

44. L-alpha-dppc

45. Einecs 200-567-6

46. L-alpha-dipalmitoyl Phosphatidylcholine

47. Palmitate De Colfosceril [inn-french]

48. Colfosceril Palmitate [usan:inn:ban]

49. L-a-dipalmitoylecithin

50. L-a-dipalmitoyllecithin

51. Palmitato De Colfoscerilo [inn-spanish]

52. L-a-dppc

53. Sn-3-dipalmitoyllecithin

54. Dipalmitoyl-l-a-lecithin

55. L-alpha-dipalmitoylecithin

56. Ncgc00167568-01

57. L-alpha-dipalmitoyllecithin

58. Colfosceril [vandf]

59. Dipalmitoyl-l-alpha-lecithin

60. Dsstox_cid_26720

61. Dsstox_rid_81850

62. Dsstox_gsid_46720

63. Schembl24980

64. L-b,g-dipalmitoyl-a-lecithin

65. Mls000028586

66. Surfaxin Component Dppc

67. 1,2-dipalmitoyl-l-a-lecithin

68. L-1,2-dipalmitoyl-a-lecithin

69. L-a-1,2-dipalmitoyl Lecithin

70. Chembl1200737

71. Dtxsid5046720

72. B,g-dipalmitoyl-l-(a)-lecithin

73. Lucinactant Component Dppc

74. L-a-dipalmitoylphosphatidylcholine

75. L-b,g-dipalmitoyl-alpha-lecithin

76. Phosphatidylcholine 16:0/16:0

77. 1,2-dipalmitoyl-l-alpha-lecithin

78. Colfosceril Palmitate (usan/inn)

79. Colfosceril Palmitate [mi]

80. Hms2231h14

81. Hms3650o14

82. L-1,2-dipalmitoyl-alpha-lecithin

83. L-alpha-1,2-dipalmitoyl Lecithin

84. Colfosceril Palmitate [inn]

85. Dipalmitoyl L-a-phosphatidylcholine

86. Dipalmitoyl-l-a-phosphatidylcholine

87. Amy37583

88. L-b,g-dipalmitoylphosphatidylcholine

89. Colfosceril Palmitate [usan]

90. Dipalmitoyl-sn-3-phosphatidylcholine

91. Tox21_112563

92. B,g-dipalmitoyl-l-phosphatidylcholine

93. Colfosceril Palmitate [vandf]

94. L-1,2-dipalmitoylphosphatidylcholine

95. L-alpha-dipalmitoylphosphatidylcholine

96. Lmgp01010564

97. [(2r)-2,3-di(hexadecanoyloxy)propyl] 2-(trimethylazaniumyl)ethyl Phosphate

98. 1,2-dipalmitoyl-l-phosphatidylcholine

99. Akos016013969

100. Colfosceril Palmitate [who-dd]

101. Dipalmitoyl L-alpha-phosphatidylcholine

102. Dipalmitoyl-l-alpha-phosphatidylcholine

103. 1,2-dipalmitoyl-sn-phosphatidylcholine

104. 1,2-l-a-dipalmitoylphosphatidylcholine

105. B,g-dipalmitoyl L-a-phosphatidylcholine

106. Db09114

107. L-b,g-dipalmitoyl-a-phosphatidylcholine

108. (r)-(4-oxido-10-oxo-7-palmitoyl-3,5,9-trioxa-4-phosphapentacosyl)trimethylammonium 4-oxide

109. 1,2-dipalmitoylglycero-3-phosphocholine

110. Cas-63-89-8

111. 1,2-dipalmitoyl-l-3-phosphatidylcholine

112. 1,2-dipalmitoyl-l-a-phosphatidylcholine

113. 1,2-dipalmitoyl-sn-glycerophosphocholine

114. Dipalmitoyl-l-3-glycerylphosphorylcholine

115. Dihexadecanoyl-sn-glycero-3-phosphocholine

116. Smr000058951

117. 1,2-l-alpha-dipalmitoylphosphatidylcholine

118. Colfosceril Palmitate [orange Book]

119. 1,2-dipalmitoyl-l-alpha-phosphatidylcholine

120. 1,2-dipalmitoyl-sn-3-glycerophosphocholine

121. 1,2-dipalmitoyl-sn-glycerophosphorylcholine

122. B,g-dipalmitoyl L-alpha-phosphatidylcholine

123. Gpc(16:0/16:0)

124. Hy-109506

125. L-b,g-dipalmitoyl-alpha-phosphatidylcholine

126. Cs-0031214

127. D3925

128. 1,2-dipalmitoyl-sn-glycerol-3-phosphocholine

129. 1,2-dipalmitoyl-sn-glyceryl-3-phosphocholine

130. D03585

131. Dipalmitoyl Glycerophosphocholine [inci]

132. H10481

133. Op0201 Component Colfosceril Palmitate

134. 1,2-bis(palmitoyl)-sn-glycero-3-phosphocholine

135. Op-0201 Component Colfosceril Palmitate

136. 1,2-bis(hexadecanoyl)-sn-glycero-3-phosphocholine

137. 1,2-dihexadecanoyl-sn-glycerol-3-phosphorylcholine

138. Q5144764

139. Exosurf Neonatal Component Colfosceril Palmitate

140. 1.2 Dipalmitoyl-sn-glycero-3-phosphatidylcholine

141. Colfosceril Palmitate Component Of Exosurf Neonatal

142. 1,2-dipalmitoyl-sn-glycero-3-phosphocholine, >=99% (tlc)

143. 1.2 Dipalmitoyl-sn-glycero-3-phosphatidylcholine (dppc)

144. (r)-2,3-bis(palmitoyloxy)propyl 2-(trimethylammonio)ethyl Phosphate

145. 1,2-dipalmitoyl-sn-glycero-3-phosphocholine, Semisynthetic, >=99%

146. (2-{[2.3-bis(hexadecanoyloxy)propyl Phosphono]oxy}ethyl)trimethylazanium

147. (2r)-2,3-bis(hexadecanoyloxy)propyl 2-(trimethylammonio)ethyl Phosphate

148. (2r)-2,3-bis(hexadecanoyloxy)propyl 2-(trimethylazaniumyl)ethyl Phosphate

149. 16:0 Pc (dppc), 1,2-dipalmitoyl-sn-glycero-3-phosphocholine, Powder

150. 2-[[(2r)-2,3-di(hexadecanoyloxy)propoxy]-hydroxy-phosphoryl]oxyethyl-trimethyl-ammonium

151. (r)-4-hydroxy-n,n,n-trimethyl-10-oxo-7-[(1-oxohexadecyl)oxy]-3,5,9-trioxa-4-phosphapentacosan-1-aminium 4-oxide Hydroxide Inner Salt

152. (r)-4-hydroxy-n,n,n-trimethyl-10-oxo-7-[(1-oxohexadecyl)oxy]-3,5,9-trioxa-4-phosphapentacosan-1-aminium 4-oxide Inner Salt

2.3.2 Other Synonyms

1. Dppc

2. Dppc (dipalmitoyl Phosphatidylcholine)

3. (+-)-beta,gamma-dipalmitoyl-alpha-lecithin

4. Dihexadecanoyl Phosphatidylcholine

2.4 Create Date

2005-07-19

3 Chemical and Physical Properties

Molecular Formula	C₄₀H₈₀NO₈P
Molecular Weight	734.0 g/mol
XLogP3	13.5
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	40
Exact Mass	733.56215551 g/mol
Monoisotopic Mass	733.56215551 g/mol
Topological Polar Surface Area	111 Å²
Heavy Atom Count	50
Formal Charge	0
Complexity	826
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
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 Indication

Colfosceril palmitate is indicated for the treatment of respiratory distress syndrome (RDS) in premature infants. The official label is referred as a intratracheal suspension for prophylactic treatment of infants of less than 1350 grams of birth weight under risk of developing RDS, or in infants with birth weight greater than 1350 grams with pulmonary immaturity, or as rescue treatment of infants that already developed RDS. The central feature of RDS is a surfactant deficiency due to lung immaturity. This lung condition is more frequently presented due to risk factors like prematurity, delayed lung maturation caused by maternal diabetes or male gender, or surfactant dysfuntion due to perinatal asphyxia, pulmonary infection or delivery without labor.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Colfosceril palmitate has shown to significantly reduce the risk of pneumothoraces, pulmonary interstitial emphysema and mortality. Unlike naturals surfactants, colfosceril palmitate reduces the risk of bronchopulmonary dysplasia, intraventricular hemorrhage and patent ductus arteriosus. In clinical placebo-controlled trials, there was a significant reduction in the number of deaths attributed to hyaline membrane disease, the incidence of pulmonary air leaks, oxygen requirements and mean airway pressure. Some reports have indicated a lack of therapeutic effect due to the absence of surfactant protein.

5.2 ATC Code

R - Respiratory system

R07 - Other respiratory system products

R07A - Other respiratory system products

R07AA - Lung surfactants

R07AA01 - Colfosceril palmitate

5.3 Absorption, Distribution and Excretion

Absorption

The absorption is done directly in the alveolus into the lung tissue. As the lung surfactant is distributed in the bronchi, bronchioles and alveoli, its highest concentration is at the alveolar air-fluid interface where it remains as a monolayer.

Route of Elimination

After 5 days, most of the administered dose (56%) is distributed throughout the body with renal and fecal excretion being the minor elimination pathway representing the 4 and 2% of the eliminated dose respectively. The major route of elimination is by expelled air which accounts for 28% of the administered dose.

Volume of Distribution

Colfosceril palmitate is distributed uniformly to all lobes of the lung, distal airways and alveolar spaces. It will not enter the systemic circulation in healthy lungs, however when the integrity of the tissue is distrupted colfosceril can reach systemic circulation. Even 5 days after administration, there are traces of colfosceril palmitate retained in the body that represented 72% of the administered dose which by then have entered pathways of lipid metabolism to become tissue associated.

Clearance

After 5 days of drug administration, the lung and liver would contain 10% of the administered dose and the elimination via renal excretion accounts only for 8% of the administered dose. This proved a very small renal clearance and confirmed that the major elimination route is by expired air.

5.4 Metabolism/Metabolites

Colfosceril palmitate is catabolized and reutilized for further synthesis and secretion in lung tissues.

5.5 Biological Half-Life

The half-life of colfosceril palmitate is registered to be in the range of 20-36 hours.

5.6 Mechanism of Action

Treatment with colfosceril palmitate aims to reinflate a collapsed area of the lung, improve compliance and reduce intrapulmonary shunting. The actions of colfosceril palmitate are perfomed by replacing the defficient or innefective endogenous lung surfactant and thus, reducing the tension and stabilizing the alveoli from collapsing. Colfosceril palmitate will form a very thin film that will cover the surface of the alveolar cells and therefore it will reduce surface tension.

API SUPPLIERS

01

Sanofi

France

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02

Avanti Polar Lipids

U.S.A

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03

NOF CORPORATION

Japan

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07

CordenPharma

Germany

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01

Genzyme Pharmaceuticals

France

Medlab Asia & Asia Health

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France

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Digital Content

Sn-1, 2-dipalmitoy1-3-phosphatidylcholine (dpp...

GDUFA

DMF Review : N/A

Rev. Date :

Pay. Date :

DMF Number : 10598

Submission : 1993-12-02

Status : Inactive

Type : II

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02

Avanti Polar Lipids Inc

U.S.A

Medlab Asia & Asia Health

Not Confirmed

03

Corden Pharma Switzerland Llc

Germany

Medlab Asia & Asia Health

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04

Lipoid Gmbh

Germany

U.S.A

Medlab Asia & Asia Health

Not Confirmed

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EU WC

01

Vav Life Science

India

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API Reference Price

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17 API Suppliers

14 USDMF

1 EU WC

2 NDC API

2 Listed Suppliers

$ API Reference Price

DEVELOPMENTS

3 Drugs in Development

FINISHED DOSAGE FORMULATIONS

8 FDF Dossiers

1 FDA Orange Book

4 South Africa

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RELATED EXCIPIENT COMPANIES

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1 Topical

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Average Price (USD/KGS)

Number of Transactions

Total Quantity (KGS)

Total Value (USD)

Quantity (KGS) & Unit rate (USD/KGS) over time

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