Details
Stereochemistry | RACEMIC |
Molecular Formula | C40H80NO8P |
Molecular Weight | 734.0389 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCCCCCCCCCCCCC(=O)OCC(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCC
InChI
InChIKey=KILNVBDSWZSGLL-UHFFFAOYSA-N
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
DescriptionSources: http://www.ncbi.nlm.nih.gov/pubmed/1723378Curator's Comment: Description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/2057244
Sources: http://www.ncbi.nlm.nih.gov/pubmed/1723378
Curator's Comment: Description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/2057244
Dipalmitoylphosphatidylcholine (DPPC) is the main lipid component of surfactant, it reduces surface tension, preventing collapse of the alveoli. It is used in the treatment of neonatal respiratory distress. It is an important constituent of the number of surfactant, such as Curosurf®, Lucinactant, Exosurf.
Porcine-derived lung surfactant Curosurf® (poractant alfa) intratracheal suspension is indicated for the rescue treatment of respiratory distress syndrome (RDS) in premature infants. Each milliliter of suspension contains 80 mg of poractant alfa that includes 76 mg of phospholipids and 1 mg of protein of which 0.45 mg is SP-B and 0.59 mg is SP-C. The amount of phospholipids is calculated from the content of phosphorus and contains 55 mg of phosphatidylcholine of which 30 mg is dipalmitoylphosphatidylcholine. Curosurf reduces mortality and pneumothoraces associated with RDS.
Lucinactant is a new synthetic peptide-containing surfactant for intratracheal use. It contains sinapultide, phospholipids (dipalmitoylphosphatidylcholine, DPPC and palmitoyloleoyl phosphatidylglycerol, POPG) and a fatty acid (palmitic acid). Intended for the prevention of RDS in premature infants at high risk for RDS. FDA approved on March 6, 2012.
Exosurf, approved by FDA in 1990, is a protein-free surfactant composed of 85% dipalmitoylphosphatidylcholine, 9% hexadecanol, and 6% tyloxapol by weight.
Originator
Sources: http://www.ncbi.nlm.nih.gov/pubmed/20276181
Curator's Comment: Dipalmitoylphosphatidylcholine was first isolated from lung by Thannhauser S.J in 1946
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: GO:0045730 Sources: http://www.ncbi.nlm.nih.gov/pubmed/11359446 |
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Target ID: CHEMBL1825 Sources: http://www.ncbi.nlm.nih.gov/pubmed/11359446 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Preventing | Surfaxin Approved UseIndicated for the prevention of respiratory distress syndrome (RDS) in premature infants at high risk for RDS. Launch Date2012 |
PubMed
Title | Date | PubMed |
---|---|---|
Initial clinical trial of EXOSURF, a protein-free synthetic surfactant, for the prophylaxis and early treatment of hyaline membrane disease. | 1991 Jul |
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Colfosceril palmitate. A review of the therapeutic efficacy and clinical tolerability of a synthetic surfactant preparation (Exosurf Neonatal) in neonatal respiratory distress syndrome. | 1991 Nov |
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Effects of surfactant protein A and surfactant lipids on lymphocyte proliferation in vitro. | 1994 Oct |
Sample Use Guides
In Vivo Use Guide
Curator's Comment: Each mL contains 30 mg phospholipids [22.50 mg dipalmitoylphosphatidylcholine (DPPC) and 7.50 mgpalmitoyloleoylphosphatidylglycerol, sodium salt (POPG, Na)], 4.05 mg palmitic acid (PA), and 0.862 mg sinapultide.
The recommended dose of SURFAXIN is 5.8 mL per kg birth weight. Up to 4 doses of SURFAXIN can be administered in the first 48 hours of life. Doses should be given no more frequently than every 6 hours.
Route of Administration:
Intratracheal
In Vitro Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/7943339
50-250 ug/ml of Dipalmitoylphosphatidylcholine suppressed mitogen-induced lymphocyte proliferation
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EU-Orphan Drug |
EU/3/04/217
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SUBSTANCE RECORD