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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
Structure of DIPALMITOYLPHOSPHATIDYLCHOLINE, DL-

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

HIDE SMILES / InChI

Description
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

Curator's Comment: Dipalmitoylphosphatidylcholine was first isolated from lung by Thannhauser S.J in 1946

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Surfaxin

Approved Use

Indicated for the prevention of respiratory distress syndrome (RDS) in premature infants at high risk for RDS.

Launch Date

2012
PubMed

PubMed

TitleDatePubMed
Initial clinical trial of EXOSURF, a protein-free synthetic surfactant, for the prophylaxis and early treatment of hyaline membrane disease.
1991 Jul
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
Effects of surfactant protein A and surfactant lipids on lymphocyte proliferation in vitro.
1994 Oct
Patents

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
50-250 ug/ml of Dipalmitoylphosphatidylcholine suppressed mitogen-induced lymphocyte proliferation
Name Type Language
DIPALMITOYLPHOSPHATIDYLCHOLINE, DL-
Common Name English
DPPC, DL
Common Name English
DIPALMITOYL PHOSPHATIDYLCHOLINE
Common Name English
DL-DIPALMITOYLLECITHIN
Common Name English
DIPALMITOYLPHOSPHATIDYLCHOLINE, (±)-
Common Name English
1,2-DIPALMITOYL-PHOSPHATIDYLCHOLINE
Common Name English
3,5,9-TRIOXA-4-PHOSPHAPENTACOSAN-1-AMINIUM, 4-HYDROXY-N,N,N-TRIMETHYL-10-OXO-7-((1-OXOHEXADECYL)OXY)-, INNER SALT, 4-OXIDE
Common Name English
1,2-DIPALMITOYL-DL-PHOSPHATIDYLCHOLINE
Common Name English
1,2-DIPALMITOYLPHOSPHATIDYLCHOLINE, DL-
Common Name English
DPPC
Common Name English
RAC-1,2-DIPALMITOYLGLYCEROL-3-PHOSPHORYLCHOLINE
Common Name English
RAC-1,2-DIPALMITOYLGLYCERO-3-PHOSPHOCHOLINE
Common Name English
1,2-DIPALMITOYLPHOSPHATIDYLCHOLINE
Common Name English
DIPALMITOYL LECITHIN, DL-
Common Name English
Classification Tree Code System Code
EU-Orphan Drug EU/3/04/217
Created by admin on Fri Dec 15 15:59:05 GMT 2023 , Edited by admin on Fri Dec 15 15:59:05 GMT 2023
Code System Code Type Description
FDA UNII
2W15RT5V7V
Created by admin on Fri Dec 15 15:59:05 GMT 2023 , Edited by admin on Fri Dec 15 15:59:05 GMT 2023
PRIMARY
CHEBI
40265
Created by admin on Fri Dec 15 15:59:05 GMT 2023 , Edited by admin on Fri Dec 15 15:59:05 GMT 2023
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DAILYMED
2W15RT5V7V
Created by admin on Fri Dec 15 15:59:05 GMT 2023 , Edited by admin on Fri Dec 15 15:59:05 GMT 2023
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CHEBI
72999
Created by admin on Fri Dec 15 15:59:05 GMT 2023 , Edited by admin on Fri Dec 15 15:59:05 GMT 2023
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CAS
2644-64-6
Created by admin on Fri Dec 15 15:59:05 GMT 2023 , Edited by admin on Fri Dec 15 15:59:05 GMT 2023
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ECHA (EC/EINECS)
220-153-9
Created by admin on Fri Dec 15 15:59:05 GMT 2023 , Edited by admin on Fri Dec 15 15:59:05 GMT 2023
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EPA CompTox
DTXSID50910226
Created by admin on Fri Dec 15 15:59:05 GMT 2023 , Edited by admin on Fri Dec 15 15:59:05 GMT 2023
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PUBCHEM
6138
Created by admin on Fri Dec 15 15:59:05 GMT 2023 , Edited by admin on Fri Dec 15 15:59:05 GMT 2023
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RXCUI
1926948
Created by admin on Fri Dec 15 15:59:05 GMT 2023 , Edited by admin on Fri Dec 15 15:59:05 GMT 2023
PRIMARY