Identification
- Summary
1-Palmitoyl-2-oleoyl-sn-glycero-3-(phospho-rac-(1-glycerol)) is a synthetic lung surfactant used to treat infant respiratory distress syndrome.
- Generic Name
- 1-Palmitoyl-2-oleoyl-sn-glycero-3-(phospho-rac-(1-glycerol))
- DrugBank Accession Number
- DB11331
- Background
Palmitoyloleoyl-phosphatidylglycerol was a component of Surfaxin, discontinued in 2017, which acted as a surfactant [FDA Label]. The product was meant to compensate for alveolar surfactant deficiency and reduce to likelihood of alveolar collapse leading to acute respiratory collapse.
- Type
- Small Molecule
- Groups
- Approved, Experimental
- Structure
Structure for 1-Palmitoyl-2-oleoyl-sn-glycero-3-(phospho-rac-(1-glycerol)) (DB11331)
- Weight
- Average: 749.02
Monoisotopic: 748.525435677 - Chemical Formula
- C40H77O10P
- Synonyms
- 1-Palmitoyl-2-oleoyl-sn-glycero-3-(phospho-rac-(1-glycerol))
- 1-Palmitoyl-2-oleoyl-sn-glycero-3-phosphatidylglycerol
- 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphoglycerol
- l-Alpha-1-palmitoyl-2-oleoylglycerophosphoglycerol
- Palmitoyloleoyl-phosphatidylglycerol
- PG(16:0/18:1(9Z))
- PG(16:0/18:1)
- POPG
Pharmacology
- Indication
Palmitoyloleoyl-phosphatidylglycerol was a component of Surfaxin which was indicated for the prevention of respiratory distress syndrome in premature infants.
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Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
Palmitoyloleoyl-phosphatidylglycerol is a replacement surfactant which prevents alveolar collapse when administered intratracheally.
- Mechanism of action
Palmitoyloleoyl-phosphatidylglycerol reduces interfacial tension at the air/water interfaces in the alveoli [FDA Label]. This prevents the tension from pulling the alveolar membranes inwards which would collapse them and lead to respiratory distress.
- Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
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Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Products
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Ingredient UNII CAS InChI Key 1-palmitoyl-2-oleoyl-sn-glycero-3-(phospho-rac-(1-glycerol)), sodium salt T52TI8BMQ6 268550-95-4 FJXDNGDRHUDFST-XQYKCTAGSA-M - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Surfaxin 1-palmitoyl-2-oleoyl-sn-glycero-3-(phospho-rac-(1-glycerol)), sodium salt (7.50 mg/1mL) + Colfosceril palmitate (22.50 mg/1mL) + Palmitic Acid (4.05 mg/1mL) + Sinapultide (0.862 mg/1mL) Suspension Endotracheal Discovery Health 2013-11-01 2016-01-19 US 
Categories
- Drug Categories
- Not Available
- Classification
- Not classified
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- F72017VPR7
- CAS number
- 185435-28-3
- InChI Key
- PAZGBAOHGQRCBP-DDDNOICHSA-N
- InChI
- InChI=1S/C40H77O10P/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-40(44)50-38(36-49-51(45,46)48-34-37(42)33-41)35-47-39(43)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h17-18,37-38,41-42H,3-16,19-36H2,1-2H3,(H,45,46)/b18-17-/t37?,38-/m1/s1
- IUPAC Name
- (2,3-dihydroxypropoxy)[(2R)-3-(hexadecanoyloxy)-2-[(9Z)-octadec-9-enoyloxy]propoxy]phosphinic acid
- SMILES
- CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OCC(O)CO)OC(=O)CCCCCCC\C=C/CCCCCCCC
References
- General References
- Not Available
- External Links
- FDA label
- Download (218 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 2 Completed Treatment Hypoxemic Acute Respiratory Failure 1 2 Terminated Prevention Chronic Lung Disease of Prematurity / Premature Births / Respiratory Distress Syndrome, Newborn 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Suspension Endotracheal - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Not Available
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.000102 mg/mL ALOGPS logP 8.16 ALOGPS logP 11.46 ChemAxon logS -6.9 ALOGPS pKa (Strongest Acidic) 1.89 ChemAxon pKa (Strongest Basic) -3 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 6 ChemAxon Hydrogen Donor Count 3 ChemAxon Polar Surface Area 148.82 Å2 ChemAxon Rotatable Bond Count 41 ChemAxon Refractivity 205.63 m3·mol-1 ChemAxon Polarizability 89.21 Å3 ChemAxon Number of Rings 0 ChemAxon Bioavailability 0 ChemAxon Rule of Five No ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Not Available
Drug created at December 03, 2015 16:52 / Updated at June 12, 2020 16:53