1-Palmitoyl-2-oleoyl-sn-glycero-3-(phospho-rac-(1-glycerol))

Identification

Name
1-Palmitoyl-2-oleoyl-sn-glycero-3-(phospho-rac-(1-glycerol))
Accession Number
DB11331  (DB14095)
Type
Small Molecule
Groups
Approved
Description

Palmitoyloleoyl-phosphatidylglycerol was a component of Surfaxin, discontinued in 2017, which acted as a surfactant [Label]. The product was meant to compensate for alveolar surfactant deficiency and reduce to likelihood of alveolar collapse leading to acute respiratory collapse.

Structure
Thumb
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
  • POPG, L-
  • POPG, R-
Product Ingredients
IngredientUNIICASInChI Key
1-palmitoyl-2-oleoyl-sn-glycero-3-(phospho-rac-(1-glycerol)), sodium saltT52TI8BMQ6268550-95-4FJXDNGDRHUDFST-XQYKCTAGSA-M
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Surfaxin1-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)SuspensionEndotrachealDiscovery Health2013-11-012016-01-19Us
Categories
Not Available
UNII
F72017VPR7
CAS number
185435-28-3
Weight
Average: 749.02
Monoisotopic: 748.525435677
Chemical Formula
C40H77O10P
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

Pharmacology

Indication

Palmitoyloleoyl-phosphatidylglycerol was a component of Surfaxin which was indicated for the prevention of respiratory distress syndrome in premature infants.

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 [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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
ChemSpider
4446626
ChEBI
34080
FDA label
Download (218 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
SuspensionEndotracheal
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.000102 mg/mLALOGPS
logP8.16ALOGPS
logP11.46ChemAxon
logS-6.9ALOGPS
pKa (Strongest Acidic)1.89ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area148.82 Å2ChemAxon
Rotatable Bond Count41ChemAxon
Refractivity205.63 m3·mol-1ChemAxon
Polarizability89.21 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Taxonomy

Classification
Not classified

Drug created on December 03, 2015 09:52 / Updated on September 21, 2018 00:18