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

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
Thumb
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.

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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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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Toxicity

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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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 EndRegionImage
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 flag

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
ChemSpider
4446626
RxNav
1440971
ChEBI
34080
FDA label
Download (218 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentHypoxemic Acute Respiratory Failure1
2TerminatedPreventionChronic Lung Disease of Prematurity / Premature Births / Respiratory Distress Syndrome, Newborn1

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

Drug created on December 03, 2015 16:52 / Updated on June 12, 2020 16:53