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Synopsis

ACTIVE PHARMA INGREDIENTS

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Also known as: Popg, Popg, l-, Popg, r-, 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphatidylglycerol, 185435-28-3, F72017vpr7

Molecular Formula

C₄₀H₇₇O₁₀P

Molecular Weight

749.0 g/mol

InChI Key

PAZGBAOHGQRCBP-DDDNOICHSA-N

FDA UNII

F72017VPR7

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

1 2D Structure

Popg, L-

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[(2R)-1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-hexadecanoyloxypropan-2-yl] (Z)-octadec-9-enoate

2.1.2 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

2.1.3 InChI Key

PAZGBAOHGQRCBP-DDDNOICHSA-N

2.1.4 Canonical SMILES

CCCCCCCCCCCCCCCC(=O)OCC(COP(=O)(O)OCC(CO)O)OC(=O)CCCCCCCC=CCCCCCCCC

2.1.5 Isomeric SMILES

CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)OCC(CO)O)OC(=O)CCCCCCC/C=C\CCCCCCCC

2.2 Other Identifiers

2.2.1 UNII

F72017VPR7

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. Popg

2. Popg, L-

3. Popg, R-

4. 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphatidylglycerol

5. 185435-28-3

6. F72017vpr7

7. L-alpha-1-palmitoyl-2-oleoylglycerophosphoglycerol

8. 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphoglycerol

9. 1-palmitoyl-2-oleoyl-sn-glycero-3-phospho-rac-glycerol

10. 1-hexadecanoyl-2-(9z-octadecenoyl)-sn-glycero-3-phospho-(1'-rac-glycerol)

11. [(2r)-1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-hexadecanoyloxypropan-2-yl] (z)-octadec-9-enoate

12. 9-octadecenoic Acid (9z)-, (1r)-1-((((2,3-dihydroxypropoxy)hydroxyphosphinyl)oxy)methyl)-2-((1-oxohexadecyl)oxy)ethyl Ester

13. 9-octadecenoic Acid (z)-, 1-((((2,3-dihydroxypropoxy)hydroxyphosphinyl)oxy)methyl)-2-((1-oxohexadecyl)oxy)ethyl Ester, (1r)-

14. Pg(16:0/18:1)

15. 1-palmitoyl-2-oleoyl-sn-glycero-3-phospho-rac-glycerol Sodium Salt

16. Unii-f72017vpr7

17. 1-hexadecanoyl-2-(9z-octadecenoyl)-sn-glycero-3-phospho-sn-glycerol

18. Chebi:34080

19. Palmitoyloleoyl-phosphatidylglycerol

20. Lmgp04010002

21. 1-palmitoyl-2-oleoyl-sn-glycero-3-phospho-(1'-rac-glycerol)

22. Db11331

23. 1-palmitoyl-2-oleoyl-phosphatidylglycerol

24. Hy-142991

25. Cs-0374728

26. 16:0-18:1 Pg

27. 490h053

28. Q27115796

29. L-.alpha.-1-palmitoyl-2-oleoylglycerophosphoglycerol

30. 1-o-(1-o-palmitoyl-2-o-oleoyl-l-glycero-3-phospho)glycerol

31. {1-hexadecanoyl-2-[(z)-octadec-9-enoyl]-sn-glycero-3-phospho}glycerol

32. (19r)-22,25,26-trihydroxy-16,22-dioxo-17,21,23-trioxa-22lambda(5)-phosphahexacosan-19-yl (9z)-octadec-9-enoate

33. 1-hexadecanoyl-2-[cis-9-octadecanoyl]-sn-glycero-3-[phospho-rac-(1-glycerol)] Ammonium Salt

34. 9-octadecenoic Acid (9z)-, 1-[[[(2,3-dihydroxypropoxy)hydroxyphosphinyl]oxy]methyl]-2-[(1-oxohexadecyl)oxy]ethyl Ester

2.4 Create Date

2006-01-13

3 Chemical and Physical Properties

Molecular Formula	C₄₀H₇₇O₁₀P
Molecular Weight	749.0 g/mol
XLogP3	12.3
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	10
Rotatable Bond Count	41
Exact Mass	748.52543565 g/mol
Monoisotopic Mass	748.52543565 g/mol
Topological Polar Surface Area	149 Å²
Heavy Atom Count	51
Formal Charge	0
Complexity	868
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

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

FDA Label

5 Pharmacology and Biochemistry

5.1 Pharmacology

Palmitoyloleoyl-phosphatidylglycerol is a replacement surfactant which prevents alveolar collapse when administered intratracheally.

5.2 Mechanism of Action

Palmitoyloleoyl-phosphatidylglycerol reduces interfacial tension at the air/water interfaces in the alveoli. This prevents the tension from pulling the alveolar membranes inwards which would collapse them and lead to respiratory distress.

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