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Lipoprotein Lipase Activator

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Also known as: 133208-93-2, No-1886, Lipoprotein lipase activator, Opf 009, Opf-009, Diethyl (4-((4-bromo-2-cyanophenyl)carbamoyl)benzyl)phosphonate

Molecular Formula

C₁₉H₂₀BrN₂O₄P

Molecular Weight

451.2 g/mol

InChI Key

KPRTURMJVWXURQ-UHFFFAOYSA-N

FDA UNII

07H1561618

Ibrolipim is a lipoprotein lipase (LPL) activator with antihyperlipidemic activity. Activation of LDL by ibrolipim lowers plasma triglycerides, with a concomitant elevation of high-density lipoprotein cholesterol.

1 2D Structure

Lipoprotein Lipase Activator

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

N-(4-bromo-2-cyanophenyl)-4-(diethoxyphosphorylmethyl)benzamide

2.1.2 InChI

InChI=1S/C19H20BrN2O4P/c1-3-25-27(24,26-4-2)13-14-5-7-15(8-6-14)19(23)22-18-10-9-17(20)11-16(18)12-21/h5-11H,3-4,13H2,1-2H3,(H,22,23)

2.1.3 InChI Key

KPRTURMJVWXURQ-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CCOP(=O)(CC1=CC=C(C=C1)C(=O)NC2=C(C=C(C=C2)Br)C#N)OCC

2.2 Other Identifiers

2.2.1 UNII

07H1561618

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 4-diethoxyphosphorylmethyl-n-(4-bromo-2-cyanophenyl)benzamide

2. No 1886

3. No-1886

2.3.2 Depositor-Supplied Synonyms

1. 133208-93-2

2. No-1886

3. Lipoprotein Lipase Activator

4. Opf 009

5. Opf-009

6. Diethyl (4-((4-bromo-2-cyanophenyl)carbamoyl)benzyl)phosphonate

7. Phosphonic Acid, ((4-(((4-bromo-2-cyanophenyl)amino)carbonyl)phenyl)methyl)-, Diethyl Ester

8. Phosphonic Acid, [[4-[[(4-bromo-2-cyanophenyl)amino]carbonyl]phenyl]methyl]-, Diethyl Ester

9. Diethyl 4-((4-bromo-2-cyanophenyl)carbamoyl)benzylphosphonate

10. 07h1561618

11. Diethyl 4-[(4-bromo-2-cyanoanilino)carbonyl]benzylphosphonate

12. Diethyl 4-[(4-bromo-2-cyanophenyl)carbamoyl]benzylphosphonate

13. Ibrolipim [usan:inn]

14. 4-diethoxyphosphorylmethyl-n-(4-bromo-2-cyanophenyl)benzamide

15. No 1886

16. Ibrolipim [usan]

17. Unii-07h1561618

18. Ibrolipim [inn]

19. N-(4-bromo-2-cyanophenyl)-4-(diethoxyphosphorylmethyl)benzamide

20. Ibrolipim (usan/inn)

21. Mls006011667

22. Chembl34234

23. Schembl493918

24. Dtxsid20157989

25. Zinc1552570

26. Akos005067076

27. Ss-3273

28. Ncgc00481428-01

29. Smr002529695

30. Hy-117549

31. Cs-0066427

32. D03747

33. D83803

34. J-006332

35. Q5984863

36. 4-diethoxyphosphinoylmethyl-n-(4-bromo-2-cyanophenyl)benzamide

37. Diethyl4-((4-bromo-2-cyanophenyl)carbamoyl)benzylphosphonate

38. Diethyl (4-((4-bromo-2-cyanophenyl)carbamoyl)benzyl)phosphonate

39. Diethyl 4-[n-(4-bromo-2-cyanophenyl)carbamoyl]benzylphosphonate

2.4 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₁₉H₂₀BrN₂O₄P
Molecular Weight	451.2 g/mol
XLogP3	3.5
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	8
Exact Mass	450.03441 g/mol
Monoisotopic Mass	450.03441 g/mol
Topological Polar Surface Area	88.4 Å²
Heavy Atom Count	27
Formal Charge	0
Complexity	576
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Hypolipidemic Agents

Substances that lower the levels of certain LIPIDS in the BLOOD. They are used to treat HYPERLIPIDEMIAS. (See all compounds classified as Hypolipidemic Agents.)

Lipoprotein Lipase Activators

Compounds that increase the enzymatic activity of LIPOPROTEIN LIPASE. Lipoprotein lipase activators have a potential role in the treatment of OBESITY by increasing LIPID METABOLISM. Note that substances that increase the synthesis of lipoprotein lipase are not included here. (See all compounds classified as Lipoprotein Lipase Activators.)

4.2 Metabolism/Metabolites

Ibrolipim has known human metabolites that include [4-[(4-Bromo-2-cyanophenyl)carbamoyl]phenyl]methyl-ethoxyphosphinic acid.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

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