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Licofelone

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Also known as: 156897-06-2, Ml-3000, Licofelone [inn], Ml 3000, 2-[2-(4-chlorophenyl)-6,6-dimethyl-1-phenyl-5,7-dihydropyrrolizin-3-yl]acetic acid, P5t6bys22y

Molecular Formula

C₂₃H₂₂ClNO₂

Molecular Weight

379.9 g/mol

InChI Key

UAWXGRJVZSAUSZ-UHFFFAOYSA-N

FDA UNII

P5T6BYS22Y

Developed by the German pharmaceutical company, Merckle GmbH, together with EuroAlliance partners Alfa Wassermann and Lacer, licofelone (ML3000) is a dual COX/LOX inhibitor and the first member of this new class of analgesic and anti-inflammatory drugs. It is currently under evaluation as a treatment for osteoarthritis (OA), the most common form of arthritis. Although phase III trials have been successfully completed in OA patients no dates for regulatory submission have yet been given.

1 2D Structure

Licofelone

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-[2-(4-chlorophenyl)-6,6-dimethyl-1-phenyl-5,7-dihydropyrrolizin-3-yl]acetic acid

2.1.2 InChI

InChI=1S/C23H22ClNO2/c1-23(2)13-19-22(15-6-4-3-5-7-15)21(16-8-10-17(24)11-9-16)18(12-20(26)27)25(19)14-23/h3-11H,12-14H2,1-2H3,(H,26,27)

2.1.3 InChI Key

UAWXGRJVZSAUSZ-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC1(CC2=C(C(=C(N2C1)CC(=O)O)C3=CC=C(C=C3)Cl)C4=CC=CC=C4)C

2.2 Other Identifiers

2.2.1 UNII

P5T6BYS22Y

2.3 Synonyms

2.3.1 MeSH Synonyms

1. (2,2-dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1h-pyrrolizine-5-yl)acetic Acid

2. Ml 3000

3. Ml-3000

2.3.2 Depositor-Supplied Synonyms

1. 156897-06-2

2. Ml-3000

3. Licofelone [inn]

4. Ml 3000

5. 2-[2-(4-chlorophenyl)-6,6-dimethyl-1-phenyl-5,7-dihydropyrrolizin-3-yl]acetic Acid

6. P5t6bys22y

7. (6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1h-pyrrolizin-5-yl)acetic Acid

8. [6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1h-pyrrolizin-5-yl]acetic Acid

9. Chembl300982

10. 2-(6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1h-pyrrolizin-5-yl)acetic Acid

11. Lcf

12. 2-[6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1h-pyrrolizin-5-yl]acetic Acid

13. Unii-p5t6bys22y

14. Brn 6823674

15. 6-(4-chlorophenyl)-2,3-dihydro-2,2-dimethyl-7-phenyl-1h-pyrrolizine-5-acetic Acid

16. 2,2-dimethyl-6-(4-chlorophenyl-7-phenyl-2,3-dihydro-1h-pyrrolizine-5-yl)acetic Acid

17. 2,3-dihydro-6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-1h-pyrrolizine-5-acetic Acid

18. Licofelone [mi]

19. Licofelone [mart.]

20. Mls006011224

21. Schembl237833

22. Dtxsid40166154

23. Hms3655d21

24. Bcp06598

25. Hy-b1452

26. Zinc3805769

27. Bdbm50038649

28. Ml3000

29. S2121

30. Akos027250758

31. Db04725

32. Sb19520

33. (6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1h-pyrrolizine-5-yl)-acetic Acid

34. 1h-pyrrolizine-5-acetic Acid, 2,3-dihydro-6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-

35. Ncgc00250374-01

36. Ncgc00250374-02

37. Ac-33111

38. As-73938

39. Smr004702985

40. Cs-0013159

41. Ft-0670787

42. Sw219543-1

43. Ab01566204_02

44. 897l062

45. A809783

46. J-009352

47. Q3832015

48. [2-(4-chloro-phenyl)-6,6-dimethyl-1-phenyl-6,7-dihydro-5h-pyrrolizin-3-yl]-acetic Acid

49. 1h-pyrrolizine-5-acetic Acid, 6-(4-chlorophenyl)-2,3-dihydro-2,2-dimethyl-7-phenyl-

50. 6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1h-pyrrolizin-5-ylacetic Acid

2.4 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₂₃H₂₂ClNO₂
Molecular Weight	379.9 g/mol
XLogP3	5.2
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	4
Exact Mass	379.1339066 g/mol
Monoisotopic Mass	379.1339066 g/mol
Topological Polar Surface Area	42.2 Å²
Heavy Atom Count	27
Formal Charge	0
Complexity	537
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 Drug and Medication Information

4.1 Drug Indication

For the management of osteoarthritis.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Licofelone belongs to a novel class of dual-acting anti-inflammatory drugs called COX/LO inhibitors. This group of drugs simultaneously inhibits the enzymes cyclooxygenase (COX) and 5-lipoxygenase (LO).

5.2 MeSH Pharmacological Classification

Cyclooxygenase Inhibitors

Compounds or agents that combine with cyclooxygenase (PROSTAGLANDIN-ENDOPEROXIDE SYNTHASES) and thereby prevent its substrate-enzyme combination with arachidonic acid and the formation of eicosanoids, prostaglandins, and thromboxanes. (See all compounds classified as Cyclooxygenase Inhibitors.)

Analgesics

Compounds capable of relieving pain without the loss of CONSCIOUSNESS. (See all compounds classified as Analgesics.)

Anti-Inflammatory Agents

Substances that reduce or suppress INFLAMMATION. (See all compounds classified as Anti-Inflammatory Agents.)

Lipoxygenase Inhibitors

Compounds that bind to and inhibit that enzymatic activity of LIPOXYGENASES. Included under this category are inhibitors that are specific for lipoxygenase subtypes and act to reduce the production of LEUKOTRIENES. (See all compounds classified as Lipoxygenase Inhibitors.)

5.3 Metabolism/Metabolites

Licofelone has known human metabolites that include (2S,3S,4S,5R)-6-[2-[2-(4-chlorophenyl)-6,6-dimethyl-1-phenyl-5,7-dihydropyrrolizin-3-yl]acetyl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid, Licofelone M2, and Licofelone M4.

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

5.4 Mechanism of Action

Licofelone, through combined 5-LOX/COX-inhibition, reduces levels of inflammatory prostaglandins and leukotrienes.

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