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CAS-68767-14-6

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Also known as: 68767-14-6, 2-(4-((2-oxocyclopentyl)methyl)phenyl)propanoic acid, Loxoprofene, Loxoprofeno, Koloxo, Loxoprofen [inn]

Molecular Formula

C₁₅H₁₈O₃

Molecular Weight

246.30 g/mol

InChI Key

YMBXTVYHTMGZDW-UHFFFAOYSA-N

FDA UNII

3583H0GZAP

Loxoprofen is a propionic acid derivative non-steroidal anti-inflammatory drug. It is marketed under the trade name Loxonin in Brazil, Mexico and Japan by Sankyo, as Loxomac in India, and as Oxeno in Argentina. A transdermal preparation was approved for use in Japan in January 2006.

1 2D Structure

CAS 68767-14-6

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-[4-[(2-oxocyclopentyl)methyl]phenyl]propanoic acid

2.1.2 InChI

InChI=1S/C15H18O3/c1-10(15(17)18)12-7-5-11(6-8-12)9-13-3-2-4-14(13)16/h5-8,10,13H,2-4,9H2,1H3,(H,17,18)

2.1.3 InChI Key

YMBXTVYHTMGZDW-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC(C1=CC=C(C=C1)CC2CCCC2=O)C(=O)O

2.2 Other Identifiers

2.2.1 UNII

3583H0GZAP

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 156-s

2. 2-(4-((2-oxocyclopentyl)methyl)phenyl)propionic Acid

3. 2-ocppp

4. Cs 600

5. Cs-600

6. Loxoprofen Alcohol

7. Loxoprofen Sodium Dihydrate

8. Loxoprofen Sodium, (r*,s*)-isomer

9. Sodium 2-(4-(2-oxocyclopentylmethyl)phenyl)propionate Dihydrate

10. Sodium Loxoprofen

2.3.2 Depositor-Supplied Synonyms

1. 68767-14-6

2. 2-(4-((2-oxocyclopentyl)methyl)phenyl)propanoic Acid

3. Loxoprofene

4. Loxoprofeno

5. Koloxo

6. Loxoprofen [inn]

7. Loxoprofenum

8. Sodium Loxoprofen

9. Loxoprofen Sodium

10. 2-[4-[(2-oxocyclopentyl)methyl]phenyl]propanoic Acid

11. 2-{4-[(2-oxocyclopentyl)methyl]phenyl}propanoic Acid

12. Loxoprofen Acid

13. Mfcd00864331

14. Chembl19299

15. 3583h0gzap

16. Loxoprofen Sodium Hydrate

17. Chebi:76172

18. Loxoprofen (inn)

19. Ncgc00015594-02

20. Dsstox_cid_25164

21. Dsstox_rid_80714

22. Dsstox_gsid_45164

23. Loxoprofene [french]

24. Loxoprofenum [latin]

25. 2-(4-((2-oxocyclopentyl)methyl)-phenyl)propanoic Acid

26. Loxoprofeno [spanish]

27. Cas-68767-14-6

28. Unii-3583h0gzap

29. Loxoprofen, Solid

30. Alpha-methyl-4-[(2-oxocyclopentyl)methyl]benzeneacetic Acid

31. Loxoprofen [mi]

32. Loxoprofen [who-dd]

33. Lopac0_000677

34. Schembl24423

35. (+-)-p-((2-oxocyclopentyl)methyl)hydratropic Acid

36. Dtxsid1045164

37. Hms3262g15

38. Hms3885n16

39. Loxoprofen (low-melting Polymorph)

40. Bcp10971

41. Hy-b0578

42. Loxoprofen (high-melting Polymorph)

43. Tox21_110178

44. Tox21_500677

45. Bdbm50140320

46. S4682

47. Akos015906359

48. Tox21_110178_1

49. Ac-8108

50. Ccg-204763

51. Db09212

52. Gs-3193

53. Lp00677

54. Sdccgsbi-0050656.p002

55. Ncgc00015594-03

56. Ncgc00015594-04

57. Ncgc00015594-08

58. Ncgc00094037-01

59. Ncgc00094037-02

60. Ncgc00261362-01

61. Ncgc00263577-01

62. Ac-15776

63. Sy113439

64. Db-055188

65. Eu-0100677

66. Ft-0641207

67. L0244

68. Cs-600; Cs600; Cs 600

69. D08149

70. L 0664

71. (+-)-((2-oxocyclopentyl)methyl)hydratropic Acid

72. 767l146

73. A836244

74. Sr-01000075955

75. Q-201324

76. Q-300011

77. Q2759348

78. Sr-01000075955-1

79. 2-[4-[(2-oxocyclopentyl)methyl]phenyl]propionic Acid

80. 2-[4-(2-oxo-cyclopentylmethyl)-phenyl]-propionic Acid

81. 2-[4-(2-oxocyclopentan-1-ylmethyl)phenyl]propionic Acid

82. (+/-)-p-((2-oxocyclopentyl)methyl)hydratropic Acid

83. 2-[4-(2-oxocyclopentan-1-ylmethyl)phenyl]-propionic Acid

84. 2-(4-((2-oxocyclopentan-1-yl)methyl)phenyl)propionic Acid

85. Benzeneacetic Acid, .alpha.-methyl-4-[(2-oxocyclopentyl)methyl]-

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₅H₁₈O₃
Molecular Weight	246.30 g/mol
XLogP3	2.4
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	4
Exact Mass	246.125594432 g/mol
Monoisotopic Mass	246.125594432 g/mol
Topological Polar Surface Area	54.4 Å²
Heavy Atom Count	18
Formal Charge	0
Complexity	316
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	2
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Loxoprofen is non-steroidal anti-inflammatory medication (NSAID) indicated for pain and inflammation related to musculoskeletal and joint disorders. In addition to its effects on pain, it is an antipyretic and anti-inflammatory medication.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Loxoprofen is a non-selective inhibitor of cyclooxygenase enzymes, which are responsible for the formation of various biologically active pain, fever, and inflammatory mediators. These include prostaglandins, prostacyclin, thromboxane, and arachidonic acid.

5.2 MeSH Pharmacological Classification

Anti-Inflammatory Agents, Non-Steroidal

Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects. (See all compounds classified as Anti-Inflammatory Agents, Non-Steroidal.)

5.3 ATC Code

M - Musculo-skeletal system

M02 - Topical products for joint and muscular pain

M02A - Topical products for joint and muscular pain

M02AA - Antiinflammatory preparations, non-steroids for topical use

M02AA31 - Loxoprofen

5.4 Absorption, Distribution and Excretion

Absorption

Loxoprofen is rapidly and completely absorbed from the GI tract with a bioavailability of 95%. The absorption phase of the medication occurs in the first 4-6 hours after ingestion. Food ingestion with the medication causes a slight decrease in the rate of loxoprofen absorption.

Route of Elimination

50% renal excretion. This drug is 20% - 30% excreted in the stool.

Volume of Distribution

Loxoprofen has a volume of distribution of 0.16 L/kg.

Clearance

Most of the drug as unchanged loxoprofen, 6-0-desmethyl loxoprofen (less than 1%) and glucuronide or other conjugates (66-92%). In patients with renal failure, metabolites may accumulate.

5.5 Metabolism/Metabolites

Loxoprofen is a prodrug that is rapidly converted to its active trans-alcohol metabolite by carbonyl reductase in the liver. This same process also results in a cis-alcohol metabolite, though this isomer carries little pharmacological activity. The parent drug has also been observed to undergo oxidation via CYP3A4/5 to two hydroxylated metabolites (M3 and M4) and glucuronidation by UGT2B7 to two glucuronide metabolites (M5 and M6). The alcohol metabolites of loxoprofen also undergo glucuronide conjugation via UGT2B7 to two glucuronide metabolites (M7 and M8) prior to excretion. When applied in topical formulations, loxoprofen is metabolized to its active trans-alcohol form by carbonyl reductase in the skin.

5.6 Biological Half-Life

The elimination half-life of Loxoprofen is approximately 15 hours. Steady concentration is achieved after 2-3 doses.

5.7 Mechanism of Action

Loxoprofen itself is a prodrug and carries little-to-no pharmacological activity - it is rapidly metabolized to its trans-alcohol form, which is a potent and non-selective inhibitor of cyclooxygenase. Cyclooxygenase (COX) is present in 2 forms, COX-1 and COX-2, with each serving different functions. COX-1 is present in human cells and is constitutively released, performing cellular housekeeping functions such as mucus production and platelet aggregation. COX-2 is induced in human cells post-injury or due to other stimuli, is triggered to appear in large quantities at the sites of injury/stimuli, and is ultimately responsible for the mediation of inflammation and pain. Loxoprofen's active metabolite inhibits both COX isoforms, resulting in reduced expression of several mediators of pain, inflammation, and fever (e.g. prostaglandins, prostacyclin, thromboxane, etc).

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