Loxoprofen

Last updated
Loxoprofen
Loxoprofen.svg
Loxoprofen 3D ball-and-stick from crystal.png
Clinical data
AHFS/Drugs.com International Drug Names
Routes of
administration
Oral, transdermal
ATC code
Legal status
Legal status
  • JP: Class 1 OTC
    BR: Red Stripe (Rx only)
Pharmacokinetic data
Protein binding 97%
Metabolism Liver glucuronidation
Elimination half-life 75 minutes
Excretion Kidney
Identifiers
  • (RS)-2-{4-[(2-oxocyclopentyl)methyl]phenyl}propanoic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C15H18O3
Molar mass 246.306 g·mol−1
3D model (JSmol)
Chirality Racemic mixture
  • O=C2C(Cc1ccc(cc1)C(C(=O)O)C)CCC2
  • 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) Yes check.svgY
  • Key:YMBXTVYHTMGZDW-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Loxoprofen is a nonsteroidal anti-inflammatory drug (NSAID) in the propionic acid derivatives group, which also includes ibuprofen and naproxen among others. It is available in some countries for oral administration. A transdermal preparation was approved for sale in Japan in January 2006; [1] medicated tape and gel formulations followed in 2008 and 2010.

Contents

It was patented in 1977 and approved for medical use in 1986. [2]

Pharmacokinetics

Loxoprofen is a prodrug. It is quickly converted to its active trans-alcohol metabolite following oral administration, and reaches its peak plasma concentration within 30 to 50 minutes.

Mechanism of action

As most NSAIDs, loxoprofen is a non-selective cyclooxygenase inhibitor, and works by reducing the synthesis of prostaglandins from arachidonic acid.

Interactions

Loxoprofen should not be administered at the same time as second-generation quinolone antibiotics such as ciprofloxacin and norfloxacin, as it increases their inhibition of GABA and this may cause seizures. [3] It may also increase the plasma concentration of warfarin, methotrexate, sulfonylurea derivatives and lithium salts, so care should be taken when loxoprofen is administered to patients taking any of these drugs. [3]

Brand names

It is marketed in Brazil, Mexico, China and Japan by Sankyo as its sodium salt, loxoprofen sodium, under the trade name Loxonin; in Argentina as Oxeno; in India as Loxomac; in Thailand as Japrolox; and in Saudi Arabia as Roxonin and Roxonin Tape.

A generic drug is marketed in Brazil by Aché as Oxotron. In Japan, two fixed dose combinations are available: Loxonin S Plus, with magnesium oxide, and Loxonin S Premium, with apronal, caffeine, and aluminium magnesium silicate.

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Bromfenac is a nonsteroidal anti-inflammatory drug (NSAID) marketed in the US as an ophthalmic solution by ISTA Pharmaceuticals for short-term, local use. Prolensa and Bromday are the once-daily formulation of bromfenac, while Xibrom was approved for twice-daily administration. In the European Union, the brand name is Yellox. Bromfenac is indicated for the treatment of ocular inflammation and pain after cataract surgery.

Cyclooxygenases are enzymes that take part in a complex biosynthetic cascade that results in the conversion of polyunsaturated fatty acids to prostaglandins and thromboxane(s). Their main role is to catalyze the transformation of arachidonic acid into the intermediate prostaglandin H2, which is the precursor of a variety of prostanoids with diverse and potent biological actions. Cyclooxygenases have two main isoforms that are called COX-1 and COX-2. COX-1 is responsible for the synthesis of prostaglandin and thromboxane in many types of cells, including the gastro-intestinal tract and blood platelets. COX-2 plays a major role in prostaglandin biosynthesis in inflammatory cells and in the central nervous system. Prostaglandin synthesis in these sites is a key factor in the development of inflammation and hyperalgesia. COX-2 inhibitors have analgesic and anti-inflammatory activity by blocking the transformation of arachidonic acid into prostaglandin H2 selectively.

References

  1. Daiichi Sankyo Co. (January 24, 2006). "Percutaneous Absorption-Type Analgesic and Anti-inflammatory Drug Loxonin Poultice 100mg Receives Approval for Manufacture" (Press release). Doctor's Guide Global Edition. Retrieved 2007-04-19.
  2. Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 521. ISBN   9783527607495.
  3. 1 2 "LOXONIN - Bula do Medicamento [Label Information]" (in Portuguese). Centralx. 2007. Retrieved 2007-04-19.