Loxoprofen

Loxoprofen

Clinical data
AHFS/Drugs.com	International Drug Names
Routes of administration	Oral, transdermal
ATC code	M02AA31 (WHO)
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
IUPAC name (RS)-2-{4-[(2-oxocyclopentyl)methyl]phenyl}propanoic acid
CAS Number	68767-14-6 N
PubChem CID	3965
DrugBank	DB09212 Y
ChemSpider	3828 Y
UNII	3583H0GZAP
KEGG	D08149 Y
ChEBI	CHEBI:76172 N
ChEMBL	ChEMBL19299 Y
CompTox Dashboard (EPA)	DTXSID1045164
Chemical and physical data
Formula	C15H18O3
Molar mass	246.306 g·mol−1
3D model (JSmol)	Interactive image
Chirality	Racemic mixture
SMILES O=C2C(Cc1ccc(cc1)C(C(=O)O)C)CCC2
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) Y Key:YMBXTVYHTMGZDW-UHFFFAOYSA-N Y
NY (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; medicated tape and gel formulations followed in 2008 and 2010.

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

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. 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.

Brand names

It is marketed in Brazil, Mexico 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.

Wikimedia Commons has media related to Loxoprofen.