Loxoprofen

Loxoprofen

Systematic (IUPAC) name
(RS)-2-{4-[(2-oxocyclopentyl)methyl]phenyl}propanoic acid
Clinical data
AHFS/Drugs.com	International Drug Names
Legal status	Red Stripe (Brazil)
Routes of administration	Oral, transdermal
Pharmacokinetic data
Protein binding	97%
Metabolism	Hepatic glucuronidation
Biological half-life	75 minutes
Excretion	Renal
Identifiers
CAS Number	68767-14-6 N
ATC code	M01AE (WHO)
PubChem	CID: 3965
ChemSpider	3828 Y
UNII	3583H0GZAP Y
KEGG	D08149 Y
ChEBI	CHEBI:76172 N
ChEMBL	CHEMBL19299 Y
Chemical data
Formula	C15H18O3
Molecular mass	246.302 g/mol 304.314 g/mol (sodium salt)
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 (INN) is a non-steroidal anti-inflammatory drug in the propionic acid derivatives group, which also includes ibuprofen and naproxen among others. It is marketed in Brazil, Mexico and Japan by Sankyo as its sodium salt, loxoprofen sodium, under the trade name Loxonin, Argentina as Oxeno and in India as Loxomac. It is available in these countries for oral administration, and a transdermal preparation was approved for sale in Japan on January 2006.

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.