Lornoxicam

Lornoxicam

File:Lornoxicam skeletal.svg
File:Lornoxicam ball-and-stick.png
Systematic (IUPAC) name
(3E)-6-chloro-3-[hydroxy(pyridin-2-ylamino)methylene]-2-methyl-2,3-dihydro-4H-thieno[2,3-e][1,2]thiazin-4-one 1,1-dioxide
Clinical data
AHFS/Drugs.com	International Drug Names
Pregnancy category	Not recommended; contraindicated in months 7–9
Legal status	℞ (Prescription only)
Routes of administration	Oral, parenteral
Pharmacokinetic data
Bioavailability	90–100%
Protein binding	99%
Metabolism	CYP2C9
Biological half-life	3–4 hours
Excretion	2/3 hepatic, 1/3 renal
Identifiers
ATC code	M01AC05 (WHO)
PubChem	CID: 5282204
DrugBank	DB06725 Y
ChemSpider	10442760
UNII	ER09126G7A Y
KEGG	D01866 Y
ChEBI	CHEBI:31783 N
Chemical data
Formula	C13H10ClN3O4S2
Molecular mass	371.8192 g/mol
SMILES CN1C(=C(C2=C(S1(=O)=O)C=C(S2)Cl)O)C(=O)NC3=CC=CC=N3
InChI InChI=1S/C13H10ClN3O4S2/c1-17-10(13(19)16-9-4-2-3-5-15-9)11(18)12-7(23(17,20)21)6-8(14)22-12/h2-6,18H,1H3,(H,15,16,19) Key:WLHQHAUOOXYABV-UHFFFAOYSA-N
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Lornoxicam (INN, or chlortenoxicam; trade name Xefo, among others) is a non-steroidal anti-inflammatory drug (NSAID) of the oxicam class with analgesic (pain relieving), anti-inflammatory and antipyretic (fever reducing) properties. It is available in oral and parenteral formulations.

Indications

Lornoxicam is used for the treatment of various types of pain, especially resulting from inflammatory diseases of the joints, osteoarthritis, surgery, sciatica, and other inflammations.

Contraindications

The drug is contraindicated in patients that must not take other NSAIDs, possible reasons including salicylate sensitivity, gastrointestinal bleeding and bleeding disorders, and severe impairment of heart, liver or kidney function. Lornoxicam is not recommended during pregnancy and breastfeeding and is contraindicated during the last third of pregnancy.

Adverse effects

Lornoxicam has side effects similar to other NSAIDs, most commonly mild ones like gastrointestinal disorders (nausea and diarrhea) and headache. Severe but seldom side effects include bleeding, bronchospasms and the extremely rare Stevens–Johnson syndrome.

Interactions

Interactions with other drugs are typical of NSAIDs. Combination with vitamin K antagonists like warfarin increases the risk of bleeding. Combination with ciclosporin can lead to reduced kidney function, and to acute renal failure in rare cases. Lornoxicam can also increase the adverse effects of lithium, methotrexate and digoxin and its derivatives. The effect of diuretics, ACE inhibitors and angiotensin II receptor antagonists can be reduced, but this is only relevant in patients with special risks like heart failure. As with piroxicam, cimetidine can increase plasma levels but is unlikely to cause relevant interactions.