Meloxicam

Meloxicam

Clinical data
Trade names	Mobic
AHFS/Drugs.com	Monograph
MedlinePlus	a601242
Pregnancy category	AU: C US: C (Risk not ruled out)
Routes of administration	Oral
ATC code	M01AC06 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	89%
Protein binding	99.4%
Metabolism	Hepatic (CYP2C9 and 3A4-mediated)
Biological half-life	20 hours
Excretion	Urine and faeces equally
Identifiers
IUPAC name 4-hydroxy-2-methyl-N-(5-methyl-2-thiazolyl)-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide.
CAS Number	71125-38-7 Y
PubChem (CID)	5281106
IUPHAR/BPS	7220
DrugBank	DB00814 Y
ChemSpider	10442740 Y
UNII	VG2QF83CGL Y
KEGG	D00969 Y
ChEBI	CHEBI:6741 N
ChEMBL	CHEMBL599 Y
PDB ligand ID	MXM (PDBe, RCSB PDB)
ECHA InfoCard	100.113.257
Chemical and physical data
Formula	C14H13N3O4S2
Molar mass	351.403 g/mol
3D model (Jmol)	Interactive image
SMILES Cc1cnc(s1)NC(=O)C\3=C(/O)c2ccccc2S(=O)(=O)N/3C
InChI InChI=1S/C14H13N3O4S2/c1-8-7-15-14(22-8)16-13(19)11-12(18)9-5-3-4-6-10(9)23(20,21)17(11)2/h3-7,18H,1-2H3,(H,15,16,19) Y Key:ZRVUJXDFFKFLMG-UHFFFAOYSA-N Y
NY (what is this?)

Meloxicam is a nonsteroidal anti-inflammatory drug (NSAID) with analgesic and fever reducer effects. It is a derivative of oxicam, closely related to piroxicam, and falls in the enolic acid group of NSAIDs. It was developed by Boehringer-Ingelheim. Meloxicam starts to relieve pain about 30–60 minutes after administration.

As of 2015 the cost for a typical month of medication in the United States is less than $25 USD.

Meloxicam use can result in gastrointestinal toxicity and bleeding, headaches, rash, and very dark or black stool (a sign of intestinal bleeding). Like other NSAIDs, its use is associated with an increased risk of cardiovascular events such as heart attack and stroke. It has fewer gastrointestinal side effects than diclofenac,piroxicam,naproxen, and perhaps all other NSAIDs which are not COX-2 selective. Although meloxicam inhibits formation of thromboxane A, it does not appear to do so at levels that would interfere with platelet function.

A pooled analysis of randomized, controlled studies of meloxicam therapy of up to 60 days duration found that meloxicam was associated with a statistically significantly lower number of thromboembolic complications than the NSAID diclofenac (0.2% versus 0.8% respectively) but a similar incidence of thromboembolic events to naproxen and piroxicam.

Persons with hypertension, high cholesterol, or diabetes are at risk for cardiovascular side effects. Persons with family history of heart disease, heart attack, or stroke must tell their treating physician as the potential for serious cardiovascular side effects is significant.