Meloxicam

Meloxicam
Clinical data
Pregnancy; category	D in third trimester;
Routes of; administration	Oral
ATC code	M01AC06 (WHO) ;
Legal status
Legal status	UK: POM (Prescription only); US: WARNINGRx-only;
Pharmacokinetic data
Bioavailability	89%
Protein binding	99.4%
Metabolism	Hepatic (CYP2C9 and 3A4-mediated)
Elimination half-life	15 to 20 hours
Excretion	Urine and faeces equally
Identifiers
	IUPAC name (8E)-8-[hydroxy-[(5-methyl-1,3-thiazol-2-yl)amino]; methylidene]-9-methyl-10,10-dioxo-10λ6-thia-9-; azabicyclo[4.4.0]deca-1,3,5-trien-7-one;
CAS Number	71125-38-7;
PubChem CID	5281106;
DrugBank	APRD00529;
ChemSpider	10442740;
CompTox Dashboard (EPA)	DTXSID1020803 ;
ECHA InfoCard	100.113.257
Chemical and physical data
Formula	C14H13N3O4S2
Molar mass	351.403 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Cc1cnc(s1)NC(=O)C1=C(O)c2ccccc2S(=O)(=O)N1C;

Meloxicam is a nonsteroidal anti-inflammatory drug of the oxicam class, used to relieve the symptoms of arthritis, primary dysmenorrhea, fever; and as an analgesic, especially where there is an inflammatory component. It has been developed by Boehringer-Ingelheim. It is closely related to piroxicam.

In Europe it is marketed under the brand names Movalis, Melox, and Recoxa. In the Philippines it is generally marketed as the brand name Moxen. In the UK, U.S., Middle East, Thailand and Australia it is generally marketed under the brand name Mobic, in Germany as Mobec, and in Canada as Mobicox. In Latin America, the drug is marketed as Tenaron, Ilacox or Melocam. A veterinary formulation of the drug is marketed in the U.S. and in France as Metacam by the Vetmedica division of Boehringer-Ingelheim.

Box and strip of Meloxicam (Mobic) 7.5mg

Mechanism of action

Meloxicam inhibits cyclooxygenase (COX), the enzyme responsible for converting arachidonic acid into prostaglandin H₂—the first step in the synthesis of prostaglandins, which are mediators of inflammation. Meloxicam has been shown, especially at its low therapeutic dose, selectively to inhibit COX-2 over COX-1.

A primary advantage of the oxicam family of drugs is their long half-life which permits once-day dosing.

Adverse effects

Meloxicam use can result in gastrointestinal toxicity and bleeding, tinnitus, headache, rash, very dark or black stool (sign of intestinal bleeding). The risk of adverse side effects is lower than with piroxicam, diclofenac, or naproxen. Although meloxicam does inhibit thromboxane A, it does not appear to do so at levels that would interfere with platelet function.

In rare situations, it could cause serious liver disease. If there is a sensation of fatigue and/or liver pain, intake must be ceased.

Two Meloxicam pills, showing either side

Approval status

Meloxicam is licensed in Europe for treatment of rheumatoid arthritis, for short term use in osteoarthritis and for ankylosing spondylitis. As of 2004 it has been approved for use in treating osteoarthritis in the United States of America and is marketed in the under the name of Metacam by Boehringer Ingelheim Vetmedica.

Veterinary use

Under the brand name Metacam, meloxicam is also used in the veterinary field, most commonly in dogs and cattle, but also in other animals such as cats and exotics; in the U.S. is indicated for management of pain and inflammation associated with osteoarthritis in dogs (FDA.gov), and in Europe, where the product has been available since the early 1990s, it is also prescribed and licensed for other anti-inflammatory benefits including relief from both acute and chronic pain in dogs and cats. Side effects in animals are similar to those found in humans; the principal side effect is gastrointestinal irritation (vomiting, diarrhea and ulceration). Rarer but important side effects include liver and kidney toxicity.

For many years, both injectable and oral (liquid and tablet) formulations of meloxicam have been licensed for use in dogs, and injectable ones for use in cats. In June 2007, a new oral version of Metacam was licensed in Europe for the long-term relief of pain in cats. As of June 2008, Meloxicam is registered for long term use in cats in Australia, New Zealand, and throughout Europe. 'Metacam oral suspension 1.5 is not approved or recommended (according to the manufacture insert) for use in cats in the U.S.

Generic form of Metacam

Metacam is marketed in a generic form in Canada under the trade name Petcam.

References

^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.

[FDA-AllBoxedWarnings-1] "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.

[1]

v t e Non-steroidal anti-inflammatory drugs (NSAIDs) (primarily M01A and M02A, also N02BA)
pyrazolones / pyrazolidines	Aminophenazone Ampyrone Azapropazone Clofezone Difenamizole Famprofazone Feprazone Kebuzone Metamizole Mofebutazone Morazone Nifenazone Oxyphenbutazone Phenazone Phenylbutazone Propyphenazone Sulfinpyrazone Suxibuzone^‡
salicylates	Aspirin (acetylsalicylic acid)^# Aloxiprin Benorylate Carbasalate calcium Diflunisal Dipyrocetyl Ethenzamide Guacetisal Magnesium salicylate Methyl salicylate Salsalate Salicin Salicylamide Salicylic acid (salicylate) Sodium salicylate
acetic acid derivatives and related substances	Aceclofenac Acemetacin Alclofenac Amfenac Bendazac Bromfenac Bufexamac Bumadizone Diclofenac Difenpiramide Etodolac Felbinac Fenclozic acid Fentiazac Indometacin Indometacin farnesil Isoxepac Ketorolac Lonazolac Mofezolac Oxametacin Prodolic acid Proglumetacin Sulindac Tiopinac Tolmetin Zomepirac^†
oxicams	Ampiroxicam Droxicam Isoxicam Lornoxicam Meloxicam Piroxicam Pivoxicam Tenoxicam
propionic acid derivatives (profens)	Alminoprofen Benoxaprofen^† Carprofen^‡ Dexibuprofen Dexketoprofen Fenbufen Fenoprofen Flunoxaprofen Flurbiprofen Ibuprofen^# Ibuproxam Indoprofen^† Ketoprofen Loxoprofen Miroprofen Naproxen Oxaprozin Pelubiprofen Piketoprofen Pirprofen Suprofen Tarenflurbil Tepoxalin^‡ Tiaprofenic acid Vedaprofen^‡ Zaltoprofen COX-inhibiting nitric oxide donator: Naproxcinod
n-arylanthranilic acids (fenamates)	Azapropazone Clonixin Etofenamate Floctafenine Flufenamic acid Flunixin Flutiazin Glafenine^† Meclofenamic acid Mefenamic acid Morniflumate Niflumic acid Tolfenamic acid
COX-2 inhibitors (coxibs)	Apricoxib Celecoxib (+tramadol) Cimicoxib^‡ Deracoxib^‡ Etoricoxib Firocoxib^‡ Lumiracoxib^† Mavacoxib^‡ Parecoxib Robenacoxib^‡ Rofecoxib^† Valdecoxib^†
other	Aminopropionitrile Benzydamine Chondroitin sulfate Diacerein Fluproquazone Glucosamine Glycosaminoglycan Hyperforin Nabumetone Nimesulide Oxaceprol Proquazone Superoxide dismutase / orgotein Tenidap
NSAID combinations	Ibuprofen/famotidine Ibuprofen/hydrocodone Ibuprofen/oxycodone Ibuprofen/paracetamol Meloxicam/bupivacaine Naproxen/diphenhydramine Naproxen/esomeprazole
Key: underline indicates initially developed first-in-class compound of specific group; ^#WHO-Essential Medicines; ^†withdrawn drugs; ^‡veterinary use.
category commons portal

v t e Non-steroidal anti-inflammatory drugs (NSAIDs) (primarily M01A and M02A, also N02BA)
pyrazolones / pyrazolidines	Aminophenazone Ampyrone Azapropazone Clofezone Difenamizole Famprofazone Feprazone Kebuzone Metamizole Mofebutazone Morazone Nifenazone Oxyphenbutazone Phenazone Phenylbutazone Propyphenazone Sulfinpyrazone Suxibuzone^‡
salicylates	Aspirin (acetylsalicylic acid)^# Aloxiprin Benorylate Carbasalate calcium Diflunisal Dipyrocetyl Ethenzamide Guacetisal Magnesium salicylate Methyl salicylate Salsalate Salicin Salicylamide Salicylic acid (salicylate) Sodium salicylate
acetic acid derivatives and related substances	Aceclofenac Acemetacin Alclofenac Amfenac Bendazac Bromfenac Bufexamac Bumadizone Diclofenac Difenpiramide Etodolac Felbinac Fenclozic acid Fentiazac Indometacin Indometacin farnesil Isoxepac Ketorolac Lonazolac Mofezolac Oxametacin Prodolic acid Proglumetacin Sulindac Tiopinac Tolmetin Zomepirac^†
oxicams	Ampiroxicam Droxicam Isoxicam Lornoxicam Meloxicam Piroxicam Pivoxicam Tenoxicam
propionic acid derivatives (profens)	Alminoprofen Benoxaprofen^† Carprofen^‡ Dexibuprofen Dexketoprofen Fenbufen Fenoprofen Flunoxaprofen Flurbiprofen Ibuprofen^# Ibuproxam Indoprofen^† Ketoprofen Loxoprofen Miroprofen Naproxen Oxaprozin Pelubiprofen Piketoprofen Pirprofen Suprofen Tarenflurbil Tepoxalin^‡ Tiaprofenic acid Vedaprofen^‡ Zaltoprofen COX-inhibiting nitric oxide donator: Naproxcinod
n-arylanthranilic acids (fenamates)	Azapropazone Clonixin Etofenamate Floctafenine Flufenamic acid Flunixin Flutiazin Glafenine^† Meclofenamic acid Mefenamic acid Morniflumate Niflumic acid Tolfenamic acid
COX-2 inhibitors (coxibs)	Apricoxib Celecoxib (+tramadol) Cimicoxib^‡ Deracoxib^‡ Etoricoxib Firocoxib^‡ Lumiracoxib^† Mavacoxib^‡ Parecoxib Robenacoxib^‡ Rofecoxib^† Valdecoxib^†
other	Aminopropionitrile Benzydamine Chondroitin sulfate Diacerein Fluproquazone Glucosamine Glycosaminoglycan Hyperforin Nabumetone Nimesulide Oxaceprol Proquazone Superoxide dismutase / orgotein Tenidap
NSAID combinations	Ibuprofen/famotidine Ibuprofen/hydrocodone Ibuprofen/oxycodone Ibuprofen/paracetamol Meloxicam/bupivacaine Naproxen/diphenhydramine Naproxen/esomeprazole
Key: underline indicates initially developed first-in-class compound of specific group; ^#WHO-Essential Medicines; ^†withdrawn drugs; ^‡veterinary use.
category commons portal