Meloxicam
| 250px | |
| Systematic (IUPAC) name | |
|---|---|
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4-hydroxy-2-methyl-N-(5-methyl-2-thiazolyl)-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide. | |
| Clinical data | |
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| Routes of administration | Oral |
| Legal status | |
| Legal status | |
| Pharmacokinetic data | |
| Bioavailability | 89% |
| Protein binding | 99.4% |
| Metabolism | Hepatic (CYP2C9 and 3A4-mediated) |
| Biological half-life | 15 to 20 hours |
| Excretion | Urine and faeces equally |
| Identifiers | |
| CAS Number | 71125-38-7 |
| ATC code | M01AC06 (WHO) |
| PubChem | CID 5281106 |
| DrugBank | APRD00529 |
| ChemSpider | 10442740 |
| Chemical data | |
| Formula | C14H13N3O4S2 |
| Molar mass | 351.403 g/mol[[Script error: No such module "String".]] |
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Meloxicam is a nonsteroidal anti-inflammatory drug 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.[1] It was developed by Boehringer-Ingelheim.
Contents
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.[2]
Meloxicam concentrations in synovial fluid range from 40% to 50% of those in plasma. The free fraction in synovial fluid is 2.5 times higher than in plasma, due to the lower albumin content in synovial fluid as compared to plasma. The significance of this penetration is unknown,[1] but it may account for the fact that it performs exceptionally well in treatment of arthritis in animal models.[3]
Adverse effects
Meloxicam use can result in gastrointestinal toxicity and bleeding, tinnitus, blinding headaches, rash, very dark or black stool (sign of intestinal bleeding). It has fewer gastrointestinal side effects than diclofenac,[4] piroxicam,[5] naproxen,[6] and perhaps all other NSAIDs which are not COX-2 selective.[4] Although meloxicam does inhibit thromboxane A, it does not appear to do so at levels that would interfere with platelet function.
Veterinary use
Under the brand name Metacam, meloxicam is also used in the veterinary field, most commonly in dogs, but also sees off-label use in other animals such as cattle, cats and exotics, [7][8] however the U.S. Food and Drug Administration sent a Notice of Violation to the manufacturer for its promotional materials which included promotion of the drug for off-label use.[9] In the U.S. the drug is indicated for management of pain and inflammation associated with osteoarthritis in dogs only. 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. 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.
Since 2003, the oral (liquid) formulations of Metacam have been licensed for use in dogs only,[10] with the January 2005 product insert specifically warning in bold-face type: "Do not use in cats."[11] An injectable formulation for use in dogs was approved by the FDA November 2003,[12] with a formulation for cats, for surgical use only, approved in October, 2004.[13]
In the U.S., per the manufacturer's clinical instructions as of July 2010, injectable Metacam is indicated in operative use with felines as a single, one-time dose only, with specific and repeated warnings not to administer a second dose.[14] 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, Metacam is registered for long term use in cats in Australia, New Zealand, and throughout Europe.
Consumer confidence
As issues arise with any drug used off-label, the off-label use of Metacam in cats has led to many anecdotal reports of irreversible renal damage and death.[15] One peer-reviewed journal cites feline consumption of NSAIDs, and specifically oral Metacam, as being a common source of severe kidney damage in cats.[16]
Brands
In Europe, meloxicam is marketed under the brand names Movalis, Melox, and Recoxa. In the UK, U.S., Middle East, Argentina, Paraguay, Uruguay and Australia it is 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, Mavicam, or Melocam. A veterinary formulation of the drug is marketed as Metacam, Meloxidyl or Petcam. In the Philippines, it is generally marketed under the brand name Moxen. In Pakistan it is marketed under the brand name Maxicam (Reco).
References
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ar:ميلوكسيكامde:Meloxicam es:Meloxicam it:Meloxicam nl:Meloxicam pl:Meloksykam pt:Meloxicam ro:Meloxicam ru:Мелоксикам sv:Meloxicam th:มีลอกซิแคม tr:Meloksikam zh:美洛昔康
uk:Мелоксикам- ↑ 1.0 1.1 "Meloxicam official FDA information, side effects, and uses". Drugs.com. March 2010. Retrieved 17 March 2010.
- ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
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- ↑ Dequeker, J; Hawkey, C; Kahan, A; Steinbruck, K; Alegre, C; Baumelou, E; Begaud, B; Isomaki, H; Littlejohn, G; Mau, J; Papazoglou, S (1998). "Improvement in gastrointestinal tolerability of the selective cyclooxygenase (COX)-2 inhibitor, meloxicam, compared with piroxicam: results of the Safety and Efficacy Large-scale Evaluation of COX- inhibiting Therapies (SELECT) trial in osteoarthritis". The British Journal of Rheumatology. 37: 946–51.
- ↑ Wojtulewski, JA; Schattenkirchner, M; Barceló, P; Le Loët, X; Bevis, PJR; Bluhmki, E; Distel, M. "A Six-Month Double-Blind Trial to Compare the Efficacy and Safety of Meloxicam 7.5 mg Daily and Naproxen 750 mg Daily in Patients with Rheumatoid Arthritis". Rheumatology. 35, Supplement 1: 22–8.
- ↑ Off-label use discussed in: Arnold Plotnick MS, DVM, ACVIM, ABVP, Pain Management using Metacam, and Stein, Robert, Perioperative Pain Managemment Part IV, Looking Beyond Butorphanol, Sep 2006.
- ↑ For off-label use example in rabbits, see Krempels, Dana, Hind Limb Paresis and Paralysis in Rabbits, University of Miami Biology Department.
- ↑ US FDA Notice of Violation for off-label use promotion, April 2005.
- ↑ "NADA 141-213: New Animal Drug Application Approval (for Metacam® (meloxicam) 0.5 mg/mL and 1.5 mg/mL Oral Suspension)" (PDF). US Food and Drug Administration. April 15, 2003. Retrieved 24 July 2010.
- ↑ Metacam Client Information Sheet, product description: "Non-steroidal anti-inflammatory drug for oral use in dogs only", and in the "What Is Metacam" section in bold-face type: "Do not use in cats.", January 2005.
- ↑ Metacam 5 mg/mL Solution for Injection
- ↑ Metacam 5 mg/mL Solution for Injection, Supplemental Approval October 28, 2004.
- ↑ See the manufacturer's FAQ on its website, and its clinical dosing instructions for cats.
- ↑ Discussion of Metacam use at persiancats.org in Metacam Risks In Cats, and at the consumer site metacamkills.com.
- ↑ Merola, Valentina, DVM, DABT, and Dunayer Eric, MS, VMD, DABT, The 10 most common toxicoses in cats, Toxicology Brief, Veterinary Medicine, pp. 340-342, June, 2006.
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- Dog health
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- Non-steroidal anti-inflammatory drugs
- Thiazoles
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- Amides
- Benzothiazines
