Chemistry:Meloxicam

From HandWiki

Meloxicam, sold under the brand name Mobic among others, is a nonsteroidal anti-inflammatory drug (NSAID) used to treat pain and inflammation in rheumatic diseases and osteoarthritis.[1][2] It is taken by mouth or given by injection into a vein.[2][3] It is recommended that it be used for as short a period as possible and at a low dose.[2]

Common side effects include abdominal pain, dizziness, swelling, headache, and a rash.[2] Serious side effects may include heart disease, stroke, kidney problems, and stomach ulcers.[2] Use is not recommended in the third trimester of pregnancy.[2] It blocks cyclooxygenase-2 (COX-2) more than it blocks cyclooxygenase-1 (COX-1).[2] It is in the oxicam family of chemicals and is closely related to piroxicam.[2]

It is available as a generic medication.[2] In 2023, it was the 27th most commonly prescribed medication in the United States, with more than 20 million prescriptions.[4][5] An intravenous version of meloxicam (Anjeso) was approved for medical use in the United States in February 2020.[6][3] Meloxicam is available in combination with bupivacaine as bupivacaine/meloxicam and in combination with rizatriptan as meloxicam/rizatriptan.

Medical uses

Meloxicam is indicated for the treatment of osteoarthritis, rheumatoid arthritis, and juvenile rheumatoid arthritis.[7]

Adverse effects

See also: Chemistry:Nonsteroidal anti-inflammatory drug

Meloxicam use can result in gastrointestinal toxicity and bleeding, headaches, rash, and very dark or black stool (a sign of intestinal bleeding). It has fewer gastrointestinal side effects than diclofenac,[8] piroxicam,[9] naproxen,[10] and perhaps all other NSAIDs which are not COX-2 selective.[8]

In October 2020, the US Food and Drug Administration (FDA) required the prescribing information to be updated for all nonsteroidal anti-inflammatory medications to describe the risk of kidney problems in unborn babies that result in low amniotic fluid.[11][12] They recommend avoiding NSAIDs in pregnant women at 20 weeks or later in pregnancy.[11][12]

Cardiovascular

Like other NSAIDs, its use is associated with an increased risk of cardiovascular events such as heart attack and stroke.[13] Although meloxicam inhibits formation of thromboxane A, it does not appear to do so at levels that would interfere with platelet function.[14][15] 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.[16]

People with hypertension, high cholesterol, or diabetes are at risk for cardiovascular side effects. People with family history of heart disease, heart attack, or stroke should tell their treating physician as the potential for serious cardiovascular side effects is significant.[2][17]

Gastrointestinal

NSAIDs cause an increase in the risk of serious gastrointestinal adverse events including bleeding, ulceration, and perforation of the stomach or intestines, which can be fatal. Elderly patients are at greater risk for serious gastrointestinal events.[2]

Mechanism of action

Meloxicam blocks 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 low therapeutic doses, to selectively inhibit COX-2 over COX-1.[18]

X-ray crystallographic analyses and molecular modelling studies of meloxicam´s binding to cyclooxygenase isoforms showed that the methyl group of the thiazole ring in meloxicam exploits the „flexible extra space" at the top of the COX-2 chanel. The substitution of the second shell amino acid residue Ile434 in COX-1 by Val in COX-2 allows the side chain of Phe518 (a residue at the active side) to open „extra space“, which favors the binding of meloxicam to COX-2. Site-directed mutagenesis studies in which Ile434 was substituted for Val434 in COX-2 confirmed this hypothesis. [19]  Other oxicams also occupy this binding site, albeit nonselectively because of the missing methyl group in the side chain.[20]

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 compared to plasma. The significance of this penetration is unknown,[2] but it may account for the fact that it performs exceptionally well in treatment of arthritis in animal models.[21]

Pharmacokinetics

Absorption

The bioavailability of meloxicam is decreased when administered orally compared to an equivalent IV bolus dose. Different oral formulations of meloxicam are not bioequivalent.[2] Use of oral meloxicam following a high-fat breakfast increases the mean peak drug levels by about 22%; however, the manufacturer does not make any specific meal recommendations. In addition, the use of antacids does not show pharmacokinetic interactions.[7] With chronic dosing, the time to maximum plasma concentration following oral administration is approximately 5–6 hours.[22]

Distribution

The mean volume of distribution of meloxicam is approximately 10 L. It is highly protein-bound, mainly to albumin.[15][22]

Metabolism

Meloxicam is extensively metabolized in the liver by the enzymes CYP2C9 and CYP3A4 (minor) into four inactive metabolites. Peroxidase activity is thought to be responsible for the other two remaining metabolites.[2][7]

Excretion

Meloxicam is predominantly excreted in the form of metabolites and occurs to equal extents in the urine and feces.[7] Traces of unchanged parent drug are found in urine and feces.[7] The mean elimination half-life ranges from 15 to 20 hours.[7]

Adverse events are dose-dependent and associated with length of treatment.[7][23]

Research and development

In the 1970s, chemists at Dr. Karl Thomas GmbH, a subsidiary of Boehringer-Ingelheim in Germany, synthesized a variety of enol carboxamides with the aim of obtaining active ingredients with anti-inflammatory or antithrombotic properties.[24] A compound belonging to the oxicams (UH-AC 62, meloxicam) stood out, exhibiting antiinflammatory activity in the pharmacological adjuvant arthritis model, but only low antithrombotic efficacy as measured by platelet aggregation.[15] Dr. Karl Thomas GmbH filed the German basic patent DE2756113 (1979) and Boehringer Ingelheim US patent 4,233,299 (1980) and patents in many other countries.[25]

Veterinary use

Meloxicam is used in veterinary medicine mainly to treat dogs,[26][27] but also sees off-label use in other animals such as cattle and exotics.[28][29] In the European Union and other countries it is not considered off-label and can be used in cattle, pigs, horses, dogs, cats and guinea pigs.[30] It has also been investigated as an alternative to diclofenac by the Royal Society for the Protection of Birds (RSPB) to prevent deaths of vultures.[31]

Depending on the animal species, each country or union of countries applies different guidelines or legal frameworks for the use of the drug, as well as different recorded side effects. The most common side effects in dogs include gastrointestinal irritation (vomiting, diarrhea, and ulceration).[26] As far as the perioperative administration is concerned, in healthy dogs given meloxicam, no perioperative adverse effects on the cardiovascular system have been reported at recommended dosages.[32] Perioperative administration of meloxicam to cats did not affect postoperative respiratory rate nor heart rate.[33]

Use of meloxicam in cats

The issue of using meloxicam in cats involves conflicting guidelines, differing legislation, and a narrow therapeutic safety margin that can easily turn the drug from cure to poison. More specifically:

US policy vs EU policy

The US Food and Drug Administration (FDA) approves the use of meloxicam in cats only in injectable form and only as a one-time injection given before surgery.[34][35] It does not approve meloxicam oral suspension for cats and it does not approve meloxicam spray for cats because after reviewing numerous reports of meloxicam side effects in cats, it has identified many cases of acute renal failure and death and has added the following boxed warning to the prescription label: "Repeated use of meloxicam in cats has been associated with acute renal failure and death. Do not administer additional injectable or oral meloxicam to cats. See Contraindications, Warnings, and Precautions for detailed information."[36]

In contrast, in the European Union and other continents or countries, the use of the drug in cats is allowed with no such warning.[37][38] The product instruction leaflet for meloxicam for cats in the form of oral suspension 0.5 mg/ml states that: "Typical adverse reactions of NSAIDs such as loss of appetite, vomiting, diarrhoea, faecal occult blood, apathy, and renal failure have occasionally been reported. These side effects are in most cases transient and disappear following termination of the treatment but in very rare cases may be serious or fatal."[39]

Dosage and safety margin

The data sheets for meloxicam products for cats also state that: "Meloxicam has a narrow therapeutic safety margin in cats and clinical signs of overdose may be seen at relatively small overdose levels."[39]

Additional studies

Some additional information about giving meloxicam to cats from researchers is as follows: A peer-reviewed journal article cites NSAIDs, including meloxicam, as causing gastrointestinal upset and, at high doses, acute kidney injury and CNS signs such as seizures and comas in cats. It adds that cats have a low tolerance for NSAIDs.[40][41] Also, in another scientific journal there is talk of research according to which cats that received meloxicam had greater proteinuria at 6 months than cats that received placebo. It was concluded that meloxicam should be used with caution in cats with chronic kidney disease.[42]

Pharmacokinetics

In dogs, the absorption of meloxicam from the stomach is not affected by the presence of food,[43] with the peak concentration (Cmax) of meloxicam occurring in the blood 7–8 hours after administration.[43] The half-life of meloxicam is approximately 24 hours in dogs.[43] In the koala (Phascolarctos cinereus), very little meloxicam is absorbed into the blood after oral administration (that is, it has poor bioavailability).[44]

United States

2003: Meloxicam was approved in the US for use in dogs for the management of pain and inflammation associated with osteoarthritis, as an oral (liquid) formulation of meloxicam.[45]

2003 (November): An injectable formulation for use in dogs was approved by the US Food and Drug Administration (FDA).[46]

2004 (October): A formulation for use in cats was approved for use before surgery only.[47] This is an injectable meloxicam, indicated for as a single, one-time dose only, with specific and repeated warnings not to administer a second dose.[48]

2005 (January): The product insert added a warning in bold-face type: "Do not use in cats."[49]

2005: The FDA sent a Notice of Violation to the manufacturer for its promotional materials which included promotion of the drug for off-label use.[50]

2020 (February): A meloxicam injection was approved for use in the United States. Specifically, the FDA granted the approval of Anjeso to Baudax Bio.[3][51]

European Union

In the European Union, meloxicam is licensed for other anti-inflammatory benefits including relief from both acute and chronic pain in dogs. Meloxicam is also licensed for use in horses, to relieve the pain associated with musculoskeletal disorders.[52]

1998 (January): Meloxicam was authorised for use in cattle throughout the European Union, via a centralised marketing authorisation.[53]

2006: The first generic meloxicam product was approved.[53]

2024 (January): EMA issued an 'Opinion'[54] on a change to this medicine's authorisation concerning the follow-up oral treatment after initial injectable administration in cats. This change remains as an 'Opinion', while the medication continues to be approved as usual.[55]

Other countries

As of June 2008, meloxicam was registered for long-term use in cats in Australia, New Zealand, and Canada.[56]

In the United Kingdom, meloxicam is licensed for use in cats, guinea pigs, horses, and livestock including pigs and cattle.[57]

See also

  • Bupivacaine/meloxicam

References

  1. ↑ British national formulary: BNF 76 (76 ed.). Pharmaceutical Press. 2018. pp. 1112–1113. ISBN 978-0-85711-338-2. 
  2. ↑ 2.00 2.01 2.02 2.03 2.04 2.05 2.06 2.07 2.08 2.09 2.10 2.11 2.12 2.13 "Meloxicam Monograph for Professionals". AHFS. 10 June 2025. https://www.drugs.com/monograph/meloxicam.html. 
  3. ↑ 3.0 3.1 3.2 "Baudax Bio Announces FDA Approval of Anjeso for the Management of Moderate to Severe Pain". Baudax Bio, Inc. (Press release). 20 February 2020. Archived from the original on 21 February 2020. Retrieved 20 February 2020.
  4. ↑ "Top 300 of 2023". https://clincalc.com/DrugStats/Top300Drugs.aspx. 
  5. ↑ "Meloxicam Drug Usage Statistics, United States, 2014 - 2023". https://clincalc.com/DrugStats/Drugs/Meloxicam. 
  6. ↑ "Anjeso- meloxicam injection". DailyMed. U.S. National Library of Medicine. 22 February 2022. https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=6f517ef8-9478-494e-adfd-4944b9900df4. 
  7. ↑ 7.0 7.1 7.2 7.3 7.4 7.5 7.6 Cite error: Invalid <ref> tag; no text was provided for refs named Mobic FDA label
  8. ↑ 8.0 8.1 "Gastrointestinal tolerability of meloxicam compared to diclofenac in osteoarthritis patients. International MELISSA Study Group. Meloxicam Large-scale International Study Safety Assessment". British Journal of Rheumatology 37 (9): 937–945. September 1998. doi:10.1093/rheumatology/37.9.937. PMID 9783757. 
  9. ↑ "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". British Journal of Rheumatology 37 (9): 946–951. September 1998. doi:10.1093/rheumatology/37.9.946. PMID 9783758. 
  10. ↑ "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". British Journal of Rheumatology 35 Suppl 1 (Suppl 1): 22–28. April 1996. doi:10.1093/rheumatology/35.suppl_1.22. PMID 8630632. 
  11. ↑ 11.0 11.1 "FDA Warns that Using a Type of Pain and Fever Medication in Second Half of Pregnancy Could Lead to Complications". U.S. Food and Drug Administration (FDA) (Press release). 15 October 2020. Archived from the original on 16 October 2020. Retrieved 15 October 2020. Public Domain This article incorporates text from this source, which is in the public domain.
  12. ↑ 12.0 12.1 "NSAIDs may cause rare kidney problems in unborn babies". 21 July 2017. https://www.fda.gov/drugs/drug-safety-and-availability/fda-recommends-avoiding-use-nsaids-pregnancy-20-weeks-or-later-because-they-can-result-low-amniotic.  Public Domain This article incorporates text from this source, which is in the public domain.
  13. ↑ "Development of a special electrode for continuous subcutaneous pH measurement in the infant scalp". American Journal of Obstetrics and Gynecology 124 (2): 193–195. January 1976. doi:10.1016/S0002-9378(16)33297-5. PMID 2012. 
  14. ↑ "A review of the efficacy, safety, and cost-effectiveness of COX-2 inhibitors for Africa and the Middle East region". Pain Practice 13 (4): 316–331. April 2013. doi:10.1111/j.1533-2500.2012.00591.x. PMID 22931375. 
  15. ↑ 15.0 15.1 15.2 "Meloxicam: a reappraisal of pharmacokinetics, efficacy and safety". Expert Opinion on Pharmacotherapy 6 (12): 2117–2140. October 2005. doi:10.1517/14656566.6.12.2117. PMID 16197363. "Meloxicam is extensively bound to plasma proteins (99.4%), primarily to albumin. Meloxicam has an apparent volume of distribution (Vd) 10 – 15 L in humans (0.1 – 0.2 L/kg) after oral administration and a mean volume of distribution at steady-state of 0.2 L/kg after intravenous administration."
    "None of the meloxicam treatment groups demonstrated inhibition of platelet aggregation to either arachidonic acid (AC) or adenosine diphosphate (ADP). However, there were no significant changes in the platelet count, prothrombin, and activated partial thromboplastin time in any of the meloxicam and indomethacin groups. Other crossover studies also confirmed that meloxicam 15 mg/day caused a major reduction of maximum thromboxane production, but no reduction in collagen- or AC-induced platelet aggregation.".     
  16. ↑ "Risk of serious upper gastrointestinal and cardiovascular thromboembolic complications with meloxicam". The American Journal of Medicine 117 (2): 100–106. July 2004. doi:10.1016/j.amjmed.2004.03.012. PMID 15234645. 
  17. ↑ "Meloxicam". MedlinePlus. https://www.medlineplus.gov/druginfo/meds/a601242.html. 
  18. ↑ "Meloxicam". Drugs 51 (3): 424–30; discussion 431–32. March 1996. doi:10.2165/00003495-199651030-00007. PMID 8882380. 
  19. ↑ "Oxicams bind in a novel mode to the cyclooxygenase active site via a two-water-mediated H-bonding Network". The Journal of Biological Chemistry 289 (10): 6799–6808. March 2014. doi:10.1074/jbc.M113.517987. PMID 24425867. 
  20. ↑ "Oxicams, a class of nonsteroidal anti-inflammatory drugs and beyond". IUBMB Life 66 (12): 803–811. December 2014. doi:10.1002/iub.1334. PMID 25537198. 
  21. ↑ "Anti-inflammatory, analgesic, antipyretic and related properties of meloxicam, a new non-steroidal anti-inflammatory agent with favourable gastrointestinal tolerance". Inflammation Research 44 (10): 423–433. October 1995. doi:10.1007/BF01757699. PMID 8564518. 
  22. ↑ 22.0 22.1 "Meloxicam in the management of post-operative pain: Narrative review". Journal of Anaesthesiology Clinical Pharmacology 34 (4): 450–457. 2018. doi:10.4103/joacp.JOACP_133_18. PMID 30774225. 
  23. ↑ By the 2019 American Geriatrics Society Beers Criteria® Update Expert Panel (April 2019). "American Geriatrics Society 2019 Updated AGS Beers Criteria® for Potentially Inappropriate Medication Use in Older Adults". Journal of the American Geriatrics Society 67 (4): 674–694. doi:10.1111/jgs.15767. PMID 30693946. 
  24. ↑ "Effect of structural modification of enol-carboxamide-type nonsteroidal antiinflammatory drugs on COX-2/COX-1 selectivity". Journal of Medicinal Chemistry 40 (6): 980–989. March 1997. doi:10.1021/jm9607010. PMID 9083488. 
  25. ↑ "Meloxicam". PubChem, US National Library of Medicine. 27 September 2025. https://pubchem.ncbi.nlm.nih.gov/compound/54677470. 
  26. ↑ 26.0 26.1 "Metacam- meloxicam suspension". DailyMed. U.S. National Library of Medicine. https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=ed2227e6-8c69-4057-a8b2-94f74cb11264. 
  27. ↑ "Metacam- meloxicam injection, solution". DailyMed. U.S. National Library of Medicine. https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=ca78caf5-2b47-46c1-abec-0f925b39f455. 
  28. ↑ Off-label use discussed in: Arnold Plotnick MS, DVM, ACVIM, ABVP, Pain Management using Metacam , and Stein, Robert, Perioperative Pain Management Part IV, Looking Beyond Butorphanol, Sep 2006, Veterinary Anesthesia & Analgesia Support Group.
  29. ↑ For off-label use example in rabbits, see Krempels, Dana, Hind Limb Paresis and Paralysis in Rabbits , University of Miami Biology Department.
  30. ↑ "Metacam". 31 July 2006. https://www.ema.europa.eu/en/medicines/veterinary/EPAR/metacam. 
  31. ↑ "Removing the threat of diclofenac to critically endangered Asian vultures". PLOS Biology 4 (3): e66. March 2006. doi:10.1371/journal.pbio.0040066. PMID 16435886. 
  32. ↑ "Effects of meloxicam on renal function in dogs with hypotension during anaesthesia". Veterinary Anaesthesia and Analgesia 33 (1): 62–69. January 2006. doi:10.1111/j.1467-2995.2005.00208.x. PMID 16412133. 
  33. ↑ "Effect of non-steroidal anti-inflammatory drugs on postoperative respiratory and heart rate in cats subjected to ovariohysterectomy". Journal of Feline Medicine and Surgery 20 (10): 980–984. October 2018. doi:10.1177/1098612X17742290. PMID 29165006. 
  34. ↑ "Get the Facts about Pain Relievers for Pets". 29 September 2022. https://www.fda.gov/animal-veterinary/animal-health-literacy/get-facts-about-pain-relievers-pets. 
  35. ↑ "What Veterinarians Should Advise Clients About Pain Control and Nonsteroidal Anti-Inflammatory Drugs (NSAIDs) in Dogs and Cats". 15 August 2023. https://www.fda.gov/animal-veterinary/resources-you/what-veterinarians-should-advise-clients-about-pain-control-and-nonsteroidal-anti-inflammatory-drugs. 
  36. ↑ "Information about the Boxed Warning on Meloxicam Labels regarding Safety Risks in Cats". 14 August 2023. https://www.fda.gov/animal-veterinary/product-safety-information/information-about-boxed-warning-meloxicam-labels-regarding-safety-risks-cats. 
  37. ↑ "Metacam". 31 July 2006. https://www.ema.europa.eu/en/medicines/veterinary/EPAR/metacam. 
  38. ↑ "Cats: Meloxicam Question for Department for Environment, Food and Rural Affairs". UK Parliament Written questions, answers and statements. https://questions-statements.parliament.uk/written-questions/detail/2021-05-11/HL10/. 
  39. ↑ 39.0 39.1 "Clinical particulars - Meloxidyl 0.5 mg/ml oral suspension for cats". https://www.noahcompendium.co.uk/?id=-474521. 
  40. ↑ "Toxicology Brief: The 10 most common toxicoses in cats". Dvm360. 1 June 2006. http://veterinarymedicine.dvm360.com/toxicology-brief-10-most-common-toxicoses-cats?id=&sk=&date=&pageID=3. Retrieved 16 September 2018. 
  41. ↑ "The 10 most common toxicoses in cats". Veterinary Medicine: 340–342. June 2006. https://www.aspcapro.org/sites/default/files/zl-vetm0606_339-342.pdf. Retrieved 9 August 2019. 
  42. ↑ "Effects of low-dose meloxicam in cats with chronic kidney disease". Journal of Feline Medicine and Surgery 23 (2): 138–148. February 2021. doi:10.1177/1098612X20935750. PMID 32594827. 
  43. ↑ 43.0 43.1 43.2 "Toxicology of frequently encountered nonsteroidal anti-inflammatory drugs in dogs and cats". The Veterinary Clinics of North America. Small Animal Practice 42 (2): 289–306, vi–vii. March 2012. doi:10.1016/j.cvsm.2012.01.003. PMID 22381180. 
  44. ↑ "Pharmacokinetics of meloxicam in koalas (Phascolarctos cinereus) after intravenous, subcutaneous and oral administration". Journal of Veterinary Pharmacology and Therapeutics 36 (5): 486–493. October 2013. doi:10.1111/jvp.12038. PMID 23406022. 
  45. ↑ "NADA 141-213: New Animal Drug Application Approval (for Metacam (meloxicam) 0.5 mg/mL and 1.5 mg/mL Oral Suspension)". U.S. Food and Drug Administration (FDA). 15 April 2003. https://www.fda.gov/downloads/AnimalVeterinary/Products/ApprovedAnimalDrugProducts/FOIADrugSummaries/ucm118006.pdf. 
  46. ↑ "NADA 141-219: Metacam (meloxicam) 5 mg/mL Solution for Injection". U.S. Food and Drug Administration (FDA). 12 November 2003. https://www.fda.gov/downloads/AnimalVeterinary/Products/ApprovedAnimalDrugProducts/FOIADrugSummaries/ucm118026.pdf. 
  47. ↑ "Metacam 5 mg/mL Solution for Injection, Supplemental Approval". U.S. Food and Drug Administration (FDA). 28 October 2004. https://www.fda.gov/downloads/AnimalVeterinary/Products/ApprovedAnimalDrugProducts/FOIADrugSummaries/ucm118027.pdf. 
  48. ↑ See the manufacturer's FAQ on its website, and its clinical dosing instructions for cats.
  49. ↑ "Client Information Sheet For Metacam (meloxicam) 1.5 mg/mL Oral Suspension". U.S. Food and Drug Administration (FDA). January 2005. https://www.fda.gov/downloads/AnimalVeterinary/Products/ApprovedAnimalDrugProducts/DrugLabels/UCM050394.pdf. "Metacam is a prescription non-steroidal anti-inflammatory drug (NSAID) that is used to control pain and inflammation (soreness) due to osteoarthritis in dogs. Osteoarthritis (OA) is a painful condition caused by “wear and tear” of cartilage and other parts of the joints that may result in the following changes or signs in your dog: Limping or lameness, decreased activity or exercise (reluctance to stand, climb stairs, jump or run, or difficulty in performing these activities), stiffness or decreased movement of joints. Metacam is given to dogs by mouth. Do not use Metacam Oral Suspension in cats. Acute kidney injury and death have been associated with the use of meloxicam in cats." 
  50. ↑ "Notice of Violation". U.S. Food and Drug Administration (FDA). 19 April 2005. https://www.fda.gov/downloads/AnimalVeterinary/GuidanceComplianceEnforcement/ComplianceEnforcement/ucm042460.pdf. 
  51. ↑ "Anjeso (meloxicam) injection, for intravenous use". U.S. Food and Drug Administration (FDA). February 2020. https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/210583s000lbl.pdf. 
  52. ↑ "Meloxicam". Small animal clinical pharmacology (2nd ed.). Edinburgh: Saunders/Elsevier. 2008. pp. 301–302. ISBN 978-0-7020-2858-8. https://archive.org/details/smallanimalclini00mrcv. 
  53. ↑ 53.0 53.1 "Generic and biosimilar medicinal products in the European Union". Chemistry Today 25 (2): 4–6. March 2007. https://www.hoganlovells.com/~/media/hogan-lovells/pdf/publication/chemistrytodayapr07_pdf.pdf. Retrieved 28 January 2020. 
  54. ↑ "Meeting highlights from the Committee for Veterinary Medicinal Products (CVMP) 16-17 January 2024 | European Medicines Agency (EMA)" (in en). 19 January 2024. https://www.ema.europa.eu/en/news/meeting-highlights-committee-veterinary-medicinal-products-cvmp-16-17-january-2024. 
  55. ↑ "Metacam". 31 July 2006. https://www.ema.europa.eu/en/medicines/veterinary/EPAR/metacam. 
  56. ↑ "Recent NSAID developments". Clinical medicine of the dog and cat (3rd ed.). CRC Press. 2016. pp. <!––no page numbers in ebook––>. ISBN 978-1-4822-2606-5. https://books.google.com/books?id=fjqLDQAAQBAJ&dq=meloxicam+cat+australia&pg=PT2004. Retrieved 28 January 2020. 
  57. ↑ "Product Information Database". DEFRA. https://www.vmd.defra.gov.uk/ProductInformationDatabase/current?page=79&order=ActiveSubstances&descending=True. 



Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:Meloxicam&oldid=4176362"