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Meloxicam

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Meloxicam
Clinical data
Trade namesMobic, others
AHFS/Drugs.comMonograph
MedlinePlusa601242
License data
Pregnancy
category
Routes of
administration		By mouth,intravenous
ATC code
Legal status
Legal status
Pharmacokineticdata
Bioavailability89%[7]
Protein binding99.4%[7]
MetabolismLiver(CYP2C9and3A4-mediated)[7]
Eliminationhalf-life20 hours[7]
ExcretionUrineandfecesequally[7]
Identifiers
  • 4-Hydroxy-2-methyl-N-(5-methyl-2-thiazolyl)-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide
CAS Number
PubChemCID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
CompTox Dashboard(EPA)
ECHA InfoCard100.113.257Edit this at Wikidata
Chemical and physical data
FormulaC14H13N3O4S2
Molar mass351.40g·mol−1
3D model (JSmol)
  • Cc1cnc(s1)NC(=O)C\3=C(/O)c2ccccc2S(=O)(=O)N/3C
  • 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)checkY
  • Key:ZRVUJXDFFKFLMG-UHFFFAOYSA-NcheckY
☒NcheckY(what is this?)(verify)

Meloxicam,sold under the brand nameMobicamong others, is anonsteroidal anti-inflammatory drug(NSAID) used to treat pain and inflammation inrheumatic diseasesandosteoarthritis.[8][9]It is used by mouth or byinjection into a vein.[9][10]It is recommended that it be used for as short a period as possible and at a low dose.[9]

Common side effects include abdominal pain, dizziness, swelling, headache, and a rash.[9]Serious side effects may includeheart disease,stroke,kidney problems, andstomach ulcers.[9]Use is not recommended in thethird trimester of pregnancy.[9]It blockscyclooxygenase-2(COX-2) more than it blockscyclooxygenase-1(COX-1).[9]It is in theoxicamfamily of chemicals and is closely related topiroxicam.[9]

Meloxicam was patented in 1977 and approved for medical use in the United States in 2000.[9][11]It was developed byBoehringer Ingelheim;however, it is also available as ageneric medication.[9]In 2021, it was the 32nd most commonly prescribed medication in the United States, with more than 18million prescriptions.[12][13]An intravenous version of meloxicam (Anjeso) was approved for medical use in the United States in February 2020.[14][10]

Adverse effects[edit]

See also:Nonsteroidal anti-inflammatory drug

Meloxicam use can result ingastrointestinaltoxicity and bleeding, headaches, rash, andvery dark or black stool(a sign of intestinal bleeding). It has fewer gastrointestinal side effects thandiclofenac,[15]piroxicam,[16]naproxen,[17]and perhaps all other NSAIDs which are not COX-2 selective.[15]

In October 2020, the U.S.Food and Drug Administration(FDA) required thedrug labelto be updated for all nonsteroidal anti-inflammatory medications to describe the risk of kidney problems in unborn babies that result in low amniotic fluid.[18][19]They recommend avoiding NSAIDs in pregnant women at 20 weeks or later in pregnancy.[18][19]

Cardiovascular[edit]

Like otherNSAIDs,its use is associated with an increased risk of cardiovascular events such asheart attackandstroke.[20]Although meloxicam inhibits formation ofthromboxaneA, it does not appear to do so at levels that would interfere withplateletfunction.[21][22]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 ofthromboemboliccomplications than the NSAID diclofenac (0.2% versus 0.8% respectively) but a similar incidence of thromboembolic events to naproxen and piroxicam.[23]

People withhypertension,high cholesterol,ordiabetesare 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.[24][25]

Gastrointestinal[edit]

NSAIDscause an increase in the risk of seriousgastrointestinaladverse 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.[26]

Mouth[edit]

It is recommended to withhold meloxicam use for at least four to six half-lives prior to surgical or dental procedures due to increased risk fortaste perversion,ulcerative stomatitisanddry mouth.[medical citation needed]

Mechanism of action[edit]

Main article:Non-steroidal anti-inflammatory drug

Meloxicam blockscyclooxygenase(COX), theenzymeresponsible for convertingarachidonic acidintoprostaglandin H2—the first step in the synthesis ofprostaglandins,which are mediators of inflammation. Meloxicam has been shown, especially at lowtherapeutic doses,to selectively inhibitCOX-2overCOX-1.[7]

Meloxicam concentrations insynovial fluidrange from 40% to 50% of those inplasma.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,[26]but it may account for the fact that it performs exceptionally well in treatment of arthritis in animal models.[27]

Pharmacokinetics[edit]

Absorption[edit]

Thebioavailabilityof meloxicam is decreased when administered orally compared to an equivalent IV bolus dose. Different oral formulations of meloxicam are notbioequivalent.[9]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 ofantacidsdoes not show pharmacokinetic interactions.[4]With chronic dosing, the time to maximum plasma concentration following oral administration is approximately 5–6 hours.[28]

Distribution[edit]

The mean volume of distribution of meloxicam is approximately 10 L. It is highly protein-bound, mainly toalbumin.[22][28]

Metabolism[edit]

Meloxicam is extensively metabolized in the liver by the enzymesCYP2C9andCYP3A4(minor) into four inactive metabolites.Peroxidaseactivity is thought to be responsible for the other two remaining metabolites.[4][29]

Excretion[edit]

Meloxicam is predominantly excreted in the form of metabolites and occurs to equal extents in the urine and feces.[4]Traces of unchanged parent drug are found in urine and feces.[4]The mean elimination half-life ranges from 15 to 20 hours.[4]

Specific populations[edit]

Use of meloxicam is not recommended in people with peptic ulcer disease or increased gastrointestinal bleed risk, including those over 75 years of age or those taking medications associated with bleeding risk.[30]

Adverse events have been found to be dose-dependent and associated with length of treatment.[30][4]

Veterinary use[edit]

Meloxicam is used inveterinary medicineto treat dogs,[31][32]but also seesoff-label usein other animals such as cattle and exotics.[33][34]

The most common side effects include gastrointestinal irritation (vomiting, diarrhea, andulceration).[31]

In healthy dogs given meloxicam, no perioperative adverse effects on the cardiovascular system have been reported at recommended dosages.[35]Perioperative administration of meloxicam to cats did not affect postoperative respiratory rate nor heart rate.[36]

Meloxicam has been investigated as an alternative todiclofenacby theRoyal Society for the Protection of Birds(RSPB) to prevent deaths ofvultures.[37]

The Use of Meloxicam in Cats[edit]

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:

TheFDA(Food & Drug Administration) approves the use of meloxicam in catsonly in injectable formand only as a one-time injection given before surgery.[38][39]Itdoes not approvemeloxicam oral suspension for cats and itdoes not approvemeloxicam spray for cats because after reviewing numerous reports of meloxicam side effects in cats, it has identified many cases ofacute renal failureanddeathand has added the following boxed warning to the products' 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."[40]In contrast, in the European Union and other continents or countries, the use of the drug in cats is allowed.[41][42]

Another conflicting guideline concerns a specific meloxicam oral suspension product for cats. Its instruction sheet states that: "Typical adverse reactions ofNSAIDssuch 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. "[43]However, the main page of the official website of the same meloxicam product states: "Important Safety Information: DO NOT USE [...] ORAL SUSPENSION IN CATS. Acute renal failure and death have been associated with the use of meloxicam in cats."[44]

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."[43]The dosage policy for meloxicam oral suspension products for cats as described in the data sheets defines the amount administered as proportional to body weight.There is no separate dosage guideline for overweight or obese cats.This is worth mentioning on the one hand because the articleDrug dosing in obese adults[45]advocates that the use of total body weight in obese adults may lead to drug toxicity and suggests individualised dosing based on the patient's ideal rather than actual body weight, and, on the other hand, precisely because the range safety of meloxicam for cats is so limited.

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 injuryandCNSsigns such as seizures and comas in cats. It adds that cats have a low tolerance for NSAIDs.[46][47]Also, in another scientific journal there is talk of research according to which cats that received meloxicam had greaterproteinuriaat 6 months than cats that received placebo. It was concluded that meloxicam should be used with caution in cats with chronic kidney disease.[48]

Pharmacokinetics[edit]

In dogs, theabsorptionof meloxicam from the stomach is not affected by the presence of food,[49]with the peak concentration (Cmax) of meloxicam occurring in the blood 7–8 hours after administration.[49]Thehalf-lifeof meloxicam is approximately 24 hours in dogs.[49]

In thekoala(Phascolarctos cinereus), very little meloxicam is absorbed into the blood afteroral administration(that is, it has poorbioavailability).[50]

Legal status[edit]

United States[edit]

In 2003, meloxicam was approved in the U.S. for use in dogs for the management of pain and inflammation associated withosteoarthritis,as anoral(liquid) formulation of meloxicam.[51]In January 2005, the product insert added a warning in bold-face type: "Do not use in cats."[52]Aninjectableformulation for use in dogs was approved by the U.S.Food and Drug Administration(FDA) in November 2003.[53]

In October 2004, a formulation for use in cats was approved for use prior to surgery only.[54]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.[55]

In 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.[56]

In February 2020, meloxicam injection was approved for use in the United States. The FDA granted the approval of Anjeso toBaudax Bio.[10][57]

European Union[edit]

In Europe the product is licensed for other anti-inflammatory benefits including relief from bothacuteandchronic painin dogs. Meloxicam is also licensed for use in horses, to relieve the pain associated withmusculoskeletaldisorders.[58]

Meloxicam was authorised for use in cattle throughout the European Union in January 1998, via acentralised marketing authorisation.[59]The firstgenericmeloxicam product was approved in 2006.[59]

Other countries[edit]

As of June 2008,meloxicam is registered for long-term use in cats in Australia, New Zealand, and Canada.[60]In the United Kingdom, meloxicam is licensed for use in cats, guinea pigs, horses, and livestock including pigs and cattle.[61]

See also[edit]

References[edit]

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  4. ^abcdefg"Mobic- meloxicam tablet".DailyMed.Retrieved15 May2021.
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  10. ^abc"Baudax Bio Announces FDA Approval of Anjeso for the Management of Moderate to Severe Pain".Baudax Bio,Inc.(Press release). 20 February 2020.Archivedfrom the original on 21 February 2020.Retrieved20 February2020.
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  12. ^"The Top 300 of 2021".ClinCalc.Archivedfrom the original on 15 January 2024.Retrieved14 January2024.
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  15. ^abHawkey C, Kahan A, Steinbrück K, Alegre C, Baumelou E, Bégaud B, et al. (September 1998)."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): 937–45.doi:10.1093/rheumatology/37.9.937.PMID9783757.
  16. ^Dequeker J, Hawkey C, Kahan A, Steinbrück K, Alegre C, Baumelou E, et al. (September 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".British Journal of Rheumatology.37(9): 946–51.doi:10.1093/rheumatology/37.9.946.PMID9783758.
  17. ^Wojtulewski JA, Schattenkirchner M, Barceló P, Le Loët X, Bevis PJ, Bluhmki E, et al. (April 1996)."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): 22–8.doi:10.1093/rheumatology/35.suppl_1.22.PMID8630632.
  18. ^ab"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.Retrieved15 October2020.Public DomainThis article incorporates text from this source, which is in thepublic domain.
  19. ^ab"NSAIDs may cause rare kidney problems in unborn babies".U.S. Food and Drug Administration.21 July 2017.Retrieved15 October2020.Public DomainThis article incorporates text from this source, which is in thepublic domain.
  20. ^Stamm O, Latscha U, Janecek P, Campana A (January 1976). "Development of a special electrode for continuous subcutaneous pH measurement in the infant scalp".American Journal of Obstetrics and Gynecology.124(2): 193–195.doi:10.1016/S0002-9378(16)33297-5.PMID2012.
  21. ^Zeidan AZ, Al Sayed B, Bargaoui N, Djebbar M, Djennane M, Donald R, et al. (April 2013). "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.doi:10.1111/j.1533-2500.2012.00591.x.PMID22931375.S2CID205715393.
  22. ^abGates BJ, Nguyen TT, Setter SM, Davies NM (October 2005). "Meloxicam: a reappraisal of pharmacokinetics, efficacy and safety".Expert Opinion on Pharmacotherapy.6(12): 2117–2140.doi:10.1517/14656566.6.12.2117.PMID16197363.S2CID25512189.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.
  23. ^Singh G, Lanes S, Triadafilopoulos G (July 2004). "Risk of serious upper gastrointestinal and cardiovascular thromboembolic complications with meloxicam".The American Journal of Medicine.117(2): 100–106.doi:10.1016/j.amjmed.2004.03.012.PMID15234645.
  24. ^"Meloxicam".MedlinePlus.Archivedfrom the original on 29 November 2014.Retrieved15 November2014.
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  26. ^ab"Meloxicam official FDA information, side effects, and uses".Drugs.com. March 2010.Archivedfrom the original on 16 March 2010.Retrieved17 March2010.
  27. ^Engelhardt G, Homma D, Schlegel K, Utzmann R, Schnitzler C (October 1995). "Anti-inflammatory, analgesic, antipyretic and related properties of meloxicam, a new non-steroidal anti-inflammatory agent with favourable gastrointestinal tolerance".Inflammation Research.44(10): 423–33.doi:10.1007/BF01757699.PMID8564518.S2CID37937305.
  28. ^abBekker A, Kloepping C, Collingwood S (2018)."Meloxicam in the management of post-operative pain: Narrative review".Journal of Anaesthesiology Clinical Pharmacology.34(4): 450–457.doi:10.4103/joacp.JOACP_133_18.PMC6360894.PMID30774225.
  29. ^"Meloxicam (Professional Patient Advice)".Drugs.com.Archivedfrom the original on 6 August 2019.Retrieved6 August2019.
  30. ^ab2019 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.PMID30693946.S2CID59338182.
  31. ^ab"Metacam- meloxicam suspension".DailyMed.Retrieved15 May2021.
  32. ^"Metacam- meloxicam injection, solution".DailyMed.Retrieved15 May2021.
  33. ^Off-label use discussed in: Arnold Plotnick MS, DVM, ACVIM, ABVP,Pain Management using MetacamArchived14 July 2011 at theWayback Machine,and Stein, Robert,Perioperative Pain ManagementArchived18 April 2010 at theWayback MachinePart IV, Looking Beyond Butorphanol, Sep 2006, Veterinary Anesthesia & Analgesia Support Group.
  34. ^For off-label use example in rabbits, see Krempels, Dana,Hind Limb Paresis and Paralysis in RabbitsArchived17 June 2010 at theWayback Machine,University of Miami Biology Department.
  35. ^Boström IM, Nyman G, Hoppe A, Lord P (January 2006). "Effects of meloxicam on renal function in dogs with hypotension during anaesthesia".Veterinary Anaesthesia and Analgesia.33(1): 62–9.doi:10.1111/j.1467-2995.2005.00208.x.PMID16412133.
  36. ^Höglund OV, Dyall B, Gräsman V, Edner A, Olsson U, Höglund K (October 2018)."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.doi:10.1177/1098612X17742290.PMC11129237.PMID29165006.S2CID30649716.
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  40. ^Center for Veterinary Medicine (14 August 2023)."Information about the Boxed Warning on Meloxicam Labels regarding Safety Risks in Cats".FDA.
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  42. ^"Cats: Meloxicam Question for Department for Environment, Food and Rural Affairs".UK Parliament Written questions, answers and statements.
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  44. ^"Meloxidyl® from Ceva Animal Health".Retrieved29 March2024.
  45. ^Barras M, Legg A (October 2017)."Drug dosing in obese adults".Australian Prescriber.40(5): 189–193.doi:10.18773/austprescr.2017.053.PMC5662437.PMID29109603.
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  48. ^KuKanich K, George C, Roush JK, Sharp S, Farace G, Yerramilli M, et al. (February 2021)."Effects of low-dose meloxicam in cats with chronic kidney disease".Journal of Feline Medicine and Surgery.23(2): 138–148.doi:10.1177/1098612X20935750.PMC10741344.PMID32594827.S2CID220256059.
  49. ^abcKhan SA, McLean MK (March 2012). "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.doi:10.1016/j.cvsm.2012.01.003.PMID22381180.
  50. ^Kimble B, Black LA, Li KM, Valtchev P, Gilchrist S, Gillett A, et al. (October 2013)."Pharmacokinetics of meloxicam in koalas (Phascolarctos cinereus) after intravenous, subcutaneous and oral administration".Journal of Veterinary Pharmacology and Therapeutics.36(5): 486–93.doi:10.1111/jvp.12038.PMID23406022.
  51. ^"NADA 141-213: New Animal Drug Application Approval (for Metacam (meloxicam) 0.5 mg/mL and 1.5 mg/mL Oral Suspension)"(PDF).Food and Drug Administration(FDA). 15 April 2003. Archived fromthe original(PDF)on 6 April 2017.Retrieved24 July2010.
  52. ^"Client Information Sheet For Metacam (meloxicam) 1.5 mg/mL Oral Suspension"(PDF).Food and Drug Administration(FDA). January 2005. Archived fromthe original(PDF)on 15 November 2017.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 injuryand death have been associated with the use of meloxicam in cats.
  53. ^"NADA 141-219: Metacam (meloxicam) 5 mg/mL Solution for Injection"(PDF).U.S.Food and Drug Administration(FDA). 12 November 2003. Archived fromthe original(PDF)on 15 November 2017.Retrieved8 August2019.
  54. ^"Metacam 5 mg/mL Solution for Injection, Supplemental Approval"(PDF).U.S.Food and Drug Administration(FDA). 28 October 2004. Archived fromthe original(PDF)on 15 November 2017.Retrieved8 August2019.
  55. ^See the manufacturer'sFAQArchived2 July 2011 at theWayback Machineon its website, and itsclinical dosing instructions for cats.Archived6 September 2008 at theWayback Machine
  56. ^"Notice of Violation"(PDF).U.S.Food and Drug Administration(FDA). 19 April 2005. Archived fromthe original(PDF)on 13 January 2017.Retrieved8 August2019.
  57. ^"Anjeso (meloxicam) injection, for intravenous use"(PDF).U.S.Food and Drug Administration(FDA). February 2020.Archived(PDF)from the original on 22 February 2020.Retrieved21 February2020.
  58. ^Maddison JE, Page SW, Church D, eds. (2008). "Meloxicam".Small animal clinical pharmacology(2nd ed.). Edinburgh: Saunders/Elsevier. pp.301–302.ISBN9780702028588.
  59. ^abWright E (March 2007)."Generic and biosimilar medicinal products in the European Union"(PDF).Chemistry Today.25(2): 4–6.Archived(PDF)from the original on 28 January 2020.Retrieved28 January2020.
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  61. ^"Product Information Database".Veterinary Medicines Directorate.DEFRA.Retrieved29 March2023.
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