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Meloxicam

Alias:

Parocin; reumoxicam; Movicox; Mobic; Mobicox; Movalis; Meloxicamum; Uticox;

Cat No.:V1044 Purity: ≥98%
Meloxicam (Parocin; Movicox; Meloxicamum;Mobic; Mobicox; reumoxicam;Movalis; Uticox), an approved medication used to treat pain and inflammation in rheumatic arthritis and osteoarthritis,is a potent non-steroidal anti-inflammatory drug (NSAID)which acts as a selective COX inhibitor withIC50s of 0.49 µM and 36.6 µM for COX-2 and COX-1, respectively.
Meloxicam
Meloxicam Chemical Structure CAS No.: 71125-38-7
Product category: COX
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
250mg
500mg
1g
2g
5g
10g
25g
Other Sizes

Other Forms of Meloxicam:

  • Meloxicam D4
  • Meloxicam-d3-1 (meloxicam d3-1)
  • Meloxicam sodium
  • Meloxicam-13C,d3
Official Supplier of:
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Top Publications Citing lnvivochem Products
InvivoChem's Meloxicam has been cited by 1 publication
Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Meloxicam (Parocin; Movicox; Meloxicamum; Mobic; Mobicox; reumoxicam; Movalis; Uticox), an approved medication used to treat pain and inflammation in rheumatic arthritis and osteoarthritis, is a potent non-steroidal anti-inflammatory drug (NSAID) which acts as a selective COX inhibitor with IC50s of 0.49 µM and 36.6 µM for COX-2 and COX-1, respectively. I is used to relieve pain and fever effects. Studies suggest that Meloxicam is Cox-2 preferential, therefore it will probably not display a lower gastrointestinal toxicity than non-selective anti-inflammatory agents. This compound has been shown to also inhibit prostanoid synthesis in inflammatory cells. It shows potent anti-inflammatory, antipyretic, and analgesic effects with low gastrointestinal toxicity in animal models.

Biological Activity I Assay Protocols (From Reference)
ln Vitro
Compound 5, meloxicam, is a non-steroidal anti-inflammatory drug that suppresses COX activity. Its IC50 values for COX-2 and COX-1 are 0.49 µM and 36.6 µM, respectively[1]. At 0.25–25 µg/mL, meloxicam does not exhibit any cytotoxicity on MDCK or CF41.Mg tumor cells, but it suppresses COX+ tumor cells. Additionally, doxorubicin and meloxicam do not work synergistically on CF41.Mg cells. Meloxicam (0.25 µg/mL) inhibits the migration and invasion of CF41.Mg cells, reduces the production of MMP-2, and increases β-catenin phophorylation in CF41.Mg cells; however, it has no effect on apoptosis in CF41.Mg cells[2].
ln Vivo
In mice, paw liking time is considerably reduced by meloxicam (10 mg/kg) alone or in combination with rutin on the first day by 55% and 49%, respectively, compared to the formalin-treated group; however, the combination does not significantly reduce time on the third day. Additionally, meloxicam alone or in combination with rutin reduces MDA contents, activates liver SOD activities, lowers relative liver weights, inhibits IL-1β content, and considerably lowers the number of positive caspase-3 immunoreactive cells in mice[3].
Animal Protocol
N/A
Mice, horse, and dogs
ADME/Pharmacokinetics
Absorption, Distribution and Excretion
The absolute bioavailability oral capsules after a dose was 89% in one pharmacokinetic study. Cmax was reached 5–6 hours after administration of a single dose given after the first meal of the day. The Cmax doubled when the drug was administered in the fasting state. Despite this, meloxicam can be taken without regard to food, unlike many other NSAIDS. Meloxicam formulated for instillation with [bupivacaine] produced varied systemic measures following a single dose of varying strength. In patients undergoing bunionectomy, 1.8 mg of meloxicam produced a Cmax of 26 ± 14 ng/mL, a median Tmax of 18 h, and an AUC∞ of 2079 ± 1631 ng\*h/mL. For a 9 mg dose used in herniorrhaphy, the corresponding values were 225 ± 96 ng/mL, 54 h, and the AUC∞ was not reported. Lastly, a 12 mg dose used in total knee arthroplasty produced values of 275 ± 134 ng/mL, 36 h, and 25,673 ± 17,666 ng\*h/mL.
Meloxicam is mainly eliminated through metabolism. Its metabolites are cleared through renal and fecal elimination. Less than <0.25% of a dose is eliminated in the urine as unchanged drug. About 1.6% of the parent drug is excreted in the feces.
The volume of distribution of meloxicam is 10-15L. Because of its high binding to albumin, it is likely to be distributed in highly perfused tissues, such as the liver and kidney. Meloxicam concentrations in synovial fluid, measured after an oral dose, is estimated at 40% to 50% of the concentrations measured in the plasma. This drug is known to cross the placenta in humans.
After an oral dose, the total clearance of meloxicam is 0.42–0.48 L/h. The FDA label indicates a plasma clearance from 7 to 9 mL/min. No dose changes are required in mild to moderate renal or hepatic impairment. The use of meloxicam in patients with severe renal or hepatic impairment has not been studied. FDA prescribing information advises against it.
The absolute bioavailability of meloxicam capsules was 89% following a single oral dose of 30 mg compared with 30 mg iv bolus injection. Following single intravenous doses, dose-proportional pharmacokinetics were shown in the range of 5 mg to 60 mg. After multiple oral doses the pharmacokinetics of meloxicam capsules were dose-proportional over the range of 7.5 mg to 15 mg. Mean Cmax was achieved within four to five hours after a 7.5 mg meloxicam tablet was taken under fasted conditions, indicating a prolonged drug absorption. With multiple dosing, steady state concentrations were reached by Day 5. A second meloxicam concentration peak occurs around 12 to 14 hours post-dose suggesting biliary recycling.
Administration of meloxicam capsules following a high fat breakfast (75 g of fat) resulted in mean peak drug levels (ie, Cmax) being increased by approximately 22% while the extent of absorption (AUC) was unchanged. The time to maximum concentration (Tmax) was achieved between 5 and 6 hours.
The mean volume of distribution (Vss) of meloxicam is approximately 10 L. Meloxicam is about 99.4% bound to human plasma proteins (primarily albumin) within the therapeutic dose range. The fraction of protein binding is independent of drug concentration, over the clinically relevant concentration range, but decreases to about 99% in patients with renal disease.
Meloxicam penetration into human red blood cells, after oral dosing, is less than 10%. Following a radiolabeled dose, over 90% of the radioactivity detected in the plasma was present as unchanged meloxicam.
For more Absorption, Distribution and Excretion (Complete) data for Meloxicam (14 total), please visit the HSDB record page.
Metabolism / Metabolites
Meloxicam is almost completely metabolized. CYP2C9 is the main enzyme responsible for the metabolism of meloxicam with minor contributions from CYP3A4. Meloxicam has 4 major metabolites with no activity determined. About 60% of the ingested dose is metabolized to 5'-carboxy meloxicam from hepatic cytochrome enzyme oxidation of an intermediate metabolite, 5’-hydroxymethylmeloxicam. Two other metabolites are likely produced via peroxidation.
Meloxicam is almost completely metabolized to four pharmacologically inactive metabolites. The major metabolite, 5'-carboxy meloxicam (60% of dose), from P-450 mediated metabolism was formed by oxidation of an intermediate metabolite 5'-hydroxymethyl meloxicam which is also excreted to a lesser extent (9% of dose). In vitro studies indicate that cytochrome P-450 2C9 plays an important role in this metabolic pathway with a minor contribution of the CYP 3A4 isozyme.
Patients' peroxidase activity is probably responsible for /two other/ metabolites which account for 16% and 4% of the administered dose, respectively.
Meloxicam is extensively metabolized to inactive metabolites in the liver, principally via the cytochrome P-450 (CYP) 2C9 isoenzyme, with minor contribution by CYP3A4. The drug and its metabolites are excreted in urine and feces, and meloxicam undergoes substantial biliary secretion and enterohepatic recirculation.
The metabolism of Meloxicam (ME) and the cytochrome(s) P450 (CYPs) involved were analysed by using primary human hepatocytes, human liver microsomes and microsomes from recombinant human B-lymphoblastoid cell lines. While human hepatocytes were capable of converting ME to a 5-hydroxymethyl metabolite (M7) and then to a 5-carboxyderivative (M5), human liver microsomes formed mostly only the 5-hydroxymethylderivative. The kinetics of the formation of M7 by human liver microsomes were biphasic with Km = 13.6 +/- 9.5 and 381 +/- 55.2 uM respectively. The corresponding Vmax were 33.7 +/- 24.2 and 143 +/- 83.9 pmol/min/mg protein respectively. CYP2C9 and, to a much lesser extent, CYP3A4 were found to convert ME to M7. The involvement of 2C9 was demonstrated by inhibition of tolbutamide hydroxylase activity in the presence of ME, inhibition of ME metabolism by sulphaphenazole, correlation between ME metabolism and tolbutamide hydroxylase activity and active metabolism of ME by recombinant 2C9. The involvement of 3A4 was shown by inhibition of ME metabolism by ketoconazole, correlation between ME metabolism and nifedipine oxidase activity and metabolism of ME by recombinant 3A4. Kinetics of the formation of M7 by the individual enzymes resulted in a Km = 9.6 uM and Vmax = 8.4 pmol/min/mg protein for 2C9 and a Km = 475 uM and Vmax = 23 pmol/min/mg protein for 3A4.
For more Metabolism/Metabolites (Complete) data for Meloxicam (6 total), please visit the HSDB record page.
Meloxicam has known human metabolites that include 5-Hydroxymethyl meloxicam.
Biological Half-Life
The half-life of meloxicam is approximately 20 hours, which is considerably longer than most other NSAIDS. It can therefore be dosed without the need for slow-release formulations. Meloxicam applied together with [bupivacaine] for postsurgical analgesia had a median half-life of 33-42 hours, depending on dose and application site.
The mean elimination half-life (t1/2) ranges from 15 hours to 20 hours. The elimination half-life is constant across dose levels indicating linear metabolism within the therapeutic dose range.
... The twenty volunteers can be classified into extensive metabolizers and poor metabolizers according to pharmacokinetic parameters. The main parameters in the two groups obtained were as follows: T 1/2 were 21 +/- 4 and 38 +/- 9 hr, respectively. ...
Toxicity/Toxicokinetics
Hepatotoxicity
Prospective studies found that up to 7% of patients taking meloxicam experienced at least transient serum aminotransferase elevations. These frequently resolved even while continuing the drug and without dose modification. Aminotransferase elevations above 3 fold elevated occurred in 1% of patients. Clinically apparent liver injury with jaundice from meloxicam is rare and only individual case reports have been published. The latency to onset in reported cases was short (1 to 5 weeks) and both cholestatic and hepatocellular patterns of enzyme elevations were described. Immunoallergic features are usually not prominent and autoantibodies are rare, although a single case report of autoimmune hepatitis apparently triggered by meloxicam therapy has been published. Recovery is typically rapid once meloxicam is stopped. Meloxicam is rarely mentioned as an etiologic agent in large case series on drug induced liver injury and acute liver failure.
Likelihood score: C (probable rare cause of clinical apparent liver injury).
Effects During Pregnancy and Lactation
◉ Summary of Use during Lactation
Because no information is available on the use of meloxicam during breastfeeding, other agents may be preferred, especially while nursing a newborn or preterm infant.
◉ Effects in Breastfed Infants
Relevant published information was not found as of the revision date.
◉ Effects on Lactation and Breastmilk
Relevant published information was not found as of the revision date.
Protein Binding
Meloxicam is about 99.4% protein bound, primarily to albumin.
Interactions
When meloxicam is administered with aspirin to healthy volunteers, it tended to increase the AUC (10%) and Cmax (24%) of meloxicam. The clinical significance of this interaction is not known; however, as with other NSAIDs concomitant administration of meloxicam and aspirin is not generally recommended because of the potential for increased adverse effects.
Concomitant administration of low-dose aspirin with meloxicam may result in an increased rate of GI ulceration or other complications, compared to use of meloxicam alone. Meloxicam is not a substitute for aspirin for cardiovascular prophylaxis.
Pretreatment for four days with cholestyramine significantly increased the clearance of meloxicam by 50%. This resulted in a decrease in t1/2, from 19.2 hours to 12.5 hours, and a 35% reduction in AUC.
In a study conducted in healthy subjects, mean pre-dose lithium concentration and AUC were increased by 21% in subjects receiving lithium ... BID with meloxicam ... QD as compared to subjects receiving lithium alone. These effects have been attributed to inhibition of renal prostaglandin synthesis by meloxicam. Patients on lithium treatment should be closely monitored for signs of lithium toxicity when meloxicam is introduced, adjusted, or withdrawn.
For more Interactions (Complete) data for Meloxicam (7 total), please visit the HSDB record page.
References

[1]. Effect of structural modification of enol-carboxamide-type nonsteroidal antiinflammatory drugs on COX-2/COX-1 selectivity. J Med Chem. 1997 Mar 14;40(6):980-9.

[2]. Meloxicam decreases the migration and invasion of CF41.Mg canine mammary carcinoma cells. Oncol Lett. 2017 Aug;14(2):2198-2206.

[3]. Rutin and meloxicam attenuate paw inflammation in mice: Affecting sorbitol dehydrogenase activity. J Biochem Mol Toxicol. 2018 Feb;32(2).

Additional Infomation
Therapeutic Uses
Thiazines, Thiazoles; Isoenzymes/antagonists & inhibitors
Meloxicam is indicated for relief of the signs and symptoms of osteoarthritis. Use the lowest effective dose for the shortest duration consistent with individual patient treatment goals. /Included in US product label/
Meloxicam is used for the management of the signs and symptoms of rheumatoid arthritis in adults. In the management of rheumatoid arthritis in adults, NSAIAs may be useful for initial symptomatic treatment; however, NSAIAs do not alter the course of the disease or prevent joint destruction. /Included in US product label/
Meloxicam is used for the management of the signs and symptoms of pauciarticular or polyarticular course juvenile rheumatoid arthritis in children 2 years of age or older. /NOT included in US product label/
For more Therapeutic Uses (Complete) data for Meloxicam (7 total), please visit the HSDB record page.
Drug Warnings
/BOXED WARNING/ WARNING: Cardiovascular Risk NSAIDs may cause an increased risk of serious cardiovascular thrombotic events, myocardial infarction, and stroke, which can be fatal. This risk may increase with duration of use. Patients with cardiovascular disease or risk factors for cardiovascular disease may be at greater risk. Meloxicam is contraindicated for the treatment of peri-operative pain in the setting of coronary artery bypass graft (CABG) surgery.
/BOXED WARNING/ WARNING: Gastrointestinal Risk: NSAIDs cause an increased risk of serious gastrointestinal adverse events including bleeding, ulceration, and perforation of the stomach or intestines, which can be fatal. These events can occur at any time during use and without warning symptoms. Elderly patients are at greater risk for serious gastrointestinal events.
Contraindications: Known hypersensitivity to meloxicam or any ingredient in the formulation. History of urticaria, angioedema, bronchospasm, severe rhinitis, or shock precipitated by aspirin or other NSAIAs. History of aspirin triad (aspirin sensitivity, asthma, and nasal polyps). Treatment of perioperative pain in the setting of coronary artery bypass graft (CABG) surgery.
Selective COX-2 inhibitors have been associated with an increased risk of serious adverse cardiovascular thrombotic events in certain situations. Several prototypical NSAIAs also have been associated with an increased risk of cardiovascular events. Findings from a recent systematic review of controlled observational studies and a meta-analysis of published and unpublished data from randomized studies of these agents suggest that use of celecoxib (dosage exceeding 200 mg daily), diclofenac, or indomethacin is associated with an increased risk of cardiovascular events. The possibility exists that meloxicam and ibuprofen also are associated with increased cardiovascular risk.
For more Drug Warnings (Complete) data for Meloxicam (25 total), please visit the HSDB record page.
Pharmacodynamics
Meloxicam is an anti-inflammatory, analgesic analgesic with antipyretic effects in fever. Prostaglandins are substances that contribute to inflammation. This drug also exerts preferential actions against COX-2, which may reduce the possible gastrointestinal effects of this drug. In humans, meloxicam has demonstrated the ability to decrease erythrocyte sedimentation rate(ESR) in patients with rheumatoid arthritis, and to decrease ESR, C-reactive protein (CRP), as well as aquaporin-1 expression. As with other NSAIDS, prolonged use of meloxicum can result in renal or cardiovascular impairment or thrombotic cardiovascular events. A note on gastrointestinal effects As meloxicam preferentially inhibits COX-2, it is thought to cause less gastrointestinal irritation compared to other NSAIDS. Despite this, it still carries a risk of gastric inflammation, bleeding and ulceration. In one study, patients on meloxicam suffered from gastrointestinal symptoms at a rate of 13% compared to 19% of those on [diclofenac]. GI events were found to be less severe in the meloxicam-treated patients.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C14H13N3O4S2
Molecular Weight
351.4
Exact Mass
351.034
CAS #
71125-38-7
Related CAS #
Meloxicam-d3;942047-63-4;Meloxicam-d3-1;1227358-55-5;Meloxicam sodium;71125-39-8;Meloxicam-13C,d3;1309936-00-2
PubChem CID
54677470
Appearance
Light yellow to green yellow solid powder
Density
1.6±0.1 g/cm3
Boiling Point
581.3±60.0 °C at 760 mmHg
Melting Point
255ºC
Flash Point
305.4±32.9 °C
Vapour Pressure
0.0±1.7 mmHg at 25°C
Index of Refraction
1.735
LogP
3.35
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
7
Rotatable Bond Count
2
Heavy Atom Count
23
Complexity
628
Defined Atom Stereocenter Count
0
InChi Key
DWMREKMVXIFPFM-ACCUITESSA-N
InChi Code
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/h3-7,19H,1-2H3,(H,15,16)/b13-11+
Chemical Name
(E)-3-(hydroxy((5-methylthiazol-2-yl)amino)methylene)-2-methyl-2H-benzo[e][1,2]thiazin-4(3H)-one 1,1-dioxide
Synonyms

Parocin; reumoxicam; Movicox; Mobic; Mobicox; Movalis; Meloxicamum; Uticox;

HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO: 30 mg/mL (85.4 mM)
Water:<1 mg/mL
Ethanol:<1 mg/mL
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (7.11 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

Solubility in Formulation 2: ≥ 1 mg/mL (2.85 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 10.0 mg/mL clear DMSO stock solution to 400 μL of PEG300 and mix evenly; then add 50 μL of Tween-80 to the above solution and mix evenly; then add 450 μL of normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.8458 mL 14.2288 mL 28.4576 mL
5 mM 0.5692 mL 2.8458 mL 5.6915 mL
10 mM 0.2846 mL 1.4229 mL 2.8458 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Working concentration mg/mL;

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Clinical Trial Information
NCT Number Recruitment interventions Conditions Sponsor/Collaborators Start Date Phases
NCT05702827 Recruiting Drug: Bupivacaine-Meloxicam Stress Urinary Incontinence
Surgical Incision
TriHealth Inc. January 23, 2023 Phase 3
NCT01161147 Completed Drug: Meloxicam Healthy Dr. Reddy's Laboratories Limited October 2004 Phase 1
NCT01161134 Completed Drug: Meloxicam Healthy Dr. Reddy's Laboratories Limited September 2004 Phase 1
NCT01801735 Completed Has Results Drug: Meloxicam Test Capsules Osteoarthritis Iroko Pharmaceuticals, LLC March 2013 Phase 3
Biological Data
  • Expression of COX-2 in MDCK and CF41.Mg cells. (A) Representative immunofluorescence images of the (left panel) negative control, where the nuclei were visualized by DAPI, and COX-2 expression in MDCK and CF41.Mg cells respectively (central and right panel). Scale bar, 32 µm. (B) Representative Western blot of the expression of COX-2 in cell lysates, demonstrating a band at 72 kDa in both cell lines. Results are representative of 3 independent experiments. COX, cycloooxgenase; MDCK, Madin-Darby Canine Kidney.
  • Cell viability following incubation with different concentrations of meloxicam and/or doxorubicin. (A) CF41.Mg and (B) MDCK cells were incubated for 24 and 48 h with meloxicam (0–25 µg/ml). The percentage of viable cells was determined by MTS assay. Control cells were treated with DMSO alone. (C) Viability of CF41.Mg cells incubated for 24 and 48 h with meloxicam (0–25 µg/ml) and 500 ng/ml doxorubicin. (D) CF41.Mg cells were incubated with meloxicam (0–1 µg/ml) and 24 h later 500 ng/ml doxorubicin was added. Cell viability was measured at 24 and 48 h. Values are presented as the mean ± standard deviation of ≥3 independent experiments performed in triplicate. *P<0.05.
  • Meloxicam (0.25 µg/ml) has no effect on CF41.Mg cell apoptosis. Doxorubicin alone (500 ng/ml) was used as a positive control. A total of 3 independent experiments were performed and values are presented as the mean ± standard deviation. Flow cytometry plots and analysis of the data are illustrated. *P<0.05 vs. the control group.
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