Identification

Name
Meloxicam
Accession Number
DB00814
Description

Meloxicam is a nonsteroidal anti-inflammatory drug (NSAID) used to relieve various types of pain, including pain caused by musculoskeletal conditions, osteoarthritis, and rheumatoid arthritis.1 With a longer half-life than most other NSAIDS, it is a favorable option for those who require once-daily dosing. Meloxicam is available in oral, transdermal, and intravenous formulations. It is a preferential COX-2 inhibitor, purportedly reducing the risk of adverse gastrointestinal tract effects, however, this is a topic of controversy.4,5

Type
Small Molecule
Groups
Approved, Vet approved
Structure
Thumb
Weight
Average: 351.401
Monoisotopic: 351.034747299
Chemical Formula
C14H13N3O4S2
Synonyms
  • Méloxicam
  • Meloxicam
  • Meloxicamum
External IDs
  • N-1539
  • N1539
  • UH-AC 62XX
  • UH-AC-62 XX
  • UH-AC62

Pharmacology

Indication

Meloxicam is indicated for the symptomatic treatment of arthritis and osteoarthritis. In addition, it is indicated for the pauciarticular and polyarticular course of Juvenile Rheumatoid Arthritis (JRA) in patients aged 2 years old or above.10 Off-label uses include the treatment of dental or post-surgical pain. In addition to the above, meloxicam has also been studied in the treatment of neuropathic pain. 1

Associated Conditions
Contraindications & Blackbox Warnings
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Pharmacodynamics

Meloxicam is an anti-inflammatory, analgesic analgesic with antipyretic effects in fever.1 Prostaglandins are substances that contribute to inflammation.7 This drug also exerts preferential actions against COX-23, 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.1 As with other NSAIDS, prolonged use of meloxicum can result in renal or cardiovascular impairment or thrombotic cardiovascular events.10

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.5,10 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.1

Mechanism of action

Meloxicam inhibits prostaglandin synthetase (cylooxygenase 1 and 2) enzymes leading to a decreased synthesis of prostaglandins, which normally mediate painful inflammatory symptoms.7 As prostaglandins sensitize neuronal pain receptors, inhibition of their synthesis leads to analgesic and inflammatory effects. Meloxicam preferentially inhibits COX-2, but also exerts some activity against COX-1, causing gastrointestinal irritation.1,10

TargetActionsOrganism
AProstaglandin G/H synthase 2
inhibitor
Humans
UProstaglandin G/H synthase 1
inhibitor
Humans
Absorption

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.1,10

Volume of distribution

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.1 Meloxicam concentrations in synovial fluid, measured after an oral dose, is estimated at 40% to 50% of the concentrations measured in the plasma.10 This drug is known to cross the placenta in humans.9

Protein binding

Meloxicam is about 99.4% protein bound, primarily to albumin.1,3,10

Metabolism

Meloxicam is almost completely metabolized. CYP2C9 is the main enzyme responsible for the metabolism of meloxicam1,6 with minor contributions from CYP3A4.10 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.6,8 Two other metabolites are likely produced via peroxidation.6,10

Hover over products below to view reaction partners

Route of elimination

Meloxicam is mainly eliminated through metabolism. Its metabolites are cleared through renal and fecal elimination.3 Less than <0.25% of a dose is eliminated in the urine as unchanged drug.10 About 1.6% of the parent drug is excreted in the feces.1

Half-life

The half-life of meloxicam is approximately 20 hours3, which is considerably longer than most other NSAIDS. It can therefore be dosed without the need for slow-release formulations.1

Clearance

After an oral dose, the total clearance of meloxicam is 0.42–0.48 L/h.1,3 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.10

Adverse Effects
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Toxicity

The oral LD50 in rats is 98 mg/kg.11 Signs and symptoms of overdose with meloxicam may include shallow breathing, seizure, decreased urine output, gastrointestinal irritation, nausea, vomiting, gastrointestinal bleeding, and black tarry stools.12 In the case of an overdose, offer supportive treatment and attempt to remove gastrointestinal contents. Cholestyramine has been shown to enhance the elimination of meloxicam.11

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Meloxicam Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbacavirMeloxicam may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbametapirThe serum concentration of Meloxicam can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Meloxicam can be increased when combined with Abatacept.
AbciximabThe risk or severity of bleeding and hemorrhage can be increased when Meloxicam is combined with Abciximab.
AbirateroneThe metabolism of Meloxicam can be decreased when combined with Abiraterone.
AcarboseMeloxicam may decrease the excretion rate of Acarbose which could result in a higher serum level.
AcebutololMeloxicam may decrease the antihypertensive activities of Acebutolol.
AceclofenacThe risk or severity of adverse effects can be increased when Meloxicam is combined with Aceclofenac.
AcemetacinThe risk or severity of adverse effects can be increased when Meloxicam is combined with Acemetacin.
AcenocoumarolThe risk or severity of bleeding can be increased when Meloxicam is combined with Acenocoumarol.
Additional Data Available
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  • Severity
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  • Evidence Level
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  • Action
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Food Interactions
  • Avoid alcohol. The risk of gastrointestinal bleeding may be increased.
  • Take with or without food. The absorption is unaffected by food.

Products

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Product Images
International/Other Brands
Achefree (Achefree) / Acticam (Acromax Dominicana) / Aflamid (Anchor) / Afloxx (Lusa) / Aglan (Zentiva) / Ainecox (Cheminter) / Aldoron (Ivax) / Alentum (Lafrancol) / Algiflex (Biogen) / Aliviodol (Centrum) / Anaxicam (Caferma) / Anposel (Medipharm) / Antrend (Labormed) / Aponip (Pharmatec) / Areloger (Gerard) / Aremil (Magma) / Armex (Qintar Pharma) / Arrox (Xepa-Soul Pattinson) / Arsitec (Arsmedendi) / Artex (Pharmedic) / Arthrobic (Mekophar) / Arthrox (Pharmanel) / Articam (Standpharm) / Artipro (Helix) / Artriclox (Garmisch) / Artrifilm (G&R) / Artriflam (Sherfarma) / Artrilom (Pro.Med.CS) / Artrilox (Combiphar) / Artrox (PharmaBrand) / Aspicam (Biofarm) / Atiflam (Doctor Andreu) / Atrozan (Pharmstandard) / Auroxicam (Aurora) / Axius (Hersil)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Act MeloxicamTabletOralTEVA Canada Limited2004-08-12Not applicableCanada flag
Act MeloxicamTabletOralTEVA Canada Limited2004-08-12Not applicableCanada flag
AnjesoInjection30 mg/1mLIntravenousBaudax Bio, Inc.2020-02-24Not applicableUS flag
MeloxicamTablet15 mgOralCobalt LaboratoriesNot applicableNot applicableCanada flag
MeloxicamTablet7.5 mg/1OralWatson Laboratories Inc.2007-03-30Not applicableUS flag
MeloxicamTablet15 mg/1OralRanbaxy Inc.2007-05-23Not applicableUS flag
MeloxicamTablet7.5 mg/1OralMylan Pharmaceuticals Inc.2007-01-162007-01-16US flag
MeloxicamTablet15 mgOralPro Doc Limitee2009-06-102017-05-05Canada flag
MeloxicamTablet7.5 mg/1OralCaraco Pharmaceutical Laboratories, Ltd.2008-11-12Not applicableUS flag
MeloxicamTablet7.5 mgOralCobalt LaboratoriesNot applicableNot applicableCanada flag
Additional Data Available
  • Application Number
    Application Number
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    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code
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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Apo-meloxicamTabletOralApotex Corporation2004-02-13Not applicableCanada flag
Apo-meloxicamTabletOralApotex Corporation2004-02-13Not applicableCanada flag
Auro-meloxicamTabletOralAuro Pharma Inc2012-10-18Not applicableCanada flag
Auro-meloxicamTabletOralAuro Pharma Inc2012-10-19Not applicableCanada flag
Ava-meloxicamTabletOralAvanstra Inc2011-11-082014-08-21Canada flag
Ava-meloxicamTabletOralAvanstra Inc2011-08-112014-08-21Canada flag
Comfort Pac with MeloxicamKit15 mg/1OralPD-Rx Pharmaceuticals, Inc.2013-07-092018-07-13US flag
Comfort Pac with MeloxicamKit15 mg/1OralPD-Rx Pharmaceuticals, Inc.2010-06-302018-12-17US flag
Dom-meloxicamTabletOralDominion Pharmacal2004-02-06Not applicableCanada flag
Dom-meloxicamTabletOralDominion Pharmacal2004-02-06Not applicableCanada flag
Additional Data Available
  • Application Number
    Application Number
    Available for Purchase

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code
    Available for Purchase

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
NuDroxiPAK M-15Meloxicam (15 mg/1) + Capsaicin (0.25 mg/1mL) + Levomenthol (60 mg/1mL) + Methyl salicylate (250 mg/1mL)KitOral; TopicalNuCare pharmceuticals,Inc.2007-03-07Not applicableUS flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Trepoxicam-7.5Meloxicam (7.5 mg/1) + Histidine (50 mg/1)KitOralPhysician Therapeutics Llc2011-01-31Not applicableUS flag

Categories

ATC Codes
M01AC56 — Meloxicam, combinationsM01AC06 — Meloxicam
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as benzothiazines. These are organic compounds containing a benzene fused to a thiazine ring (a six-membered ring with four carbon atoms, one nitrogen atom and one sulfur atom).
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzothiazines
Sub Class
Not Available
Direct Parent
Benzothiazines
Alternative Parents
Alpha amino acids and derivatives / N-arylamides / 2,5-disubstituted thiazoles / Organosulfonamides / Benzenoids / 1,2-thiazines / Vinylogous acids / Heteroaromatic compounds / Secondary carboxylic acid amides / Azacyclic compounds
show 4 more
Substituents
2,5-disubstituted 1,3-thiazole / Alpha-amino acid or derivatives / Aromatic heteropolycyclic compound / Azacycle / Azole / Benzenoid / Benzothiazine / Carbonyl group / Carboxamide group / Carboxylic acid derivative
show 16 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
monocarboxylic acid amide, 1,3-thiazole, benzothiazine (CHEBI:6741)

Chemical Identifiers

UNII
VG2QF83CGL
CAS number
71125-38-7
InChI Key
ZRVUJXDFFKFLMG-UHFFFAOYSA-N
InChI
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)
IUPAC Name
4-hydroxy-2-methyl-N-(5-methyl-1,3-thiazol-2-yl)-1,1-dioxo-2H-1λ⁶,2-benzothiazine-3-carboxamide
SMILES
CN1C(C(=O)NC2=NC=C(C)S2)=C(O)C2=C(C=CC=C2)S1(=O)=O

References

Synthesis Reference

Laura Coppi, "Crystalline forms of meloxicam and processes for their preparation and interconversion." U.S. Patent US20030109701, issued June 12, 2003.

US20030109701
General References
  1. Bekker A, Kloepping C, Collingwood S: Meloxicam in the management of post-operative pain: Narrative review. J Anaesthesiol Clin Pharmacol. 2018 Oct-Dec;34(4):450-457. doi: 10.4103/joacp.JOACP_133_18. [PubMed:30774225]
  2. Moore RA, Derry S, McQuay HJ: Single dose oral meloxicam for acute postoperative pain in adults. Cochrane Database Syst Rev. 2009 Oct 7;(4):CD007552. doi: 10.1002/14651858.CD007552.pub2. [PubMed:19821429]
  3. Turck D, Roth W, Busch U: A review of the clinical pharmacokinetics of meloxicam. Br J Rheumatol. 1996 Apr;35 Suppl 1:13-6. doi: 10.1093/rheumatology/35.suppl_1.13. [PubMed:8630630]
  4. Katz JA: COX-2 inhibition: what we learned--a controversial update on safety data. Pain Med. 2013 Dec;14 Suppl 1:S29-34. doi: 10.1111/pme.12252. [PubMed:24373107]
  5. Seddik H, Rabhi M: [Meloxicam-induced colitis revealed by acute abdominal pain]. Ann Pharm Fr. 2013 Mar;71(2):119-22. doi: 10.1016/j.pharma.2012.12.003. Epub 2013 Mar 8. [PubMed:23537413]
  6. Chesne C, Guyomard C, Guillouzo A, Schmid J, Ludwig E, Sauter T: Metabolism of Meloxicam in human liver involves cytochromes P4502C9 and 3A4. Xenobiotica. 1998 Jan;28(1):1-13. doi: 10.1080/004982598239704. [PubMed:9493314]
  7. Ricciotti E, FitzGerald GA: Prostaglandins and inflammation. Arterioscler Thromb Vasc Biol. 2011 May;31(5):986-1000. doi: 10.1161/ATVBAHA.110.207449. [PubMed:21508345]
  8. Prasad GS, Srisailam K, Sashidhar RB: Metabolic inhibition of meloxicam by specific CYP2C9 inhibitors in Cunninghamella blakesleeana NCIM 687: in silico and in vitro studies. Springerplus. 2016 Feb 24;5:166. doi: 10.1186/s40064-016-1794-4. eCollection 2016. [PubMed:27026863]
  9. Carl P. Weiner MD, MBA, FACOG, Clifford Mason PhD (2019). Drugs for Pregnant and Lactating Women (3rd ed.). Elsevier.
  10. FDA approved products: Mobic (meloxicam) oral tablets [Link]
  11. Medsafe NZ: Mobictab (meloxicam) oral tablets [Link]
  12. American College of Cardiology: Meloxicam [Link]
Human Metabolome Database
HMDB0014952
KEGG Drug
D00969
KEGG Compound
C08169
PubChem Compound
54677470
PubChem Substance
46506624
ChemSpider
10442740
BindingDB
50056998
RxNav
41493
ChEBI
6741
ChEMBL
CHEMBL599
ZINC
ZINC000013129998
Therapeutic Targets Database
DAP000971
PharmGKB
PA450353
PDBe Ligand
MXM
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Meloxicam
AHFS Codes
  • 28:08.04.92 — Other Nonsteroidal Antiimflammatory Agents
PDB Entries
4m11 / 4o1z
FDA label
Download (45.4 KB)
MSDS
Download (35.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentBiliary Atresia, Kasai Portoenterostomy Status1
4CompletedTreatmentHealthy Volunteers1
4CompletedTreatmentOsteoarthritis (OA)3
4CompletedTreatmentOsteoarthritis (OA) / Rheumatoid Arthritis1
4CompletedTreatmentPharyngitis1
4TerminatedTreatmentAnkylosing Spondylitis (AS) / Spondyloarthritis, Axial1
3CompletedNot AvailableRheumatoid Arthritis1
3CompletedTreatmentAnkylosing Spondylitis (AS)1
3CompletedTreatmentBack Pain Lower Back1
3CompletedTreatmentLumbar Sciatic Pain1

Pharmacoeconomics

Manufacturers
  • Boehringer ingelheim pharmaceuticals inc
  • Actavis totowa llc
  • Apotex inc etobicoke site
  • Aurobindo pharma ltd
  • Beijing double crane pharmaceutical co ltd
  • Beijing yabao biopharmaceutical co ltd
  • Breckenridge pharmaceutical inc
  • Caraco pharmaceutical laboratories ltd
  • Carlsbad technology inc
  • Corepharma llc
  • Dr reddys laboratories inc
  • Genpharm inc
  • Glenmark generics ltd
  • Lupin pharmaceuticals inc
  • Mutual pharmaceutical co inc
  • Mylan pharmaceuticals inc
  • Roxane laboratories inc
  • Strides arcolab ltd
  • Taro pharmaceutical industries ltd
  • Teva pharmaceuticals usa
  • Unichem laboratories ltd
  • Watson laboratories inc
  • Zydus pharmaceuticals usa inc
Packagers
  • 4uOrtho LLC
  • Advanced Pharmaceutical Services Inc.
  • Aidarex Pharmacuticals LLC
  • Apotex Inc.
  • Apotheca Inc.
  • A-S Medication Solutions LLC
  • Aurobindo Pharma Ltd.
  • Blenheim Pharmacal
  • Boehringer Ingelheim Ltd.
  • Breckenridge Pharmaceuticals
  • Bryant Ranch Prepack
  • Cadila Healthcare Ltd.
  • Cadista Pharmaceuticals Inc.
  • Caraco Pharmaceutical Labs
  • Carlsbad Technology Inc.
  • Cipla Ltd.
  • Corepharma LLC
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Doctor Reddys Laboratories Ltd.
  • Dorx LLC
  • Genpharm LP
  • Glenmark Generics Ltd.
  • H.J. Harkins Co. Inc.
  • Innoviant Pharmacy Inc.
  • International Laboratories Inc.
  • Keltman Pharmaceuticals Inc.
  • Lake Erie Medical and Surgical Supply
  • Lannett Co. Inc.
  • Lupin Pharmaceuticals Inc.
  • Mallinckrodt Inc.
  • Medisca Inc.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Mylan
  • Nucare Pharmaceuticals Inc.
  • Palmetto Pharmaceuticals Inc.
  • PD-Rx Pharmaceuticals Inc.
  • Physicians Total Care Inc.
  • Preferred Pharmaceuticals Inc.
  • Prepak Systems Inc.
  • Rebel Distributors Corp.
  • Remedy Repack
  • Resource Optimization and Innovation LLC
  • Roxane Labs
  • Sandoz
  • Southwood Pharmaceuticals
  • St Mary's Medical Park Pharmacy
  • Stat Rx Usa
  • Strides Arcolab Limited
  • Taro Pharmaceuticals USA
  • Teva Pharmaceutical Industries Ltd.
  • UDL Laboratories
  • Unichem Laboratories Ltd.
  • Vangard Labs Inc.
  • Yung Shin Pharmaceutical Industry Ltd.
  • Zydus Pharmaceuticals
Dosage Forms
FormRouteStrength
InjectionIntravenous30 mg/1mL
Capsule, liquid filledOral7.5 mg
Capsule, liquid filledOral15 mg
KitOral15 mg/1
SolutionIntramuscular15 mg
GelTopical1 g
InjectionIntramuscular15 mg/1.5ml
Tablet, film coatedOral
Tablet, orally disintegratingOral15 mg
Injection15 mg/1.5ml
Tablet, solubleOral15 mg
Tablet, coatedOral22.275 mg
Tablet, solubleOral7.5 mg
Tablet, coatedOral20 mg
Injection, solutionIntramuscular15 mg/1.5ml
SuspensionOral7.5 mg/5mL
TabletOral15 mg/1
TabletOral7.5 mg/1
TabletOral15 MG
TabletOral7.5 MG
Injection, solutionParenteral15 mg/1.5ml
Tablet, coatedOral15 mg
CapsuleOral15 MG
CapsuleOral7.5 mg
Injection, solution15 mg
SuppositoryRectal15 MG
SuppositoryRectal7.5 mg
TabletOral
Injection
Capsule, coatedOral7.5 mg
Capsule, coatedOral15 mg
KitOral; Topical
Tablet, delayed releaseOral7.5 mg
SolutionConjunctival; Ophthalmic0.3 mg
Tablet, orally disintegratingOral15 mg/1
Tablet, orally disintegratingOral7.5 mg/1
SuspensionOral1.5 mg/ml
TabletOral2.5 mg
Capsule, coatedOral20 mg
KitOral
CapsuleOral10 mg/1
CapsuleOral5 mg/1
Prices
Unit descriptionCostUnit
Meloxicam 7.5 mg/5ml Suspension 100ml Bottle86.99USD bottle
Meloxicam bp powder56.61USD g
Mobic 15 mg tablet7.37USD tablet
Meloxicam 15 mg tablet4.94USD tablet
Mobic 7.5 mg tablet4.74USD tablet
Meloxicam 7.5 mg tablet3.23USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US6184220Yes2001-02-062019-09-25US flag
US9649318No2017-05-162035-03-31US flag
US9526734No2016-12-272033-03-31US flag
US9808468No2017-11-072035-03-31US flag
US8545879No2013-10-012030-08-31US flag
US9974746No2018-05-222030-05-26US flag
US8512727No2013-08-202022-12-25US flag
US10471067No2019-11-122024-02-24US flag
US10463673No2019-11-052024-02-24US flag
US10709713No2010-05-262030-05-26US flag
Additional Data Available
  • Filed On
    Filed On
    Available for Purchase

    The date on which a patent was filed with the relevant government.

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Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)256http://www.guildlink.com.au/gc/ws/by/pi.cfm?product=bypmobic10517
boiling point (°C)581.3±60.0 https://www.chemsrc.com/en/cas/71125-38-7_1083007.html
water solubility22 mg/mlhttps://www.chemicalbook.com/ChemicalProductProperty_US_CB2191355.aspx
logP0.1https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/20938s004lbl.pdf
Caco2 permeability-4.71ADME Research, USCD
pKa4.08https://www.chemicalbook.com/ChemicalProductProperty_US_CB2191355.aspx
Predicted Properties
PropertyValueSource
Water Solubility0.154 mg/mLALOGPS
logP2.28ALOGPS
logP1.6ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)4.47ChemAxon
pKa (Strongest Basic)0.47ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area99.6 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity88.62 m3·mol-1ChemAxon
Polarizability34.25 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9156
Blood Brain Barrier-0.9811
Caco-2 permeable+0.8484
P-glycoprotein substrateSubstrate0.5181
P-glycoprotein inhibitor INon-inhibitor0.7516
P-glycoprotein inhibitor IINon-inhibitor0.7491
Renal organic cation transporterNon-inhibitor0.9275
CYP450 2C9 substrateSubstrate0.5637
CYP450 2D6 substrateNon-substrate0.9117
CYP450 3A4 substrateNon-substrate0.6649
CYP450 1A2 substrateNon-inhibitor0.9271
CYP450 2C9 inhibitorInhibitor0.5511
CYP450 2D6 inhibitorNon-inhibitor0.9322
CYP450 2C19 inhibitorNon-inhibitor0.8948
CYP450 3A4 inhibitorNon-inhibitor0.8191
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7316
Ames testNon AMES toxic0.8576
CarcinogenicityNon-carcinogens0.7052
BiodegradationNot ready biodegradable0.9312
Rat acute toxicity3.4619 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9579
hERG inhibition (predictor II)Non-inhibitor0.7999
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0009000000-d860614369de32fc5b55
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00kf-0901000000-0d362af6b48e1604f3c0
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0006-0900000000-f79d2bd45c77067c33bf
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0006-0900000000-385da9c2b565923f3591
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0006-0900000000-24d8592c133da8552647
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0uxr-0905000000-155a653652a8dc132b5c
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0uxu-2905000000-a1d5ee29626527977b8e
MS/MS Spectrum - , positiveLC-MS/MSsplash10-014l-3900000000-835e2ce927e75b3bb1fb
MS/MS Spectrum - , positiveLC-MS/MSsplash10-014l-3910000000-cf38e48efa983293e01f

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Prostaglandin-endoperoxide synthase activity
Specific Function
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Constitutively expressed in some tissues in physiological conditions, such as the endothelium, kidney and...
Gene Name
PTGS2
Uniprot ID
P35354
Uniprot Name
Prostaglandin G/H synthase 2
Molecular Weight
68995.625 Da
References
  1. Poulsen Nautrup B, Horstermann D: [Pharmacodynamic and pharmacokinetic aspects of the non-inflammatory non-steroidal agent meloxicam in dogs]. Dtsch Tierarztl Wochenschr. 1999 Mar;106(3):94-100. [PubMed:10220944]
  2. Tegeder I, Lotsch J, Krebs S, Muth-Selbach U, Brune K, Geisslinger G: Comparison of inhibitory effects of meloxicam and diclofenac on human thromboxane biosynthesis after single doses and at steady state. Clin Pharmacol Ther. 1999 May;65(5):533-44. [PubMed:10340919]
  3. Blanco FJ, Guitian R, Moreno J, de Toro FJ, Galdo F: Effect of antiinflammatory drugs on COX-1 and COX-2 activity in human articular chondrocytes. J Rheumatol. 1999 Jun;26(6):1366-73. [PubMed:10381057]
  4. Panara MR, Renda G, Sciulli MG, Santini G, Di Giamberardino M, Rotondo MT, Tacconelli S, Seta F, Patrono C, Patrignani P: Dose-dependent inhibition of platelet cyclooxygenase-1 and monocyte cyclooxygenase-2 by meloxicam in healthy subjects. J Pharmacol Exp Ther. 1999 Jul;290(1):276-80. [PubMed:10381787]
  5. Gross JM, Dwyer JE, Knox FG: Natriuretic response to increased pressure is preserved with COX-2 inhibitors. Hypertension. 1999 Nov;34(5):1163-7. [PubMed:10567199]
  6. Bekker A, Kloepping C, Collingwood S: Meloxicam in the management of post-operative pain: Narrative review. J Anaesthesiol Clin Pharmacol. 2018 Oct-Dec;34(4):450-457. doi: 10.4103/joacp.JOACP_133_18. [PubMed:30774225]
  7. Gates BJ, Nguyen TT, Setter SM, Davies NM: Meloxicam: a reappraisal of pharmacokinetics, efficacy and safety. Expert Opin Pharmacother. 2005 Oct;6(12):2117-40. doi: 10.1517/14656566.6.12.2117. [PubMed:16197363]
  8. FDA approved products: Mobic (meloxicam) oral tablets [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Prostaglandin-endoperoxide synthase activity
Specific Function
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gas...
Gene Name
PTGS1
Uniprot ID
P23219
Uniprot Name
Prostaglandin G/H synthase 1
Molecular Weight
68685.82 Da
References
  1. Blanco FJ, Guitian R, Moreno J, de Toro FJ, Galdo F: Effect of antiinflammatory drugs on COX-1 and COX-2 activity in human articular chondrocytes. J Rheumatol. 1999 Jun;26(6):1366-73. [PubMed:10381057]
  2. Panara MR, Renda G, Sciulli MG, Santini G, Di Giamberardino M, Rotondo MT, Tacconelli S, Seta F, Patrono C, Patrignani P: Dose-dependent inhibition of platelet cyclooxygenase-1 and monocyte cyclooxygenase-2 by meloxicam in healthy subjects. J Pharmacol Exp Ther. 1999 Jul;290(1):276-80. [PubMed:10381787]
  3. Bekker A, Kloepping C, Collingwood S: Meloxicam in the management of post-operative pain: Narrative review. J Anaesthesiol Clin Pharmacol. 2018 Oct-Dec;34(4):450-457. doi: 10.4103/joacp.JOACP_133_18. [PubMed:30774225]
  4. Gates BJ, Nguyen TT, Setter SM, Davies NM: Meloxicam: a reappraisal of pharmacokinetics, efficacy and safety. Expert Opin Pharmacother. 2005 Oct;6(12):2117-40. doi: 10.1517/14656566.6.12.2117. [PubMed:16197363]
  5. FDA approved products: Mobic (meloxicam) oral tablets [Link]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Chesne C, Guyomard C, Guillouzo A, Schmid J, Ludwig E, Sauter T: Metabolism of Meloxicam in human liver involves cytochromes P4502C9 and 3A4. Xenobiotica. 1998 Jan;28(1):1-13. doi: 10.1080/004982598239704. [PubMed:9493314]
  2. Ludwig E, Schmid J, Beschke K, Ebner T: Activation of human cytochrome P-450 3A4-catalyzed meloxicam 5'-methylhydroxylation by quinidine and hydroquinidine in vitro. J Pharmacol Exp Ther. 1999 Jul;290(1):1-8. [PubMed:10381752]
  3. Bekker A, Kloepping C, Collingwood S: Meloxicam in the management of post-operative pain: Narrative review. J Anaesthesiol Clin Pharmacol. 2018 Oct-Dec;34(4):450-457. doi: 10.4103/joacp.JOACP_133_18. [PubMed:30774225]
  4. Flockhart Table of Drug Interactions [Link]
  5. FDA approved products: Mobic (meloxicam) oral tablets [Link]
  6. Meloxicam FDA label [File]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Chesne C, Guyomard C, Guillouzo A, Schmid J, Ludwig E, Sauter T: Metabolism of Meloxicam in human liver involves cytochromes P4502C9 and 3A4. Xenobiotica. 1998 Jan;28(1):1-13. doi: 10.1080/004982598239704. [PubMed:9493314]
  2. Ludwig E, Schmid J, Beschke K, Ebner T: Activation of human cytochrome P-450 3A4-catalyzed meloxicam 5'-methylhydroxylation by quinidine and hydroquinidine in vitro. J Pharmacol Exp Ther. 1999 Jul;290(1):1-8. [PubMed:10381752]
  3. FDA approved products: Mobic (meloxicam) oral tablets [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Curator comments
Data in the literature are limited regarding this enzyme action.
General Function
Phosphogluconate dehydrogenase (decarboxylating) activity
Specific Function
Catalyzes the oxidative decarboxylation of 6-phosphogluconate to ribulose 5-phosphate and CO(2), with concomitant reduction of NADP to NADPH.
Gene Name
PGD
Uniprot ID
P52209
Uniprot Name
6-phosphogluconate dehydrogenase, decarboxylating
Molecular Weight
53139.56 Da
References
  1. Akkemik E, Budak H, Ciftci M: Effects of some drugs on human erythrocyte 6-phosphogluconate dehydrogenase: an in vitro study. J Enzyme Inhib Med Chem. 2010 Aug;25(4):476-9. doi: 10.3109/14756360903257900. [PubMed:20235752]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Curator comments
Pharmocogenomic studies indicate that meloxicam may be a substrate of CYP2C8 in certain patients. More research is warranted. Clinical relevance of this enzyme action is undetermined.
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Agundez JA, Garcia-Martin E, Martinez C: Genetically based impairment in CYP2C8- and CYP2C9-dependent NSAID metabolism as a risk factor for gastrointestinal bleeding: is a combination of pharmacogenomics and metabolomics required to improve personalized medicine? Expert Opin Drug Metab Toxicol. 2009 Jun;5(6):607-20. doi: 10.1517/17425250902970998 . [PubMed:19422321]
  2. Rodrigues AD: Impact of CYP2C9 genotype on pharmacokinetics: are all cyclooxygenase inhibitors the same? Drug Metab Dispos. 2005 Nov;33(11):1567-75. Epub 2005 Aug 23. [PubMed:16118328]
  3. Jaja C, Bowman L, Wells L, Patel N, Xu H, Lyon M, Kutlar A: Preemptive Genotyping of CYP2C8 and CYP2C9 Allelic Variants Involved in NSAIDs Metabolism for Sickle Cell Disease Pain Management. Clin Transl Sci. 2015 Aug;8(4):272-80. doi: 10.1111/cts.12260. Epub 2015 Feb 2. [PubMed:25640739]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Bekker A, Kloepping C, Collingwood S: Meloxicam in the management of post-operative pain: Narrative review. J Anaesthesiol Clin Pharmacol. 2018 Oct-Dec;34(4):450-457. doi: 10.4103/joacp.JOACP_133_18. [PubMed:30774225]
  2. Trynda-Lemiesz L, Wiglusz K: Interactions of human serum albumin with meloxicam: characterization of binding site. J Pharm Biomed Anal. 2010 Jun 5;52(2):300-4. doi: 10.1016/j.jpba.2009.12.025. Epub 2010 Jan 4. [PubMed:20089378]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Atpase activity, coupled to transmembrane movement of substances
Specific Function
May be an organic anion pump relevant to cellular detoxification.
Gene Name
ABCC4
Uniprot ID
O15439
Uniprot Name
Multidrug resistance-associated protein 4
Molecular Weight
149525.33 Da
References
  1. Uchida Y, Kamiie J, Ohtsuki S, Terasaki T: Multichannel liquid chromatography-tandem mass spectrometry cocktail method for comprehensive substrate characterization of multidrug resistance-associated protein 4 transporter. Pharm Res. 2007 Dec;24(12):2281-96. Epub 2007 Oct 16. [PubMed:17939016]
2. Human vesicular glutamate transporters
Kind
Group
Organism
Humans
Pharmacological action
Unknown
Actions
Modulator
Curator comments
Meloxicam modulates these transporters in rats, and likely produces similar effects in humans.
This group is comprised of various human vesicular glutamate transporters, such as VGLUT1, VGLUT2 and VGLUT3.
References
  1. Llorente IL, Landucci E, Pellegrini-Giampietro DE, Fernandez-Lopez A: Glutamate receptor and transporter modifications in rat organotypic hippocampal slice cultures exposed to oxygen-glucose deprivation: the contribution of cyclooxygenase-2. Neuroscience. 2015 Apr 30;292:118-28. doi: 10.1016/j.neuroscience.2015.02.040. Epub 2015 Feb 28. [PubMed:25732138]
  2. Llorente IL, Perez-Rodriguez D, Burgin TC, Gonzalo-Orden JM, Martinez-Villayandre B, Fernandez-Lopez A: Age and meloxicam modify the response of the glutamate vesicular transporters (VGLUTs) after transient global cerebral ischemia in the rat brain. Brain Res Bull. 2013 May;94:90-7. doi: 10.1016/j.brainresbull.2013.02.006. Epub 2013 Feb 28. [PubMed:23458738]

Drug created on June 13, 2005 07:24 / Updated on November 30, 2020 13:38

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