Meloxicam

Basic Info

Common NameMeloxicam(F05809)
2D Structure
FRCD IDF05809
CAS Number71125-38-7
PubChem CID54677470
FormulaC14H13N3O4S2
IUPAC Name

4-hydroxy-2-methyl-N-(5-methyl-1,3-thiazol-2-yl)-1,1-dioxo-1$l^{6},2-benzothiazine-3-carboxamide

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)

Canonical SMILES

CC1=CN=C(S1)NC(=O)C2=C(C3=CC=CC=C3S(=O)(=O)N2C)O

Isomeric SMILES

CC1=CN=C(S1)NC(=O)C2=C(C3=CC=CC=C3S(=O)(=O)N2C)O

Synonyms
        
            Mobec
        
            meloxicam
        
            71125-38-7
        
            Mobic
        
            Metacam
        
            Movalis
        
            Mobicox
        
            Meloxicam (Mobic)
        
            Meloxicamum
        
            Movatec
Classifies
                

                  
                    Predicted: Plant Toxin
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganoheterocyclic compounds
ClassBenzothiazines
SubclassNot available
Intermediate Tree NodesNot available
Direct ParentBenzothiazines
Alternative Parents
Molecular FrameworkAromatic heteropolycyclic compounds
SubstituentsAlpha-amino acid or derivatives - Benzothiazine - N-arylamide - 2,5-disubstituted 1,3-thiazole - Ortho-thiazine - Benzenoid - Organosulfonic acid amide - Azole - Heteroaromatic compound - Vinylogous acid - Thiazole - Organosulfonic acid or derivatives - Organic sulfonic acid or derivatives - Carboxamide group - Secondary carboxylic acid amide - Azacycle - Carboxylic acid derivative - Organic oxygen compound - Organic nitrogen compound - Carbonyl group - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organonitrogen compound - Organooxygen compound - Aromatic heteropolycyclic compound
DescriptionThis 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).

Properties

Property NameProperty Value
Molecular Weight351.395
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count7
Rotatable Bond Count2
Complexity628
Monoisotopic Mass351.035
Exact Mass351.035
XLogP3
Formal Charge0
Heavy Atom Count23
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB-0.9811
Human Intestinal AbsorptionHIA+0.9156
Caco-2 PermeabilityCaco2+0.8484
P-glycoprotein SubstrateSubstrate0.5181
P-glycoprotein InhibitorNon-inhibitor0.7516
Non-inhibitor0.7491
Renal Organic Cation TransporterNon-inhibitor0.9275
Distribution
Subcellular localizationMitochondria0.4348
Metabolism
CYP450 2C9 SubstrateSubstrate0.5637
CYP450 2D6 SubstrateNon-substrate0.9117
CYP450 3A4 SubstrateNon-substrate0.6649
CYP450 1A2 InhibitorNon-inhibitor0.9271
CYP450 2C9 InhibitorInhibitor0.5511
CYP450 2D6 InhibitorNon-inhibitor0.9322
CYP450 2C19 InhibitorNon-inhibitor0.8948
CYP450 3A4 InhibitorNon-inhibitor0.8191
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.7316
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9579
Non-inhibitor0.7999
AMES ToxicityNon AMES toxic0.8576
CarcinogensNon-carcinogens0.7052
Fish ToxicityHigh FHMT0.8811
Tetrahymena Pyriformis ToxicityHigh TPT0.9476
Honey Bee ToxicityLow HBT0.7855
BiodegradationNot ready biodegradable0.9312
Acute Oral ToxicityII0.6971
Carcinogenicity (Three-class)Non-required0.6941
Model Value Unit
Absorption
Aqueous solubility-3.7597LogS
Caco-2 Permeability1.2073LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity3.4619LD50, mol/kg
Fish Toxicity1.6914pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.5386pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
MilkJapan0.01ppm
Other Terrestrial Mammals,Edible OffalJapan0.07ppm
Pig,Edible OffalJapan0.06ppm
Cattle,Edible OffalJapan0.07ppm
Other Terrestrial Mammals,KidneyJapan0.07ppm
Pig,KidneyJapan0.09ppm
Cattle,KidneyJapan0.1ppm
Other Terrestrial Mammals,LiverJapan0.07ppm
Pig,LiverJapan0.06ppm
Cattle,LiverJapan0.07ppm
Other Terrestrial Mammals,FatJapan0.02ppm
Pig,FatJapan0.1ppm
Pig,MuscleJapan0.02ppm
Cattle,MuscleJapan0.02ppm
Cattle,FatJapan0.02ppm
Other Terrestrial Mammals,MuscleJapan0.02ppm

References

TitleJournalDatePubmed ID
Changes in feeding, social, and lying behaviors in dairy cows with metritisfollowing treatment with a nonsteroidal anti-inflammatory drug as adjunctivetreatment to an antimicrobial.J Dairy Sci2018 May29477521
Gastroscopic Study of Meloxicam, Tramadol, and Their Combined Administration onthe Development of Gastric Injuries in Dogs.Top Companion Anim Med2017 Sep29291772
Evaluation of in-feed larch sawdust anti-inflammatory effect in sows.Pol J Vet Sci2017 Mar 128865211
Clinical trial of local anesthetic protocols for acute pain associated withcaustic paste disbudding in dairy calves.J Dairy Sci2017 Aug28551190
YY-1224, a terpene trilactone-strengthened Ginkgo biloba, attenuatesneurodegenerative changes induced by β-amyloid (1-42) or double transgenicoverexpression of APP and PS1 via inhibition of cyclooxygenase-2.J Neuroinflammation2017 Apr 2728449688
Evaluation of meloxicam for the treatment of obstructive feline idiopathiccystitis.J Feline Med Surg2016 Nov26672127
Addition of meloxicam to the treatment of clinical mastitis improves subsequentreproductive performance.J Dairy Sci2016 Mar26778316
Hot topic: Early postpartum treatment of commercial dairy cows with nonsteroidal antiinflammatory drugs increases whole-lactation milk yield.J Dairy Sci2016 Jan26519977
Meloxicam inhibits fipronil-induced apoptosis via modulation of the oxidativestress and inflammatory response in SH-SY5Y cells.J Appl Toxicol2016 Jan25772694
Experimental study on the effect of oral meloxicam administration in sows onpre-weaning mortality and growth and immunoglobulin G transfer to piglets.Prev Vet Med2016 Apr 126874363
Development of Analytical Method and Monitoring of Veterinary Drug Residues inKorean Animal Products.Korean J Food Sci Anim Resour201627433102
A multiresidue liquid chromatographic/tandem mass spectrometric method for thedetection and quantitation of 15 nonsteroidal anti-inflammatory drugs (NSAIDs) inbovine meat and milk.Anal Bioanal Chem2015 Jun25814273
Toxic influence.Nature2014 Oct 2325341753
Comparison of meloxicam and a glucosamine-chondroitin supplement in management offeline osteoarthritis. A double-blind randomised, placebo-controlled, prospectivetrial.Vet Comp Orthop Traumatol201424146058
Hemodynamic and behavioral differences after administration of meloxicam,buprenorphine, or tramadol as analgesics for telemeter implantation in mice.J Am Assoc Lab Anim Sci2013 Sep24041211
Effects of meloxicam on milk production, behavior, and feed intake in dairy cows following assisted calving.J Dairy Sci2013 Jun23567050
Pharmacokinetics and milk secretion of gabapentin and meloxicam co-administeredorally in Holstein-Friesian cows.J Vet Pharmacol Ther2013 Feb22372845
Aspirin augments IgE-mediated histamine release from human peripheral basophilsvia Syk kinase activation.Allergol Int2013 Dec24153330
Target animal safety study of meloxicam administered via transmucosal oral spray (Promist(®) technology) for 6 months in dogs.J Vet Pharmacol Ther2013 Aug23009183
Effects of buprenorphine and meloxicam analgesia on induced cerebral ischemia in C57BL/6 male mice.Comp Med2013 Apr23582417