Tmic
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Record Information
Version2.0
Creation Date2009-07-21 20:27:43 UTC
Update Date2014-12-24 20:25:53 UTC
Accession NumberT3D2899
Identification
Common NameMeloxicam
ClassSmall Molecule
DescriptionMeloxicam is a nonsteroidal anti-inflammatory drug (NSAID) used to relieve the symptoms of arthritis, primary dysmenorrhea, fever; and as an analgesic, especially where there is an inflammatory component. It is closely related to piroxicam. In Europe it is marketed under the brand names Movalis, Melox, and Recoxa. In North America it is generally marketed under the brand name Mobic. In Latin America, the drug is marketed as Tenaron. [Wikipedia]
Compound Type
  • Amide
  • Amine
  • Analgesic
  • Anti-Inflammatory Agent, Non-Steroidal
  • Antiemetic
  • Antineoplastic Agent
  • Cyclooxygenase Inhibitor
  • Drug
  • Ester
  • Growth Inhibitor
  • Metabolite
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
Synonym
Achefree
Acticam
Aflamid
Afloxx
Aglan
Ainecox
Aldoron
Alentum
Algiflex
Aliviodol
Anaxicam
Anposel
Antrend
Aponip
Areloger
Aremil
Armex
Arrox
Arsitec
Artex
Arthrobic
Arthrox
Articam
Artipro
Artriclox
Artrifilm
Artriflam
Artrilom
Artrilox
Artrox
Aspicam
Atiflam
Atrozan
Auroxicam
Axius
Meloxicamum
Mobic
UNII-vg2qf83cgl
Chemical FormulaC14H13N3O4S2
Average Molecular Mass351.401 g/mol
Monoisotopic Mass351.035 g/mol
CAS Registry Number71125-38-7
IUPAC Name4-hydroxy-2-methyl-N-(5-methyl-1,3-thiazol-2-yl)-1,1-dioxo-2H-1λ⁶,2-benzothiazine-3-carboxamide
Traditional Namemeloxicam
SMILESCN1C(C(O)=NC2=NC=C(C)S2)=C(O)C2=CC=CC=C2S1(=O)=O
InChI IdentifierInChI=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)
InChI KeyInChIKey=ZRVUJXDFFKFLMG-UHFFFAOYSA-N
Chemical Taxonomy
Description 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).
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzothiazines
Sub ClassNot Available
Direct ParentBenzothiazines
Alternative Parents
Substituents
  • Alpha-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
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
Meloxicam PathwayNot AvailableNot Available
Applications
Biological Roles
Chemical Roles
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point254 dec°C
Boiling PointNot Available
Solubility7.15 mg/L
LogP3.43
Predicted Properties
PropertyValueSource
Water Solubility0.15 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity88.62 m³·mol⁻¹ChemAxon
Polarizability34.25 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-2902000000-442e82736bdaa71629b1View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-001i-4290100000-70369ef9629adcb66252View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0uxr-0905000000-155a653652a8dc132b5cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-001i-1390000000-e476bc93f0f2236bccdcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0006-3910000000-5a451a906b9cf9bd15b8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0009000000-d860614369de32fc5b55View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00kf-0901000000-0d362af6b48e1604f3c0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0006-0900000000-f79d2bd45c77067c33bfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0006-0900000000-385da9c2b565923f3591View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0006-0900000000-24d8592c133da8552647View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0uxr-0905000000-155a653652a8dc132b5cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0uxu-2905000000-a1d5ee29626527977b8eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-014l-3900000000-835e2ce927e75b3bb1fbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-014l-3910000000-cf38e48efa983293e01fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0w29-0709000000-28418136a19ad7e133bfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1900000000-09c918b92fb04726ae80View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ikc-8900000000-b213c50ee4ed1505df38View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0229000000-acae128204108b962183View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ik9-1496000000-6b38c2d88b94b6dcf7cbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03g0-6900000000-cedcff29bec701cd8ff3View in MoNA
Toxicity Profile
Route of ExposureOral. Absolute bioavailability = 89%
Mechanism of ToxicityAnti-inflammatory effects of meloxicam are believed to be due to inhibition of prostaglandin synthetase (cylooxygenase), leading to the inhibition of prostaglandin synthesis. As prostaglandins sensitize pain receptors, inhibition of their synthesis may be associated with the analgesic and antipyretic effects of meloxicam.
MetabolismMeloxicam is almost completely metabolized into inactive metabolites by the cytochrome P450 (CYP450) isozymes. CYP2C9 is primarily responsible for metabolism of meloxicam while CYP3A4 plays a minor role. An intermediate metabolite, 5'-hydroxymethyl meloxicam, is further metabolized to 5'-carboxy meloxicam, the major metabolite. Peroxidase activity is thought to produce the two other inactive metabolites of meloxicam. Route of Elimination: Meloxicam is almost completely metabolized to four pharmacologically inactive metabolites. Meloxicam excretion is predominantly in the form of metabolites, and occurs to equal extents in the urine and feces. Only traces of the unchanged parent compound are excreted in the urine (0.2%) and feces (1.6%). The extent of the urinary excretion was confirmed for unlabeled multiple 7.5 mg doses: 0.5%, 6% and 13% of the dose were found in urine in the form of meloxicam, and the 5'-hydroxymethyl and 5'-carboxy metabolites, respectively. Half Life: 15-20 hours
Toxicity ValuesLD50: 84 mg/kg (Oral, Rat) (1) LD50: 470 mg/kg (Oral, Mouse) (1) LD50: 320 mg/kg (Oral, Rabbit) (1)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesUsed to relieve the symptoms of arthritis, primary dysmenorrhea, fever; and as an analgesic, especially where there is an inflammatory component.
Minimum Risk LevelNot Available
Health EffectsCan result in gastrointestinal toxicity and bleeding, tinnitus, headache, rash, very dark or black stool (sign of intestinal bleeding). [Wikipedia]
SymptomsNot Available
TreatmentPatients should be managed with symptomatic and supportive care following an NSAID overdose. In cases of acute overdose, gastric lavage followed by activated charcoal is recommended. Gastric lavage performed more than one hour after overdose has little benefit in the treatment of overdose. Administration of activated charcoal is recommended for patients who present 1-2 hours after overdose. For substantial overdose or severely symptomatic patients, activated charcoal may be administered repeatedly. Accelerated removal of meloxicam by 4 gm oral doses of cholestyramine given three times a day was demonstrated in a clinical trial. Administration of cholestyramine may be useful following an overdose. Forced diuresis, alkalinization of urine, hemodialysis, or hemoperfusion may not be useful due to high protein binding. (3)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB00814
HMDB IDHMDB14952
PubChem Compound ID5281106
ChEMBL IDCHEMBL599
ChemSpider ID4444553
KEGG IDC08169
UniProt IDNot Available
OMIM ID
ChEBI ID120496
BioCyc IDNot Available
CTD IDNot Available
Stitch IDMeloxicam
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkMeloxicam
References
Synthesis Reference

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

MSDSLink
General References
  1. Wishart DS, Knox C, Guo AC, Cheng D, Shrivastava S, Tzur D, Gautam B, Hassanali M: DrugBank: a knowledgebase for drugs, drug actions and drug targets. Nucleic Acids Res. 2008 Jan;36(Database issue):D901-6. Epub 2007 Nov 29. [18048412 ]
  2. Drugs.com [Link]
  3. RxList: The Internet Drug Index (2009). [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

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 brain, and in pathological conditions, such as in cancer. PTGS2 is responsible for production of inflammatory prostaglandins. Up-regulation of PTGS2 is also associated with increased cell adhesion, phenotypic changes, resistance to apoptosis and tumor angiogenesis. In cancer cells, PTGS2 is a key step in the production of prostaglandin E2 (PGE2), which plays important roles in modulating motility, proliferation and resistance to apoptosis.
Gene Name:
PTGS2
Uniprot ID:
P35354
Molecular Weight:
68995.625 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory0.7 uMNot AvailableBindingDB 50056998
IC500.16 uMNot AvailableBindingDB 50056998
IC500.49 uMNot AvailableBindingDB 50056998
IC500.7 uMNot AvailableBindingDB 50056998
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. [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. [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. [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. [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. [10567199 ]
  6. Lazer ES, Sorcek R, Cywin CL, Thome D, Possanza GJ, Graham AG, Churchill L: Antiinflammatory 2-benzyl-4-sulfonyl-4H-isoquinoline-1,3-diones: novel inhibitors of COX-2. Bioorg Med Chem Lett. 1998 May 19;8(10):1181-6. [9871731 ]
  7. Lazer ES, Miao CK, Cywin CL, Sorcek R, Wong HC, Meng Z, Potocki I, Hoermann M, Snow RJ, Tschantz MA, Kelly TA, McNeil DW, Coutts SJ, Churchill L, Graham AG, David E, Grob PM, Engel W, Meier H, Trummlitz G: 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. [9083488 ]
  8. Prasit P, Wang Z, Brideau C, Chan CC, Charleson S, Cromlish W, Ethier D, Evans JF, Ford-Hutchinson AW, Gauthier JY, Gordon R, Guay J, Gresser M, Kargman S, Kennedy B, Leblanc Y, Leger S, Mancini J, O'Neill GP, Ouellet M, Percival MD, Perrier H, Riendeau D, Rodger I, Zamboni R, et al.: The discovery of rofecoxib, [MK 966, Vioxx, 4-(4'-methylsulfonylphenyl)-3-phenyl-2(5H)-furanone], an orally active cyclooxygenase-2-inhibitor. Bioorg Med Chem Lett. 1999 Jul 5;9(13):1773-8. [10406640 ]
  9. Chan CC, Boyce S, Brideau C, Charleson S, Cromlish W, Ethier D, Evans J, Ford-Hutchinson AW, Forrest MJ, Gauthier JY, Gordon R, Gresser M, Guay J, Kargman S, Kennedy B, Leblanc Y, Leger S, Mancini J, O'Neill GP, Ouellet M, Patrick D, Percival MD, Perrier H, Prasit P, Rodger I, et al.: Rofecoxib [Vioxx, MK-0966; 4-(4'-methylsulfonylphenyl)-3-phenyl-2-(5H)-furanone]: a potent and orally active cyclooxygenase-2 inhibitor. Pharmacological and biochemical profiles. J Pharmacol Exp Ther. 1999 Aug;290(2):551-60. [10411562 ]
  10. Riendeau D, Percival MD, Brideau C, Charleson S, Dube D, Ethier D, Falgueyret JP, Friesen RW, Gordon R, Greig G, Guay J, Mancini J, Ouellet M, Wong E, Xu L, Boyce S, Visco D, Girard Y, Prasit P, Zamboni R, Rodger IW, Gresser M, Ford-Hutchinson AW, Young RN, Chan CC: Etoricoxib (MK-0663): preclinical profile and comparison with other agents that selectively inhibit cyclooxygenase-2. J Pharmacol Exp Ther. 2001 Feb;296(2):558-66. [11160644 ]
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 gastric epithelial cells, it is a key step in the generation of prostaglandins, such as prostaglandin E2 (PGE2), which plays an important role in cytoprotection. In platelets, it is involved in the generation of thromboxane A2 (TXA2), which promotes platelet activation and aggregation, vasoconstriction and proliferation of vascular smooth muscle cells.
Gene Name:
PTGS1
Uniprot ID:
P23219
Molecular Weight:
68685.82 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
IC501.4 uMNot AvailableBindingDB 50056998
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. [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. [10381787 ]
  3. Prasit P, Wang Z, Brideau C, Chan CC, Charleson S, Cromlish W, Ethier D, Evans JF, Ford-Hutchinson AW, Gauthier JY, Gordon R, Guay J, Gresser M, Kargman S, Kennedy B, Leblanc Y, Leger S, Mancini J, O'Neill GP, Ouellet M, Percival MD, Perrier H, Riendeau D, Rodger I, Zamboni R, et al.: The discovery of rofecoxib, [MK 966, Vioxx, 4-(4'-methylsulfonylphenyl)-3-phenyl-2(5H)-furanone], an orally active cyclooxygenase-2-inhibitor. Bioorg Med Chem Lett. 1999 Jul 5;9(13):1773-8. [10406640 ]