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

• ChemBase ID: 693
• Molecular Formular: C14H13N3O4S2
• Molecular Mass: 351.40072
• Monoisotopic Mass: 351.03474791
• SMILES: c12c(S(=O)(=O)N(C(=C1O)C(=O)Nc1ncc(s1)C)C)cccc2
• Canonical SMILES: Cc1cnc(s1)NC(=O)C1=C(O)c2ccccc2S(=O)(=O)N1C
• 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)
• InChIKey: ZRVUJXDFFKFLMG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-hydroxy-2-methyl-N-(5-methyl-1,3-thiazol-2-yl)-1,1-dioxo-2H-1$l^{6},2-benzothiazine-3-carboxamide; 4-hydroxy-2-methyl-N-(5-methyl-1,3-thiazol-2-yl)-1,1-dioxo-2H-1λ^6,2-benzothiazine-3-carboxamide
• IUPAC Traditional name: 4-hydroxy-2-methyl-N-(5-methyl-1,3-thiazol-2-yl)-1,1-dioxo-2H-1λ^6,2-benzothiazine-3-carboxamide; @meloxicam; 4-hydroxy-2-methyl-N-(5-methyl-1,3-thiazol-2-yl)-1,1-dioxo-2H-1$l^{6},2-benzothiazine-3-carboxamide; meloxicam
• Brand Name: Mobic; Mobicox; Movalis; Movatec; Novo-meloxicam; PHL-meloxicam; PMS-meloxicam; Parocin; Ratio-meloxicam; Tenaron; Metacam; Gen-meloxicam; Dom-meloxicam; Co Meloxicam; Apo-meloxicam
• Synonyms: 4-Hydroxy-2-methyl-N-(5-methyl-2-thiazolyl)-2H-1,2-benzothiazine-3-carboxamide 1,1-Dioxide; Mobicox; Movalis; Movatec; Melox; Recoxa; Tenaron; Meloxicam; Mobic; Metacam; Parocin; Meloxicamum [latin]; Meloxicam; 4-hydroxy-2-methyl-N-(5-methylthiazol-2-yl)-2H-benzo[e][1,2]thiazine-3-carboxamide 1,1-dioxide; 4-hydroxy-2-methyl-N-(5-methyl-1,3-thiazol-2-yl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide

Database IDs

• CAS Number: 71125-38-7
• MDL Number: MFCD00868752
• PubChem SID: 46506624; 160964156
• PubChem CID: 5281106; 54677470

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.47116
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 0.53962874
• LogD (pH = 7.4): -0.97548914
• Log P: 1.6005814
• Molar Refractivity: 88.6249 cm^3
• Polarizability: 33.15376 Å^3
• Polar Surface Area: 99.6 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.28
• LOG S: -3.36
• Solubility (Water): 1.54e-01 g/l

PROPERTIES

Physical Property

• Solubility: 7.15 mg/L; DMSO
• Apperance: Light Yellow Solid
• Melting Point: 240-242°C
• Hydrophobicity(logP): 1.9; 2.853

Safety Information

• Storage Condition: -20°C; -20°C Freezer; Room Temperature (15-30°C)

Pharmacology Properties

• Mechanism of Action: Cyclooxygenase inhibitor; Prostaglandin antagonist

Product Information

• Purity: 95%; 95+%
• Salt Data: Free Base
• Application(s): Analgesic; Antiinflammatory agent; Antipyretic

DETAILS

MP Biomedicals - 02199147

Non-Steroidal Anti-Inflamantory Drug (N.S.A.I.D). Cyclooxygenase (COX-2) Inhibitor. Used in Osteoarthritis research and to treat pain from rheumatoid arthritis.

DrugBank - DB00814

• Drug Groups: approved
• Description: Meloxicam 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]
• Indication: For symptomatic treatment of arthritis and osteoarthritis.
• Pharmacology: Meloxicam is an nonsteroidal anti-inflammatory drug (NSAID) with analgesic and antipyretic properties. Prostaglandins are substances that contribute to inflammation of joints. Meloxicam inhibits prostaglandin synthetase (cylooxygenase 1 and 2) and leads to a decrease of the synthesis of prostaglandins, therefore, inflammation is reduced.
• Toxicity: LD₅₀, Acute: 84 mg/kg (Rat); Oral 470 mg/kg (Mouse); Oral 320 mg/kg (Rabbit)
• Affected Organisms: Humans and other mammals
• Biotransformation: Meloxicam 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.
• Absorption: Absolute bioavailability = 89%
• Half Life: 15-20 hours
• Protein Binding: 99.4% bound, primarily to albumin
• 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.
• Distribution: * 10 L
• Clearance: * 8.8 mL/min [Healthy Male Adults (Fed) oral 7.5 mg tablets]; * 9.9 mL/min [Eldery Male (Fed) oral 15 mg capsules]; * 5.1 mL/min [Eldery Female (Fed) oral 15 mg capsules]; * 19 mL/min [Renal Failure (Fasted) oral 15 mg capsules]; * 11 mL/min [Hepatic Insufficiency (Fasted) oral 15 mg capsules]
• External Links: Wikipedia; RxList; Drugs.com

Selleck Chemicals - S1734

Research Area: Inflammation
Biological Activity:
Meloxicam (Mobic) is a nonsteroidal anti-inflammatory drug with analgesic and fever reducer effects. Meloxicam inhibits cyclooxygenase (COX), the enzyme responsible for converting arachidonic acid into prostaglandin H2--the first step in the synthesis of prostaglandins, which are mediators of inflammation. Meloxicam has been shown, especially at its low therapeutic dose, selectively to inhibit COX-2 over COX-1. [1]

Toronto Research Chemicals - M216100

Preferential cyclooxygenase (COX-2) inhibitor. Sudoxicam and Meloxicam are nonsteroidal anti-inflammatory drugs (NSAIDs) from the enol-carboxamide class.

REFERENCES

• http://en.wikipedia.org/wiki/Meloxicam
• Hawkey, C., et al.: Br. J. Rheumatol., 35, Suppl. 1, 1 (1996)
• Fleischmann, R., et al.: Expert Opin. Pharmacother., 3, 1501 (1996)
• Ger. Pat., 1979, Dr Karl Thomae, 2 756 113; CA, 91, 91656m, (synth, pharmacol)
• Busch, U. et al., Drugs Exp. Clin. Res., 1990, 16, 49; 53, (metab)
• Tsai, R. et al., Helv. Chim. Acta, 1993, 76, 842, (uv, pKa, props)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 1386
• Noble, S. et al., Drugs, 1996, 51, 424
• Busch, U. et al., Drug Metab. Dispos., 1998, 26, 576-584, (metab)