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

• ChemBase编号: 693
• 分子式: C14H13N3O4S2
• 平均质量: 351.40072
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 4-hydroxy-2-methyl-N-(5-methyl-1,3-thiazol-2-yl)-1,1-dioxo-2H-1$l^{6},2-benzothiazine-3-carboxamide; 4-hydroxy-2-methyl-N-(5-methyl-1,3-thiazol-2-yl)-1,1-dioxo-2H-1λ^6,2-benzothiazine-3-carboxamide
• IUPAC传统名: 4-hydroxy-2-methyl-N-(5-methyl-1,3-thiazol-2-yl)-1,1-dioxo-2H-1λ^6,2-benzothiazine-3-carboxamide; @meloxicam; 4-hydroxy-2-methyl-N-(5-methyl-1,3-thiazol-2-yl)-1,1-dioxo-2H-1$l^{6},2-benzothiazine-3-carboxamide; meloxicam
• 商标名: Mobic; Mobicox; Movalis; Movatec; Novo-meloxicam; PHL-meloxicam; PMS-meloxicam; Parocin; Ratio-meloxicam; Tenaron; Metacam; Gen-meloxicam; Dom-meloxicam; Co Meloxicam; Apo-meloxicam
• 别名: 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

登记号

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

理论计算性质

JChem

• Acid pKa: 4.47116
• 质子受体: 5
• 质子供体: 2
• LogD (pH = 5.5): 0.53962874
• LogD (pH = 7.4): -0.97548914
• Log P: 1.6005814
• 摩尔折射率: 88.6249 cm^3
• 极化性: 33.15376 Å^3
• 极化表面积: 99.6 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 2.28
• LOG S: -3.36
• 溶解度: 1.54e-01 g/l

分子性质

理化性质

• 溶解度: 7.15 mg/L; DMSO
• 外观: Light Yellow Solid
• 熔点: 240-242°C
• 疏水性(logP): 1.9; 2.853

安全信息

• 保存条件: -20°C; -20°C Freezer; Room Temperature (15-30°C)

药理学性质

• 生物活性机理: Cyclooxygenase inhibitor; Prostaglandin antagonist

产品相关信息

• 纯度: 95%; 95+%
• 成盐信息: Free Base
• 应用领域: Analgesic; Antiinflammatory agent; Antipyretic

详细说明

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.

参考文献

• 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)