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

• ChemBase编号: 72791
• 分子式: C15H13N3O4S
• 平均质量: 331.34642
• 单一同位素质量: 331.06267691
• SMILES: c1cnc(cc1)NC(=O)C1=C(c2c(S(=O)(=O)N1C)cccc2)O
• Canonical SMILES: O=C(C1=C(O)c2ccccc2S(=O)(=O)N1C)Nc1ccccn1
• InChI: InChI=1S/C15H13N3O4S/c1-18-13(15(20)17-12-8-4-5-9-16-12)14(19)10-6-2-3-7-11(10)23(18,21)22/h2-9,19H,1H3,(H,16,17,20)
• InChIKey: QYSPLQLAKJAUJT-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 4-hydroxy-2-methyl-1,1-dioxo-N-(pyridin-2-yl)-2H-1$l^{6},2-benzothiazine-3-carboxamide; 4-hydroxy-2-methyl-1,1-dioxo-N-(pyridin-2-yl)-2H-1λ^6,2-benzothiazine-3-carboxamide
• IUPAC传统名: piroxicam; 4-hydroxy-2-methyl-1,1-dioxo-N-(pyridin-2-yl)-2H-1λ^6,2-benzothiazine-3-carboxamide
• 商标名: Feldene
• 别名: 2-甲基-4-羟基-N-(2-吡啶基)-2H-1,2-苯并噻嗪-3-甲酰胺-1,1-二氧化物; 吡罗昔康; 4-Hydroxy-2-methyl-N-(pyridin-2-yl)-2H-benzo[e][1,2]thiazine-3-carboxamide 1,1-dioxide; Feldene; Roxam; Piroxicam; 4-Hydroxy-2-methyl-3[pyrid-2-yl-carbamoyl]-2H-1,2-benzothiazine 1,1-dioxide; 4-Hydroxy-2-methyl-3-(pyrid-2-yl-carbamoyl)-2H-1,2-benzothiazine 1,1-dioxide; Piroxicam; Brexin; Cycladol; Fasax; Flamatrol; Improntal; Larapam; Piroflam; Pirox; Pirozip; Reudene;; 4-Hydroxy-2-methyl-N-2-pyridinyl-2H-1,2-benzothiazine-3-carboxamide 1,1-Dioxide; Artroxicam; Baxo; Bruxicam; CHF 1251; CP 16171; Caliment; Roxicam; Roxiden; Sasulen; Solocalm

登记号

• CAS号: 36322-90-4
• EC号: 252-974-3
• MDL号: MFCD00057317
• PubChem SID: 162037712; 24898132; 24278641
• PubChem CID: 5280452; 54676228
• CHEBI ID: 8249
• ATC码: M01AC01; S01BC06; M02AA07
• CHEMBL: 527
• Chemspider ID: 10442653
• DrugBank ID: DB00554
• KEGG ID: D00127
• 美国药典/FDA物质标识码: 13T4O6VMAM
• 维基百科标题: Piroxicam
• Medline Plus: a684045

理论计算性质

• Acid pKa: 4.7604237
• 质子受体: 5
• 质子供体: 2
• LogD (pH = 5.5): 0.033200305
• LogD (pH = 7.4): -1.5190158
• Log P: 0.59988385
• 摩尔折射率: 87.0435 cm^3
• 极化性: 32.634167 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

分子性质

理化性质

• 溶解度: Chloroform; Ethyl Acetate
• 外观: Off-White to Pale Yellow Solid
• 熔点: 198-200°C; 198-200°C

安全信息

• 保存条件: -20°C; -20°C Freezer; 2-8°C
• RTECS编号: DL0705000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 联合国危险货物编号: 2811
• 德国WGK号: 3
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): 3; III
• 澳大利亚Hazchem: 2X
• 危险公开号: 22; R:22
• 安全公开号: 26-36; S:36/37/39
• 欧盟危险货物分类: T2
• 欧盟危险识别号(EUHIN): 6.1B
• 美国ERG指导号: 154
• GHS危险品标识: GHS06
• GHS警示词: Danger
• GHS危险声明: H301
• GHS警示性声明: P301 + P310
• 个人保护装置: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2811 6.1/PG 3
• 保存温度: 2-8°C

药理学性质

• 作用靶点: COX
• 给药途径: PO
• 排泄: 4 to 10% renal
• 半衰期: 30 to 86 hours
• 代谢: 4 to 10% renal
• 法定药品分级: POM
• 妊娠期药物分类: C, D if used in the third trimester or near delivery
• 相关基因信息: human ... PTGS1(5742), PTGS2(5743)rat ... Alox5(25290)
• 生物活性机理: Piroxicam also inhibits the migration of leukocytes into sites of inflammation and prevents the formation of thromboxane A2, an aggregating agent, by the platelets; Piroxicam blocks the Cox-1 enzyme, resulting into the disruption of production of prostaglandins.; Reversible inhibitor of cyclooxygenase, causing the peripheral inhibition of prostaglandin synthesis.; The prostaglandins are produced by an enzyme called Cox-1.

产品相关信息

• 纯度: ≥98% (TLC); 95+%
• 成盐信息: Free Base
• 适用性: meets USP testing specifications
• 应用领域: Antiinflammatory agent
• Empirical Formula (Hill Notation): C15H13N3O4S

详细说明

MP Biomedicals - 02156277

Cyclooxygenase inhibitor

Selleck Chemicals - S1713

Research Area: Inflammtion
Biological Activity:
Piroxicam (Feldene) is a non-selective COX inhibitor with an IC50 of 6 mM. It is a non-steroidal anti-inflammatory drug used to relieve the symptoms of rheumatoid and osteoarthritis, primary dysmenorrhoea, postoperative pain; and acts as an analgesic, especially where there is an inflammatory component. [1][2]References on Piroxicam (Feldene)[] Life Sciences , 2003, 73:333–1346

Sigma Aldrich - P5654

Biochem/physiol Actions
Non-steroidal anti-inflamatory agent (NSAID) shown to be effective in the prevention of colon cancer.
环加氧酶抑制剂。

Sigma Aldrich - P0847

Biochem/physiol Actions
环加氧酶抑制剂。

Toronto Research Chemicals - P510000

Non-steroidal anti-inflammatory with long half-life. Cyclooxygenase inhibitor. Clinically useful NSAID.

参考文献

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