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

• ChemBase ID: 72791
• Molecular Formular: C15H13N3O4S
• Molecular Mass: 331.34642
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 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 Traditional name: piroxicam; 4-hydroxy-2-methyl-1,1-dioxo-N-(pyridin-2-yl)-2H-1λ^6,2-benzothiazine-3-carboxamide
• Brand Name: Feldene
• Synonyms: 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; 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

Database IDs

• CAS Number: 36322-90-4
• EC Number: 252-974-3
• MDL Number: MFCD00057317
• PubChem SID: 162037712; 24898132; 24278641
• PubChem CID: 54676228; 5280452
• CHEBI ID: 8249
• ATC CODE: S01BC06; M01AC01; M02AA07
• CHEMBL: 527
• Chemspider ID: 10442653
• DrugBank ID: DB00554
• KEGG ID: D00127
• Unique Ingredient Identifier: 13T4O6VMAM
• Wikipedia Title: Piroxicam
• Medline Plus: a684045

CALCULATED PROPERTIES

• Acid pKa: 4.7604237
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 0.033200305
• LogD (pH = 7.4): -1.5190158
• Log P: 0.59988385
• Molar Refractivity: 87.0435 cm^3
• Polarizability: 32.634167 Å^3
• Polar Surface Area: 99.6 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 198-200°C; 198-200°C

Safety Information

• Storage Condition: -20°C; -20°C Freezer; 2-8°C
• RTECS: DL0705000
• European Hazard Symbols: Harmful (Xn)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3; III
• Australian Hazchem: 2X
• Risk Statements: 22; R:22
• Safety Statements: 26-36; S:36/37/39
• EU Classification: T2
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 154
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301
• GHS Precautionary statements: P301 + P310
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target: COX
• Admin Routes: PO
• Excretion: 4 to 10% renal
• Half Life: 30 to 86 hours
• Metabolism: 4 to 10% renal
• Legal Status: POM
• Pregnancy Category: C, D if used in the third trimester or near delivery
• Gene Information: human ... PTGS1(5742), PTGS2(5743)rat ... Alox5(25290)
• Mechanism of Action: 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.

Product Information

• Purity: ≥98% (TLC); 95+%
• Salt Data: Free Base
• Suitability: meets USP testing specifications
• Application(s): Antiinflammatory agent
• Empirical Formula (Hill Notation): C15H13N3O4S

DETAILS

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
Cyclooxygenase inhibitor.
Non-steroidal anti-inflamatory agent (NSAID) shown to be effective in the prevention of colon cancer.

Sigma Aldrich - P0847

Biochem/physiol Actions
Cyclooxygenase inhibitor.

Toronto Research Chemicals - P510000

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

REFERENCES

• Oyanagui Y et al. Life Sci. 2003 Jul 25; 73(10)
• Carty, T.J., et al.: Prostaglandins, 47, 55 (1980)
• Brogden, R.N., et al.: Drugs, 22, 165 (1980)
• Mihalic, M., et al.: Anal. Profiles Drug Subs., 15, 509 (1980)
• Laneauville., O., et al.: J. Pharmacol. Exp. Ther., 271, 927 (1980)
• Bernhard, E. et al., Arzneim.-Forsch., 1984, 34, 647, (pKa)
• Brogden, R.N. et al., Drugs, 1984, 28, 292, (rev, pharmacol)
• U.S. Pat., 1984, 4 434 164; CA, 100, 191894, (salts)
• Mihalic, M. et al., Anal. Profiles Drug Subst., 1986, 15, 509, (rev, synth, anal)
• Svoboda, J. et al., Coll. Czech. Chem. Comm., 1986, 51, 1133, (synth)
• Tsai, R. et al., Helv. Chim. Acta, 1993, 76, 842, (props)
• Lee, C.R. et al., Drugs, 1994, 48, 907, (rev)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 7th edn., Akademie-Verlag, 1994, 4443, (synonyms)
• Takcs-Novk, K. et al., Helv. Chim. Acta, 1995, 78, 553, (props, bibl)
• Maya, M.T. et al., J. Pharm. Biomed. Anal., 1995, 13, 319; 785, (hplc)
• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 80
• Lombardino, J.G. et al., J. Med. Chem., 1973, 16, 493, (synth, pharmacol)
• Whipple, E.B., Org. Magn. Reson., 1977, 10, 23, (cmr)
• Wiseman, E.H. et al., Pharmacol. Biochem. Prop. Drug Subst., 1981, 3, 524, (rev, pharmacol)
• Kojic-Prodic, B. et al., Acta Cryst. B, 1982, 38, 2948, (cryst struct)
• Bordner, J. et al., Acta Cryst. C, 1984, 40, 989, (cryst struct)