(3E)-3-{hydroxy[(pyridin-2-yl)amino]methylidene}-2-methyl-3,4-dihydro-2H-1$l^{6},2-benzothiazine-1,1,4-trione

• ChemBase ID: 436
• Molecular Formular: C15H13N3O4S
• Molecular Mass: 331.34642
• Monoisotopic Mass: 331.06267691
• SMILES: S1(=O)(=O)N(/C(=C(/O)\Nc2ncccc2)/C(=O)c2c1cccc2)C
• Canonical SMILES: O/C(=C/1\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/h2-9,20H,1H3,(H,16,17)/b15-13+
• InChIKey: LDJVNWFKNMYYNT-FYWRMAATSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3E)-3-{hydroxy[(pyridin-2-yl)amino]methylidene}-2-methyl-3,4-dihydro-2H-1$l^{6},2-benzothiazine-1,1,4-trione
• IUPAC Traditional name: akten
• Brand Name: Apo-Piroxicam; Artroxicam; Baxo; Bruxicam; Caliment; Erazon; Feldene; Flogobene; Geldene; Improntal; Larapam; Pipoxicam; Pirkam; Piroflex; Reudene; Riacen; Roxicam; Roxiden; Sasulen; Solocalm; Zunden; piroxicam usp; Akten
• Synonyms: piroxicam; AK1015; Piroxicam

Database IDs

• CAS Number: 36322-90-4
• PubChem SID: 160963899
• PubChem CID: 54676228

CALCULATED PROPERTIES

JChem

• Acid pKa: 7.5554237
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 1.230431
• LogD (pH = 7.4): 1.0765729
• Log P: 1.3089457
• Molar Refractivity: 96.1692 cm^3
• Polarizability: 32.561253 Å^3
• Polar Surface Area: 99.6 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.81
• LOG S: -3.74
• Solubility (Water): 6.05e-02 g/l

PROPERTIES

Physical Property

• Solubility: 23 mg/L
• Hydrophobicity(logP): 3

DETAILS

DrugBank - DB00554

• Drug Groups: approved; investigational
• Description: A cyclooxygenase inhibiting, non-steroidal anti-inflammatory agent (NSAID) that is well established in treating rheumatoid arthritis and osteoarthritis and used for musculoskeletal disorders, dysmenorrhea, and postoperative pain. Its long half-life enables it to be administered once daily. [PubChem]
• Indication: For treatment of osteoarthritis and rheumatoid arthritis.
• Pharmacology: Piroxicam is in a class of drugs called nonsteroidal anti-inflammatory drugs (NSAIDs). Piroxicam works by reducing hormones that cause inflammation and pain in the body. Piroxicam is used to reduce the pain, inflammation, and stiffness caused by rheumatoid arthritis and osteoarthritis.
• Toxicity: Symptoms of overdose include drowsiness, nausea, stomach pain, and/or vomiting.
• Affected Organisms: Humans and other mammals
• Biotransformation: Renal
• Absorption: Well absorbed following oral administration.
• Half Life: 30 to 86 hours
• Elimination: Piroxicam and its biotransformation products are excreted in urine and feces, with about twice as much appearing in the urine as in the feces. Approximately 5% of a piroxicam dose is excreted unchanged. However, a substantial portion of piroxicam elimination occurs by hepatic metabolism. Piroxicam is excreted into human milk.
• Distribution: * 0.14 L/kg
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com