Piroxicam

Base Information

• Chemical Name: Piroxicam
• CAS No.: 36322-90-4
• Molecular Formula: C15H13N3O4S
• Molecular Weight: 331.352
• Hs Code.: 29349990
• Mol file: 36322-90-4.mol

Synonyms:(4-Hydroxy-2-methyl-1,1-dioxobenzo[e]1,2-thiazin-3-yl)-N-(2-pyridyl)carboxamide;Prestwick_573;Piroxicam (JP14/USP);CP 16171;Feldene;Roxicam;4-Hydroxy-2-methyl-N-2-pyridinyl-2H-1,2-benzothiazine-3-carboxamide, 1,1-dioxide;Piroxicam [USAN:BAN:INN:JAN];2H-1,2-Benzothiazine-3-carboxamide, 4-hydroxy-2-methyl-N-2-pyridinyl-, 1,1-dioxide;Piroftal;Pyroxycam;BAXO;Feldene (TN);Piroxicamum [INN-Latin];4-Hydroxy-2-methyl-N-2-pyridyl-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide;4-Hydroxy-2-methyl-N-(2-pyridyl)-2H-1,2-benzothiazin-3-caboxyamid-1,1-dioxid [German];

Chemical Property of Piroxicam

Chemical Property:

• Appearance/Colour: Off-white to pale yellow solid
• Melting Point: 198-200 °C
• Refractive Index: 1.714
• PKA: 6.3 (2:1 dioxane-water)
• PSA: 107.98000
• Density: 1.563 g/cm³
• LogP: 2.67270
• Storage Temp.: 2-8°C
• Solubility.: Practically insoluble in water, soluble in methylene chloride, slightly soluble in anhydrous ethanol. It shows polymorphism (5.9).
• Water Solubility.: Soluble in water, ethanol, chloroform, ethyl acetate.

Purity/Quality:

97%~103% ^*data from raw suppliers

Piroxicam ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, F
• Hazard Codes: Xn,F,T
• Statements: 22-25
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Description: Piroxieam is a non-steroidal anti-inflammatory drug, of the oxieam class. A contact and photocontact sensitizer, which induced contact dermatitis in a physieal therapist. Piroxieam generally cross reacts with thiosalicylic acid and also with thiomersal. Cross sensitivity is not observed to tenoxicam.
• Uses: Piroxicam is used in inflammatory and degenerative diseases of the musculoskeletal system that are accompanied by painful symptoms. It is used for rheumatic heart disease, nonspecific infectious polyarthritis, gouty arthritis, rheumatoid arthritis, osteoarthritis, ankylosing spondylitis, arthrosis, back pain, neuralgia, myalgia, and other diseases associated with inflammation. Piroxicam is an effective and potent inhibitor of prostaglandin synthesis and a Cox-1 and Cox-2 inhibitor. Studies show that Piroxicam blocks release of platelet ADP, and inhibits Cox-1 more potently than Cox-2. Non-steroidal anti-inflammatory with long half-life. Cyclooxygenase inhibitor. Clinically useful NSAID
• Indications: Piroxicam (Feldene) is indicated for the treatment of rheumatoid arthritis and osteoarthritis. Piroxicam is a nonspecific COX inhibitor that has a much higher affinity for COX-1 than COX-2. This may account for the large proportion (over 30%) of patients receiving long-term therapy who have reported side effects.Adverse GI reactions have been the most frequently reported side effect, but edema, dizziness, headache, rash, and changes in hematological parameters have also occurred in 1 to 6% of patients. Piroxicam can cause serious GI bleeding, ulceration, and perforation, particularly in the elderly, if the recommended dosage is exceeded or if aspirin is being taken concurrently.
• Therapeutic Function: Antiinflammatory, Analgesic
• Clinical Use: NSAID and analgesic
• Drug interactions: Potentially hazardous interactions with other drugs ACE inhibitors and angiotensin-II antagonists: antagonism of hypotensive effect; increased risk of nephrotoxicity and hyperkalaemia. Analgesics: avoid concomitant use of 2 or more NSAIDs, including aspirin (increased side effects); avoid with ketorolac (increased risk of side effects and haemorrhage). Antibacterials: possibly increased risk of convulsions with quinolones. Anticoagulants: effects of coumarins and phenindione enhanced; possibly increased risk of bleeding with heparins, dabigatran and edoxaban - avoid long term use with edoxaban. Antidepressants: increased risk of bleeding with SSRIs and venlaflaxine. Antidiabetic agents: effects of sulphonylureas enhanced. Antiepileptics: possibly increased phenytoin concentration. Antivirals: increased risk of haematological toxicity with zidovudine; concentration increased by ritonavir. Ciclosporin: may potentiate nephrotoxicity. Cytotoxics: reduced excretion of methotrexate; increased risk of bleeding with erlotinib. Diuretics: increased risk of nephrotoxicity; antagonism of diuretic effect; hyperkalaemia with potassium-sparing diuretics. Lithium: excretion decreased. Pentoxifylline: increased risk of bleeding. Tacrolimus: increased risk of nephrotoxicity.

Technology Process of Piroxicam

There total 29 articles about Piroxicam which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

2-aminopyridine (504-29-0) + methoxyethyl 2-methyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide (80201-74-7) → Piroxicam (36322-90-4)

Guidance literature:

In xylene; for 6h; Heating;

Reference yield: 96.0%

2-aminopyridine (504-29-0) + 2-methoxyethyl 4-hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide (80201-73-6) → Piroxicam (36322-90-4)

Guidance literature:

In 5,5-dimethyl-1,3-cyclohexadiene;

Reference yield: 92.0%

2-aminopyridine (504-29-0) + 4-Hydroxy-2-methyl-1,1-dioxo-1,2-dihydro-1λ6-benzo[e][1,2]thiazine-3-carboxylic acid 2-ethoxy-ethyl ester (107124-73-2) → Piroxicam (36322-90-4)

Guidance literature:

In xylene; for 6h; Heating;

upstream raw materials:

2-aminopyridine

methoxyethyl 2-methyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide

4-Hydroxy-2-methyl-1,1-dioxo-1,2-dihydro-1λ⁶-benzo[e][1,2]thiazine-3-carboxylic acid 2-ethoxy-ethyl ester

4-methoxy-2-methyl-N-(pyridin-2-yl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide

Downstream raw materials:

droxicam

Ampiroxicam

[Ni(II)(4-hydroxy-2-methyl-N-(2-pyridyl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide)(DL-phenylalaninate)(H₂O)2]Cl

[Zn(II)(4-hydroxy-2-methyl-N-(2-pyridyl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide)(DL-phenylalaninate)(H₂O)2](acetate)*H₂O

Refernces

• 1、 -. "Solid Pharmaceutical Preparations Containing Copolymers Based On Polyethers Combined With Poorly Water-Soluble Polymers". . . Retrieved 2012/03/12.
• 2、 -. "Topical and transdermal delivery system utilizing submicron oil spheres". . . Retrieved 2008/06/13.