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Piroxicam

Piroxicam Structure
CAS No.
36322-90-4
Chemical Name:
Piroxicam
Synonyms
Feldene;Pipoxicam;Prioxicam;4-HYDROXY-2-METHYL-3-(PYRID-2-YL-CARBAMOYL)-2H-1,2-BENZOTHIAZINE 1,1-DIOXIDE;Baxo;Erazon;Pirkam;Riacen;Zunden;chf1251
CBNumber:
CB1375282
Molecular Formula:
C15H13N3O4S
Molecular Weight:
331.35
MOL File:
36322-90-4.mol
MSDS File:
SDS
Modify Date:
2024/7/2 8:55:00

Piroxicam Properties

Melting point 198-200°C
Density 1.3664 (rough estimate)
refractive index 1.6320 (estimate)
storage temp. 2-8°C
solubility Practically insoluble in water, soluble in methylene chloride, slightly soluble in anhydrous ethanol. It shows polymorphism (5.9).
form Solid
pka 6.3 (2:1 dioxane-water)
color White to Light yellow
Water Solubility Soluble in water, ethanol, chloroform, ethyl acetate.
λmax 358nm(H2O)(lit.)
Merck 14,7506
BCS Class 2
InChIKey QYSPLQLAKJAUJT-UHFFFAOYSA-N
CAS DataBase Reference 36322-90-4(CAS DataBase Reference)
NIST Chemistry Reference Piroxicam(36322-90-4)
EPA Substance Registry System 2H-1,2-Benzothiazine-3-carboxamide, 4-hydroxy-2-methyl-N-2-pyridinyl-, 1,1-dioxide (36322-90-4)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS06,GHS08
Signal word  Danger
Hazard statements  H301-H373
Precautionary statements  P260-P264-P270-P301+P310-P314-P405
Hazard Codes  Xn,F,T
Risk Statements  22-25
Safety Statements  26-36
RIDADR  UN 2811
WGK Germany  3
RTECS  DL0705000
HazardClass  6.1(b)
PackingGroup  III
HS Code  29349990
Toxicity LD50 orally in mice: 360 mg/kg (Wiseman)
NFPA 704
0
2 0

Piroxicam price More Price(8)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) P5654 Piroxicam ≥98% (TLC) 36322-90-4 1G ₹6051.18 2022-06-14 Buy
Sigma-Aldrich(India) PHR1588 Piroxicam Pharmaceutical Secondary Standard; Certified Reference Material 36322-90-4 200MG ₹13704.45 2022-06-14 Buy
Sigma-Aldrich(India) P5654 Piroxicam ≥98% (TLC) 36322-90-4 5G ₹21097.93 2022-06-14 Buy
Sigma-Aldrich(India) P5654 Piroxicam ≥98% (TLC) 36322-90-4 10G ₹27289.83 2022-06-14 Buy
Sigma-Aldrich(India) P0847 Piroxicam meets USP testing specifications 36322-90-4 1G ₹6062 2022-06-14 Buy
Product number Packaging Price Buy
P5654 1G ₹6051.18 Buy
PHR1588 200MG ₹13704.45 Buy
P5654 5G ₹21097.93 Buy
P5654 10G ₹27289.83 Buy
P0847 1G ₹6062 Buy

Piroxicam Chemical Properties,Uses,Production

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.

Chemical Properties

Off-White to Pale Yellow Solid

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.

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.

Definition

ChEBI: A monocarboxylic acid amide resulting from the formal condensation of the carboxy group of 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylic acid 1,1-dioxide with the exocyclic nitrogen of 2-aminopyridine.

brand name

Feldene (Mack/Pfizer, Germany), Brexidol (Pharmacia & Upjohn, Germany), Brexin (Pharmacia & Upjohn, Austria), Doblexan (Organon, Spain), Durapirox (Durachemie, Germany), Piro-Phlogont (Azupharma, Germany), Ruvamed (Coup, Greece).

General Description

Piroxicam (Feldene) is the most widely used oxicam becauseof its once-daily dosing schedule. It is well absorbedafter oral administration and has a plasma half-life of 50hours, thus requiring a dose of only 20 to 30 mg oncedaily. It undergoes extensive hepatic metabolism, catalyzedby CYP2C9 to give 5-hydroxypiroxicam as its majormetabolite. Several piroxicam prodrugshave been synthesized via derivatization of the enol alcoholgroup (amipiroxicam, droxicam, and pivoxicam) to reducepiroxicam-induced GI irritation.

Biological Activity

Anti-inflammatory; highly selective inhibitor of COX-1 (ratio of IC 50 values for COX-2/COX-1 ~ 600).

Clinical Use

NSAID and analgesic. Piroxicam, the first of a new class of NSAIDs known as “oxicams,” was introduced in 1979 for the treatment of rheumatoid arthritis, osteoarthritis, ankylosing spondylitis, gout, and acute musculoskeletal disorders. This compound was the result of a long and intensive effort to develop a potent NSAID having a novel structure and a plasma half-life sufficiently long to maintain continuous therapeutic blood levels on a once-a-day dosing regimen. Piroxicam is a potent competitive inhibitor of cyclooxygenase and lowers blood levels of prostaglandins in humans. Its ability to inhibit the infiltration of polymorphonuclear leukocytes into inflamed joints has been demonstrated in animals. Its potency and long plasma half-life of 40 h in humans allow for once-a-day dosing at 20 mg. A high incidence of gastric irritation results from this agent.

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Piroxicam Spectrum

4-HYDROXY-2-METHYL-3-(PYRID-2-YL-CARBAMOYL)-2H-1,2-BENZOTHIAZINE 1,2-DIOXIDE 4-HYDROXY-2-METHYL-N-2-PYRIDINYL-2H-1,2-BENZOTHIAZINE-3-CARBOXAMIDE 4-hydroxy-2-methyl-n-2-pyridinyl-2h-1,2-benzothiazine-3-carboxamide 1,1-dioxide 3,4-DIHYDRO-2-METHYL-4-OXO-N-2-PYRIDYL-2H-1,2-BENZOTHIAZINE-3-CARBOXAMIDE 1,1-DIOXIDE AURORA KA-6753 4-Hydroxy-2-Methyl-1,2-Benzothiazine-3-Carboxylic Acid Ethylester-1,1-Dioxide Piroxicam, Feldene PIROXICAM ASSAY STANDARD BP(CRM STANDARD) PIROXICAM EPP(CRM STANDARD) PIROXICAM USP EP PIROXICAM USP(CRM STANDARD) PIROXICAM(RG) 4-HYDROXY-2-METHYL-N-2-PYRIDINYL-2H-1,2-BENZOTHIAZINE-3-CARBOXAMIDE(PIROXICAM) PIROXICAM PIROXICAMUM 2H-1,2-Benzothiazine-3-carboxamide, 4-hydroxy-2-methyl-N-2-pyridinyl-, 1,1-dioxide 2h-1,2-benzothiazine-3-carboxamide,4-hydroxy-2-methyl-n-2-pyridinyl-,1,1-diox 4-Hydroxy-2-methyl-N-(2-pyridyl)-2H-1,2-benzothiazin-3-caboxyamid-1,1-dioxid 4-hydroxy-2-methyl-n-(2-pyridyl)-2h-1,2-benzothiazine-3-carboxamide-1,1-diox 4-Hydroxy-2-methyl-N-(2-pyridyl)-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide Artroxicam Baxo Bruxicam Caliment chf1251 CP 16171 cp16171 Erazon Flogobene Geldene Improntal Larapam Pirkam Piroflex piroftal piroxicamusp pyroxycam Reudene Riacen Roxicam Roxiden Sasulen Solocalm Zunden PiroxicaMbcd Piroxicam (125 mg) 4-Hydroxy-2-methyl-3-(2-pyridylcarbamoyl)-2H-1,2-benzothiazine 1,1-dioxide Piroxicam (200 mg) 4-hydroxy-2-Methyl-1,1-dioxo-N-(pyridin-2-yl)-2H-1$l^{6},2-benzothiazine-3-carboxaMide PiroxicaMUSP30 4-Hydroxy-2-methyl-3-(2-pyridylcarbamoyl)-2H-1,2-benzothiazine 1,1-Dioxide 4-Hydroxy-2-methyl-N-(2-pyridyl)-2H-1,2-benzothiazine-3-carboxamide 1,1-Dioxide piroxicaM us 4-Hydroxy-2-Methyl-N-(pyridin-2-yl)-2H-benzo[e][1,2]thiazine-3-carboxaMide 1,1-dioxide 4-hydroxy-2-methyl-N-2-pyridinyl-1,1-dioxide-2H-1,2-benzothiazine-3-carboxamide Piroxicam Solution, 100ppm Piroxicam 36322-90-4 4-Hydroxy-2-methyl-N-(pyridin-2-yl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide piroxicam pyroxycam roxicam piroxicam usp