Piroxicam
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Piroxicam
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CAS No:
36322-90-4
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Formula:
C15H13N3O4S
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Chemical Name:
Piroxicam
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Synonyms:
2H-1,2-Benzothiazine-3-carboxamide,4-hydroxy-2-methyl-N-2-pyridinyl-,1,1-dioxide;Piroxicam;Pyroxycam;Baxo;Feldene;Piroftal;CHF 1251;Roxicam;4-Hydroxy-2-methyl-N-(2-pyridyl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide;NSC 666076;Sasulen;Doblexan;Improntal;Piroflex;Bruxicam;Erazon;Flogobene;Geldene;Reudene;Artroxicam;Roxiden;Solocalm;Riacen;Larapam;Zunden;Caliment;Pirkam;CP 16171;Felden gel;Feldene Zydis;Dolibid;Feldene Melt;Felvin 20;Pixicam;Feloxin;Nkoyo piroxicam;Felxicam;Neoxicam;Uphaxicam;Maxvin;Laxidene;Rheugesic;Piroxidine;Dispercam;Murupe;Feledene;Feldoral;Piroxitas-DT;Nesprex-DT;Flogosan;Inflacin
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CAS No:
Description
Piroxicam is a non-steroidal anti-inflammatory drugs, acts as a COX inhibitor, with IC50s of 47, 25 μM for human monocyte COX-1 and COX-2, respectively.
Solid
Piroxicam is 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. A non-steroidal anti-inflammatory drug of the oxicam class, it is used to relieve pain and works by preventing the production of endogenous prostaglandins involved in the mediation of pain, stiffness, tenderness and swelling. It has a role as an analgesic, a cyclooxygenase 1 inhibitor, a non-steroidal anti-inflammatory drug, an EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor and an antirheumatic drug. It is a benzothiazine, a member of pyridines and a monocarboxylic acid amide.|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.|Piroxicam is a Nonsteroidal Anti-inflammatory Drug. The mechanism of action of piroxicam is as a Cyclooxygenase Inhibitor.|Piroxicam is a commonly used nonsteroidal antiinflammatory drug (NSAID) that is available by prescription only and is used in therapy of chronic arthritis. Piroxicam can cause mild serum aminotransferase elevations and, in rare instances, leads to clinically apparent acute liver injury that can be severe and even fatal.|Piroxicam is a nonsteroidal oxicam derivative with anti-inflammatory, antipyretic and analgesic properties. As a non-selective, nonsteroidal anti-inflammatory drug (NSAID), piroxicam binds and chelates both isoforms of cyclooxygenases (COX1 and COX2), thereby stalling phospholipase A2 activity and conversion of arachidonic acid into prostaglandin precursors at the rate limiting cyclooxygenase enzyme step. This results in inhibition of prostaglandin biosynthesis. As a second, independent effect, piroxicam inhibits the activation of neutrophils thereby contributing to its overall anti-inflammatory effects.
Piroxicam Basic Attributes
331.34600
331.35
252-974-3
13T4O6VMAM
757284|666076
DTXSID5021170
C751
M01AC01|M - Musculo-skeletal system|S - Sensory organs
3005101000
Characteristics
107.98000
3.1
Off-white to pale yellow solid
1.563 g/cm3
198-200 °C
297.6±32.9 °C
1.714
Soluble in water, ethanol, chloroform, ethyl acetate.
2-8ºC
LD50 orally in mice: 360 mg/kg (Wiseman)
6.3
170.9 Ų [M+H]+ [CCS Type: TW, Method: Major Mix IMS/Tof Calibration Kit (Waters)]|170.7 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]|170.9 Ų [M+H]+ [CCS Type: TW]
Safety Information
III
6.1(b)
UN 2811
3
R22
S26-S36
DL0705000
Xn
Stable at normal temperatures and pressures.
Missing Phrase - N15.00950417
H301
|Danger|H301 (99.01%): Toxic if swallowed [Danger Acute toxicity, oral]|P201, P202, P260, P264, P270, P281, P301+P310, P308+P313, P314, P321, P330, P405, and P501|Aggregated GHS information provided by 202 companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Toxicity
Symptoms of overdose include drowsiness, nausea, stomach pain, and/or vomiting.
Elevated serum aminotransferase levels have been reported in 3% to 18% of patients taking piroxicam, but symptomatic liver disease with jaundice is rare (estimated at 1 to 5 cases per 100,000 prescriptions). The latency to onset of symptoms of clinically apparent liver injury due to piroxicam is variable from a few days to several months, but is generally within the first 1 to 6 weeks of treatment. The pattern of injury is predominantly cholestatic, although cases presenting with mixed or hepatocellular patterns have been reported (Case 1). Eosinophilia, rash and fever can occur, but are not always present and are usually not prominent. Autoantibodies are rarely found. The injury is usually self-limited and recovery occurs within 1 to 2 months. Rare cases of acute liver failure have been reported.
Drug Information
For treatment of osteoarthritis and rheumatoid arthritis.|FDA Label
Piroxicam is a commonly used nonsteroidal antiinflammatory drug (NSAID) that is available by prescription only and is used in therapy of chronic arthritis. Piroxicam can cause mild serum aminotransferase elevations and, in rare instances, leads to clinically apparent acute liver injury that can be severe and even fatal.
Nonsteroidal Antiinflammatory Drugs
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.
Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions.They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects. (See all compounds classified as Anti-Inflammatory Agents, Non-Steroidal.)|Compounds or agents that combine with cyclooxygenase (PROSTAGLANDIN-ENDOPEROXIDE SYNTHASES) and thereby prevent its substrate-enzyme combination with arachidonic acid and the formation of eicosanoids, prostaglandins, and thromboxanes. (See all compounds classified as Cyclooxygenase Inhibitors.)
Well absorbed following oral administration.|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.|0.14 L/kg
Renal|Piroxicam has known human metabolites that include 5'-Hydroxypiroxicam.
30 to 86 hours
The antiinflammatory effect of Piroxicam may result from the reversible inhibition of cyclooxygenase, causing the peripheral inhibition of prostaglandin synthesis. The prostaglandins are produced by an enzyme called Cox-1. Piroxicam blocks the Cox-1 enzyme, resulting into the disruption of production of prostaglandins. Piroxicam also inhibits the migration of leukocytes into sites of inflammation and prevents the formation of thromboxane A2, an aggregating agent, by the platelets.
CP 16171
Piroxicam Use and Manufacturing
Piroxicam (INN, BAN, USAN, AAN; in some countries it is spelt piroksikam or piroxikam) is a non-steroidal anti-inflammatory drug (NSAID) of the oxicam class used to relieve the symptoms of painful, inflammatory conditions like arthritis. Piroxicam works by preventing the production of a certain type of body chemical called prostaglandins which are involved in the mediation of pain, stiffness, tenderness and swelling. The medicine is available as capsules, tablets and (not in all countries) as a prescription-free gel 0.5%. It is also available in a betadex formulation, which allows a more rapid absorption of piroxicam from the digestive tract.It was originally brought to market by Pfizer under the tradename Feldene in 1980, became generic in 1992, and is marketed worldwide under many brandnames.
Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients|Pharmaceuticals
Computed Properties
Molecular Weight:331.3
XLogP3:3.1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:2
Exact Mass:331.06267708
Monoisotopic Mass:331.06267708
Topological Polar Surface Area:108
Heavy Atom Count:23
Complexity:611
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Drug Function and Efficacy
It is a non-steroidal anti-inflammatory drug with analgesic, anti-inflammatory and antipyretic effects. This product exerts its pharmacological effects by inhibiting cyclooxygenase, reducing the synthesis of prostaglandins in local tissues, and inhibiting the chemotaxis of leukocytes and the release of lysosomal enzymes.
Registered Holders
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APEX HEALTHCARE LTD
Active
United States
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ARCH PHARMALABS LTD
Active
United States
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ARCH PHARMALABS LIMITED
Active
India
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