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Details

Stereochemistry ACHIRAL
Molecular Formula C15H13N3O4S
Molecular Weight 331.346
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PIROXICAM

SMILES

CN1C(C(=O)NC2=CC=CC=N2)=C(O)C3=C(C=CC=C3)S1(=O)=O

InChI

InChIKey=QYSPLQLAKJAUJT-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Molecular Formula C15H13N3O4S
Molecular Weight 331.346
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Piroxicam is in a class of drugs called nonsteroidal anti-inflammatory drugs (NSAIDs). 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. 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. 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. Piroxicam is used for treatment of osteoarthritis and rheumatoid arthritis.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
0.414 mM [IC50]
4.4 µM [IC50]
70.0 µM [IC50]
73.8 µM [IC50]
7.0 µM [IC50]
1.3 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
FELDENE
Primary
FELDENE

Cmax

ValueDoseCo-administeredAnalytePopulation
2.3 μg/mL
20 mg single, oral
PIROXICAM plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
135.8 μg × h/mL
20 mg single, oral
PIROXICAM plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
40.5 h
20 mg single, oral
PIROXICAM plasma
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG




OverviewOther

Other InhibitorOther SubstrateOther Inducer





Drug as perpetrator​

Drug as victim

Tox targets

PubMed

Sample Use Guides

In Vivo Use Guide
Recommended dose: 20 mg orally once a day
Route of Administration: Oral
In Vitro Use Guide
Contractions induced by bradykinin in guinea-pig gallbladder smooth muscle strips were significantly attenuated by the cyclooxygenase inhibitor piroxicam (10 muM).
Substance Class Chemical
Record UNII
13T4O6VMAM
Record Status Validated (UNII)
Record Version