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Compound Detail

CHEMBL527

PIROXICAM
💊 Approved Drug
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💊 Approved Drug
CN1C(C(=O)Nc2ccccn2)=C(O)c2ccccc2S1(=O)=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL527
Name PIROXICAM
Phase Approved
Structure Type MOL
InChI Key QYSPLQLAKJAUJT-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Brexidol CP-16,171 CP-16171 Feldene Feldene 20 Feldene p Flamatrol Kentene Larapam NSC-666076 Piroflam 10 Piroflam 20 +3 more
13
Targets
26
Activities
2
Assay Types
4
PK Parameters
20
Publications
15
Known Names
11
Indications
1
Mechanisms

Molecular Properties

331.4
MW (Da)
1.58
ALogP
5
HBA
2
HBD
99.6
PSA (Ų)
0.87
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1982
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Black Box Warning Natural Product
USAN Stem -icam
USAN Year 1974

Extended Properties

Molecular Formula C15H13N3O4S
MW 331.35
Aromatic Rings 2
Heavy Atoms 23
NP-Likeness -1.18

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Cyclooxygenase inhibitor INHIBITOR Cyclooxygenase ✓ ✓

Indications

Arthralgia Arthritis, Rheumatoid Eye Diseases Myalgia Osteoarthritis Rheumatic Diseases Renal Colic Wounds and Injuries Osteoarthritis, Knee Tennis Elbow Pain

ATC Classification

M01AC01
piroxicam
Level 1: MUSCULO-SKELETAL SYSTEM
Level 2: ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS
M02AA07
piroxicam
Level 1: MUSCULO-SKELETAL SYSTEM
Level 2: TOPICAL PRODUCTS FOR JOINT AND MUSCULAR PAIN
S01BC06
piroxicam
Level 1: SENSORY ORGANS
Level 2: OPHTHALMOLOGICALS

Drug Warnings

Black Box Warning
cardiotoxicity
Country: United States
Black Box Warning
neurotoxicity
Country: United States
Black Box Warning
gastrointestinal toxicity
Country: United States

Activity Summary

IC50 21 meas. best 7.0
Ki 5 meas. best 5.31

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Cyclooxygenase
CHEMBL2095157
 IC50 7.0 7.0 100.0 1
Rattus norvegicus
CHEMBL376
 IC50 7.0 7.0 100.0 1
Prostaglandin G/H synthase 1
CHEMBL221
 IC50 5.89 5.28 1300.0 3
Organic anion transporter 3
CHEMBL1641348
 Ki 5.31 5.31 4880.0 1
Plasmodium falciparum
CHEMBL364
 IC50 5.0 4.9667 10000.0 3
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 4.75 4.75 18000.0 1
THP-1
CHEMBL614245
 IC50 4.74 4.705 18100.0 2
Solute carrier family 22 member 6
CHEMBL1641347
 Ki 4.7 4.7 19800.0 1
Solute carrier family 22 member 6
CHEMBL1641347
 IC50 4.69 4.69 20500.0 1
Prostaglandin G/H synthase 1
CHEMBL2949
 IC50 4.68 4.68 21000.0 1
Solute carrier family 22 member 6
CHEMBL1777665
 Ki 4.28 4.28 52000.0 1
Unchecked
CHEMBL612545
 IC50 4.2 4.2 62600.0 1
Cyclooxygenase
CHEMBL2096674
 IC50 4.19 4.19 65000.0 1
Prostaglandin G/H synthase 2
CHEMBL230
 IC50 4.05 4.05 89125.1 1

Pharmacokinetic Data

Parameter Value Units Species
Cmax 47.8 nmol/g Rattus norvegicus
F 100.0 % Homo sapiens
F 100.0 % Homo sapiens
F 100.0 % Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Cyclooxygenase IC50 = 100.0 nM 7.0 In vitro inhibitory activity against Prostaglandin G/H synthase in rat neutrophi... 3086558
Rattus norvegicus IC50 = 100.0 nM 7.0 Compound is evaluated for inhibitory effect on the generation of Prostaglandin E... 3118023
Prostaglandin G/H synthase 1 IC50 = 1300.0 nM 5.89 Concentration of drug that causes a 50% decrease in the maximal inhibition of Pr... 9083488
Prostaglandin G/H synthase 1 IC50 = 1313.0 nM 5.88 DRUGMATRIX: Cyclooxygenase COX-1 enzyme inhibition (substrate: Arachidonic acid) -
Organic anion transporter 3 Ki = 4880.0 nM 5.31 TP_TRANSPORTER: inhibition of Ochratoxin A uptake in OAT3-expressing S2 cells 11669456
Plasmodium falciparum IC50 = 10000.0 nM 5.0 Antiplasmodial activity against Plasmodium falciparum 7G8 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 10000.0 nM 5.0 Antiplasmodial activity against Plasmodium falciparum GB4 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 12589.25 nM 4.9 Antiplasmodial activity against Plasmodium falciparum W2 after 72 hrs by SYBR gr... 19734910
NON-PROTEIN TARGET IC50 = 18000.0 nM 4.75 Antiinflammatory activity in human THP1 cells assessed as inhibition of PMA-indu... 24780595
THP-1 IC50 = 18100.0 nM 4.74 Anti-inflammatory activity in human THP1 cells assessed as inhibition of PMA-ind... 26748696
Solute carrier family 22 member 6 Ki = 19800.0 nM 4.7 TP_TRANSPORTER: inhibition of Ochratoxin A uptake in OAT1-expressing S2 cells 11669456
Solute carrier family 22 member 6 IC50 = 20500.0 nM 4.69 TP_TRANSPORTER: inhibition of Adefovir uptake in OAT1-expressing CHO cells 10991954
Prostaglandin G/H synthase 1 IC50 = 21000.0 nM 4.68 Tested for inhibitory activity against Prostaglandin G/H synthase 1 from ovine 7562922
THP-1 IC50 = 21330.0 nM 4.67 Antiinflammatory activity in human THP1 cells assessed as inhibition of PMA-indu... 23811092
Solute carrier family 22 member 6 Ki = 52000.0 nM 4.28 TP_TRANSPORTER: inhibition of PAH uptake in Xenopus laevis oocytes 10220563
Unchecked IC50 = 62600.0 nM 4.2 Inhibition of soybean 15-LOX 37862815
Cyclooxygenase IC50 = 65000.0 nM 4.19 Inhibition of bovine Prostaglandin G/H synthase after oral administration 3133478
Prostaglandin G/H synthase 1 IC50 = 85113.8 nM 4.07 Inhibition of COX-1 (unknown origin) using arachidonic acid as substrate preincu... 27842798
Prostaglandin G/H synthase 2 IC50 = 89125.09 nM 4.05 Inhibition of COX-2 (unknown origin) using arachidonic acid as substrate preincu... 27842798

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 252
16472241 10.2174/1570163043334794 Hepatotoxicity 18
3118023 10.1021/jm00394a011 Rattus norvegicus 17
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
1552506 10.1021/jm00084a019 Rattus norvegicus 12
3086558 10.1021/jm00156a032 Rattus norvegicus 11
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
30852078 10.1016/j.bmc.2019.03.007 Mus musculus 10
38747896 10.1021/acs.jmedchem.4c00596 No relevant target 9
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
- 10.1016/S0960-894X(00)80397-2 Rattus norvegicus 6
9526560 10.1021/jm9704311 ADMET 6
18433939 10.1016/j.ejmech.2008.02.034 Rattus norvegicus 6
31995375 10.1021/acs.jmedchem.0c00046 Albumin 6
27842798 10.1016/j.bmc.2016.10.036 Prostaglandin G/H synthase 1 6
19818539 10.1016/j.ejmech.2009.09.026 NON-PROTEIN TARGET 5
17418579 10.1016/j.bmc.2007.03.040 ADMET 5
27842798 10.1016/j.bmc.2016.10.036 Prostaglandin G/H synthase 2 5
26454648 10.1016/j.ejmech.2015.09.036 NON-PROTEIN TARGET 5
9083488 10.1021/jm9607010 Prostaglandin G/H synthase 1 5

Data from ChEMBL 36 via Core Engine