piroxicam Indications/Contra | FAERs | Orange Book | BioActivity |

Stem definitionDrug idCAS RN
anti-inflammatory, isoxicam derivatives 2210 36322-90-4

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • piroxicam olamine
  • piroxicam betadex
  • brexicam
  • brexidol
  • brexin
  • cicladol
  • piroxicam-beta-cyclodextrin complex
  • piroxicam beta-cyclodextrin
  • feldene
  • CP16171
  • CP-16171
  • piroxicam
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.
  • Molecular weight: 331.35
  • Formula: C15H13N3O4S
  • CLOGP: 1.89
  • LIPINSKI: 0
  • HAC: 7
  • HDO: 2
  • TPSA: 99.60
  • ALOGS: -3.37
  • ROTB: 2

Drug dosage:

DoseUnitRoute
20 mg O
20 mg P
20 mg R

Approvals:

DateAgencyCompanyOrphan
April 6, 1982 FDA PFIZER

FDA Adverse Event Reporting System

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Drug hypersensitivity 1070.31 32.75 286 950 68114 4569642
Urticaria 147.87 32.75 57 1179 39516 4598240
Gastrointestinal haemorrhage 143.28 32.75 52 1184 30483 4607273
Drug interaction 111.79 32.75 54 1182 64454 4573302
Gastric ulcer 94.76 32.75 26 1210 6097 4631659
Melaena 90.66 32.75 28 1208 9930 4627826
Therapeutic product cross-reactivity 89.03 32.75 17 1219 788 4636968
Acute generalised exanthematous pustulosis 86.70 32.75 21 1215 3009 4634747
Fixed eruption 84.26 32.75 15 1221 470 4637286
Rash 78.04 32.75 51 1185 108337 4529419
Duodenal ulcer 75.93 32.75 19 1217 3111 4634645
Intestinal diaphragm disease 73.62 32.75 11 1225 110 4637646
Angioedema 68.34 32.75 27 1209 19738 4618018
Acute kidney injury 65.37 32.75 39 1197 70392 4567364
Mast cell activation syndrome 64.15 32.75 9 1227 55 4637701
Stevens-Johnson syndrome 60.87 32.75 20 1216 8619 4629137
Hyponatraemia 55.99 32.75 25 1211 24705 4613051
Toxic epidermal necrolysis 54.57 32.75 17 1219 6175 4631581
Haemoglobin decreased 54.55 32.75 28 1208 37629 4600127
Chest expansion decreased 51.97 32.75 7 1229 30 4637726
Pruritus 51.70 32.75 34 1202 72538 4565218
Drug reaction with eosinophilia and systemic symptoms 51.20 32.75 19 1217 11694 4626062
Spondylitis 49.88 32.75 10 1226 596 4637160
Hyperkalaemia 49.04 32.75 20 1216 15817 4621939
Colitis ischaemic 48.76 32.75 13 1223 2722 4635034
Haematemesis 48.25 32.75 17 1219 9026 4628730
Sacroiliitis 45.78 32.75 9 1227 485 4637271
Ankylosing spondylitis 45.20 32.75 11 1225 1601 4636155
Renal failure 43.81 32.75 25 1211 41344 4596412
Peptic ulcer 43.01 32.75 10 1226 1198 4636558
Vitreous haemorrhage 42.95 32.75 10 1226 1205 4636551
Oedema 42.55 32.75 19 1217 18732 4619024
Musculoskeletal stiffness 42.41 32.75 19 1217 18883 4618873
Toxicity to various agents 42.36 32.75 30 1206 72010 4565746
Benign abdominal neoplasm 41.97 32.75 5 1231 5 4637751
Completed suicide 40.56 32.75 24 1212 42421 4595335
Condition aggravated 38.35 32.75 26 1210 58145 4579611
Gastritis erosive 38.17 32.75 10 1226 1955 4635801
Quadriparesis 38.09 32.75 8 1228 600 4637156
Haematochezia 37.79 32.75 15 1221 11049 4626707
Enthesopathy 37.47 32.75 7 1229 287 4637469
Anaphylactic reaction 37.00 32.75 17 1219 17893 4619863
Thermal burn 36.52 32.75 9 1227 1379 4636377
Axial spondyloarthritis 36.01 32.75 5 1231 28 4637728
Oedema peripheral 35.63 32.75 22 1214 41950 4595806
Abdominal pain 35.27 32.75 25 1211 59999 4577757
Erythema multiforme 34.71 32.75 11 1225 4212 4633544
Cardiac arrest 34.51 32.75 20 1216 33987 4603769
Drug ineffective 33.82 32.75 40 1196 186021 4451735
Face oedema 33.48 32.75 12 1224 6678 4631078

Pharmacologic Action:

SourceCodeDescription
ATC M01AC01 MUSCULO-SKELETAL SYSTEM
ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS
ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS
Oxicams
ATC M02AA07 MUSCULO-SKELETAL SYSTEM
TOPICAL PRODUCTS FOR JOINT AND MUSCULAR PAIN
TOPICAL PRODUCTS FOR JOINT AND MUSCULAR PAIN
Antiinflammatory preparations, non-steroids for topical use
ATC S01BC06 SENSORY ORGANS
OPHTHALMOLOGICALS
ANTIINFLAMMATORY AGENTS
Antiinflammatory agents, non-steroids
MeSH PA D000700 Analgesics
MeSH PA D018712 Analgesics, Non-Narcotic
CHEBI has role CHEBI:35842 antirheumatic drug
CHEBI has role CHEBI:35475 non-steroidal anti-inflammatory drug
CHEBI has role CHEBI:35480 analgesic
MeSH PA D000893 Anti-Inflammatory Agents
MeSH PA D000894 Anti-Inflammatory Agents, Non-Steroidal
MeSH PA D018501 Antirheumatic Agents
MeSH PA D016861 Cyclooxygenase Inhibitors
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D018373 Peripheral Nervous System Agents
MeSH PA D018689 Sensory System Agents
FDA EPC N0000175722 Nonsteroidal Anti-inflammatory Drug
FDA Chemical/Ingredient N0000175721 Nonsteroidal Anti-inflammatory Compounds

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Rheumatoid arthritis indication 69896004 DOID:7148
Osteoarthritis indication 396275006
Ankylosing spondylitis off-label use 9631008 DOID:7147
Juvenile rheumatoid arthritis off-label use 410795001
Alcoholism contraindication 7200002
Asthenia contraindication 13791008
Myocardial infarction contraindication 22298006 DOID:5844
Hypertensive disorder contraindication 38341003 DOID:10763
Gastrointestinal ulcer contraindication 40845000
Body fluid retention contraindication 43498006
Chronic heart failure contraindication 48447003
Disorder of cardiovascular system contraindication 49601007 DOID:1287
Gastrointestinal perforation contraindication 51875005
Acute nephropathy contraindication 58574008
Blood coagulation disorder contraindication 64779008 DOID:1247
Gastrointestinal hemorrhage contraindication 74474003
Kidney disease contraindication 90708001 DOID:557
Liver function tests abnormal contraindication 166603001
Acute hepatic failure contraindication 197270009
Cerebrovascular accident contraindication 230690007
Coronary artery bypass graft contraindication 232717009
Disease of liver contraindication 235856003 DOID:409
Drug-induced hepatitis contraindication 235876009
Edema contraindication 267038008
Anemia contraindication 271737000 DOID:2355
Pregnancy, function contraindication 289908002
Cardiovascular event risk contraindication 395112001
Visual impairment contraindication 397540003
Thrombosis contraindication 439127006
Smokes tobacco daily contraindication 449868002

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 2.31 acidic
pKa2 8.26 acidic
pKa3 5.18 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Prostaglandin G/H synthase 1 Enzyme INHIBITOR IC50 5.18 WOMBAT-PK CHEMBL
Prostaglandin G/H synthase 2 Enzyme INHIBITOR IC50 4.70 WOMBAT-PK CHEMBL
Prostaglandin G/H synthase 1 Enzyme IC50 4.68 CHEMBL
Cyclooxygenase Enzyme IC50 7 CHEMBL
Cyclooxygenase Enzyme IC50 4.19 CHEMBL

External reference:

IDSource
C0687717 UMLSCUI
D00127 KEGG_DRUG
13T4O6VMAM UNII
3713 INN_ID
27754002 SNOMEDCT_US
4018626 VANDF
1529 MMSL
8356 RXNORM
387153005 SNOMEDCT_US
5308 MMSL
d00343 MMSL
002389 NDDF
CHEMBL527 ChEMBL_ID
DB00554 DRUGBANK_ID
85056-47-9 SECONDARY_CAS_RN
CHEBI:8249 CHEBI
54676228 PUBCHEM_CID
D010894 MESH_DESCRIPTOR_UI
CHEMBL2106953 ChEMBL_ID
CHEMBL2108444 ChEMBL_ID
7273 IUPHAR_LIGAND_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Feldene HUMAN PRESCRIPTION DRUG LABEL 1 0069-3220 CAPSULE 10 mg ORAL NDA 20 sections
Feldene HUMAN PRESCRIPTION DRUG LABEL 1 0069-3230 CAPSULE 20 mg ORAL NDA 20 sections
Piroxicam HUMAN PRESCRIPTION DRUG LABEL 1 0093-0756 CAPSULE 10 mg ORAL ANDA 19 sections
Piroxicam HUMAN PRESCRIPTION DRUG LABEL 1 0093-0757 CAPSULE 20 mg ORAL ANDA 19 sections
Piroxicam HUMAN PRESCRIPTION DRUG LABEL 1 0143-3107 CAPSULE 10 mg ORAL ANDA 19 sections
Piroxicam HUMAN PRESCRIPTION DRUG LABEL 1 0143-3108 CAPSULE 20 mg ORAL ANDA 19 sections
Piroxicam HUMAN PRESCRIPTION DRUG LABEL 1 0378-0466 CAPSULE 10 mg ORAL ANDA 19 sections
Piroxicam HUMAN PRESCRIPTION DRUG LABEL 1 0378-0467 CAPSULE 20 mg ORAL ANDA 19 sections
PIROXICAM HUMAN PRESCRIPTION DRUG LABEL 1 16590-187 CAPSULE 10 mg ORAL ANDA 13 sections
PIROXICAM HUMAN PRESCRIPTION DRUG LABEL 1 16590-188 CAPSULE 20 mg ORAL ANDA 13 sections
Piroxicam HUMAN PRESCRIPTION DRUG LABEL 1 21695-285 CAPSULE 20 mg ORAL ANDA 13 sections
Piroxicam HUMAN PRESCRIPTION DRUG LABEL 1 21695-520 CAPSULE 10 mg ORAL ANDA 13 sections
Piroxicam HUMAN PRESCRIPTION DRUG LABEL 1 29033-012 CAPSULE 10 mg ORAL ANDA 19 sections
Piroxicam HUMAN PRESCRIPTION DRUG LABEL 1 29033-013 CAPSULE 20 mg ORAL ANDA 19 sections
Piroxicam HUMAN PRESCRIPTION DRUG LABEL 1 29300-255 CAPSULE 10 mg ORAL ANDA 19 sections
Piroxicam HUMAN PRESCRIPTION DRUG LABEL 1 29300-256 CAPSULE 20 mg ORAL ANDA 19 sections
Piroxicam HUMAN PRESCRIPTION DRUG LABEL 1 42254-062 CAPSULE 20 mg ORAL ANDA 14 sections
Piroxicam HUMAN PRESCRIPTION DRUG LABEL 1 42254-143 CAPSULE 10 mg ORAL ANDA 14 sections
Piroxicam HUMAN PRESCRIPTION DRUG LABEL 1 42291-674 CAPSULE 10 mg ORAL ANDA 19 sections
Piroxicam HUMAN PRESCRIPTION DRUG LABEL 1 42291-677 CAPSULE 20 mg ORAL ANDA 19 sections
Piroxicam HUMAN PRESCRIPTION DRUG LABEL 1 42543-114 CAPSULE 10 mg ORAL ANDA 19 sections
Piroxicam HUMAN PRESCRIPTION DRUG LABEL 1 42543-115 CAPSULE 20 mg ORAL ANDA 19 sections
PIROXICAM HUMAN PRESCRIPTION DRUG LABEL 1 42549-542 CAPSULE 20 mg ORAL ANDA 13 sections
PIROXICAM HUMAN PRESCRIPTION DRUG LABEL 1 42571-176 CAPSULE 10 mg ORAL ANDA 19 sections
PIROXICAM HUMAN PRESCRIPTION DRUG LABEL 1 42571-177 CAPSULE 20 mg ORAL ANDA 19 sections
PIROXICAM HUMAN PRESCRIPTION DRUG LABEL 1 50090-4779 CAPSULE 20 mg ORAL ANDA 19 sections
Piroxicam HUMAN PRESCRIPTION DRUG LABEL 1 52959-232 CAPSULE 20 mg ORAL ANDA 13 sections
Piroxicam HUMAN PRESCRIPTION DRUG LABEL 1 52959-398 CAPSULE 10 mg ORAL ANDA 13 sections
Piroxicam HUMAN PRESCRIPTION DRUG LABEL 1 54868-2198 CAPSULE 10 mg ORAL ANDA 13 sections
Piroxicam HUMAN PRESCRIPTION DRUG LABEL 1 54868-2199 CAPSULE 20 mg ORAL ANDA 13 sections