piroxicam Indications/Contra | FAERs-F | FAERs-M | Orange Bk | 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

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
20 mg O
20 mg P
20 mg R

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.01 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 5 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 1.51 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 99 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

DateAgencyCompanyOrphan
April 6, 1982 FDA PFIZER

FDA Adverse Event Reporting System (Female)

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 867.95 33.03 220 471 46423 2310971
Intestinal diaphragm disease 77.38 33.03 10 681 30 2357364
Gastric ulcer 67.28 33.03 17 674 2999 2354395
Gastrointestinal haemorrhage 61.99 33.03 22 669 12413 2344981
Therapeutic product cross-reactivity 54.93 33.03 10 681 368 2357026
Stevens-Johnson syndrome 47.90 33.03 14 677 4245 2353149
Fixed eruption 47.73 33.03 8 683 180 2357214
Drug interaction 43.89 33.03 22 669 29141 2328253
Haemoglobin decreased 43.81 33.03 19 672 18132 2339262
Quadriparesis 43.63 33.03 8 683 306 2357088
Rash 43.60 33.03 28 663 59530 2297864
Urticaria 41.56 33.03 20 671 24241 2333153
Colitis ischaemic 40.32 33.03 10 681 1627 2355767
Melaena 39.64 33.03 12 679 4094 2353300
Thermal burn 35.99 33.03 8 683 810 2356584
Toxicity to various agents 35.89 33.03 20 671 32734 2324660

FDA Adverse Event Reporting System (Male)

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 169.07 52.84 49 371 15086 1731275
Acute generalised exanthematous pustulosis 84.07 52.84 17 403 1105 1745256
Urticaria 82.22 52.84 27 393 12214 1734147
Mast cell activation syndrome 67.94 52.84 8 412 7 1746354
Drug interaction 63.77 52.84 28 392 27930 1718431
Chest expansion decreased 55.22 52.84 7 413 17 1746344

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