ketoprofen Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
anti-inflammatory agents, ibuprofen derivatives 1528 22071-15-4

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • RP 19583
  • RP-19583
  • ketoprofen
  • ketoprofene
  • ketoprophen
An IBUPROFEN-type anti-inflammatory analgesic and antipyretic. It is used in the treatment of rheumatoid arthritis and osteoarthritis.
  • Molecular weight: 254.29
  • Formula: C16H14O3
  • CLOGP: 2.76
  • LIPINSKI: 0
  • HAC: 3
  • HDO: 1
  • TPSA: 54.37
  • ALOGS: -4.08
  • ROTB: 4

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
0.15 g O
0.15 g P
0.15 g R

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.18 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 0.50 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 19.66 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 90 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 0.13 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 1.60 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.01 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 2.10 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Jan. 9, 1986 FDA

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
Acute kidney injury 258.91 50.09 81 712 28041 2329251
Temperature regulation disorder 236.29 50.09 32 761 129 2357163
Food allergy 199.65 50.09 33 760 598 2356694
Erythema 191.96 50.09 63 730 25096 2332196
Coeliac disease 190.54 50.09 33 760 799 2356493
Immunodeficiency 182.06 50.09 33 760 1043 2356249
Bursitis 157.25 50.09 32 761 1876 2355416
Asthma 152.63 50.09 44 749 11270 2346022
Rash erythematous 140.30 50.09 36 757 5940 2351352
Hepatic enzyme increased 131.55 50.09 38 755 9764 2347528
Drug hypersensitivity 123.65 50.09 54 739 46589 2310703
Hypersensitivity 117.09 50.09 43 750 23550 2333742
Fluid retention 115.67 50.09 32 761 7014 2350278
Hyperhidrosis 114.58 50.09 38 755 15384 2341908
Hepatitis 109.64 50.09 30 763 6307 2350985
Back pain 108.25 50.09 44 749 31615 2325677
Constipation 105.70 50.09 39 754 21590 2335702
Upper respiratory tract infection 104.07 50.09 31 762 8820 2348472
Vomiting 98.74 50.09 53 740 71549 2285743
Hepatocellular injury 97.83 50.09 25 768 4030 2353262
Melaena 87.79 50.09 23 770 4083 2353209
Rheumatoid arthritis 84.23 50.09 32 761 19108 2338184
Angioedema 79.83 50.09 25 768 8371 2348921
Urticaria 73.50 50.09 31 762 24230 2333062
Poisoning deliberate 69.26 50.09 15 778 1176 2356116
Pain 69.16 50.09 40 753 61817 2295475
Suicide attempt 68.70 50.09 24 769 11258 2346034
Intentional overdose 68.62 50.09 24 769 11297 2345995
Peripheral nerve injury 67.88 50.09 10 783 80 2357212
Aspirin-exacerbated respiratory disease 67.17 50.09 11 782 185 2357107
Headache 66.98 50.09 43 750 80136 2277156
Abdominal pain upper 62.78 50.09 27 766 22073 2335219
Lactic acidosis 59.63 50.09 18 775 5312 2351980
Overdose 55.46 50.09 24 769 19883 2337409
Fatigue 55.17 50.09 39 754 84834 2272458
Intentional self-injury 55.17 50.09 16 777 4111 2353181
Nasal disorder 54.57 50.09 10 783 331 2356961
Spinal epidural haemorrhage 54.26 50.09 7 786 17 2357275
Hepatitis cholestatic 53.07 50.09 12 781 1145 2356147
Toxicity to various agents 52.64 50.09 27 766 32727 2324565
Cholestasis 52.29 50.09 15 778 3706 2353586
Somnolence 51.65 50.09 24 769 23461 2333831
Toxic epidermal necrolysis 50.17 50.09 14 779 3130 2354162

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
Acute kidney injury 187.95 52.61 75 649 34869 1711188
Angioedema 129.11 52.61 41 683 9623 1736434
Vomiting 100.54 52.61 50 674 38265 1707792
Erythema 91.49 52.61 35 689 14153 1731904
Pruritus 87.54 52.61 39 685 23183 1722874
Poisoning deliberate 85.27 52.61 18 706 824 1745233
Coma 73.32 52.61 25 699 7237 1738820
Vascular purpura 71.01 52.61 13 711 280 1745777
Melaena 64.78 52.61 21 703 5189 1740868
Eyelid oedema 61.67 52.61 15 709 1298 1744759
Hepatitis cholestatic 56.51 52.61 14 710 1307 1744750

Pharmacologic Action:

SourceCodeDescription
ATC M01AE03 MUSCULO-SKELETAL SYSTEM
ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS
ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS
Propionic acid derivatives
ATC M01AE53 MUSCULO-SKELETAL SYSTEM
ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS
ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS
Propionic acid derivatives
ATC M02AA10 MUSCULO-SKELETAL SYSTEM
TOPICAL PRODUCTS FOR JOINT AND MUSCULAR PAIN
TOPICAL PRODUCTS FOR JOINT AND MUSCULAR PAIN
Antiinflammatory preparations, non-steroids for topical use
FDA Chemical/Ingredient N0000175721 Nonsteroidal Anti-inflammatory Compounds
FDA EPC N0000175722 Nonsteroidal Anti-inflammatory Drug
MeSH PA D000700 Analgesics
MeSH PA D018712 Analgesics, Non-Narcotic
CHEBI has role CHEBI:88188 drug allergen
CHEBI has role CHEBI:35475 non-steroidal anti-inflammatory drug
CHEBI has role CHEBI:35493 antipyretic
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

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Pain indication 22253000
Rheumatoid arthritis indication 69896004 DOID:7148
Dysmenorrhea indication 266599000
Osteoarthritis indication 396275006
Ankylosing spondylitis off-label use 9631008 DOID:7147
Gout off-label use 90560007 DOID:13189
Vascular headache off-label use 128187005
Peptic ulcer contraindication 13200003 DOID:750
Myocardial infarction contraindication 22298006 DOID:5844
Hypertensive disorder contraindication 38341003 DOID:10763
Gastrointestinal ulcer contraindication 40845000
Chronic heart failure contraindication 48447003
Disorder of cardiovascular system contraindication 49601007 DOID:1287
Hepatic failure contraindication 59927004
Blood coagulation disorder contraindication 64779008 DOID:1247
Gastrointestinal hemorrhage contraindication 74474003
Kidney disease contraindication 90708001 DOID:557
Hypoalbuminemia contraindication 119247004
Coronary artery bypass graft contraindication 232717009
Pregnancy, function contraindication 289908002
Cardiovascular event risk contraindication 395112001
Smokes tobacco daily contraindication 449868002

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 4.28 acidic

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 7.33 WOMBAT-PK CHEMBL
Prostaglandin G/H synthase 2 Enzyme INHIBITOR IC50 6.62 WOMBAT-PK CHEMBL
Cyclooxygenase Enzyme IC50 5.47 CHEMBL
Prostaglandin G/H synthase 1 Enzyme IC50 6.10 CHEMBL

External reference:

IDSource
4018064 VUID
N0000146405 NUI
C0022635 UMLSCUI
D00132 KEGG_DRUG
10099000 SNOMEDCT_US
3365 MMSL
6142 RXNORM
386832008 SNOMEDCT_US
4946 MMSL
d00028 MMSL
4018064 VANDF
002394 NDDF
90Y4QC304K UNII
3284 INN_ID
CHEBI:6128 CHEBI
CHEMBL571 ChEMBL_ID
DB01009 DRUGBANK_ID
3825 PUBCHEM_CID
D007660 MESH_DESCRIPTOR_UI
4795 IUPHAR_LIGAND_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Ketoprofen HUMAN PRESCRIPTION DRUG LABEL 1 0378-8200 CAPSULE, EXTENDED RELEASE 200 mg ORAL ANDA 13 sections
KETOPROFEN HUMAN PRESCRIPTION DRUG LABEL 1 16590-136 CAPSULE 50 mg ORAL ANDA 13 sections
KETOPROFEN HUMAN PRESCRIPTION DRUG LABEL 1 16590-137 CAPSULE 75 mg ORAL ANDA 13 sections
Ketoprofen HUMAN PRESCRIPTION DRUG LABEL 1 21695-340 CAPSULE 50 mg ORAL ANDA 13 sections
Ketoprofen HUMAN PRESCRIPTION DRUG LABEL 1 21695-341 CAPSULE 75 mg ORAL ANDA 13 sections
ketoprofen HUMAN PRESCRIPTION DRUG LABEL 1 23155-020 CAPSULE 25 mg ORAL ANDA 13 sections
ketoprofen HUMAN PRESCRIPTION DRUG LABEL 1 23155-021 CAPSULE 50 mg ORAL ANDA 13 sections
ketoprofen HUMAN PRESCRIPTION DRUG LABEL 1 23155-022 CAPSULE 75 mg ORAL ANDA 13 sections
Ketoprofen HUMAN PRESCRIPTION DRUG LABEL 1 33261-064 CAPSULE 75 mg ORAL ANDA 13 sections
Ketoprofen HUMAN PRESCRIPTION DRUG LABEL 1 42254-037 CAPSULE 75 mg ORAL ANDA 13 sections
Ketoprofen HUMAN PRESCRIPTION DRUG LABEL 1 45865-379 CAPSULE 75 mg ORAL ANDA 13 sections
Ketoprofen HUMAN PRESCRIPTION DRUG LABEL 1 45865-485 CAPSULE 50 mg ORAL ANDA 13 sections
Ketoprofen HUMAN PRESCRIPTION DRUG LABEL 1 50090-0453 CAPSULE 75 mg ORAL ANDA 13 sections
Ketoprofen HUMAN PRESCRIPTION DRUG LABEL 1 50090-2729 CAPSULE 50 mg ORAL ANDA 13 sections
Ketoprofen HUMAN PRESCRIPTION DRUG LABEL 1 52959-245 CAPSULE 50 mg ORAL ANDA 13 sections
Ketoprofen HUMAN PRESCRIPTION DRUG LABEL 1 53217-221 CAPSULE 50 mg ORAL ANDA 13 sections
Ketoprofen HUMAN PRESCRIPTION DRUG LABEL 1 54868-2414 CAPSULE 50 mg ORAL ANDA 13 sections
Ketoprofen HUMAN PRESCRIPTION DRUG LABEL 1 54868-2415 CAPSULE 75 mg ORAL ANDA 13 sections
Ketoprofen HUMAN PRESCRIPTION DRUG LABEL 1 54868-4826 CAPSULE, EXTENDED RELEASE 200 mg ORAL ANDA 13 sections
Ketoprofen HUMAN PRESCRIPTION DRUG LABEL 1 63187-018 CAPSULE 75 mg ORAL ANDA 13 sections
Ketoprofen HUMAN PRESCRIPTION DRUG LABEL 1 67296-0369 TABLET 75 mg ORAL ANDA 13 sections
Ketoprofen HUMAN PRESCRIPTION DRUG LABEL 1 69336-127 CAPSULE 25 mg ORAL ANDA 13 sections
KETOPHENE HUMAN PRESCRIPTION DRUG LABEL 1 70332-101 KIT 33.50 g None unapproved drug other 2 sections