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
Temperature regulation disorder 350.72 13.76 101 16160 3259 46666542
Food allergy 282.54 13.76 102 16159 6831 46662970
Coeliac disease 279.32 13.76 102 16159 7059 46662742
Immunodeficiency 229.11 13.76 105 16156 13001 46656800
Bursitis 196.12 13.76 108 16153 19734 46650067
Rash erythematous 153.02 13.76 113 16148 34237 46635564
Acute kidney injury 127.37 13.76 264 15997 235591 46434210
Erythema 106.98 13.76 184 16077 142636 46527165
Fluid retention 97.71 13.76 104 16157 50942 46618859
Upper respiratory tract infection 91.97 13.76 112 16149 63444 46606357
Hyperhidrosis 85.89 13.76 129 16132 89179 46580622
Hepatic enzyme increased 84.22 13.76 122 16139 81665 46588136
Asthma 80.69 13.76 127 16134 91415 46578386
Constipation 74.74 13.76 178 16083 173919 46495882
Hepatocellular injury 72.74 13.76 69 16192 29453 46640348
Acute generalised exanthematous pustulosis 65.93 13.76 41 16220 9364 46660437
Hypersensitivity 51.28 13.76 141 16120 150180 46519621
Poisoning deliberate 49.20 13.76 32 16229 7894 46661907
Angioedema 48.42 13.76 64 16197 39278 46630523
Back pain 47.64 13.76 171 16090 209868 46459933
Peripheral nerve injury 46.87 13.76 13 16248 364 46669437
Lactic acidosis 44.59 13.76 57 16204 33852 46635949
Goitre 44.50 13.76 26 16235 5305 46664496
Spinal epidural haemorrhage 40.17 13.76 9 16252 101 46669700
Product dose omission issue 39.10 13.76 6 16255 168514 46501287
Hepatic adenoma 35.30 13.76 10 16251 303 46669498
Cholestasis 35.03 13.76 45 16216 26848 46642953
Rheumatoid arthritis 34.42 13.76 170 16091 240045 46429756
Completed suicide 34.30 13.76 5 16256 145915 46523886
Aspirin-exacerbated respiratory disease 34.22 13.76 12 16249 736 46669065
Death 34.17 13.76 40 16221 335508 46334293
Suicide attempt 33.60 13.76 65 16196 54971 46614830
Face oedema 33.09 13.76 37 16224 19116 46650685
Hepatic function abnormal 30.62 13.76 48 16213 34373 46635428
Epidural haemorrhage 28.50 13.76 7 16254 120 46669681
Burning mouth syndrome 28.48 13.76 9 16252 399 46669402
Gastritis erosive 27.06 13.76 19 16242 5311 46664490
Pneumoperitoneum 26.43 13.76 12 16249 1450 46668351
Sinoatrial block 25.87 13.76 10 16251 808 46668993
Drug hypersensitivity 25.81 13.76 159 16102 243666 46426135
Pneumococcal sepsis 25.62 13.76 9 16252 555 46669246
Coma 25.33 13.76 60 16201 58289 46611512
Melaena 25.07 13.76 39 16222 27733 46642068
Toxic skin eruption 25.03 13.76 26 16235 12361 46657440
Femoral artery dissection 24.96 13.76 5 16256 31 46669770
Atypical haemolytic uraemic syndrome 22.98 13.76 8 16253 480 46669321
Epidural analgesia 22.67 13.76 5 16256 52 46669749
Septic shock 22.44 13.76 57 16204 57836 46611965
Foetal heart rate abnormal 22.01 13.76 8 16253 545 46669256
Oedematous pancreatitis 21.68 13.76 7 16254 333 46669468
Miosis 21.22 13.76 18 16243 6639 46663162
Fine motor skill dysfunction 20.69 13.76 14 16247 3686 46666115
Anaphylactic shock 20.47 13.76 30 16231 20244 46649557
Pancreatitis necrotising 20.24 13.76 10 16251 1459 46668342
Gastric ulcer 20.15 13.76 31 16230 21832 46647969
Glomerulonephropathy 20.07 13.76 5 16256 91 46669710
Tubulointerstitial nephritis 19.66 13.76 25 16236 14763 46655038
Upper respiratory tract inflammation 19.12 13.76 12 16249 2783 46667018
Hypertransaminasaemia 19.03 13.76 13 16248 3475 46666326
Nasal disorder 19.01 13.76 11 16250 2203 46667598
Contraindicated product administered 18.85 13.76 66 16195 79881 46589920
Intentional overdose 18.34 13.76 57 16204 64887 46604914
Linear IgA disease 17.97 13.76 9 16252 1352 46668449
Upper gastrointestinal haemorrhage 17.24 13.76 25 16236 16713 46653088
Vanishing bile duct syndrome 17.00 13.76 7 16254 667 46669134
Drug interaction 17.00 13.76 125 16136 202969 46466832
Enteritis infectious 16.98 13.76 10 16251 2069 46667732
Gastroenteropancreatic neuroendocrine tumour disease 16.97 13.76 4 16257 57 46669744
Social anxiety disorder 16.88 13.76 6 16255 383 46669418
Drug level increased 16.79 13.76 26 16235 18415 46651386
Azotaemia 16.46 13.76 13 16248 4338 46665463
Enterocolitis 16.30 13.76 15 16246 6153 46663648
Arthritis bacterial 15.26 13.76 14 16247 5722 46664079
Lip pruritus 15.23 13.76 6 16255 510 46669291
Intervertebral discitis 15.14 13.76 10 16251 2529 46667272
Pyelonephritis acute 14.89 13.76 12 16249 4122 46665679
Renal cortical necrosis 14.85 13.76 4 16257 100 46669701
Metabolic acidosis 14.83 13.76 38 16223 38742 46631059
Drug abuse 14.64 13.76 52 16209 63356 46606445
Overdose 14.43 13.76 72 16189 101907 46567894
Hepatitis acute 14.41 13.76 16 16245 8198 46661603
Spinal compression fracture 14.36 13.76 20 16241 12883 46656918
Posterior capsule opacification 14.13 13.76 4 16257 121 46669680
Inflammation 13.94 13.76 43 16218 48738 46621063
Mixed anxiety and depressive disorder 13.85 13.76 4 16257 130 46669671

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 95.46 14.75 243 9239 273599 29669397
Angioedema 86.73 14.75 78 9404 34306 29908690
Lactic acidosis 56.44 14.75 59 9423 31154 29911842
Anaphylactic shock 54.74 14.75 41 9441 13952 29929044
Erythema 44.14 14.75 84 9398 77367 29865629
Poisoning deliberate 41.73 14.75 25 9457 5879 29937117
Death 41.05 14.75 32 9450 357251 29585745
Hepatocellular injury 40.51 14.75 45 9437 25426 29917570
Hepatitis cholestatic 37.49 14.75 26 9456 7846 29935150
Eyelid oedema 34.72 14.75 21 9461 5024 29937972
Gastric ulcer 33.62 14.75 32 9450 15089 29927907
Vascular purpura 33.01 14.75 14 9468 1583 29941413
Pancreatitis acute 31.90 14.75 40 9442 25655 29917341
Myoclonic epilepsy 30.40 14.75 11 9471 815 29942181
Suicide attempt 30.37 14.75 47 9435 36650 29906346
Acute generalised exanthematous pustulosis 28.71 14.75 20 9462 6078 29936918
Coma 28.30 14.75 48 9434 40401 29902595
Laryngeal discomfort 27.91 14.75 7 9475 145 29942851
Fusobacterium infection 27.55 14.75 6 9476 65 29942931
Palatal oedema 27.39 14.75 10 9472 760 29942236
Drug interaction 25.78 14.75 128 9354 199440 29743556
Polyneuropathy in malignant disease 24.41 14.75 6 9476 114 29942882
Dermatitis bullous 24.12 14.75 18 9464 6086 29936910
Mixed liver injury 23.98 14.75 12 9470 1981 29941015
Pruritus 23.95 14.75 87 9395 118117 29824879
Intentional overdose 23.61 14.75 45 9437 41436 29901560
Cholestasis 23.56 14.75 34 9448 24916 29918080
Melaena 23.36 14.75 39 9443 32398 29910598
Vomiting 22.95 14.75 133 9349 219685 29723311
Tongue oedema 22.89 14.75 13 9469 2767 29940229
Liver injury 21.61 14.75 23 9459 12377 29930619
Blood lactic acid 21.57 14.75 7 9475 373 29942623
Anaemia 21.16 14.75 125 9357 207867 29735129
Dyschezia 20.16 14.75 9 9473 1151 29941845
Vitello-intestinal duct remnant 19.61 14.75 5 9477 111 29942885
Meningoencephalitis bacterial 19.24 14.75 5 9477 120 29942876
Drug level increased 18.79 14.75 26 9456 18328 29924668
Enterocolitis 18.49 14.75 16 9466 6671 29936325
Prothrombin time shortened 17.65 14.75 9 9473 1546 29941450
Anterograde amnesia 17.60 14.75 5 9477 169 29942827
Brain empyema 17.57 14.75 3 9479 7 29942989
Gastric ulcer haemorrhage 17.36 14.75 14 9468 5300 29937696
Altered state of consciousness 17.16 14.75 26 9456 19893 29923103
Hepatic function abnormal 16.33 14.75 39 9443 41906 29901090
Diarrhoea infectious 16.33 14.75 6 9476 464 29942532
Metastases to lung 16.21 14.75 16 9466 7879 29935117
Pruritus allergic 16.08 14.75 4 9478 80 29942916
Gastric cancer 16.08 14.75 13 9469 4937 29938059
Pathological fracture 15.93 14.75 12 9470 4114 29938882
Fatigue 15.54 14.75 51 9431 320622 29622374
Mediastinitis 15.50 14.75 6 9476 536 29942460
Hyperkalaemia 15.45 14.75 51 9431 65959 29877037
Allergic colitis 15.34 14.75 3 9479 18 29942978
Metastases to bone 15.23 14.75 17 9465 9641 29933355
Hyperaesthesia 15.16 14.75 11 9471 3562 29939434

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 CS M0001335 Anti-Inflammatory Agents, Non-Steroidal
FDA MoA N0000000160 Cyclooxygenase Inhibitors
FDA EPC N0000175722 Nonsteroidal Anti-inflammatory Drug
CHEBI has role CHEBI:35475 non-steroidal anti-inflammatory drugs
CHEBI has role CHEBI:35493 anti-pyretic
CHEBI has role CHEBI:35544 cyclooxygenase inhibitors
CHEBI has role CHEBI:35703 xenobiotic
CHEBI has role CHEBI:78298 environmental contaminants
CHEBI has role CHEBI:88188 allergenic drug
MeSH PA D000700 Analgesics
MeSH PA D018712 Analgesics, Non-Narcotic
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
D00132 KEGG_DRUG
4018064 VANDF
C0022635 UMLSCUI
CHEBI:6128 CHEBI
CHEMBL571 ChEMBL_ID
D007660 MESH_DESCRIPTOR_UI
DB01009 DRUGBANK_ID
4795 IUPHAR_LIGAND_ID
3284 INN_ID
90Y4QC304K UNII
3825 PUBCHEM_CID
6142 RXNORM
3365 MMSL
4946 MMSL
d00028 MMSL
002394 NDDF
10099000 SNOMEDCT_US
386832008 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Ketoprofen HUMAN PRESCRIPTION DRUG LABEL 1 0378-8200 CAPSULE, EXTENDED RELEASE 200 mg ORAL ANDA 29 sections
KETOPROFEN HUMAN PRESCRIPTION DRUG LABEL 1 16590-136 CAPSULE 50 mg ORAL ANDA 28 sections
KETOPROFEN HUMAN PRESCRIPTION DRUG LABEL 1 16590-137 CAPSULE 75 mg ORAL ANDA 28 sections
Ketoprofen HUMAN PRESCRIPTION DRUG LABEL 1 21695-340 CAPSULE 50 mg ORAL ANDA 30 sections
Ketoprofen HUMAN PRESCRIPTION DRUG LABEL 1 21695-341 CAPSULE 75 mg ORAL ANDA 30 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 28 sections
Ketoprofen HUMAN PRESCRIPTION DRUG LABEL 1 42254-037 CAPSULE 75 mg ORAL ANDA 28 sections
Ketoprofen HUMAN PRESCRIPTION DRUG LABEL 1 45865-379 CAPSULE 75 mg ORAL ANDA 28 sections
Ketoprofen HUMAN PRESCRIPTION DRUG LABEL 1 45865-485 CAPSULE 50 mg ORAL ANDA 28 sections
Ketoprofen HUMAN PRESCRIPTION DRUG LABEL 1 50090-0453 CAPSULE 75 mg ORAL ANDA 28 sections
Ketoprofen HUMAN PRESCRIPTION DRUG LABEL 1 50090-2729 CAPSULE 50 mg ORAL ANDA 28 sections
Ketoprofen HUMAN PRESCRIPTION DRUG LABEL 1 52959-245 CAPSULE 50 mg ORAL ANDA 28 sections
Ketoprofen HUMAN PRESCRIPTION DRUG LABEL 1 53217-221 CAPSULE 50 mg ORAL ANDA 28 sections
Ketoprofen HUMAN PRESCRIPTION DRUG LABEL 1 54868-2414 CAPSULE 50 mg ORAL ANDA 30 sections
Ketoprofen HUMAN PRESCRIPTION DRUG LABEL 1 54868-2415 CAPSULE 75 mg ORAL ANDA 30 sections
Ketoprofen HUMAN PRESCRIPTION DRUG LABEL 1 54868-4826 CAPSULE, EXTENDED RELEASE 200 mg ORAL ANDA 30 sections
Ketoprofen HUMAN PRESCRIPTION DRUG LABEL 1 63187-018 CAPSULE 75 mg ORAL ANDA 28 sections
Ketoprofen HUMAN PRESCRIPTION DRUG LABEL 1 67296-0369 TABLET 75 mg ORAL ANDA 28 sections
Ketoprofen HUMAN PRESCRIPTION DRUG LABEL 1 69336-127 CAPSULE 25 mg ORAL ANDA 14 sections