flurbiprofen 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | BioActivity |

Stem definitionDrug idCAS RN
anti-inflammatory agents, ibuprofen derivatives 1219 5104-49-4

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • flurbiprofen
  • (+/-)-Flurbiprofen
  • fluribiprofen
  • fluroben
  • flurofen
  • dl-Flurbiprofen
  • flurbiprofen sodium
An anti-inflammatory analgesic and antipyretic of the phenylalkynoic acid series. It has been shown to reduce bone resorption in periodontal disease by inhibiting CARBONIC ANHYDRASE.
  • Molecular weight: 244.27
  • Formula: C15H13FO2
  • CLOGP: 3.75
  • LIPINSKI: 0
  • HAC: 2
  • HDO: 1
  • TPSA: 37.30
  • ALOGS: -3.99
  • ROTB: 3
  • Status: OFP
    • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
0.20 g O
0.20 g R
44 mg O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 2.90 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 17.55 µM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 92 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
azlogd74 LogD at pH 7.4 0.992 High 1
caco2-efflux Caco-2 efflux ratio (BA/AB) 0.465 High 1
caco2-intrinsic-papp Caco-2 intrinsic apparent permeability 188.365 10^-6 cm/s High 1
dh-clint Dog hepatocyte intrinsic clearance 12.560 uL/min/10^6 cells High 1
dppb Dog plasma protein binding (% unbound) 0.390 % High 1
fcs-ppb Fetal calf serum protein binding (% unbound) 1.400 % High 1
herg hERG pIC50 4.200 pIC50 High 1
hh-clint Human hepatocyte intrinsic clearance 8.222 uL/min/10^6 cells High 1
hlm-clint Human liver microsomal intrinsic clearance 3.508 uL/min/mg protein High 1
hppb Human plasma protein binding (% unbound) 0.480 % High 1
kinase-safety-class ACVR2B,AXL,EIF2AK3,GRK2,PDK1,PDK2,PDK4,PIK3CG,PRKDC,TGFBR1 10
kinase-selectivity-class AXL 1
mdck-mdr1-efflux MDCK-MDR1 efflux ratio 1.517 High 1
mh-clint Mouse hepatocyte intrinsic clearance 77.804 High 1
mppb Mouse plasma protein binding (% unbound) 3.470 High 1
nih-mdck-mdr1-efflux NIH MDCK-MDR1 efflux ratio 0.222 High 1
pfas-class PFAS structural alert (1 = True, 0 = False) 0
pppb Pig plasma protein binding (% unbound) 1.160 % High 1
rh-clint Rat hepatocyte intrinsic clearance 9.419 uL/min/10^6 cells High 1
rh-fuinc Rat hepatocyte fraction unbound in incubation 84.210 % High 1
rppb Rat plasma protein binding (% unbound) 0.620 % High 1
solubility-dd Solubility at pH 7.4 in DMSO 950.605 uM High 1

Approvals:

DateAgencyCompanyOrphan
Dec. 31, 1986 FDA ALLERGAN

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
Angioedema 131.70 23.74 55 2641 64821 90560930
Toxic anterior segment syndrome 99.87 23.74 21 2675 2229 90623522
Acute kidney injury 85.91 23.74 73 2623 320314 90305437
Allergy test positive 76.39 23.74 14 2682 728 90625023
Central pain syndrome 71.30 23.74 13 2683 657 90625094
Drug reaction with eosinophilia and systemic symptoms 63.09 23.74 29 2667 42729 90583022
Eyelid oedema 57.68 23.74 19 2677 11515 90614236
Pancreatitis acute 44.92 23.74 21 2675 32094 90593657
Lip oedema 41.75 23.74 12 2684 4627 90621124
Hyperaesthesia 35.57 23.74 13 2683 10689 90615062
Eosinophilic myocarditis 33.90 23.74 7 2689 678 90625073
Urticaria 33.90 23.74 44 2652 312690 90313061
Altered state of consciousness 33.24 23.74 17 2679 31515 90594236
Ankylosing spondylitis 32.98 23.74 13 2683 13120 90612631
Dermo-hypodermitis 32.76 23.74 7 2689 800 90624951
Poisoning deliberate 30.13 23.74 13 2683 16473 90609278
Gingival pain 29.41 23.74 11 2685 9641 90616110
Somnolence 26.76 23.74 32 2664 209052 90416699
Anastomotic complication 26.05 23.74 5 2691 334 90625417
Hepatic cytolysis 25.07 23.74 14 2682 30902 90594849

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
Hypertrophic cardiomyopathy 56.94 28.14 12 1114 1453 42618756
Ischaemic cerebral infarction 55.57 28.14 12 1114 1631 42618578
Toxic anterior segment syndrome 34.99 28.14 8 1118 1408 42618801
Arrhythmia 34.08 28.14 18 1108 40299 42579910
Sudden death 31.55 28.14 13 1113 16616 42603593
Abnormal dreams 28.50 28.14 10 1116 8261 42611948

FDA Adverse Event Reporting System (Geriatric)

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
Angioedema 165.55 20.77 75 3515 98425 110487284
Toxic anterior segment syndrome 132.34 20.77 29 3561 3425 110582284
Allergy test positive 72.11 20.77 14 3576 909 110584800
Central pain syndrome 67.53 20.77 13 3577 807 110584902
Urticaria 65.20 20.77 65 3525 318792 110266917
Eyelid oedema 58.24 20.77 21 3569 15241 110570468
Drug reaction with eosinophilia and systemic symptoms 55.37 20.77 34 3556 82061 110503648
Lip oedema 51.04 20.77 16 3574 7584 110578125
Cross sensitivity reaction 47.11 20.77 14 3576 5553 110580156
Acute kidney injury 46.84 20.77 78 3512 635352 109950357
Ischaemic cerebral infarction 46.11 20.77 12 3578 2933 110582776
Hypertrophic cardiomyopathy 45.26 20.77 12 3578 3151 110582558
Pancreatitis acute 38.19 20.77 24 3566 60250 110525459
Ankylosing spondylitis 32.99 20.77 14 3576 15598 110570111
Hyperaesthesia 30.44 20.77 13 3577 14714 110570995
Face oedema 28.15 20.77 16 3574 33453 110552256
Dermo-hypodermitis 27.89 20.77 7 3583 1481 110584228
Sudden death 27.03 20.77 14 3576 24381 110561328
Eosinophilic myocarditis 25.55 20.77 7 3583 2078 110583631
Arrhythmia 23.76 20.77 19 3571 69556 110516153
Gingival pain 23.29 20.77 11 3579 15725 110569984
Poisoning deliberate 23.26 20.77 13 3577 26318 110559391
Anastomotic complication 22.67 20.77 5 3585 606 110585103
Altered state of consciousness 22.42 20.77 17 3573 57609 110528100
Abnormal dreams 22.25 20.77 10 3580 12770 110572939
Electrocardiogram QT prolonged 21.80 20.77 22 3568 108938 110476771
Toxicity to various agents 21.70 20.77 48 3542 480507 110105202
Intentional overdose 21.62 20.77 24 3566 132477 110453232
Spinal pain 21.59 20.77 11 3579 18504 110567205
Laryngeal oedema 21.41 20.77 9 3581 9798 110575911

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC M01AE09 MUSCULO-SKELETAL SYSTEM
ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS
ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS
Propionic acid derivatives
ATC M02AA19 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 R02AX01 RESPIRATORY SYSTEM
THROAT PREPARATIONS
THROAT PREPARATIONS
Other throat preparations
ATC S01BC04 SENSORY ORGANS
OPHTHALMOLOGICALS
ANTIINFLAMMATORY AGENTS
Antiinflammatory agents, non-steroids
FDA CS M0001335 Anti-Inflammatory Agents, Non-Steroidal
FDA MoA N0000000160 Cyclooxygenase Inhibitors
MeSH PA D000700 Analgesics
MeSH PA D000893 Anti-Inflammatory Agents
MeSH PA D000894 Anti-Inflammatory Agents, Non-Steroidal
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D016861 Cyclooxygenase Inhibitors
MeSH PA D018501 Antirheumatic Agents
MeSH PA D018689 Sensory System Agents
MeSH PA D018712 Analgesics, Non-Narcotic
CHEBI has role CHEBI:33282 antibacterial agent
CHEBI has role CHEBI:35475 non-steroidal anti-inflammatory drug
CHEBI has role CHEBI:35480 analgesic
CHEBI has role CHEBI:35481 non-narcotic analgesic
CHEBI has role CHEBI:35493 antipyretic
CHEBI has role CHEBI:35526 hypoglycemic agent
CHEBI has role CHEBI:35544 EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor
CHEBI has role CHEBI:35842 antirheumatic drug
CHEBI has role CHEBI:64946 anti-HIV agent
CHEBI has role CHEBI:66981 ophthalmology drug
CHEBI has role CHEBI:75835 anti-anaemic agent
FDA EPC N0000175722 Nonsteroidal Anti-inflammatory Drug

Related Drugs by ATC class:

M01AE Propionic acid derivatives 21 drugs
alminoprofenbenoxaprofendexibuprofendexketoprofendiphenhydramineesomeprazolefenbufenfenoprofenflunoxaprofenibuprofenibuproxamindoprofen show all 21 →
M02AA Antiinflammatory preparations, non-steroids for topical use 28 drugs
aceclofenacbendazacbenzydaminebufexamacclofezonedexketoprofendiclofenacesflurbiprofenetofenamatefelbinacfentiazacfeprazone show all 28 →
R02AX Other throat preparations 2 drugs
benzydamineibuprofen
S01BC Antiinflammatory agents, non-steroids 10 drugs
bendazacbromfenacdiclofenacindomethacinketorolacnepafenacoxyphenbutazonepiroxicampranoprofensalicylic acid

Drug Use | Suggest Off label Use Form| |View source of the data|

DiseaseRelationSNOMED_IDDOID
Rheumatoid arthritis indication 69896004 DOID:7148
Osteoarthritis indication 396275006
Prevention of Ocular Surgery-Induced Miosis indication
Dysmenorrhea off-label use 266599000
Alcoholism contraindication 7200002
Peptic ulcer contraindication 13200003 DOID:750
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
Coronary artery bypass graft contraindication 232717009
Disease of liver contraindication 235856003 DOID:409
Impaired wound healing contraindication 271618001
Pregnancy, function contraindication 289908002
Cardiovascular event risk contraindication 395112001
Smokes tobacco daily contraindication 449868002
Ocular Bleeding contraindication




🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 4.2 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 2 Enzyme INHIBITOR IC50 8.39 WOMBAT-PK CHEMBL
Prostaglandin G/H synthase 1 Enzyme INHIBITOR IC50 8.74 WOMBAT-PK CHEMBL
Aldo-keto reductase family 1 member C1 Enzyme IC50 5.69 CHEMBL
Aldo-keto reductase family 1 member C2 Enzyme IC50 4.49 CHEMBL
Aldo-keto reductase family 1 member C3 Enzyme IC50 5.81 CHEMBL
Fatty acid-binding protein, intestinal Cytosolic other Ki 4.59 CHEMBL
Aldo-keto reductase family 1 member C4 Enzyme IC50 5.53 CHEMBL
Fatty acid-binding protein, liver Cytosolic other Ki 5.93 CHEMBL
Prostaglandin G/H synthase 2 Enzyme IC50 6.30 CHEMBL
Prostaglandin G/H synthase 1 Enzyme Ki 6 CHEMBL
Prostaglandin G/H synthase 1 Enzyme IC50 6.77 CHEMBL

External reference:

IDSource
4019154 VUID
N0000147399 NUI
D00330 KEGG_DRUG
1584155-62-3 SECONDARY_CAS_RN
4019153 VANDF
4019154 VANDF
C0016377 UMLSCUI
CHEBI:5130 CHEBI
FLP PDB_CHEM_ID
CHEMBL563 ChEMBL_ID
DB00712 DRUGBANK_ID
CHEMBL3989754 ChEMBL_ID
D005480 MESH_DESCRIPTOR_UI
3394 PUBCHEM_CID
4194 IUPHAR_LIGAND_ID
3220 INN_ID
5GRO578KLP UNII
4502 RXNORM
4753 MMSL
4754 MMSL
72 MMSL
d00239 MMSL
002382 NDDF
003968 NDDF
11633008 SNOMEDCT_US
373506008 SNOMEDCT_US
54344006 SNOMEDCT_US
5GRO578KLP INXIGHT DRUGS

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
FLURBIPROFEN HUMAN PRESCRIPTION DRUG LABEL 1 16590-096 TABLET, FILM COATED 100 mg ORAL ANDA 11 sections
Flurbiprofen Sodium HUMAN PRESCRIPTION DRUG LABEL 1 21695-615 SOLUTION/ DROPS 0.24 mg OPHTHALMIC ANDA 20 sections
Flurbiprofen Sodium HUMAN PRESCRIPTION DRUG LABEL 1 24208-314 SOLUTION/ DROPS 0.30 mg OPHTHALMIC ANDA 20 sections
FLURBIPROFEN SODIUM HUMAN PRESCRIPTION DRUG LABEL 1 42254-023 SOLUTION/ DROPS 0.30 mg OPHTHALMIC NDA authorized generic 18 sections
Flurbiprofen HUMAN PRESCRIPTION DRUG LABEL 1 43063-992 TABLET, FILM COATED 100 mg ORAL ANDA 26 sections
Flurbiprofen Sodium HUMAN PRESCRIPTION DRUG LABEL 1 50090-3946 SOLUTION/ DROPS 0.30 mg OPHTHALMIC ANDA 20 sections
Flurbiprofen HUMAN PRESCRIPTION DRUG LABEL 1 54868-3362 TABLET, FILM COATED 100 mg ORAL ANDA 27 sections
Flurbiprofen Sodium HUMAN PRESCRIPTION DRUG LABEL 1 63187-937 SOLUTION/ DROPS 0.30 mg OPHTHALMIC ANDA 20 sections
Flurbiprofen HUMAN PRESCRIPTION DRUG LABEL 1 64950-218 TABLET 100 mg ORAL ANDA 29 sections
Flurbiprofen HUMAN PRESCRIPTION DRUG LABEL 1 68071-2480 TABLET, FILM COATED 100 mg ORAL ANDA 26 sections
Flurbiprofen HUMAN PRESCRIPTION DRUG LABEL 1 68071-4436 TABLET, FILM COATED 100 mg ORAL ANDA 27 sections
Flurbiprofen HUMAN PRESCRIPTION DRUG LABEL 1 68788-7341 TABLET, FILM COATED 100 mg ORAL ANDA 26 sections
Flurbiprofen Sodium HUMAN PRESCRIPTION DRUG LABEL 1 69292-722 SOLUTION/ DROPS 0.30 mg OPHTHALMIC ANDA 20 sections
Antiphlamine Pain Relieving HUMAN OTC DRUG LABEL 1 69642-1300 PATCH 33 mg TOPICAL unapproved drug other 8 sections
LURBIRO HUMAN PRESCRIPTION DRUG LABEL 1 71085-082 TABLET 100 mg ORAL ANDA 29 sections
Rinol-STroche HUMAN OTC DRUG LABEL 1 72988-0041 TROCHE 8.75 mg ORAL unapproved drug other 7 sections