flurbiprofen Indications/Contra | FAERs-F | FAERs-M | Orange Bk | 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 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 92 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

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 107.80 20.88 45 1830 39297 46644890
Toxic anterior segment syndrome 94.70 20.88 21 1854 2116 46682071
Allergy test positive 76.45 20.88 13 1862 321 46683866
Drug reaction with eosinophilia and systemic symptoms 55.61 20.88 26 1849 29522 46654665
Pancreatitis acute 44.06 20.88 21 1854 24851 46659336
Urticaria 37.99 20.88 34 1841 117858 46566329
Eosinophilic myocarditis 36.06 20.88 7 1868 366 46683821
Eyelid oedema 32.21 20.88 13 1862 10344 46673843
Symptom recurrence 29.62 20.88 6 1869 390 46683797
Altered state of consciousness 27.58 20.88 15 1860 23333 46660854
Lip oedema 24.80 20.88 8 1867 3356 46680831
Acute kidney injury 21.73 20.88 36 1839 235819 46448368

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
Toxic anterior segment syndrome 34.19 24.70 8 808 1513 29950149
Hypertrophic cardiomyopathy 32.38 24.70 7 809 926 29950736
Abnormal dreams 28.40 24.70 10 806 8105 29943557
Ischaemic cerebral infarction 26.86 24.70 6 810 923 29950739

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
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
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 D002491 Central Nervous System 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
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

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 1 Enzyme INHIBITOR IC50 8.74 WOMBAT-PK CHEMBL
Prostaglandin G/H synthase 2 Enzyme INHIBITOR IC50 8.39 WOMBAT-PK CHEMBL
Fatty acid-binding protein, intestinal Cytosolic other Ki 4.59 CHEMBL
Aldo-keto reductase family 1 member C3 Enzyme IC50 5.81 CHEMBL
Aldo-keto reductase family 1 member C2 Enzyme IC50 4.49 CHEMBL
Fatty acid-binding protein, liver Unclassified Ki 5.93 CHEMBL
Prostaglandin G/H synthase 1 Enzyme IC50 6.77 CHEMBL
Prostaglandin G/H synthase 1 Enzyme Ki 6 CHEMBL
Prostaglandin G/H synthase 2 Enzyme IC50 6.30 CHEMBL

External reference:

IDSource
4019154 VUID
N0000147399 NUI
D00330 KEGG_DRUG
4019153 VANDF
4019154 VANDF
C0016377 UMLSCUI
CHEBI:42446 CHEBI
FLP PDB_CHEM_ID
3394 PUBCHEM_CID
CHEMBL563 ChEMBL_ID
CHEMBL1200990 ChEMBL_ID
CHEMBL3989754 ChEMBL_ID
DB00712 DRUGBANK_ID
D005480 MESH_DESCRIPTOR_UI
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

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Flurbiprofen HUMAN PRESCRIPTION DRUG LABEL 1 0093-0711 TABLET, FILM COATED 100 mg ORAL ANDA 26 sections
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 27 sections
Flurbiprofen HUMAN PRESCRIPTION DRUG LABEL 1 45865-918 TABLET, FILM COATED 100 mg ORAL ANDA 27 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 63629-8338 TABLET, FILM COATED 100 mg ORAL ANDA 27 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