flurbiprofen 🐶 Veterinary Use | 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 µM/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 134.65 23.48 54 2214 47911 63438843
Toxic anterior segment syndrome 101.06 23.48 21 2247 1750 63485004
Allergy test positive 76.35 23.48 14 2254 606 63486148
Drug reaction with eosinophilia and systemic symptoms 64.53 23.48 29 2239 33807 63452947
Acute kidney injury 53.78 23.48 56 2212 263359 63223395
Urticaria 46.48 23.48 42 2226 165760 63320994
Pancreatitis acute 44.62 23.48 21 2247 27145 63459609
Eyelid oedema 40.78 23.48 15 2253 10464 63476290
Ankylosing spondylitis 33.53 23.48 13 2255 10461 63476293
Eosinophilic myocarditis 33.32 23.48 7 2261 613 63486141
Altered state of consciousness 30.98 23.48 16 2252 25214 63461540
Lip oedema 28.62 23.48 9 2259 3915 63482839

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 36.36 27.43 8 934 1161 34954828
Hypertrophic cardiomyopathy 30.96 27.43 7 935 1150 34954839
Ischaemic cerebral infarction 30.43 27.43 7 935 1240 34954749
Abnormal dreams 29.17 27.43 10 932 7568 34948421

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 137.34 18.85 63 2837 75972 79665516
Toxic anterior segment syndrome 135.52 18.85 29 2871 2735 79738753
Allergy test positive 73.85 18.85 14 2886 714 79740774
Drug reaction with eosinophilia and systemic symptoms 59.56 18.85 34 2866 64210 79677278
Urticaria 51.33 18.85 47 2853 185154 79556334
Eyelid oedema 43.57 18.85 17 2883 13670 79727818
Pancreatitis acute 40.00 18.85 24 2876 49580 79691908
Lip oedema 31.81 18.85 11 2889 6305 79735183
Ankylosing spondylitis 31.38 18.85 13 2887 12192 79729296
Acute kidney injury 29.71 18.85 61 2839 519343 79222145
Eosinophilic myocarditis 28.47 18.85 7 2893 1215 79740273
Altered state of consciousness 22.54 18.85 16 2884 43806 79697682
Spinal pain 22.34 18.85 11 2889 15381 79726107
Abnormal dreams 22.25 18.85 10 2890 11402 79730086
Urticaria chronic 22.15 18.85 5 2895 601 79740887
Drug hypersensitivity 21.83 18.85 39 2861 298877 79442611
Symptom recurrence 19.69 18.85 6 2894 2308 79739180
Hypertrophic cardiomyopathy 19.63 18.85 6 2894 2334 79739154
Ischaemic cerebral infarction 19.15 18.85 6 2894 2529 79738959

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
CHEBI has role CHEBI:35475 non-steroidal anti-inflammatory agent
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
FDA EPC N0000175722 Nonsteroidal Anti-inflammatory Drug

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 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
Fatty acid-binding protein, liver Unclassified 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
56767-76-1 SECONDARY_CAS_RN
4019153 VANDF
4019154 VANDF
C0016377 UMLSCUI
CHEBI:42446 CHEBI
FLP PDB_CHEM_ID
CHEMBL563 ChEMBL_ID
DB00712 DRUGBANK_ID
CHEMBL3989754 ChEMBL_ID
CHEMBL1200990 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

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 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 43063-992 TABLET, FILM COATED 100 mg ORAL ANDA 27 sections
Flurbiprofen HUMAN PRESCRIPTION DRUG LABEL 1 43063-992 TABLET, FILM COATED 100 mg ORAL ANDA 27 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 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 25 sections
Flurbiprofen HUMAN PRESCRIPTION DRUG LABEL 1 63629-8808 TABLET, FILM COATED 100 mg ORAL ANDA 26 sections
Flurbiprofen HUMAN PRESCRIPTION DRUG LABEL 1 63629-8808 TABLET, FILM COATED 100 mg ORAL ANDA 26 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 HUMAN PRESCRIPTION DRUG LABEL 1 68788-7341 TABLET, FILM COATED 100 mg ORAL ANDA 26 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
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