fenoprofen ๐Ÿถ Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | BioActivity |

Stem definitionDrug idCAS RN
anti-inflammatory agents, ibuprofen derivatives 1154 29679-58-1

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • fenoprofen
  • (+/-)-Fenoprofen
  • 3-Phenoxyhydratropic acid
  • fenoprofen calcium
  • fenoprofen calcium salt
  • fenoprofen calcium salt dihydrate
A propionic acid derivative that is used as a non-steroidal anti-inflammatory agent.
  • Molecular weight: 242.27
  • Formula: C15H14O3
  • CLOGP: 3.52
  • LIPINSKI: 0
  • HAC: 3
  • HDO: 1
  • TPSA: 46.53
  • ALOGS: -3.48
  • ROTB: 4

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
1.20 g O

ADMET properties:

PropertyValueReference
MRTD (Maximum Recommended Therapeutic Daily Dose) 206.38 ยตM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Hosey CM, Chan R, Benet LZ
Vd (Volume of distribution) 0.10 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 0.60 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.02 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 2.24 hours Lombardo F, Berellini G, Obach RS
S (Water solubility) 0.08 mg/mL Bocci G, Oprea TI, Benet LZ
BA (Bioavailability) 85 %

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
azlogd74 LogD at pH 7.4 0.625 High 1
caco2-efflux Caco-2 efflux ratio (BA/AB) 0.358 High 1
caco2-intrinsic-papp Caco-2 intrinsic apparent permeability 118.577 10^-6 cm/s High 1
dh-clint Dog hepatocyte intrinsic clearance 8.831 uL/min/10^6 cells High 1
dppb Dog plasma protein binding (% unbound) 1.020 % High 1
fcs-ppb Fetal calf serum protein binding (% unbound) 3.090 % High 1
herg hERG pIC50 4.060 pIC50 High 1
hh-clint Human hepatocyte intrinsic clearance 11.776 uL/min/10^6 cells High 1
hlm-clint Human liver microsomal intrinsic clearance 3.304 uL/min/mg protein High 1
hppb Human plasma protein binding (% unbound) 1.300 % High 1
kinase-safety-class ACVR2B,AURKA,AXL,BTK,CDK5,CDK9,EIF2AK3,ERBB2,GRK2,ITK,MAP2K6,MAPK7,PDK1,PDK2,PDK4,PIK3CB,PIK3CG,PRKDC,TEK,TGFBR1 20
kinase-selectivity-class GRK2,PDK4 2
mdck-mdr1-efflux MDCK-MDR1 efflux ratio 1.315 High 1
mh-clint Mouse hepatocyte intrinsic clearance 110.154 High 1
mppb Mouse plasma protein binding (% unbound) 6.920 High 1
nih-mdck-mdr1-efflux NIH MDCK-MDR1 efflux ratio 0.272 High 1
pfas-class PFAS structural alert (1 = True, 0 = False) 0
pppb Pig plasma protein binding (% unbound) 2.350 % High 1
rh-clint Rat hepatocyte intrinsic clearance 31.405 uL/min/10^6 cells High 1
rh-fuinc Rat hepatocyte fraction unbound in incubation 89.360 % High 1
rppb Rat plasma protein binding (% unbound) 1.600 % High 1
solubility-dd Solubility at pH 7.4 in DMSO 866.962 uM High 1

Approvals:

DateAgencyCompanyOrphan
March 16, 1976 FDA XSPIRE

FDA Adverse Event Reporting System (Female)

None

FDA Adverse Event Reporting System (Male)

None

FDA Adverse Event Reporting System (Geriatric)

None

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC M01AE04 MUSCULO-SKELETAL SYSTEM
ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS
ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS
Propionic acid derivatives
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:35475 non-steroidal anti-inflammatory drug
CHEBI has role CHEBI:35481 non-narcotic analgesic
CHEBI has role CHEBI:35493 antipyretic
CHEBI has role CHEBI:50629 cyclooxygenase 2 inhibitor
CHEBI has role CHEBI:50630 cyclooxygenase 1 inhibitor
CHEBI has role CHEBI:88188 drug allergen
CHEBI has role CHEBI:35842 antirheumatic drug
FDA EPC N0000175722 Nonsteroidal Anti-inflammatory Drug

Related Drugs by ATC class:

M01AE Propionic acid derivatives 21 drugs

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

DiseaseRelationSNOMED_IDDOID
Pain indication 22253000
Rheumatoid arthritis indication 69896004 DOID:7148
Osteoarthritis indication 396275006
Arthritis off-label use 3723001 DOID:848
Gout off-label use 90560007 DOID:13189
Vascular headache off-label use 128187005
Alcoholism contraindication 7200002
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
Blood coagulation disorder contraindication 64779008 DOID:1247
Gastrointestinal hemorrhage contraindication 74474003
Kidney disease contraindication 90708001 DOID:557
Hearing disorder contraindication 128540005
Liver function tests abnormal contraindication 166603001
Cerebrovascular accident contraindication 230690007
Coronary artery bypass graft contraindication 232717009
Drug-induced hepatitis contraindication 235876009
Edema contraindication 267038008
Acute papillary necrosis contraindication 270494003
Anemia contraindication 271737000 DOID:2355
Pregnancy, function contraindication 289908002
Cardiovascular event risk contraindication 395112001
Visual impairment contraindication 397540003
Thrombosis contraindication 439127006
Smokes tobacco daily contraindication 449868002




๐Ÿถ Veterinary Drug Use

None

๐Ÿถ Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 4.51 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 5.23 WOMBAT-PK CHEMBL
Prostaglandin G/H synthase 1 Enzyme INHIBITOR IC50 5.36 WOMBAT-PK CHEMBL
Sodium-coupled monocarboxylate transporter 1 Transporter INHIBITOR IC50 4.57 IUPHAR
Prostaglandin G/H synthase 2 Enzyme IC50 4.58 CHEMBL
Cyclooxygenase Enzyme IC50 4.01 CHEMBL

External reference:

IDSource
4019755 VUID
N0000147846 NUI
D00968 KEGG_DRUG
53746-45-5 SECONDARY_CAS_RN
4018902 VANDF
4019755 VANDF
C0015837 UMLSCUI
CHEBI:5004 CHEBI
PFN PDB_CHEM_ID
CHEMBL249244 ChEMBL_ID
CHEMBL1297 ChEMBL_ID
DB00573 DRUGBANK_ID
CHEMBL2103736 ChEMBL_ID
D005279 MESH_DESCRIPTOR_UI
3342 PUBCHEM_CID
4820 IUPHAR_LIGAND_ID
3104 INN_ID
RA33EAC7KY UNII
267171 RXNORM
3081 MMSL
4720 MMSL
d00026 MMSL
002378 NDDF
004810 NDDF
017029 NDDF
373525006 SNOMEDCT_US
71798005 SNOMEDCT_US
77353007 SNOMEDCT_US
RA33EAC7KY INXIGHT DRUGS

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Fenoprofen Calcium HUMAN PRESCRIPTION DRUG LABEL 1 0276-0501 CAPSULE 200 mg ORAL NDA 28 sections
Fenoprofen Calcium HUMAN PRESCRIPTION DRUG LABEL 1 0276-0502 CAPSULE 300 mg ORAL NDA 28 sections
Fenoprofen Calcium HUMAN PRESCRIPTION DRUG LABEL 1 0276-0503 CAPSULE 400 mg ORAL NDA 28 sections
FENOPROFEN CALCIUM Human Prescription Drug Label 1 16571-688 CAPSULE 400 mg ORAL ANDA 25 sections
FENOPROFEN CALCIUM Human Prescription Drug Label 1 16571-886 CAPSULE 200 mg ORAL ANDA 25 sections
FENOPROFEN CALCIUM Human Prescription Drug Label 1 16571-887 CAPSULE 300 mg ORAL ANDA 25 sections
Fenoprofen Calcium HUMAN PRESCRIPTION DRUG LABEL 1 50090-3572 CAPSULE 400 mg ORAL NDA authorized generic 29 sections
Fenoprofen Calcium HUMAN PRESCRIPTION DRUG LABEL 1 53217-169 CAPSULE 400 mg ORAL NDA AUTHORIZED GENERIC 28 sections
FENOPRON TM HUMAN PRESCRIPTION DRUG LABEL 1 61825-311 CAPSULE 300 mg ORAL ANDA 27 sections
FENOPROFEN CALCIUM HUMAN PRESCRIPTION DRUG LABEL 1 69336-124 CAPSULE 200 mg ORAL NDA 28 sections
FENOPROFEN CALCIUM HUMAN PRESCRIPTION DRUG LABEL 1 71205-828 CAPSULE 400 mg ORAL ANDA 26 sections
FENOPROFEN CALCIUM HUMAN PRESCRIPTION DRUG LABEL 1 71993-308 CAPSULE 400 mg ORAL ANDA 20 sections
Fenoprofen calcium HUMAN PRESCRIPTION DRUG LABEL 1 71993-313 CAPSULE 200 mg ORAL ANDA 20 sections