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

Stem definitionDrug idCAS RN
non-steroid antiandrogens 1223 13311-84-7

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • flutamide
  • flutopharm
  • niftholide
  • niftolide
Flutamide is an acetanilid, nonsteroidal, orally active antiandrogen. It exerts its antiandrogenic action by inhibiting androgen uptake and/or by inhibiting nuclear binding of androgen in target tissues or both.
  • Molecular weight: 276.22
  • Formula: C11H11F3N2O3
  • CLOGP: 3.34
  • LIPINSKI: 0
  • HAC: 5
  • HDO: 1
  • TPSA: 74.92
  • ALOGS: -4.69
  • ROTB: 4
  • Status: OFP
    • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
0.75 g O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.01 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) 38.79 µM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 90 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
azlogd74 LogD at pH 7.4 3.429 High 1
caco2-efflux Caco-2 efflux ratio (BA/AB) 0.641 High 1
caco2-intrinsic-papp Caco-2 intrinsic apparent permeability 61.518 10^-6 cm/s High 1
dh-clint Dog hepatocyte intrinsic clearance 38.107 uL/min/10^6 cells High 1
dppb Dog plasma protein binding (% unbound) 5.450 % High 1
fcs-ppb Fetal calf serum protein binding (% unbound) 12.080 % High 1
herg hERG pIC50 4.725 pIC50 High 1
hh-clint Human hepatocyte intrinsic clearance 66.988 uL/min/10^6 cells High 1
hlm-clint Human liver microsomal intrinsic clearance 135.207 uL/min/mg protein High 1
hppb Human plasma protein binding (% unbound) 5.410 % High 1
kinase-safety-class ACVR2A,ACVR2B,AURKA,AXL,BRAF,BTK,CAMK2B,CAMK2D,CDK5,CDK9,DDR1,DYRK1B,EGFR,EIF2AK3,EPHB4,ERBB2,GRK2,GSK3B,ITK,JAK2,MAP2K6,MAP3K21,MAP3K7,MAPK10,MAPK7,MAPK9,MAPKAPK2,MET,NTRK2,PDK1,PDK2,PDK4,PDPK1,PIK3CB,PIK3CD,PIK3CG,PIM2,PRKCD,PRKDC,SIK2,STK33,SYK,TEK,TTK,ZAP70 45
kinase-selectivity-class AURKA,AXL,BRAF,CDK9,DDR1,DYRK1B,GRK2,MAPK7,MET,PDK1,PDK4,STK33,TTK 13
mdck-mdr1-efflux MDCK-MDR1 efflux ratio 1.816 High 1
mh-clint Mouse hepatocyte intrinsic clearance 71.285 High 1
mppb Mouse plasma protein binding (% unbound) 6.160 High 1
nih-mdck-mdr1-efflux NIH MDCK-MDR1 efflux ratio 1.476 High 1
pfas-class PFAS structural alert (1 = True, 0 = False) 1
pld-class Phospholipidosis risk class (1 = positive, 0 = negative) 0 High 1
pppb Pig plasma protein binding (% unbound) 10.130 % High 1
rh-clint Rat hepatocyte intrinsic clearance 35.318 uL/min/10^6 cells High 1
rh-fuinc Rat hepatocyte fraction unbound in incubation 56.520 % High 1
rppb Rat plasma protein binding (% unbound) 5.750 % High 1
solubility-dd Solubility at pH 7.4 in DMSO 58.210 uM High 1

Approvals:

DateAgencyCompanyOrphan
Jan. 27, 1989 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
Nephropathy 55.97 48.97 11 240 9224 90618972

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
Prostatic specific antigen increased 148.11 26.51 45 1550 16880 42602860
Osteonecrosis of jaw 122.30 26.51 40 1555 19009 42600731
Metastases to bone 67.17 26.51 24 1571 14785 42604955
Hormone-refractory prostate cancer 51.55 26.51 11 1584 993 42618747
Bladder tamponade 44.44 26.51 9 1586 629 42619111
Prostate cancer 41.78 26.51 24 1571 44619 42575121
Interstitial lung disease 33.81 26.51 26 1569 78436 42541304

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
Prostatic specific antigen increased 161.13 28.16 37 1534 12474 110575254
Osteonecrosis of jaw 115.89 28.16 38 1533 47979 110539749
Hormone-refractory prostate cancer 63.26 28.16 11 1560 899 110586829
Metastases to bone 56.65 28.16 20 1551 31352 110556376
Prostate cancer 53.09 28.16 20 1551 37621 110550107
Nephropathy 33.80 28.16 11 1560 13456 110574272
Interstitial lung disease 28.34 28.16 20 1551 139314 110448414

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC L02BB01 ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
ENDOCRINE THERAPY
HORMONE ANTAGONISTS AND RELATED AGENTS
Anti-androgens
FDA MoA N0000000243 Androgen Receptor Antagonists
FDA EPC N0000175560 Androgen Receptor Inhibitor
MeSH PA D000726 Androgen Antagonists
MeSH PA D000970 Antineoplastic Agents
MeSH PA D006727 Hormone Antagonists
MeSH PA D018931 Antineoplastic Agents, Hormonal
CHEBI has role CHEBI:35497 androgen antagonist
CHEBI has role CHEBI:35610 antineoplastic agent

Related Drugs by ATC class:

L02BB Anti-androgens 5 drugs
apalutamidebicalutamidedarolutamideenzalutamidenilutamide

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

DiseaseRelationSNOMED_IDDOID
Neoplasm of prostate indication 126906006 DOID:10283
Hyperbilirubinemia contraindication 14783006 DOID:2741
Methemoglobinemia contraindication 38959009 DOID:10783
Hepatic failure contraindication 59927004
Anemia due to enzyme deficiency contraindication 111577008
Deficiency of glucose-6-phosphate dehydrogenase contraindication 124134002 DOID:2862
Deficiency of cytochrome-b>5< reductase contraindication 124184009
Disease of liver contraindication 235856003 DOID:409
Pregnancy, function contraindication 289908002
Breastfeeding (mother) contraindication 413712001




🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 11.76 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
Androgen receptor Nuclear hormone receptor ANTAGONIST Ki 5.89 CHEMBL CHEMBL
Cytochrome P450 1A2 Enzyme Ki 5.36 WOMBAT-PK
5-hydroxytryptamine receptor 6 GPCR Ki 5.08 DRUG MATRIX
5-hydroxytryptamine receptor 4 GPCR Ki 5.65 DRUG MATRIX
Androgen receptor Transcription factor Ki 5.05 DRUG MATRIX
Bile salt export pump Transporter IC50 4.10 CHEMBL

External reference:

IDSource
4019377 VUID
N0000147534 NUI
D00586 KEGG_DRUG
4019377 VANDF
C0016384 UMLSCUI
CHEBI:5132 CHEBI
CHEMBL806 ChEMBL_ID
DB00499 DRUGBANK_ID
D005485 MESH_DESCRIPTOR_UI
3397 PUBCHEM_CID
6943 IUPHAR_LIGAND_ID
3483 INN_ID
76W6J0943E UNII
4508 RXNORM
42238 MMSL
4755 MMSL
d00240 MMSL
002677 NDDF
387587007 SNOMEDCT_US
96371003 SNOMEDCT_US
76W6J0943E INXIGHT DRUGS

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Eulexin HUMAN PRESCRIPTION DRUG LABEL 1 80725-143 CAPSULE 125 mg ORAL ANDA 24 sections
Eulexin HUMAN PRESCRIPTION DRUG LABEL 1 80725-600 CAPSULE 125 mg ORAL ANDA 26 sections