flutamide Indications/Contra | FAERs-F | FAERs-M | Orange Bk | 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: 3.33
  • 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 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 90 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

DateAgencyCompanyOrphan
Jan. 27, 1989 FDA

FDA Adverse Event Reporting System (Female)

None

FDA Adverse Event Reporting System (Male)

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
CHEBI has role CHEBI:35497 antiandrogen
CHEBI has role CHEBI:35610 cytostatic
MeSH PA D000726 Androgen Antagonists
MeSH PA D000970 Antineoplastic Agents
MeSH PA D018931 Antineoplastic Agents, Hormonal
MeSH PA D006727 Hormone Antagonists

Drug Use (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

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
5-hydroxytryptamine receptor 6 GPCR Ki 5.08 DRUG MATRIX
Cytochrome P450 1A2 Enzyme Ki 5.36 WOMBAT-PK
Androgen receptor Transcription factor Ki 5.05 DRUG MATRIX
5-hydroxytryptamine receptor 4 GPCR Ki 5.65 DRUG MATRIX
Bile salt export pump Unclassified 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
6943 IUPHAR_LIGAND_ID
3483 INN_ID
76W6J0943E UNII
3397 PUBCHEM_CID
4508 RXNORM
42238 MMSL
4755 MMSL
d00240 MMSL
002677 NDDF
387587007 SNOMEDCT_US
96371003 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Flutamide HUMAN PRESCRIPTION DRUG LABEL 1 49884-753 CAPSULE 125 mg ORAL ANDA 17 sections
Flutamide HUMAN PRESCRIPTION DRUG LABEL 1 60429-272 CAPSULE 125 mg ORAL ANDA 17 sections
FLUTAMIDE HUMAN PRESCRIPTION DRUG LABEL 1 69097-915 CAPSULE 125 mg ORAL ANDA 20 sections