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flutamide 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | BioActivity |
| Stem definition | Drug id | CAS RN |
|---|---|---|
| non-steroid antiandrogens | 1223 | 13311-84-7 |
Description:
| Molecule | Description |
|---|---|
|
Synonyms:
|
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.
Legend: OFP - off patent OFM - off market ONP - on patent |
Drug dosage:
| Dose | Unit | Route |
|---|---|---|
| 0.75 | g | O |
ADMET properties:
| Property | Value | Reference |
|---|---|---|
| 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):
| Property | Description | Value | Unit | Confidence | Similarity |
|---|---|---|---|---|---|
| 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:
| Date | Agency | Company | Orphan |
|---|---|---|---|
| Jan. 27, 1989 | FDA |
FDA Adverse Event Reporting System (Female)
| MedDRA adverse event term | Likelihood ratio | Likelihood ratio threshold | Patients taking drug having adverse event | Patients taking drug not having adverse event | Patients not taking drug having adverse event | Patients 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 term | Likelihood ratio | Likelihood ratio threshold | Patients taking drug having adverse event | Patients taking drug not having adverse event | Patients not taking drug having adverse event | Patients 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 term | Likelihood ratio | Likelihood ratio threshold | Patients taking drug having adverse event | Patients taking drug not having adverse event | Patients not taking drug having adverse event | Patients 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:
| Source | Code | Description |
|---|---|---|
| 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
Drug Use | Suggest Off label Use Form| |View source of the data|
| Disease | Relation | SNOMED_ID | DOID |
|---|---|---|---|
| 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 level | Dissociation constant | Type (acidic/basic) |
|---|---|---|
| pKa1 | 11.76 | acidic |
Orange Book patent data (new drug applications)
None
Orange Book exclusivity data (new drug applications)
None
Bioactivity Summary:
| Target | Class | Pharos | UniProt | Action | Type | Activity value (-log[M]) | Mechanism action | Bioact source | MoA 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:
| ID | Source |
|---|---|
| 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:
| Product | Category | Ingredients | NDC | Form | Quantity | Route | Marketing | Label |
|---|---|---|---|---|---|---|---|---|
| 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 |