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

Stem definitionDrug idCAS RN
antineoplastic, alkylating agents, (beta-chloroethyl)amine derivatives 1065 2998-57-4

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • estramustine
  • estracty
A nitrogen mustard linked to estradiol, usually as phosphate; used to treat prostatic neoplasms; also has radiation protective properties.
  • Molecular weight: 440.41
  • Formula: C23H31Cl2NO3
  • CLOGP: 4.92
  • LIPINSKI: 0
  • HAC: 4
  • HDO: 1
  • TPSA: 49.77
  • ALOGS: -6.06
  • ROTB: 6
  • Status: OFP
    • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

None

ADMET properties:

PropertyValueReference
S (Water solubility) 0.00 mg/mL Bocci G, Oprea TI, Benet LZ
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Bocci G, Oprea TI, Benet LZ
BA (Bioavailability) 60 %

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
azlogd74 LogD at pH 7.4 4.354 Moderate 0.65
caco2-efflux Caco-2 efflux ratio (BA/AB) 0.991 Moderate 0.65
caco2-intrinsic-papp Caco-2 intrinsic apparent permeability 22.284 10^-6 cm/s Moderate 0.65
dh-clint Dog hepatocyte intrinsic clearance 130.017 uL/min/10^6 cells Moderate 0.65
dppb Dog plasma protein binding (% unbound) 0.330 % Moderate 0.65
fcs-ppb Fetal calf serum protein binding (% unbound) 0.680 % Moderate 0.65
herg hERG pIC50 4.941 pIC50 Moderate 0.65
hh-clint Human hepatocyte intrinsic clearance 161.436 uL/min/10^6 cells Moderate 0.65
hlm-clint Human liver microsomal intrinsic clearance 200.909 uL/min/mg protein Moderate 0.65
hppb Human plasma protein binding (% unbound) 0.380 % Moderate 0.65
kinase-safety-class ACVR2B,BRAF,CDK5,EIF2AK3,GRK2,ITK,MAPK10,NTRK2,PDK1,PDK2,PDK4,PRKDC 12
kinase-selectivity-class EIF2AK3,PDK2 2
mdck-mdr1-efflux MDCK-MDR1 efflux ratio 0.746 Moderate 0.65
mh-clint Mouse hepatocyte intrinsic clearance 186.638 Moderate 0.65
mppb Mouse plasma protein binding (% unbound) 0.550 Moderate 0.65
nih-mdck-mdr1-efflux NIH MDCK-MDR1 efflux ratio 2.344 Moderate 0.65
pfas-class PFAS structural alert (1 = True, 0 = False) 0
pppb Pig plasma protein binding (% unbound) 1.650 % Moderate 0.65
rh-clint Rat hepatocyte intrinsic clearance 286.418 uL/min/10^6 cells Moderate 0.65
rh-fuinc Rat hepatocyte fraction unbound in incubation 6.140 % Moderate 0.65
rppb Rat plasma protein binding (% unbound) 0.590 % Moderate 0.65
solubility-dd Solubility at pH 7.4 in DMSO 1.714 uM Moderate 0.65

Approvals:

None

FDA Adverse Event Reporting System (Female)

None

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
Osteonecrosis of jaw 41.77 40.79 10 122 19039 42602164

FDA Adverse Event Reporting System (Geriatric)

None

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC L01XX11 ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
ANTINEOPLASTIC AGENTS
OTHER ANTINEOPLASTIC AGENTS
Other antineoplastic agents
FDA CS M0007772 Estradiol
FDA CS M0014901 Nitrogen Mustard Compounds
FDA MoA N0000000236 Alkylating Activity
FDA EPC N0000175558 Alkylating Drug
MeSH PA D000477 Alkylating Agents
MeSH PA D000970 Antineoplastic Agents
MeSH PA D018906 Antineoplastic Agents, Alkylating
MeSH PA D018931 Antineoplastic Agents, Hormonal
CHEBI has role CHEBI:22333 alkylating agent
CHEBI has role CHEBI:35610 antineoplastic agent
CHEBI has role CHEBI:66987 radiation protective agent

Related Drugs by ATC class:

L01XX Other antineoplastic agents 33 drugs
adagrasibafliberceptaltretamineamsacrineanagrelidearsenic trioxideasparaginasebelzutifancalaspargase pegolcelecoxibdarinaparsindenileukin diftitox show all 33 →

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

DiseaseRelationSNOMED_IDDOID
Neoplasm of prostate indication 126906006 DOID:10283
Gynecomastia contraindication 4754008 DOID:12698
Hypocalcemia contraindication 5291005
Hyperbilirubinemia contraindication 14783006 DOID:2741
Myocardial infarction contraindication 22298006 DOID:5844
Migraine contraindication 37796009 DOID:6364
Immunosuppression contraindication 38013005
Hypertensive disorder contraindication 38341003 DOID:10763
Body fluid retention contraindication 43498006
Chronic heart failure contraindication 48447003
Cerebrovascular disease contraindication 62914000 DOID:6713
Thrombophlebitis contraindication 64156001 DOID:3875
Diabetes mellitus contraindication 73211009 DOID:9351
Epilepsy contraindication 84757009 DOID:1826
Kidney disease contraindication 90708001 DOID:557
Liver function tests abnormal contraindication 166603001
Disease of liver contraindication 235856003 DOID:409
Edema contraindication 267038008
Pregnancy, function contraindication 289908002
Bone marrow depression contraindication 307762000
Thromboembolic disorder contraindication 371039008
Impotence contraindication 397803000
Breastfeeding (mother) contraindication 413712001
Disorder of coronary artery contraindication 414024009
Hypercalcemia associated with Metabolic Bone Disease contraindication




🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

None

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

None

External reference:

IDSource
4022118 VUID
N0000020124 NUI
D04066 KEGG_DRUG
4022118 VANDF
C0014921 UMLSCUI
CHEBI:4868 CHEBI
CHEMBL1575 ChEMBL_ID
D004961 MESH_DESCRIPTOR_UI
DB01196 DRUGBANK_ID
9076 IUPHAR_LIGAND_ID
2877 INN_ID
35LT29625A UNII
259331 PUBCHEM_CID
4089 RXNORM
d01351 MMSL
004824 NDDF
108768000 SNOMEDCT_US
386909008 SNOMEDCT_US
35LT29625A INXIGHT DRUGS

Pharmaceutical products:

None