diethylstilbestrol Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
estrogens 875 56-53-1

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • diethylstilbestrol
  • agostilben
  • antigestil
  • distilbene
  • estrobene
  • estromenin
  • stilbestrol
A synthetic nonsteroidal estrogen used in the treatment of menopausal and postmenopausal disorders. It was also used formerly as a growth promoter in animals. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), diethylstilbestrol has been listed as a known carcinogen. (Merck, 11th ed)
  • Molecular weight: 268.36
  • Formula: C18H20O2
  • CLOGP: 4.96
  • LIPINSKI: 0
  • HAC: 2
  • HDO: 2
  • TPSA: 40.46
  • ALOGS: -4.39
  • ROTB: 4

  • Status: OFM

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

Drug dosage:

DoseUnitRoute
0.20 mg O
1 mg V
3 mg O

ADMET properties:

None

Approvals:

DateAgencyCompanyOrphan
May 30, 1973 FDA TABLICAPS

FDA Adverse Event Reporting System (Female)

None

FDA Adverse Event Reporting System (Male)

None

Pharmacologic Action:

SourceCodeDescription
ATC G03CB02 GENITO URINARY SYSTEM AND SEX HORMONES
SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
ESTROGENS
Synthetic estrogens, plain
ATC G03CC05 GENITO URINARY SYSTEM AND SEX HORMONES
SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
ESTROGENS
Estrogens, combinations with other drugs
ATC L02AA01 ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
ENDOCRINE THERAPY
HORMONES AND RELATED AGENTS
Estrogens
CHEBI has role CHEBI:35610 antineoplastic agent
CHEBI has role CHEBI:138015 endocrine disruptor
CHEBI has role CHEBI:76988 xenoestrogen
MeSH PA D002273 Carcinogens
MeSH PA D004967 Estrogens
MeSH PA D004968 Estrogens, Non-Steroidal
MeSH PA D006728 Hormones
MeSH PA D009676 Noxae

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Hyperlipoproteinemia contraindication 3744001 DOID:1168
Hypocalcemia contraindication 5291005
Hypercholesterolemia contraindication 13644009
Myocardial infarction contraindication 22298006 DOID:5844
Chloasma contraindication 36209000
Migraine contraindication 37796009 DOID:6364
Hypertensive disorder contraindication 38341003 DOID:10763
Disorder of gallbladder contraindication 39621005 DOID:0060262
Hypothyroidism contraindication 40930008 DOID:1459
Body fluid retention contraindication 43498006
Thrombosis of retinal vein contraindication 46085004
Humoral hypercalcemia of malignancy contraindication 47709007
Disorder of cardiovascular system contraindication 49601007 DOID:1287
Dementia contraindication 52448006
Hepatic porphyria contraindication 55056006 DOID:3133
Systemic lupus erythematosus contraindication 55464009 DOID:9074
Thrombophlebitis contraindication 64156001 DOID:3875
Intermenstrual bleeding - irregular contraindication 64996003
Hypercalcemia contraindication 66931009 DOID:12678
Diabetes mellitus contraindication 73211009 DOID:9351
Heart failure contraindication 84114007 DOID:6000
Epilepsy contraindication 84757009 DOID:1826
Breast lump contraindication 89164003
Kidney disease contraindication 90708001 DOID:557
Uterine leiomyoma contraindication 95315005 DOID:13223
Neoplasm of liver contraindication 126851005 DOID:3571
Neoplasm of prostate contraindication 126906006 DOID:10283
Neoplasm of female genital organ contraindication 126907002 DOID:120
Deep venous thrombosis contraindication 128053003
Endometriosis contraindication 129103003
Mammography abnormal contraindication 168750009
Asthma contraindication 195967001 DOID:2841
Cerebrovascular accident contraindication 230690007
Pulmonary thromboembolism contraindication 233935004
Thrombophilia contraindication 234467004 DOID:2452
Disease of liver contraindication 235856003 DOID:409
Endometrial carcinoma contraindication 254878006 DOID:2871
Benign prostatic hyperplasia contraindication 266569009
Edema contraindication 267038008
Chorea contraindication 271700006
Pregnancy, function contraindication 289908002
Hypertriglyceridemia contraindication 302870006
Functional visual loss contraindication 313165001
Malignant tumor of ovary contraindication 363443007 DOID:2394
Thromboembolic disorder contraindication 371039008
Cardiovascular event risk contraindication 395112001
Breastfeeding (mother) contraindication 413712001
Disorder of coronary artery contraindication 414024009
Obesity contraindication 414916001 DOID:9970
Estrogen receptor positive tumor contraindication 416053008
Resistance to activated protein C due to Factor V Leiden contraindication 421527008
Family history of malignant neoplasm of breast contraindication 429740004
Hypertensive urgency contraindication 443482000
Carcinoma of female breast contraindication 447782002
Smokes tobacco daily contraindication 449868002
Acute Thromboembolic Stroke contraindication
Breast Carcinoma in Males contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 9.27 acidic
pKa2 9.87 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
Estrogen receptor Nuclear hormone receptor AGONIST Ki 9.66 CHEMBL CHEMBL
Estrogen-related receptor gamma Nuclear hormone receptor ANTAGONIST IC50 5.30 IUPHAR
Beta-1 adrenergic receptor GPCR Ki 4.89 DRUG MATRIX
Prostaglandin G/H synthase 1 Enzyme IC50 5.25 DRUG MATRIX
Mu-type opioid receptor GPCR Ki 5.63 DRUG MATRIX
D(1A) dopamine receptor GPCR Ki 5.41 DRUG MATRIX
D(2) dopamine receptor GPCR Ki 5.35 DRUG MATRIX
Adenosine receptor A2a GPCR Ki 5.30 DRUG MATRIX
Alpha-2A adrenergic receptor GPCR Ki 5.28 DRUG MATRIX
Sodium-dependent serotonin transporter Transporter Ki 5.18 DRUG MATRIX
Sodium-dependent noradrenaline transporter Transporter Ki 5.44 DRUG MATRIX
5-hydroxytryptamine receptor 2A GPCR Ki 5.86 DRUG MATRIX
5-hydroxytryptamine receptor 2B GPCR Ki 5.70 DRUG MATRIX
5-hydroxytryptamine receptor 2C GPCR Ki 4.57 DRUG MATRIX
5-hydroxytryptamine receptor 6 GPCR Ki 5.22 DRUG MATRIX
Alpha-2B adrenergic receptor GPCR Ki 5.27 DRUG MATRIX
D(3) dopamine receptor GPCR Ki 5.52 DRUG MATRIX
Muscarinic acetylcholine receptor M1 GPCR Ki 5.44 DRUG MATRIX
Muscarinic acetylcholine receptor M3 GPCR Ki 5.41 DRUG MATRIX
Glucocorticoid receptor Nuclear hormone receptor Ki 5.32 DRUG MATRIX
Alpha-2C adrenergic receptor GPCR Ki 5.66 DRUG MATRIX
Sodium-dependent dopamine transporter Transporter Ki 6.07 DRUG MATRIX
Adenosine receptor A1 GPCR Ki 5.78 DRUG MATRIX
Adenosine receptor A3 GPCR Ki 5.90 DRUG MATRIX
Alpha-1D adrenergic receptor GPCR Ki 5.27 DRUG MATRIX
Kappa-type opioid receptor GPCR Ki 5.74 DRUG MATRIX
Delta-type opioid receptor GPCR Ki 6.02 DRUG MATRIX
Acetylcholinesterase Enzyme IC50 4.59 DRUG MATRIX
Vasopressin V1a receptor GPCR Ki 4.98 DRUG MATRIX
Tyrosine-protein kinase Fyn Kinase IC50 4.85 DRUG MATRIX
Thromboxane-A synthase Enzyme IC50 5.36 DRUG MATRIX
Mitogen-activated protein kinase 14 Kinase IC50 4.48 DRUG MATRIX
Substance-K receptor GPCR Ki 5.50 DRUG MATRIX
Sodium/nucleoside cotransporter 1 Transporter Ki 5.32 DRUG MATRIX
Estrogen receptor beta Nuclear hormone receptor Ki 9.20 CHEMBL
UDP-glucose 4-epimerase Enzyme IC50 4.12 CHEMBL
Cysteinyl leukotriene receptor 1 GPCR Ki 5.05 CHEMBL
Nuclear receptor subfamily 1 group I member 2 Nuclear hormone receptor IC50 4.84 CHEMBL
Steroid hormone receptor ERR2 Nuclear hormone receptor ANTAGONIST IC50 5.30 IUPHAR
Arachidonate 15-lipoxygenase Enzyme IC50 5.53 DRUG MATRIX
Cysteinyl leukotriene receptor 1 GPCR Ki 5.05 DRUG MATRIX
Progesterone receptor Transcription factor Ki 6.21 DRUG MATRIX
Androgen receptor Transcription factor IC50 4.85 CHEMBL
Alpha-1A adrenergic receptor GPCR IC50 4.71 CHEMBL
Steroid hormone receptor ERR1 Nuclear hormone receptor ANTAGONIST IC50 5.30 IUPHAR

External reference:

IDSource
D004054 MESH_DESCRIPTOR_UI
4017427 VUID
N0000145815 NUI
C0012203 UMLSCUI
D00577 KEGG_DRUG
731DCA35BT UNII
388 INN_ID
1190 MMSL
3390 RXNORM
396026002 SNOMEDCT_US
4591 MMSL
d00546 MMSL
79332009 SNOMEDCT_US
4017427 VANDF
001275 NDDF
CHEBI:41922 CHEBI
CHEMBL411 ChEMBL_ID
DB00255 DRUGBANK_ID
DES PDB_CHEM_ID
2801 IUPHAR_LIGAND_ID
448537 PUBCHEM_CID

Pharmaceutical products:

None