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diethylstilbestrol 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | BioActivity |
| Stem definition | Drug id | CAS RN |
|---|---|---|
| estrogens | 875 | 56-53-1 |
Description:
| Molecule | Description |
|---|---|
|
Synonyms:
|
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)
Legend: OFP - off patent OFM - off market ONP - on patent |
Drug dosage:
| Dose | Unit | Route |
|---|---|---|
| 0.20 | mg | O |
| 1 | mg | V |
| 3 | mg | O |
ADMET properties:
None
Predicted pharmacokinetic/toxicological properties (PK-AZ):
| Property | Description | Value | Unit | Confidence | Similarity |
|---|---|---|---|---|---|
| azlogd74 | LogD at pH 7.4 | 4.697 | High | 1 | |
| caco2-efflux | Caco-2 efflux ratio (BA/AB) | 0.610 | High | 1 | |
| caco2-intrinsic-papp | Caco-2 intrinsic apparent permeability | 55.081 | 10^-6 cm/s | High | 1 |
| dh-clint | Dog hepatocyte intrinsic clearance | 346.737 | uL/min/10^6 cells | High | 1 |
| dppb | Dog plasma protein binding (% unbound) | 0.250 | % | High | 1 |
| fcs-ppb | Fetal calf serum protein binding (% unbound) | 0.830 | % | High | 1 |
| herg | hERG pIC50 | 4.978 | pIC50 | High | 1 |
| hh-clint | Human hepatocyte intrinsic clearance | 289.068 | uL/min/10^6 cells | High | 1 |
| hlm-clint | Human liver microsomal intrinsic clearance | 46.026 | uL/min/mg protein | High | 1 |
| hppb | Human plasma protein binding (% unbound) | 0.190 | % | High | 1 |
| kinase-safety-class | ACVR2A,ACVR2B,AKT2,AKT3,ALK,AURKA,AURKB,AXL,BRAF,BTK,CAMK2B,CAMK2D,CDK4,CDK5,CDK9,CSF1R,DDR1,DYRK1B,EIF2AK3,EPHB4,ERBB2,FLT3,GRK2,GSK3B,ITK,JAK1,JAK2,MAP2K6,MAP3K1,MAP3K14,MAP3K21,MAP3K7,MAP4K1,MAP4K3,MAPK10,MAPK7,MAPK9,MAPKAPK2,MARK4,MET,MTOR,NTRK2,PDK1,PDK2,PDK4,PDPK1,PIK3CA,PIK3CB,PIK3CD,PIK3CG,PIM2,PRKCD,PRKDC,SGK1,SIK2,SIK3,STK33,SYK,TEK,TGFBR1,TTK,ULK1,ZAP70 | 63 | |||
| kinase-selectivity-class | ACVR2A,ACVR2B,AXL,BRAF,CAMK2B,CAMK2D,CDK4,CDK9,DDR1,DYRK1B,EPHB4,GRK2,MAP2K6,MAPK7,MARK4,PRKDC,SIK2,SIK3,STK10,STK33,TEK,TTK,ULK1 | 23 | |||
| mdck-mdr1-efflux | MDCK-MDR1 efflux ratio | 1.959 | High | 1 | |
| mh-clint | Mouse hepatocyte intrinsic clearance | 467.735 | High | 1 | |
| mppb | Mouse plasma protein binding (% unbound) | 0.110 | High | 1 | |
| nih-mdck-mdr1-efflux | NIH MDCK-MDR1 efflux ratio | 4.027 | High | 1 | |
| pfas-class | PFAS structural alert (1 = True, 0 = False) | 0 | |||
| pppb | Pig plasma protein binding (% unbound) | 0.530 | % | High | 1 |
| rh-clint | Rat hepatocyte intrinsic clearance | 322.849 | uL/min/10^6 cells | High | 1 |
| rh-fuinc | Rat hepatocyte fraction unbound in incubation | 9.480 | % | High | 1 |
| rppb | Rat plasma protein binding (% unbound) | 0.120 | % | High | 1 |
| solubility-dd | Solubility at pH 7.4 in DMSO | 70.146 | uM | High | 1 |
Approvals:
| Date | Agency | Company | Orphan |
|---|---|---|---|
| May 30, 1973 | FDA | TABLICAPS |
FDA Adverse Event Reporting System (Female)
None
FDA Adverse Event Reporting System (Male)
None
FDA Adverse Event Reporting System (Geriatric)
None
FDA Adverse Event Reporting System (Pediatric)
None
Pharmacologic Action:
| Source | Code | Description |
|---|---|---|
| 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 |
| MeSH PA | D002273 | Carcinogens |
| MeSH PA | D004967 | Estrogens |
| MeSH PA | D004968 | Estrogens, Non-Steroidal |
| MeSH PA | D006728 | Hormones |
| CHEBI has role | CHEBI:35610 | antineoplastic agent |
| CHEBI has role | CHEBI:35718 | antifungal agent |
| CHEBI has role | CHEBI:38215 | calcium channel blocker |
| CHEBI has role | CHEBI:49200 | EC 3.6.3.10 (<em>H</em><small><sup>+</small></sup>/<em>K</em><small><sup>+</small></sup>-exchanging ATPase) inhibitor |
| CHEBI has role | CHEBI:50903 | carcinogenic agent |
| CHEBI has role | CHEBI:76988 | xenoestrogen |
| CHEBI has role | CHEBI:137626 | EC 1.1.1.146 (11β-hydroxysteroid dehydrogenase) inhibitor |
| CHEBI has role | CHEBI:138015 | endocrine disruptor |
| CHEBI has role | CHEBI:138880 | autophagy inducer |
Related Drugs by ATC class:
G03CB Synthetic estrogens, plain 3 drugs
G03CC Estrogens, combinations with other drugs 6 drugs
L02AA Estrogens 3 drugs
Drug Use | Suggest Off label Use Form| |View source of the data|
| Disease | Relation | SNOMED_ID | DOID |
|---|---|---|---|
| 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 |
🐶 Veterinary Drug Use
None
🐶 Veterinary products
None
Acid dissociation constants calculated using MoKa v3.0.0
| Dissociation level | Dissociation constant | Type (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:
| Target | Class | Pharos | UniProt | Action | Type | Activity value (-log[M]) | Mechanism action | Bioact source | MoA source |
|---|---|---|---|---|---|---|---|---|---|
| Estrogen receptor | Nuclear hormone receptor | AGONIST | Ki | 9.66 | CHEMBL | CHEMBL | |||
| 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 | 4.58 | 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 | 5.53 | 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 | |||||
| Nuclear receptor subfamily 1 group I member 2 | Nuclear hormone receptor | IC50 | 4.84 | CHEMBL | |||||
| 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 | |||||
| Estrogen receptor beta | Nuclear hormone receptor | Ki | 9.20 | CHEMBL | |||||
| Estrogen-related receptor gamma | Nuclear hormone receptor | ANTAGONIST | IC50 | 5.30 | IUPHAR | ||||
| Cysteinyl leukotriene receptor 1 | GPCR | Ki | 5.05 | CHEMBL | |||||
| 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 | |||||
| Steroid hormone receptor ERR2 | Nuclear hormone receptor | ANTAGONIST | IC50 | 5.30 | IUPHAR | ||||
| Mitogen-activated protein kinase 14 | Kinase | IC50 | 4.48 | DRUG MATRIX | |||||
| Substance-K receptor | GPCR | Ki | 5.50 | DRUG MATRIX | |||||
| UDP-glucose 4-epimerase | Enzyme | IC50 | 4.12 | CHEMBL | |||||
| Sodium/nucleoside cotransporter 1 | Transporter | Ki | 5.32 | DRUG MATRIX | |||||
| Androgen receptor | Transcription factor | IC50 | 4.85 | CHEMBL | |||||
| 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 | |||||
| Alpha-1A adrenergic receptor | GPCR | IC50 | 4.71 | CHEMBL | |||||
| Steroid hormone receptor ERR1 | Nuclear hormone receptor | ANTAGONIST | IC50 | 5.30 | IUPHAR | ||||
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | Enzyme | IC50 | 4.85 | CHEMBL |
External reference:
| ID | Source |
|---|---|
| 4017427 | VUID |
| N0000145815 | NUI |
| D00577 | KEGG_DRUG |
| 3390 | RXNORM |
| 4017427 | VANDF |
| C0012203 | UMLSCUI |
| CHEBI:41922 | CHEBI |
| DES | PDB_CHEM_ID |
| CHEMBL411 | ChEMBL_ID |
| DB00255 | DRUGBANK_ID |
| D004054 | MESH_DESCRIPTOR_UI |
| 448537 | PUBCHEM_CID |
| 2801 | IUPHAR_LIGAND_ID |
| 388 | INN_ID |
| 731DCA35BT | UNII |
| 1190 | MMSL |
| 4591 | MMSL |
| d00546 | MMSL |
| 001275 | NDDF |
| 396026002 | SNOMEDCT_US |
| 79332009 | SNOMEDCT_US |
| 731DCA35BT | INXIGHT DRUGS |
Pharmaceutical products:
None