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

Stem definition	Drug id	CAS RN
estrogens	875	56-53-1

Description:

Molecule	Description
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

Molecule

Description

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:

Dose	Unit	Route
0.20	mg	O
1	mg	V
3	mg	O

ADMET properties:

None

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
MeSH PA	D009676	Noxae
CHEBI has role	CHEBI:35610	antineoplastic agents
CHEBI has role	CHEBI:35718	antifungal agents
CHEBI has role	CHEBI:38215	calcium channel blockers
CHEBI has role	CHEBI:49200	proton pump inhibitors
CHEBI has role	CHEBI:50903	carcinogen
CHEBI has role	CHEBI:76988	xenoestrogens
CHEBI has role	CHEBI:137626	corticosteroid 11beta-dehydrogenase inhibitors
CHEBI has role	CHEBI:138015	endocrine disruptors
CHEBI has role	CHEBI:138880	autophagocytosis inducer

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])	Bioact source	MoA source
Estrogen receptor	Nuclear hormone receptor	P03372	ESR1_HUMAN	AGONIST	Ki	9.66	CHEMBL	CHEMBL
Beta-1 adrenergic receptor	GPCR	P08588	ADRB1_HUMAN		Ki	4.89	DRUG MATRIX
Prostaglandin G/H synthase 1	Enzyme	P23219	PGH1_HUMAN		IC50	5.25	DRUG MATRIX
Mu-type opioid receptor	GPCR	P35372	OPRM_HUMAN		Ki	5.63	DRUG MATRIX
D(1A) dopamine receptor	GPCR	P21728	DRD1_HUMAN		Ki	5.41	DRUG MATRIX
D(2) dopamine receptor	GPCR	P14416	DRD2_HUMAN		Ki	5.35	DRUG MATRIX
Adenosine receptor A2a	GPCR	P29274	AA2AR_HUMAN		Ki	5.30	DRUG MATRIX
Alpha-2A adrenergic receptor	GPCR	P08913	ADA2A_HUMAN		Ki	5.28	DRUG MATRIX
Sodium-dependent serotonin transporter	Transporter	P31645	SC6A4_HUMAN		Ki	5.18	DRUG MATRIX
Sodium-dependent noradrenaline transporter	Transporter	P23975	SC6A2_HUMAN		Ki	5.44	DRUG MATRIX
5-hydroxytryptamine receptor 2A	GPCR	P28223	5HT2A_HUMAN		Ki	5.86	DRUG MATRIX
5-hydroxytryptamine receptor 2B	GPCR	P41595	5HT2B_HUMAN		Ki	5.70	DRUG MATRIX
5-hydroxytryptamine receptor 2C	GPCR	P28335	5HT2C_HUMAN		Ki	4.58	DRUG MATRIX
5-hydroxytryptamine receptor 6	GPCR	P50406	5HT6R_HUMAN		Ki	5.22	DRUG MATRIX
Alpha-2B adrenergic receptor	GPCR	P18089	ADA2B_HUMAN		Ki	5.27	DRUG MATRIX
D(3) dopamine receptor	GPCR	P35462	DRD3_HUMAN		Ki	5.53	DRUG MATRIX
Muscarinic acetylcholine receptor M1	GPCR	P11229	ACM1_HUMAN		Ki	5.44	DRUG MATRIX
Muscarinic acetylcholine receptor M3	GPCR	P20309	ACM3_HUMAN		Ki	5.41	DRUG MATRIX
Glucocorticoid receptor	Nuclear hormone receptor	P04150	GCR_HUMAN		Ki	5.32	DRUG MATRIX
Alpha-2C adrenergic receptor	GPCR	P18825	ADA2C_HUMAN		Ki	5.66	DRUG MATRIX
Sodium-dependent dopamine transporter	Transporter	Q01959	SC6A3_HUMAN		Ki	6.07	DRUG MATRIX
Adenosine receptor A1	GPCR	P30542	AA1R_HUMAN		Ki	5.78	DRUG MATRIX
Adenosine receptor A3	GPCR	P0DMS8	AA3R_HUMAN		Ki	5.90	DRUG MATRIX
Nuclear receptor subfamily 1 group I member 2	Nuclear hormone receptor	O75469	NR1I2_HUMAN		IC50	4.84	CHEMBL
Alpha-1D adrenergic receptor	GPCR	P25100	ADA1D_HUMAN		Ki	5.27	DRUG MATRIX
Kappa-type opioid receptor	GPCR	P41145	OPRK_HUMAN		Ki	5.74	DRUG MATRIX
Delta-type opioid receptor	GPCR	P41143	OPRD_HUMAN		Ki	6.02	DRUG MATRIX
Acetylcholinesterase	Enzyme	P22303	ACES_HUMAN		IC50	4.59	DRUG MATRIX
Estrogen receptor beta	Nuclear hormone receptor	Q92731	ESR2_HUMAN		Ki	9.20	CHEMBL
Estrogen-related receptor gamma	Nuclear hormone receptor	P62508	ERR3_HUMAN	ANTAGONIST	IC50	5.30	IUPHAR
Cysteinyl leukotriene receptor 1	GPCR	Q9Y271	CLTR1_HUMAN		Ki	5.05	CHEMBL
Vasopressin V1a receptor	GPCR	P37288	V1AR_HUMAN		Ki	4.98	DRUG MATRIX
Tyrosine-protein kinase Fyn	Kinase	P06241	FYN_HUMAN		IC50	4.85	DRUG MATRIX
Thromboxane-A synthase	Enzyme	P24557	THAS_HUMAN		IC50	5.36	DRUG MATRIX
Steroid hormone receptor ERR2	Nuclear hormone receptor	O95718	ERR2_HUMAN	ANTAGONIST	IC50	5.30	IUPHAR
Mitogen-activated protein kinase 14	Kinase	Q16539	MK14_HUMAN		IC50	4.48	DRUG MATRIX
Substance-K receptor	GPCR	P21452	NK2R_HUMAN		Ki	5.50	DRUG MATRIX
UDP-glucose 4-epimerase	Enzyme	Q14376	GALE_HUMAN		IC50	4.12	CHEMBL
Sodium/nucleoside cotransporter 1	Transporter	O00337	S28A1_HUMAN		Ki	5.32	DRUG MATRIX
Androgen receptor	Transcription factor		ANDR_RAT		IC50	4.85	CHEMBL
Arachidonate 15-lipoxygenase	Enzyme		LOX15_RABIT		IC50	5.53	DRUG MATRIX
Cysteinyl leukotriene receptor 1	GPCR		CLTR1_CAVPO		Ki	5.05	DRUG MATRIX
Progesterone receptor	Transcription factor		Q690N0_BOVIN		Ki	6.21	DRUG MATRIX
Alpha-1A adrenergic receptor	GPCR		ADA1A_RAT		IC50	4.71	CHEMBL
Steroid hormone receptor ERR1	Nuclear hormone receptor		ERR1_MOUSE	ANTAGONIST	IC50	5.30	IUPHAR
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	Enzyme		AT2A1_RABIT		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

Pharmaceutical products:

None