DIETHYLSTILBESTROL

US Previously Marketed

First approved in 1941

Details

Stereochemistry	ACHIRAL
Molecular Formula	C18H20O2
Molecular Weight	268.3502
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC\C(C1=CC=C(O)C=C1)=C(\CC)C2=CC=C(O)C=C2

InChI

InChIKey=RGLYKWWBQGJZGM-ISLYRVAYSA-N

InChI=1S/C18H20O2/c1-3-17(13-5-9-15(19)10-6-13)18(4-2)14-7-11-16(20)12-8-14/h5-12,19-20H,3-4H2,1-2H3/b18-17+

HIDE SMILES / InChI

Molecular Formula	C18H20O2
Molecular Weight	268.3502
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Description
Sources: http://druginfosys.com/Drug.aspx?drugCode=327&drugName=&type=0https://www.drugs.com/mmx/stilbestrol.html
Curator's Comment: description was created based on several sources, including: http://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/083003.pdf | https://en.wikipedia.org/wiki/Diethylstilbestrol | http://monographs.iarc.fr/ENG/Monographs/vol100A/mono100A-16.pdf

Diethylstilbestrol is a synthetic non-steroidal estrogen. It is used in the treatment of menopausal and postmenopausal disorders, prostate cancer and in the prevention of miscarriage or premature delivery in pregnant women prone to miscarriage or premature delivery. Diethylstilbestrol is a very potent full agonist of the estrogen receptors. At the cellular level, estrogens increase the synthesis of DNA, RNA, and various proteins in target tissues. Pituitary mass is also increased. Estrogens reduce the release of gonadotropin-releasing hormone from the hypothalamus, leading to a reduction in release of follicle-stimulating hormone and luteinizing hormone from the pituitary. Adverse effects are: breast pain or tenderness, enlargement of breasts, gynecomastia, peripheral edema and others. Estrogens may interfere with the effects of bromocriptine. Dosage adjustment may be needed. Concurrent use with estrogens may alter the metabolism and protein binding of the glucocorticoids, leading to decreased clearance, increased elimination half-life, and increased therapeutic and toxic effects of the glucocorticoids.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Estrogen receptor alpha 127 Target ID: CHEMBL206 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22294742	Agonist 2678	0.18 nM [EC50]
Estrogen receptor beta 110 Target ID: CHEMBL242 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22294742	Agonist 2678	0.06 nM [EC50]
Estrogen-related receptor alpha 12 Target ID: CHEMBL3429 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15161930 \| https://www.ncbi.nlm.nih.gov/pubmed/11447273	Inverse Agonist 80	10.0 µM [EC50]
Estrogen-related receptor beta 8 Target ID: CHEMBL3751 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11447273	Inverse Agonist 80	700.0 nM [EC50]
Estrogen-related receptor gamma 11 Target ID: CHEMBL4245 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11447273	Inverse Agonist 80	700.0 nM [EC50]
estrogen receptor 1 5 Target ID: P03372 Gene Symbol: ESR1 Sources: http://www.drugbank.ca/drugs/DB00255	Agonist 2678
estrogen-related receptor alpha 5 Target ID: P11474 Gene Symbol: ESRRA Sources: http://genesdev.cshlp.org/content/15/7/833.full	Inverse Agonist 80	1.0 µM [IC50]
estrogen-related receptor beta 5 Target ID: O95718 Gene Symbol: ESRRB Sources: http://genesdev.cshlp.org/content/15/7/833.full	Inverse Agonist 80	1.0 µM [IC50]
estrogen-related receptor gamma 5 Target ID: P62508 Gene Symbol: ESRRG Sources: http://genesdev.cshlp.org/content/15/7/833.full	Inverse Agonist 80	1.0 µM [IC50]
estrogen receptor 2 (ER beta) 5 Target ID: Q92731 Gene Symbol: ESR2 Sources: http://www.drugbank.ca/drugs/DB00255	Agonist 2678

Conditions

Condition	Modality	Highest Phase	Product
Prostate cancer 178 Sources: http://www.drugbank.ca/drugs/DB00255	Primary	Approved 8429	Stilphostrol Approved Use Unknown Launch Date 1981
Prostate cancer 178 Sources: https://www.drugs.com/mmx/stilbestrol.html	Primary	Approved 8429	STILBESTROL Approved Use Used in the treatment of prostate cancer. Launch Date 1973
Miscarriage 5 Sources: http://monographs.iarc.fr/ENG/Monographs/vol100A/mono100A-16.pdf	Preventing	Approved 8429	STILBESTROL Approved Use Prevention of miscarriage or premature delivery in pregnant women prone to miscarriage or premature delivery. Launch Date 1973
Atrophic vaginitis 13 Sources: https://www.drugs.com/mmx/stilbestrol.html	Primary	Approved 8429	STILBESTROL Approved Use It is used for the treatment of senile (atrophic) vaginitis. Launch Date 1973
Vulvar dystrophy 5 Sources: https://www.drugs.com/mmx/stilbestrol.html	Primary	Approved 8429	STILBESTROL Approved Use It is used for the treatment of vulvar dystrophy. Launch Date 1973
Menopausal syndrome 6 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/083003.pdf	Primary	Approved 8429	STILBESTROL Approved Use Other therapeutic use of diethylstilbestrol was post menopause syndrome. Launch Date 1973
Amenorrhea 18 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/083003.pdf	Primary	Approved 8429	STILBESTROL Approved Use Drug is indicated for replacement therapy of estrogen deficiency associated with amenorrhea. Launch Date 1973
Female hypogonadism 5 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/083003.pdf	Primary	Approved 8429	STILBESTROL Approved Use Drug is indicated for replacement therapy of estrogen deficiency associated with female hypogonadism. Launch Date 1973
Postmenopausal osteoporosis 59 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/083003.pdf	Preventing	Approved 8429	STILBESTROL Approved Use Drug is indicated for the prevention of osteoporosis. Launch Date 1973

Doses

Dose	Population	Adverse events
1104 mg 1 times / day multiple, intravenous Recommended Dose: 1104 mg, 1 times / day Route: intravenous Route: multiple Dose: 1104 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12496896/	unhealthy, 56-87 n = 17 Health Status: unhealthy Condition: prostate cancer Age Group: 56-87 Sex: M Population Size: 17 Sources: https://pubmed.ncbi.nlm.nih.gov/12496896/	Disc. AE: Vomiting... AEs leading to discontinuation/dose reduction: Vomiting (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/12496896/
600 mg 1 times / day multiple, oral Dose: 600 mg, 1 times / day Route: oral Route: multiple Dose: 600 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10526944/	unhealthy, 59 n = 1 Health Status: unhealthy Condition: prostate cancer Age Group: 59 Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/10526944/	Disc. AE: Secondary adrenocortical insufficiency... AEs leading to discontinuation/dose reduction: Secondary adrenocortical insufficiency Sources: https://pubmed.ncbi.nlm.nih.gov/10526944/
120 mg 3 times / day multiple, oral Recommended Dose: 120 mg, 3 times / day Route: oral Route: multiple Dose: 120 mg, 3 times / day Sources: https://www.ijmpo.org/article.asp?issn=0971-5851;year=2019;volume=40;issue=1;spage=79;epage=84;aulast=Kalaiyarasi	unhealthy, 65 n = 47 Health Status: unhealthy Condition: prostate cancer Age Group: 65 Sex: M Population Size: 47 Sources: https://www.ijmpo.org/article.asp?issn=0971-5851;year=2019;volume=40;issue=1;spage=79;epage=84;aulast=Kalaiyarasi	Disc. AE: Toxic reaction (NOS), Toxic reaction (NOS)... AEs leading to discontinuation/dose reduction: Toxic reaction (NOS) (grade 2, 3 patients) Toxic reaction (NOS) (grade 3, 2 patients) Sources: https://www.ijmpo.org/article.asp?issn=0971-5851;year=2019;volume=40;issue=1;spage=79;epage=84;aulast=Kalaiyarasi
5.7 g 1 times / day multiple, intravenous MTD Dose: 5.7 g, 1 times / day Route: intravenous Route: multiple Dose: 5.7 g, 1 times / day Co-administed with:: SALICYLIC ACID(200 mg; 1/day) Sources: https://pubmed.ncbi.nlm.nih.gov/7508621/	unhealthy, 68 n = 21 Health Status: unhealthy Condition: prostate cancer Age Group: 68 Sex: M Population Size: 21 Sources: https://pubmed.ncbi.nlm.nih.gov/7508621/	DLT: Nausea and vomiting, Nausea and vomiting... Dose limiting toxicities: Nausea and vomiting (grade 1, 13 patients) Nausea and vomiting (grade 2, 4 patients) Weight gain (2 patients) Edema (2 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/7508621/
100 mg 3 times / day multiple, oral Recommended Dose: 100 mg, 3 times / day Route: oral Route: multiple Dose: 100 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10761752/	unhealthy, 70 n = 38 Health Status: unhealthy Condition: prostate cancer Age Group: 70 Sex: M Population Size: 38 Sources: https://pubmed.ncbi.nlm.nih.gov/10761752/	Other AEs: Hypertension, Gynecomastia... Other AEs: Hypertension (5%) Gynecomastia (38%) Peripheral edema (32%) Gastrointestinal discomfort (19%) Deep vein thrombosis (8%) Skin rash (5%) Transaminases increased (2%) Sources: https://pubmed.ncbi.nlm.nih.gov/10761752/
1104 mg 1 times / day multiple, intravenous Dose: 1104 mg, 1 times / day Route: intravenous Route: multiple Dose: 1104 mg, 1 times / day Co-administed with:: MEPERIDINE(75 mg; i.m; 1/day) PROCHLORPERAZINE(12.5 mg; i.m; 1/day) Sources: https://pubmed.ncbi.nlm.nih.gov/9607886/	unhealthy, 74 n = 17 Health Status: unhealthy Condition: prostate cancer Age Group: 74 Sex: M Population Size: 17 Sources: https://pubmed.ncbi.nlm.nih.gov/9607886/	Other AEs: Nausea, Bone pain... Other AEs: Nausea (17 patients) Bone pain (17 patients) Perineal pain (1 patient) Deep vein thrombosis (4 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/9607886/
4 g 1 times / day multiple, intravenous RP2D Dose: 4 g, 1 times / day Route: intravenous Route: multiple Dose: 4 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/7508621/	unhealthy Health Status: unhealthy Condition: prostate cancer Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/7508621/	Sources: https://pubmed.ncbi.nlm.nih.gov/7508621/

AEs

Sourcing

Vendor/Aggregator	ID	URL
A2Z Chemical	AZM13788
ABI Chem	AC1MHWYU
Aurora Fine Chemicals LLC	K16.450.167	http://online.aurorafinechemicals.com/info?ID=K16.450.167
BLD Pharm	BD131559	http://www.bldpharm.com/products/4719-75-9.html
BOC Sciences	4719-75-9	https://www.bocsci.com/tetrasodium-fosfestrol-cas-4719-75-9-item-15065.html
Changzhou Highassay Chemical Co., Ltd	my_sub1996
ChemMol	99096292	http://www.chemmol.com/chemmol/99096292.html
Glentham Life Sciences	GP2439	http://www.glentham.com/products/product/GP2439/
Hairui	HR110840	http://www.hairuichem.com/en/product/23519-26-8.html
NovoSeek	3034148
PubChem	3034148	https://pubchem.ncbi.nlm.nih.gov/compound/3034148
iChemical	EBD43877	http://www.ichemical.com/chemicals/cas-4719-75-9

PubMed

Title	Date	PubMed
The Veterans' Administration Cooperative Urological Research Group studies of carcinoma of the prostate: a review.	1975 Jan-Feb	1093670
Induction of urogenital anomalies and some tumors in the progeny of mice receiving diethylstilbestrol during pregnancy.	1977 Apr	14781
Effects of estrogenic agents on chitobiase activity in the epidermis and hepatopancreas of the fiddler crab, Uca pugilator.	1999 Feb	10051369
Rapid inhibition of rat brain mitochondrial proton F0F1-ATPase activity by estrogens: comparison with Na+, K+ -ATPase of porcine cortex.	1999 Feb 26	10096774
Myopia in diethylstilboestrol exposed amblyopic subjects.	1999 Jan	10209454
A phase 1-2 trial of diethylstilbestrol plus low dose warfarin in advanced prostate carcinoma.	1999 Jan	10037391
Estrogen receptor activation via activation function 2 predicts agonism of xenoestrogens in normal and neoplastic cells of the uterine myometrium.	1999 Jul 1	10397250
The role of estrogen receptor, androgen receptor and growth factors in diethylstilbestrol-induced programming of prostate differentiation.	2000 Aug	11011959
Pubertal development and reproductive functions of Crl:CD BR Sprague-Dawley rats exposed to bisphenol A during prenatal and postnatal development.	2000 Jun	10828273
Differential estrogen receptor binding of estrogenic substances: a species comparison.	2000 Nov 15	11162928
Estrogen inhibition of cystic fibrosis transmembrane conductance regulator-mediated chloride secretion.	2000 Oct	10991979
Activation of a uterine insulin-like growth factor I signaling pathway by clinical and environmental estrogens: requirement of estrogen receptor-alpha.	2000 Sep	10965916
Cell-transforming activity and estrogenicity of bisphenol-A and 4 of its analogs in mammalian cells.	2001 Jul 1	11391616
4-Hydroxytamoxifen binds to and deactivates the estrogen-related receptor gamma.	2001 Jul 17	11447273
Metabolism of bisphenol A in isolated rat hepatocytes and oestrogenic activity of a hydroxylated metabolite in MCF-7 human breast cancer cells.	2001 Mar	11465389
Modulation by estrogens and xenoestrogens of recombinant human neuronal nicotinic receptors.	2001 Nov 2	11711029
Transcriptional regulation of the estrogen-inducible pS2 breast cancer marker gene by the ERR family of orphan nuclear receptors.	2001 Sep 15	11559547
Uterine responsiveness to estradiol and DNA methylation are altered by fetal exposure to diethylstilbestrol and methoxychlor in CD-1 mice: effects of low versus high doses.	2002 Aug 15	12217638
Cirrhosis with steatohepatitis following longterm stilboestrol treatment.	2003 Aug	12890826
The immune system of geriatric mice is modulated by estrogenic endocrine disruptors (diethylstilbestrol, alpha-zearalanol, and genistein): effects on interferon-gamma.	2003 Dec 15	14636701
Oxidative DNA damage induced by toluene is involved in its male reproductive toxicity.	2003 Jan	12653219
In vitro modulation of prolactin mRNA by toxaphene and 3,3',4,4'-tetrachlorobiphenyl.	2003 Jul	12804517
Estrogenic endocrine disruptive components interfere with calcium handling and differentiation of human trophoblast cells.	2003 Jul 1	12858341
Update on cryptorchidism: endocrine, environmental and therapeutic aspects.	2003 Jun	12952375
Differential expression of c-fos and c-myc protooncogenes by estrogens, xenobiotics and other growth-stimulatory agents in primary rat hepatocytes.	2003 Mar	12632255
Prenatal exposure to estrogenic compounds alters the expression pattern of platelet-derived growth factor receptors alpha and beta in neonatal rat testis: identification of gonocytes as targets of estrogen exposure.	2003 Mar	12604637
Study of 202 natural, synthetic, and environmental chemicals for binding to the androgen receptor.	2003 Oct	14565775
Comparison of the Hershberger assay and androgen receptor binding assay of twelve chemicals.	2004 Feb 15	14751673

Patents

Sample Use Guides

In Vivo Use Guide

360-480 mg 3 times/day. Maintenance: 120-240 mg 3 times/day.

Route of Administration: Oral

In Vitro Use Guide

1–20 µg/ml

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:35:47 GMT 2023` Edited by `admin` on `Fri Dec 15 16:35:47 GMT 2023`
Record UNII	731DCA35BT
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

DIETHYLSTILBESTROL

Official Name

English

Diethylstilbestrol [WHO-DD]

Common Name

English

STILBETIN

Brand Name

English

DIETHYLSTILBESTROL [ORANGE BOOK]

Common Name

English

DIETHYLSTILBESTROL [IARC]

Common Name

English

.ALPHA.,.ALPHA.'-DIETHYL-(E)-4,4'-STILBENEDIOL

Common Name

English

STILBESTRO

Brand Name

English

PHENOL 4,4'-(1,2-DIETHYL-1,2-ETHENEDIYL)BIS-, (E)-

Common Name

English

NSC-3070

Code

English

DIETHYLSTILBESTROL [MI]

Common Name

English

STILBESTROL

Brand Name

English

DIETHYLSTILBESTROL [USP-RS]

Common Name

English

DIETHYLSTILBESTROL [EP MONOGRAPH]

Common Name

English

DIETHYLSTILBESTROL [MART.]

Common Name

English

DIETHYLSTILBESTROL [HSDB]

Common Name

English

diethylstilbestrol [INN]

Common Name

English

DIETHYLSTILBESTROL [VANDF]

Common Name

English

DIETHYLSTILBESTROL [USP MONOGRAPH]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QG03CC05