U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of DIETHYLSTILBESTROL

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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description

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 TargetPharmacologyConditionPotency
0.18 nM [EC50]
0.06 nM [EC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Stilphostrol
Primary
STILBESTROL
Preventing
STILBESTROL
Primary
STILBESTROL
Primary
STILBESTROL
Primary
STILBESTROL
Primary
STILBESTROL
Primary
STILBESTROL
Preventing
STILBESTROL

Doses

AEs

PubMed

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
Record UNII
731DCA35BT
Record Status Validated (UNII)
Record Version