Product Name

Diethylstilbestrol

CAS Number

56-53-1

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Product Name:
Diethylstilbestrol
CAS Number:
56-53-1
Indication:
Used in the treatment of prostate cancer. Previously used in the prevention of miscarriage or premature delivery in pregnant women prone to miscarriage or premature delivery.
Mode of Action:

Estrogens diffuse into their target cells and interact with a protein receptor, the estrogen receptor. Target cells include the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. The effect of Estrogen binding their receptors causes downstream increases the hepatic synthesis of sex hormone binding globulin (SHBG), thyroid-binding globulin (TBG), and other serum proteins and suppress follicle-stimulating hormone (FSH) from the anterior pituitary. The combination of an estrogen with a progestin suppresses the hypothalamic-pituitary system, decreasing the secretion of gonadotropin-releasing hormone (GnRH).

Pharmacodynamics:

Diethylstilbestrol is a synthetic estrogen that was developed to supplement a woman's natural estrogen production. In 1971, the Food and Drug Administration (FDA) issued a Drug Bulletin advising physicians to stop prescribing DES to pregnant women because it was linked to a rare vaginal cancer in female offspring.

Metabolism:

Hepatic.

Toxicity:

Symptoms of overdose include nausea and vomiting, and withdrawal bleeding may occur in females.

IUPAC:
4-[4-(4-hydroxyphenyl)hex-3-en-3-yl]phenol
ATC:
G03CB02 G03CC05 L02AA01
PubChem:
448537
DrugBank:
DB00255 (APRD00920, EXPT01164)
Formula:
C24H30N2O2
Molecular Mass:
268.3502
Synonyms:
DES Diethylstilbesterol Diethylstilbestrol BP Diethylstilboesterol Dietilestilbestrol Percutatrine oestrogenique iscovesco Rcra waste number U089 trans-Diethylstilbesterol trans-Diethylstilbestrol trans-Diethylstilboesterol
SMILES:
CCC(=C(CC)C1=CC=C(O)C=C1)C1=CC=C(O)C=C1
AHFS Code:
08:16.0
InChi:
RGLYKWWBQGJZGM-ISLYRVAYSA-N
General Reference:
General Reference:

  1. : Leuprolide versus diethylstilbestrol for metastatic prostate cancer. The Leuprolide Study Group. N Engl J Med. 1984 Nov 15;311(20):1281-6. Pubmed
  2. DIECKMANN WJ, DAVIS ME, RYNKIEWICZ LM, POTTINGER RE: Does the administration of diethylstilbestrol during pregnancy have therapeutic value? Am J Obstet Gynecol. 1953 Nov;66(5):1062-81. Pubmed
  3. Ingle JN, Ahmann DL, Green SJ, Edmonson JH, Bisel HF, Kvols LK, Nichols WC, Creagan ET, Hahn RG, Rubin J, Frytak S: Randomized clinical trial of diethylstilbestrol versus tamoxifen in postmenopausal women with advanced breast cancer. N Engl J Med. 1981 Jan 1;304(1):16-21. Pubmed
  4. Kuchera LK: Postcoital contraception with diethylstilbestrol. JAMA. 1971 Oct 25;218(4):562-3. Pubmed
  5. Herbst AL, Ulfelder H, Poskanzer DC: Adenocarcinoma of the vagina. Association of maternal stilbestrol therapy with tumor appearance in young women. N Engl J Med. 1971 Apr 15;284(15):878-81. Pubmed

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