Diethylstilbestrol

• Catalog No.: DB00255
• CAS Number: 56-53-1
• M. F.: C18H20O2
• M. W.: 268.3502

SYNONYMS

• IUPAC name: 4-[4-(4-hydroxyphenyl)hex-3-en-3-yl]phenol
• IUPAC Traditional name: diethylstilbestrol
• Brand Name: Stilbestrone; Hi-Bestrol; Synestrin; Stilboestrol; Stibilium; Antigestil; Diastyl; Dicorvin; Estril; Iscovesco; New-Estranol 1; Oestrogenine; Oestromenin; Sibol; Stilbestrol; Stilbol; Tampovagan stilboestrol; Agostilben; Comestrol estrobene; Dawe's destrol; Di-Estryl; Dibestrol; Distilbene; Domestrol; Estilben; Follidiene; Gynopharm; Micrest; Neo-Oestranol I; Oestromensil; Oestromon; Pabestrol; Sedestran; Stil; Stilbestroform; Stilboestroform; Stilphostrol; Synthoestrin; neo-Oestranol 1; strobene; Acnestrol; Bio-des; Climaterine; Cyren; Cyren A; Desma; Destrol; DiBestrol 2 Premix; Dyestrol; Estrobene; Estrogenine; Estromenin; Estrosyn; Fonatol; Grafestrol; Makarol; Menostilbeen; Microest; OeKolp; Oestrol vetag; Oestromensyl; Oestromienin; Palestrol; Protectona; Rumestrol 1; Rumestrol 2; Sintestrol; Stil-Rol; Stilbetin; Stilboefral; Stilbofolin; Stilbofollin; Stilkap; Synthestrin; Tylosterone; Vagestrol; Bufon; Comestrol; Estilbin MCO; Idroestril; Milestrol; Serral; Sexocretin; Synthofolin; Syntofolin
• Synonyms: DES; DEB; Diethylstilbesterol; Diethylstilbestrol BP; Diethylstilboesterol; Dietilestilbestrol; Percutatrine oestrogenique iscovesco; Rcra waste number U089; trans-Diethylstilbesterol; trans-Diethylstilbestrol; trans-Diethylstilboesterol

DATABASE IDS

• CAS Number: 56-53-1
• PubChem SID: 46507453
• PubChem CID: 448537

PROPERTIES

• Hydrophobicity(logP): 5.07 [HANSCH,C ET AL. (1995)]
• Solubility: 0.012 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]

DETAILS

Description (English)

• Drug Groups: approved
• Description: 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)
• 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.
• Pharmacology: 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.
• Toxicity: Symptoms of overdose include nausea and vomiting, and withdrawal bleeding may occur in females.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic.
• References: : Leuprolide versus diethylstilbestrol for metastatic prostate cancer. The Leuprolide Study Group. N Engl J Med. 1984 Nov 15;311(20):1281-6. [Pubmed] ; 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] ; 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] ; Kuchera LK: Postcoital contraception with diethylstilbestrol. JAMA. 1971 Oct 25;218(4):562-3. [Pubmed] ; 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]
• External Links: Wikipedia

REFERENCES

• : Leuprolide versus diethylstilbestrol for metastatic prostate cancer. The Leuprolide Study Group. N Engl J Med. 1984 Nov 15;311(20):1281-6. Pubmed
• 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
• 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
• Kuchera LK: Postcoital contraception with diethylstilbestrol. JAMA. 1971 Oct 25;218(4):562-3. Pubmed
• 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