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Namespace Prefixes

PrefixIRI
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Statements

Subject Item
n2:DB00255
rdf:type
n3:Drug
n3: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)
n3:generalReferences
# : Leuprolide versus diethylstilbestrol for metastatic prostate cancer. The Leuprolide Study Group. N Engl J Med. 1984 Nov 15;311(20):1281-6. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/6436700 # 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":http://www.ncbi.nlm.nih.gov/pubmed/13104505 # 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":http://www.ncbi.nlm.nih.gov/pubmed/7001242 # Kuchera LK: Postcoital contraception with diethylstilbestrol. JAMA. 1971 Oct 25;218(4):562-3. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/5171004 # 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":http://www.ncbi.nlm.nih.gov/pubmed/5549830
n3:group
approved
n3: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.
n3:manufacturer
n5:271B408A-363D-11E5-9242-09173F13E4C5 n5:271B4088-363D-11E5-9242-09173F13E4C5 n5:271B408B-363D-11E5-9242-09173F13E4C5 n5:271B4089-363D-11E5-9242-09173F13E4C5
owl:sameAs
n13:DB00255 n24:DB00255
dcterms:title
Diethylstilbestrol
adms:identifier
n10:Diethylstilbestrol n14:DES n15:PA449307 n16:C07620 n18:D00577 n19:DB00255 n20:4531 n21:2946 n25:448537 n26:46507453
n3:mechanismOfAction
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).
n3:packager
n5:271B4087-363D-11E5-9242-09173F13E4C5
n3:synonym
trans-Diethylstilbesterol 4,4'-dihydroxy-α,β-diethylstilbene Diethylstilbestrolum trans-Diethylstilbestrol alpha,Alpha'-diethyl-(e)-4,4'-stilbenediol (e)-4,4'-(1,2-Diethyl-1,2-ethenediyl)bisphenol Diethylstilbestrol Dietilestilbestrol Distilbene (E)-3,4-bis(4-hydroxyphenyl)-3-hexene α,α'-diethyl-(E)-4,4'-stilbenediol trans-4,4'-(1,2-diethyl-1,2-ethenediyl)bisphenol 4,4'-Dihydroxy-alpha,beta-diethylstilbene DES trans-Diethylstilboesterol Stilboestrol
n3:toxicity
Symptoms of overdose include nausea and vomiting, and withdrawal bleeding may occur in females.
n6:hasAHFSCode
n11:68-16-04
n3:synthesisReference
Adler, E.,Gie, G.J. and von Euler, H.; US. Patent 2,421,401; June 3, 1947; assigned to Hoffmann-La Roche, Inc.
n22:hasConcept
n23:M0006357
n3:IUPAC-Name
n4:271B4091-363D-11E5-9242-09173F13E4C5
n3:InChI
n4:271B4097-363D-11E5-9242-09173F13E4C5
n3:Molecular-Formula
n4:271B4096-363D-11E5-9242-09173F13E4C5
n3:Molecular-Weight
n4:271B4093-363D-11E5-9242-09173F13E4C5
n3:Monoisotopic-Weight
n4:271B4094-363D-11E5-9242-09173F13E4C5
n3:SMILES
n4:271B4095-363D-11E5-9242-09173F13E4C5
n3:Water-Solubility
n4:271B40A7-363D-11E5-9242-09173F13E4C5 n4:271B408F-363D-11E5-9242-09173F13E4C5
n3:logP
n4:271B408D-363D-11E5-9242-09173F13E4C5 n4:271B40A9-363D-11E5-9242-09173F13E4C5 n4:271B4090-363D-11E5-9242-09173F13E4C5
n3:logS
n4:271B408E-363D-11E5-9242-09173F13E4C5 n4:271B40AA-363D-11E5-9242-09173F13E4C5
n6:hasATCCode
n7:L02AA01 n7:G03CC05 n7:G03CB02
n3:H-Bond-Acceptor-Count
n4:271B409D-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Donor-Count
n4:271B409E-363D-11E5-9242-09173F13E4C5
n3:InChIKey
n4:271B4098-363D-11E5-9242-09173F13E4C5
n3:Polar-Surface-Area--PSA-
n4:271B4099-363D-11E5-9242-09173F13E4C5
n3:Polarizability
n4:271B409B-363D-11E5-9242-09173F13E4C5
n3:Refractivity
n4:271B409A-363D-11E5-9242-09173F13E4C5
n3:Rotatable-Bond-Count
n4:271B409C-363D-11E5-9242-09173F13E4C5
n3:affectedOrganism
Humans and other mammals
n3:casRegistryNumber
56-53-1
n3:category
n3:containedIn
n8:271B408C-363D-11E5-9242-09173F13E4C5
n3:Bioavailability
n4:271B40A3-363D-11E5-9242-09173F13E4C5
n3:Ghose-Filter
n4:271B40A5-363D-11E5-9242-09173F13E4C5
n3:MDDR-Like-Rule
n4:271B40A6-363D-11E5-9242-09173F13E4C5
n3:Melting-Point
n4:271B40A8-363D-11E5-9242-09173F13E4C5
n3:Number-of-Rings
n4:271B40A2-363D-11E5-9242-09173F13E4C5
n3:Physiological-Charge
n4:271B40A1-363D-11E5-9242-09173F13E4C5
n3:Rule-of-Five
n4:271B40A4-363D-11E5-9242-09173F13E4C5
n3:Traditional-IUPAC-Name
n4:271B4092-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-acidic-
n4:271B409F-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-basic-
n4:271B40A0-363D-11E5-9242-09173F13E4C5