CAS 56-53-1|CAS 6898-97-1|4-[(3E)-4-(4-hydroxyphenyl)hex-3-en-3-yl]phenol|estrogen|4,4'-(3-Hexene-3,4-diyl)diphenol|Stilbestrol|Diethylstilbestrol|DES|diethylstilbestrol|diethylstilboestrol|4-[4-(4-...

General Information

Structure

Molecular Formula

C₁₈H₂₀O₂

Molecular Mass

268.3502

Exact Mass

268.14632988

Charge

InChI

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

InChIKey

RGLYKWWBQGJZGM-UHFFFAOYSA-N

Canonic Smiles

CC/C(=C(\c1ccc(cc1)O)/CC)/c1ccc(cc1)O

Isomeric Smiles

Oc1ccc(/C(=C(\CC)/c2ccc(O)cc2)/CC)cc1

Calculated Properties

JChem

Acid pKa

9.129198

H Acceptors

H Donor

LogD (pH = 5.5)

5.1937814

LogD (pH = 7.4)

5.185866

Log P

5.193883

Molar Refractivity

83.2406

Polarizability

32.122524

Polar Surface Area

40.46

Rotatable Bonds

Lipinski's Rule of Five

false

ALOGPS 2.1

Log P

4.62

LOG S

-4.39

Solubility (Water)

1.09e-02 g/l

Data Source

Names and Identifiers

IUPAC name

4-[(3E)-4-(4-hydroxyphenyl)hex-3-en-3-yl]phenol 4-[4-(4-hydroxyphenyl)hex-3-en-3-yl]phenol

IUPAC Traditional name

estrogen diethylstilbestrol stil 4-[(3E)-4-(4-hydroxyphenyl)hex-3-en-3-yl]phenol

Synonyms

4,4'-(3-Hexene-3,4-diyl)diphenolStilbestrolDiethylstilbestrolDESdiethylstilboestrolDiethylstilbesterolRcra waste number U089Diethylstilboesteroltrans-Diethylstilbesteroltrans-DiethylstilbestrolDietilestilbestroltrans-DiethylstilboesterolPercutatrine oestrogenique iscovescoDiethylstilbestrol BPDEBStilbesterol, DESDIETHYLSTILBESTEROL(E)-3,4-Bis(4-hydroxyphenyl)-3-hexene己烯雌酚(E)-3,4-双(4-羟苯基)3-亚己基乙芪酚Diethylstilbestrol己烯雌酚，顺式和反式异构体混合物Diethylstilbestrol, mixture of cis and transBio-des(E)-4,4'-(1,2-Diethyl-1,2-ethenediyl)bisphenolAgostilben4,4'-Dihydroxy-α,β-diethylstilbene4,4'-[(1E)-1,2-Diethyl-1,2-ethenediyl]bisphenolComestroltrans-Diethyl StilbestrolAntigestil(E)-DiethylstilbestrolBufonBertrol4,4'-DihydroxydiethylstilbeneCyren ACyren4-[4-(4-hydroxyphenyl)hex-3-en-3-yl]phenol

Brand Name

Hi-BestrolOestromensilBio-desAgostilbenAntigestilStilbestrolPalestrolStilbolDomestrolSibolEstilbenPabestrolMicrestRumestrol 1SexocretinBufonStilbestroformComestrolSedestranMicroestOestromonDiastylSynthofolinTylosteroneStilphostrolGynopharmCyren AFonatolStilboestroformStilbofolinSerralStibiliumIscovescoDicorvinIdroestrilEstilbin MCOStilbestroneSyntofolinneo-Oestranol 1Rumestrol 2StilOestromieninProtectonaEstrosynStilboefralSintestrolFollidieneStilboestrolEstrilDi-EstrylAcnestrolMenostilbeenStilbetinSynthoestrinDyestrolStilbofollinGrafestrolMilestrolEstrobeneDestrolDibestrolstrobeneStilkapSynestrinOestrogenineStil-RolDiBestrol 2 PremixDawe's destrolMakarolNeo-Oestranol IComestrol estrobeneOeKolpNew-Estranol 1EstromeninSynthestrinTampovagan stilboestrolCyrenVagestrolOestromensylDesmaOestromeninClimaterineOestrol vetagDistilbeneEstrogenine

Names and Identifiers

Registration numbers

PubChem SID

16096360324893887248699342485310046507453

Beilstein Number

EC Number

CAS Number

MDL Number

PubChem CID

Registration numbers

Properties

Safety Information

false

Download link

Pharmacology Properties

human ... ESR1(2099), ESR2(2100), ESRRG(2104)mouse ... Esr1(13982)rat ... Ar(24208), Esr1(24890)

In the preovulatory-phase: produces changes in the tubular-mucosa

Encourages cornification of superficial vaginal-cells

The responsible for vaginal acidity caused by deposition of glycogen in the vaginal epithelium

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

DrugBank

DB00255

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]

Selleck Chemicals

S1859

Research Area: Endocrinology
Biological Activity:
Diethylstilbestrol(Stilbestrol), 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. Estrogens diffuse into their target cells and interact with a protein receptor. Target cells include the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. Estrogens increase 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. [1]

MP Biomedicals

02101560

Crystalline

Sigma Aldrich

D4628

Biochem/physiol Actions
Diethylstilbestrol is a synthetic estrogen with carcinogenic properties. Causes renal clear-cell carcinoma in Syrian hamster. In humans it causes increased risk of breast cancer, clear cell adenocarcinoma (CCA) of the vagina and cervix, and reproductive anomalies. Used in the treatment of prostate cancer to block the production of testosterone.

218944

Packaging
5 g in glass bottle

32500

Other Notes
A probe for studying the Fo "proton channel" of rat liver mitochondria1

46207

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

TRC

D445026

A synthetic, nonsteroidal estrogen.Recomended solvents are DMSO, DMF and ethanol, even in these solvents do not store in solution for any prolonged period of time.

Molecule Details

References

PubChem Literature

From Data Sources

• : 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

• Kuchera LK: Postcoital contraception with diethylstilbestrol. JAMA. 1971 Oct 25;218(4):562-3. Pubmed

• http://www.drugbank.ca/drugs/DB00255

• White, W. A. et. al.: J. Agric. Food Chem. 19(2)

• 388-390 (1971).

• Leimner, J. et al., Chem. Ber., 1982, 115, 3697, (synth, deriv)

• Oda, T. et al., Chem. Pharm. Bull., 1988, 36, 1534, (cmr)

• Solmssen, U.V., Chem. Rev., 1945, 37, 481, (rev, uv)

• Busetta, B., Acta Cryst. B, 1973, 29, 2456, (struct)

• Darden, T. et al., J.A.C.S., 1986, 108, 207, (conformn)

• Doskosch, J. et al., Monatsh. Chem., 1953, 84, 1146, (isom)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, DKA200; DKA600; DKB000; TEE300

• Metzler, M., Crit. Rev. Biochem., 1981, 10, 171, (rev, metab)

• Crawley, G.C., Kirk-Othmer Encycl. Chem. Technol., 3rd edn., Wiley, 1978, 12, 658, (pharmacol, toxicol)

• Al-Badr, A.A. et al., Anal. Profiles Drug Subst., 1990, 19, 145, (rev)

• Duax, W.L. et al., Environ. Health Perspect., 1985, 61, 111, (cryst struct)

• Schneider, M. et al., Eur. J. Med. Chem. (Chim. Ther.), 1982, 17, 49, (synth, deriv)

• Williard, P.G. et al., Tet. Lett., 1980, 21, 3731, (synth)

• Inamori, Y. et al., Chem. Pharm. Bull., 1985, 33, 4478, (pharmacol, uv, ir, pmr)

• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 4805; 4885; 5765

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 1185; 1195

• IARC Monog., 1979, 21, 131; 173; Suppl. 6, 250; Suppl. 7, 273, (rev, tox)

• Kharasch, N. et al., J.A.C.S., 1943, 65, 11, (synth)

• Engel, L.L. et al., Biomed. Mass Spectrom., 1978, 5, 582, (ms)

• Edelman, D.A., DES/Diethylstilbestrol - New Perspectives, MTP Press, 1986, (book)

References

Bioactivity

PubChem BioAssay

Bioactivity