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'''Stilbestrol''', or '''stilboestrol''', also known as '''4,4'-dihydroxystilbene''' or '''4,4'-stilbenediol''', is a [[stilbenoid]] and the [[parent compound]] of a group of [[non-steroid]]al [[estrogen]]s that includes, most notably, [[diethylstilbestrol]].<ref name="AcademicPress1945">{{cite book|title=VITAMINS AND HORMONES|url=http://books.google.com/books?id=7PrzbzO-Q2AC&pg=PA233|date=1 January 1945|publisher=Academic Press|isbn=978-0-08-086600-0|pages=233–}}</ref><ref name="Jessop2014">{{cite book|author=William John Edward Jessop|title=Fearon's Introduction to Biochemistry|url=http://books.google.com/books?id=bEGQBQAAQBAJ&pg=PA408|date=12 May 2014|publisher=Elsevier|isbn=978-1-4831-9556-8|pages=408–}}</ref> The term "stilbestrol" is often used incorrectly to refer to diethylstilbestrol, but they are not the same compound.<ref name="AcademicPress1945" />
'''Stilbestrol''', or '''stilboestrol''', also known as '''4,4'-dihydroxystilbene''' or '''4,4'-stilbenediol''', is a [[stilbenoid]] and the [[parent compound]] of a group of [[non-steroid]]al [[estrogen]]s that includes, most notably, [[diethylstilbestrol]].<ref name="AcademicPress1945">{{cite book|title=VITAMINS AND HORMONES|url=http://books.google.com/books?id=7PrzbzO-Q2AC&pg=PA233|date=1 January 1945|publisher=Academic Press|isbn=978-0-08-086600-0|pages=233–}}</ref><ref name="Jessop2014">{{cite book|author=William John Edward Jessop|title=Fearon's Introduction to Biochemistry|url=http://books.google.com/books?id=bEGQBQAAQBAJ&pg=PA408|date=12 May 2014|publisher=Elsevier|isbn=978-1-4831-9556-8|pages=408–}}</ref> The term "stilbestrol" is often used incorrectly to refer to diethylstilbestrol, but they are not the same compound.<ref name="AcademicPress1945" />


==Stilbestrol derivatives==
The stilbestrol estrogenic drugs include the following:
The stilbestrol estrogenic drugs include the following:


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** [[Methestrol dipropionate]] (promethestrol dipropionate)
** [[Methestrol dipropionate]] (promethestrol dipropionate)


Of the stilbestrol estrogens, diethylstilbestrol, hexestrol, and benzestrol were the most well-known.<ref name="Stanford">{{cite book|title=Actions and Uses of Drugs|url=http://books.google.com/books?id=02qmAAAAIAAJ&pg=PA234|publisher=Stanford University Press|isbn=978-0-8047-1505-8|pages=234–}}</ref>
Of the stilbestrol estrogens, diethylstilbestrol, hexestrol, and benzestrol are the most well-known.<ref name="Stanford">{{cite book|title=Actions and Uses of Drugs|url=http://books.google.com/books?id=02qmAAAAIAAJ&pg=PA234|publisher=Stanford University Press|isbn=978-0-8047-1505-8|pages=234–}}</ref>


===Mechanism of action===
The stilbestrol estrogens bind with high [[affinity (pharmacology)|affinity]] to both [[ERα]] and [[ERβ]].<ref name="KuiperCarlsson1997">{{cite journal|last1=Kuiper|first1=George G. J. M.|last2=Carlsson|first2=Bo|last3=Grandien|first3=Kaj|last4=Enmark|first4=Eva|last5=Häggblad|first5=Johan|last6=Nilsson|first6=Stefan|last7=Gustafsson|first7=Jan-Åke|title=Comparison of the Ligand Binding Specificity and Transcript Tissue Distribution of Estrogen Receptors α and β|journal=Endocrinology|volume=138|issue=3|year=1997|pages=863–870|issn=0013-7227|doi=10.1210/endo.138.3.4979}}</ref>
The stilbestrol estrogens bind with high [[affinity (pharmacology)|affinity]] to both [[ERα]] and [[ERβ]].<ref name="KuiperCarlsson1997">{{cite journal|last1=Kuiper|first1=George G. J. M.|last2=Carlsson|first2=Bo|last3=Grandien|first3=Kaj|last4=Enmark|first4=Eva|last5=Häggblad|first5=Johan|last6=Nilsson|first6=Stefan|last7=Gustafsson|first7=Jan-Åke|title=Comparison of the Ligand Binding Specificity and Transcript Tissue Distribution of Estrogen Receptors α and β|journal=Endocrinology|volume=138|issue=3|year=1997|pages=863–870|issn=0013-7227|doi=10.1210/endo.138.3.4979}}</ref>


===Closely related compounds===
Estrogens closely related to the stilbestrols include [[paroxypropione]] (a metabolite of diethylstilbestrol) and the [[anise]] and [[fennel]]-derived compounds [[anol]], [[dianol]], [[anethole]], [[dianethole]], and [[photoanethole]] (from which the stilbestrol estrogens were originally derived). The [[triphenylethylene]] group of estrogenic drugs such as [[estrobin]], [[chlorotrianisene]], [[broparestrol]], [[ethamoxytriphetol]], [[clomifene]], [[tamoxifen]], and more recently developed derivatives are also closely related to the stilbestrols.
Estrogens closely related to the stilbestrols include [[paroxypropione]] (a metabolite of diethylstilbestrol) and the [[anise]] and [[fennel]]-derived compounds [[anol]], [[dianol]], [[anethole]], [[dianethole]], and [[photoanethole]] (from which the stilbestrol estrogens were actually originally derived). The [[triphenylethylene]] group of estrogenic drugs that includes triphenylethylene itself, [[estrobin]], [[chlorotrianisene]], [[broparestrol]], [[ethamoxytriphetol]], [[clomifene]], [[tamoxifen]], and more recently developed derivatives is also very closely related structurally to the stilbestrols.


[[Resveratrol]] is a stilbenoid with estrogenic properties that is not a silbestrol derivative (it is 3,4',5-stilbenetriol).<ref name="pmid11606380">{{cite journal | author = Bhat KP, Lantvit D, Christov K, Mehta RG, Moon RC, Pezzuto JM | title = Estrogenic and antiestrogenic properties of resveratrol in mammary tumor models | journal = Cancer Res. | volume = 61 | issue = 20 | pages = 7456–63 | date = October 2001 | pmid = 11606380 | doi = | last2 = Lantvit | last3 = Christov | last4 = Mehta | last5 = Moon | last6 = Pezzuto }}</ref>
[[Resveratrol]] is a stilbenoid with estrogenic properties that is not technically a silbestrol derivative (it is 3,4',5-stilbenetriol).<ref name="pmid11606380">{{cite journal | author = Bhat KP, Lantvit D, Christov K, Mehta RG, Moon RC, Pezzuto JM | title = Estrogenic and antiestrogenic properties of resveratrol in mammary tumor models | journal = Cancer Res. | volume = 61 | issue = 20 | pages = 7456–63 | date = October 2001 | pmid = 11606380 | doi = | last2 = Lantvit | last3 = Christov | last4 = Mehta | last5 = Moon | last6 = Pezzuto }}</ref>


==See also==
==See also==

Revision as of 15:16, 13 September 2016

Stilbestrol
Names
IUPAC name
4-[(E)-2-(4-Hydroxyphenyl)ethenyl]phenol
Other names
4,4'-Dihydroxystilbene, 4,4'-stilbenediol
Identifiers
3D model (JSmol)
  • C1=CC(=CC=C1C=CC2=CC=C(C=C2)O)O
Properties
C14H12O2
Molar mass 212.24388 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Not to be confused with diethylstilbestrol.

Stilbestrol, or stilboestrol, also known as 4,4'-dihydroxystilbene or 4,4'-stilbenediol, is a stilbenoid and the parent compound of a group of non-steroidal estrogens that includes, most notably, diethylstilbestrol.[1][2] The term "stilbestrol" is often used incorrectly to refer to diethylstilbestrol, but they are not the same compound.[1]

Stilbestrol derivatives

The stilbestrol estrogenic drugs include the following:

Of the stilbestrol estrogens, diethylstilbestrol, hexestrol, and benzestrol are the most well-known.[3]

Mechanism of action

The stilbestrol estrogens bind with high affinity to both ERα and ERβ.[4]

Closely related compounds

Estrogens closely related to the stilbestrols include paroxypropione (a metabolite of diethylstilbestrol) and the anise and fennel-derived compounds anol, dianol, anethole, dianethole, and photoanethole (from which the stilbestrol estrogens were actually originally derived). The triphenylethylene group of estrogenic drugs that includes triphenylethylene itself, estrobin, chlorotrianisene, broparestrol, ethamoxytriphetol, clomifene, tamoxifen, and more recently developed derivatives is also very closely related structurally to the stilbestrols.

Resveratrol is a stilbenoid with estrogenic properties that is not technically a silbestrol derivative (it is 3,4',5-stilbenetriol).[5]

See also

References

  1. ^ a b VITAMINS AND HORMONES. Academic Press. 1 January 1945. pp. 233–. ISBN 978-0-08-086600-0.
  2. ^ William John Edward Jessop (12 May 2014). Fearon's Introduction to Biochemistry. Elsevier. pp. 408–. ISBN 978-1-4831-9556-8.
  3. ^ Actions and Uses of Drugs. Stanford University Press. pp. 234–. ISBN 978-0-8047-1505-8.
  4. ^ Kuiper, George G. J. M.; Carlsson, Bo; Grandien, Kaj; Enmark, Eva; Häggblad, Johan; Nilsson, Stefan; Gustafsson, Jan-Åke (1997). "Comparison of the Ligand Binding Specificity and Transcript Tissue Distribution of Estrogen Receptors α and β". Endocrinology. 138 (3): 863–870. doi:10.1210/endo.138.3.4979. ISSN 0013-7227.
  5. ^ Bhat KP, Lantvit D, Christov K, Mehta RG, Moon RC, Pezzuto JM; Lantvit; Christov; Mehta; Moon; Pezzuto (October 2001). "Estrogenic and antiestrogenic properties of resveratrol in mammary tumor models". Cancer Res. 61 (20): 7456–63. PMID 11606380.{{cite journal}}: CS1 maint: multiple names: authors list (link)



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