Dienestrol: Difference between revisions

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Dienestrol
Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
ATC code	G03CB01 (WHO) G03CC02 (WHO);
Pharmacokinetic data
Protein binding	50 to 80%
Identifiers
	IUPAC name 4-[4-(4-hydroxyphenyl)hexa-2,4-dien-3-yl]phenol; p-[(E,E)-1-Ethylidene-2-(p-hydroxyphenyl)-2-butenyl]phenol;
CAS Number	84-17-3 ;
PubChem CID	667476;
DrugBank	DB00890 ;
ChemSpider	580857 ;
UNII	RRW32X4U1F;
KEGG	D00898 ;
ChEBI	CHEBI:4518 ;
ChEMBL	ChEMBL1018 ;
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C18H18O2
Molar mass	266.334 g/mol
3D model (JSmol)	Interactive image;
	SMILES Oc2ccc(C(/C(c1ccc(O)cc1)=C/C)=C\C)cc2;
	InChI InChI=1S/C18H18O2/c1-3-17(13-5-9-15(19)10-6-13)18(4-2)14-7-11-16(20)12-8-14/h3-12,19-20H,1-2H3/b17-3+,18-4+ ; Key:NFDFQCUYFHCNBW-SCGPFSFSSA-N ;
(what is this?) (verify)

VisualWikitext

Latest revision as of 13:37, 10 April 2015

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Dienestrol is a synthetic estrogen.

Synthesis

Pinacol coupling of p-acetoxy-propiophenone.
Dehydration of the thus-obtained glycol with a mixture of acetyl chloride and acetic anhydride leads to the transoid diene system (bis-β-Methylstyrene-type).
Saponification removes the acetate groups and thus affords dienestrol.

References

↑ Template:Cite doi

[1] Template:Cite doi

[1]

@@ Line 1: / Line 1: @@
-{{Editor Help}}
+{{Drugbox
+| Verifiedfields = changed
+| Watchedfields = changed
+| verifiedrevid = 460784619
+| IUPAC_name = 4-[4-(4-hydroxyphenyl)hexa-2,4-dien-3-yl]phenol; ''p''-[(''E,E'')-1-Ethylidene-2-(''p''-hydroxyphenyl)-2-butenyl]phenol
+| image = Dienestrol.svg
+<!--Clinical data-->
+| tradename =
+| Drugs.com = {{drugs.com|CONS|dienestrol}}
+| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
+| pregnancy_US = <!-- A / B / C / D / X -->
+| pregnancy_category =
+| legal_AU = <!-- Unscheduled / S2 / S4 / S8 -->
+| legal_UK = <!-- GSL / P / POM / CD -->
+| legal_US = <!-- OTC / Rx-only -->
+| legal_status =
+| routes_of_administration =
+<!--Pharmacokinetic data-->
+| bioavailability =
+| protein_bound = 50 to 80%
+| metabolism =
+| elimination_half-life =
+| excretion =
-{{drugbox
+<!--Identifiers-->
-| IUPAC_name = 4-[4-(4-hydroxyphenyl)hexa-2,4-dien-3-yl]phenol
+| CASNo_Ref = {{cascite|correct|CAS}}
-| image = Dienestrol.svg
+| CAS_number_Ref = {{cascite|changed|??}}
 | CAS_number = 84-17-3
 | ATC_prefix = G03
 | ATC_suffix = CB01
-| ATC_supplemental = {{ATC|G03|CC02}}
+| ATC_supplemental =  {{ATC|G03|CC02}}
-| PubChem = 3049
+| PubChem = 667476
-| DrugBank = APRD00917
+| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
-| C = 18 | H = 18 | O = 2
+ | DrugBank = DB00890
+| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
+| ChemSpiderID = 580857
+| UNII_Ref = {{fdacite|correct|FDA}}
+| UNII = RRW32X4U1F
+| KEGG_Ref = {{keggcite|correct|kegg}}
+| KEGG = D00898
+| ChEBI_Ref = {{ebicite|changed|EBI}}
+| ChEBI = 4518
+| ChEMBL_Ref = {{ebicite|correct|EBI}}
+| ChEMBL = 1018
+<!--Chemical data-->
+| C=18 | H=18 | O=2
 | molecular_weight = 266.334 g/mol
-| bioavailability =
+| smiles = Oc2ccc(C(/C(c1ccc(O)cc1)=C/C)=C\C)cc2
-| protein_bound = 50 to 80%
+| InChI = 1/C18H18O2/c1-3-17(13-5-9-15(19)10-6-13)18(4-2)14-7-11-16(20)12-8-14/h3-12,19-20H,1-2H3/b17-3+,18-4+
-| metabolism =
+| InChIKey = NFDFQCUYFHCNBW-SCGPFSFSBL
-| elimination_half-life =
+| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
-| excretion =
+| StdInChI = 1S/C18H18O2/c1-3-17(13-5-9-15(19)10-6-13)18(4-2)14-7-11-16(20)12-8-14/h3-12,19-20H,1-2H3/b17-3+,18-4+
-| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
+| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
-| pregnancy_US = <!-- A / B / C / D / X -->
+| StdInChIKey = NFDFQCUYFHCNBW-SCGPFSFSSA-N
-| pregnancy_category =
-| legal_AU = <!-- Unscheduled / S2 / S4 / S8 -->
-| legal_UK = <!-- GSL / P / POM / CD -->
-| legal_US = <!-- OTC / Rx-only -->
-| legal_status =
-| routes_of_administration =
 }}
+              __NOTOC__
 {{SI}}
+{{CMG}}
+==Overview==
 '''Dienestrol''' is a synthetic [[estrogen]].
-{{SIB}}
+==Synthesis==
+[[File:Dienestrol.png|center|thumb|700px|Dienestrol synthesis:<ref>{{Cite doi|10.1098/rspb.1939.0015}}</ref>]]
+#[[Pinacol coupling]] of ''[[para isomer|p]]''-[[acetoxy]]-[[propiophenone]].
+#[[Dehydration]] of the thus-obtained [[glycol]] with a mixture of [[acetyl chloride]] and [[acetic anhydride]] leads to the [[wikt:transoid|transoid]] [[diene]] system ([[bis]]-''β''-Methyl[[styrene]]-type).
+#[[Saponification]] removes the acetate groups and thus affords dienestrol.
+==See also==
+*[[Diethylstilbestrol]]
+==References==
+{{reflist|2}}
 [[Category:Synthetic estrogens]]
-[[Category:Endocrinology]]
+[[Category:Phenols]]
-{{Sex hormones}}
+[[Category:Drug]]
-{{WikiDoc Help Menu}}
-{{WikiDoc Sources}}

Dienestrol: Difference between revisions

Latest revision as of 13:37, 10 April 2015

Overview

Synthesis

See also

References

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