Dienestrol: Difference between revisions

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{{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
| CAS_number = 84-17-3
| ATC_prefix = G03
| ATC_prefix = G03
| ATC_suffix = CB01
| 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
| 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 =  
}}
}}
{{SI}}
'''Dienestrol''' is a synthetic [[estrogen]].
'''Dienestrol''' is a synthetic [[estrogen]].


==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}}
{{Estrogenics}}
[[Category:Synthetic estrogens]]
[[Category:Synthetic estrogens]]
[[Category:Endocrinology]]
[[Category:Phenols]]
{{Sex hormones}}
 
{{WikiDoc Help Menu}}
 
{{WikiDoc Sources}}
{{genito-urinary-drug-stub}}

Revision as of 13:34, 10 April 2015

Dienestrol
Clinical data
AHFS/Drugs.comMicromedex Detailed Consumer Information
ATC code
Pharmacokinetic data
Protein binding50 to 80%
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
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
FormulaC18H18O2
Molar mass266.334 g/mol
3D model (JSmol)
 ☒N☑Y (what is this?)  (verify)

Dienestrol is a synthetic estrogen.

Synthesis

Dienestrol synthesis:[1]
  1. Pinacol coupling of p-acetoxy-propiophenone.
  2. 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).
  3. Saponification removes the acetate groups and thus affords dienestrol.

See also

References

  1. ↑ Template:Cite doi


Template:Genito-urinary-drug-stub

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