Mestranol

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'''Mestranol''' is the 3-[[methyl]] [[ether]] of [[ethinylestradiol]].  It was the [[estrogen]] used in many of the [[combined oral contraceptive pill|first oral contraceptives]].
 
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It is a biologically inactive [[prodrug]] of ethinylestradiol to which it is [[demethylation| demethylated]] in the liver with a conversion efficiency of 70% (50 µg of mestranol is [[pharmacokinetic| pharmacokinetically]] [[bioequivalent]] to 35 µg of ethinylestradiol).<ref name=faigle>{{cite book |author=Faigle, Johann W.; Schenkel, Lotte |editor=in Fraser, Ian S. (ed.) |year=1998 |chapter=Pharmacokinetics of estrogens and progestogens |title=Estrogens and Progestogens in Clinical Practice |pages=pp. 273-294 |location=London |publisher=Churchill Livingstone |id=ISBN 0-443-04706-5}}</ref>
 
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Pubchem(6291)
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==Description==
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The 3-methyl ether of ETHINYL ESTRADIOL. It must be demethylated to be  biologically active. It is used as the estrogen component of many  combination ORAL CONTRACEPTIVES.
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==General Properties==
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The 3-methyl ether of ETHINYL ESTRADIOL. It must be demethylated to be biologically active. It is used as the estrogen component of many combination ORAL CONTRACEPTIVES.
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<b>*Molecular Weight</b>
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'''KEGG'''(C07618,D00575)
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'''Activity''' Estrogen
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310.43
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{| border="1;width:100%; height:200px;style=text-align:center"
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|+'''Physiochemical properties of Mestranol:'''
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|-
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! style="background:brown; color:white" |Physical Property
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! style="background:brown; color:white" |Value
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! style="background:brown; color:white" |Units
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! style="background:brown; color:white" |Temp (deg C)
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! style="background:brown; color:white" |Source
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|-
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|Melting Point
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|150.5
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|deg C
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|  
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|EXP
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|-
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|log P (octanol-water)
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|4.680
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|(none)
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| 
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|EST
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|-
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|Atmospheric OH Rate Constant
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|9.04E-11
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|cm3/molecule-sec
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|25
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|EST
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|-
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|}
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{| border="1;width:100%; height:200px;style=text-align:center"
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|+'''Toxicity:'''
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|-
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! style="background:brown; color:white" |Organism
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! style="background:brown; color:white" |Test Type 
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! style="background:brown; color:white" |Route 
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! style="background:brown; color:white" |Reported Dose (Normalized Dose)
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! style="background:brown; color:white" |Effect
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! style="background:brown; color:white" |Source
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|-
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|mouse
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|LD50
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|intraperitoneal
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|> 3200mg/kg (3200mg/kg)
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|SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE
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BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
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<b>*Molecular Formula</b>
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SKIN AND APPENDAGES (SKIN): HAIR: OTHER
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C<sub>2</sub><sub>1</sub>H<sub>2</sub><sub>6</sub>O<sub>2</sub>
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|Oyo Yakuri. Pharmacometrics. Vol. 4, Pg. 217, 1970.
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|-
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|mouse
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|LD50
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|oral
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|> 10gm/kg (10000mg/kg)
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|SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE
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BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
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<b>*IUPAC NAME</b>
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SKIN AND APPENDAGES (SKIN): HAIR: OTHER
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(8R,9S,13S,14S,17R)-17-ethynyl-3-methoxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-ol
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|Oyo Yakuri. Pharmacometrics. Vol. 4, Pg. 217, 1970.
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|-
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|mouse
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|LD50
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|subcutaneous
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|2500mg/kg (2500mg/kg)
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|SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE
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SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE
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<b>*Canonical Smiles</b>
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SKIN AND APPENDAGES (SKIN): HAIR: OTHER
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CC12CCC3C(C1CCC2(C#C)O)CCC4=C3C=CC(=C4)OC
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|Oyo Yakuri. Pharmacometrics. Vol. 4, Pg. 217, 1970.
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|-
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|rat
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|LD50
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|intraperitoneal
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|> 3gm/kg (3000mg/kg)
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|BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
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GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS
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<b>*Isomeric Smiles</b>
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SKIN AND APPENDAGES (SKIN): HAIR: OTHER
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C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CCC4=C3C=CC(=C4)OC
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|Oyo Yakuri. Pharmacometrics. Vol. 4, Pg. 217, 1970.
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|-
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|rat
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|LD50
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|oral
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|> 10gm/kg (10000mg/kg)  
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|  
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|Oyo Yakuri. Pharmacometrics. Vol. 4, Pg. 217, 1970.
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|-
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|rat
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|LD50
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|subcutaneous
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|> 5gm/kg (5000mg/kg)
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|BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
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GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS
 
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SKIN AND APPENDAGES (SKIN): HAIR: OTHER
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==PhysioChemical Properties==
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|Oyo Yakuri. Pharmacometrics. Vol. 4, Pg. 217, 1970.
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|-
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|}
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==References==
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{{reflist}}
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{{Sex hormones}}
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<b>*Melting Point</b>
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[[Category:Hormonal contraception]]
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150.5(EXP)
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[[Category:Synthetic estrogens]]
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[[Category:Prodrugs]]
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[[de:Mestranol]]
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<b>*LogP</b>
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{{pharma-stub}}
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4.68(EST)
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<b>*Water Solubility</b>
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==External Links==
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*[http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=6291]Pubchem
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*[http://www.genome.jp/dbget-bin/www_bget?compound+C07618]KEGG Compound
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*[http://www.genome.jp/dbget-bin/www_bget?drug+D00575]KEGG Drug
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*[http://www.drugbank.ca/drugs/DB01357]Drugbank
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[[Categories:Hormones]]

Revision as of 00:00, 15 January 2001


Contents

Description

The 3-methyl ether of ETHINYL ESTRADIOL. It must be demethylated to be biologically active. It is used as the estrogen component of many combination ORAL CONTRACEPTIVES.

General Properties

*Molecular Weight

310.43

*Molecular Formula

C21H26O2

*IUPAC NAME

(8R,9S,13S,14S,17R)-17-ethynyl-3-methoxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-ol

*Canonical Smiles

CC12CCC3C(C1CCC2(C#C)O)CCC4=C3C=CC(=C4)OC

*Isomeric Smiles

C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CCC4=C3C=CC(=C4)OC


PhysioChemical Properties

*Melting Point

150.5(EXP)

*LogP

4.68(EST)

*Water Solubility


External Links

Categories:Hormones

Retrieved from "http://140949.jxltd.asia/drugpedia/index.php/Mestranol"