Mestranol

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[http://172.141.127.22/raghava/hmrbase/test_extract.php?db=arun&table=nphormonet&id=1087&show=SHOW-3D Show 3-D Structure]
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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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<uploadedFileContents>NPH187.SDF</uploadedFileContents>
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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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<b>*Molecular Weight</b>
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Pubchem(6291)
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310.43
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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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'''KEGG'''(C07618,D00575)
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<b>*Molecular Formula</b>
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'''Activity''' Estrogen
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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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C<sub>2</sub><sub>1</sub>H<sub>2</sub><sub>6</sub>O<sub>2</sub>
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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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|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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(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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BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
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<b>*Canonical Smiles</b>
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SKIN AND APPENDAGES (SKIN): HAIR: OTHER
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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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CC12CCC3C(C1CCC2(C#C)O)CCC4=C3C=CC(=C4)OC
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SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE
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<b>*Isomeric Smiles</b>
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SKIN AND APPENDAGES (SKIN): HAIR: OTHER
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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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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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GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS
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SKIN AND APPENDAGES (SKIN): HAIR: OTHER
 +
|Oyo Yakuri. Pharmacometrics. Vol. 4, Pg. 217, 1970.
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|-
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|rat
 +
|LD50
 +
|oral
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|> 10gm/kg (10000mg/kg)
 +
|  
 +
|Oyo Yakuri. Pharmacometrics. Vol. 4, Pg. 217, 1970.
 +
|-
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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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==PhysioChemical Properties==
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GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS
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<b>*Melting Point</b>
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SKIN AND APPENDAGES (SKIN): HAIR: OTHER
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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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150.5(EXP)
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{{Sex hormones}}
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<b>*LogP</b>
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[[Category:Hormonal contraception]]
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[[Category:Synthetic estrogens]]
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[[Category:Prodrugs]]
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4.68(EST)
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[[de:Mestranol]]
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<b>*Water Solubility</b>
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{{pharma-stub}}
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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]]
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Current revision

Show 3-D Structure

Mestranol is the 3-methyl ether of ethinylestradiol. It was the estrogen used in many of the first oral contraceptives.

It is a biologically inactive prodrug of ethinylestradiol to which it is demethylated in the liver with a conversion efficiency of 70% (50 µg of mestranol is pharmacokinetically bioequivalent to 35 µg of ethinylestradiol).<ref name=faigle>Template:Cite book</ref>

Pubchem(6291)

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.

KEGG(C07618,D00575)

Activity Estrogen

Physiochemical properties of Mestranol:
Physical Property Value Units Temp (deg C) Source
Melting Point 150.5 deg C EXP
log P (octanol-water) 4.680 (none) EST
Atmospheric OH Rate Constant 9.04E-11 cm3/molecule-sec 25 EST
Toxicity:
Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal > 3200mg/kg (3200mg/kg) SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

SKIN AND APPENDAGES (SKIN): HAIR: OTHER

Oyo Yakuri. Pharmacometrics. Vol. 4, Pg. 217, 1970.
mouse LD50 oral > 10gm/kg (10000mg/kg) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

SKIN AND APPENDAGES (SKIN): HAIR: OTHER

Oyo Yakuri. Pharmacometrics. Vol. 4, Pg. 217, 1970.
mouse LD50 subcutaneous 2500mg/kg (2500mg/kg) SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE

SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

SKIN AND APPENDAGES (SKIN): HAIR: OTHER

Oyo Yakuri. Pharmacometrics. Vol. 4, Pg. 217, 1970.
rat LD50 intraperitoneal > 3gm/kg (3000mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS

SKIN AND APPENDAGES (SKIN): HAIR: OTHER

Oyo Yakuri. Pharmacometrics. Vol. 4, Pg. 217, 1970.
rat LD50 oral > 10gm/kg (10000mg/kg) Oyo Yakuri. Pharmacometrics. Vol. 4, Pg. 217, 1970.
rat LD50 subcutaneous > 5gm/kg (5000mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS

SKIN AND APPENDAGES (SKIN): HAIR: OTHER

Oyo Yakuri. Pharmacometrics. Vol. 4, Pg. 217, 1970.

[edit] References

Unknown extension tag "references"

Template:Sex hormonesde:Mestranol

Template:Pharma-stub

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