Mestranol
From DrugPedia: A Wikipedia for Drug discovery
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| - | '''Mestranol''' | + | '''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) | Pubchem(6291) | ||
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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. | 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) | + | '''KEGG'''(C07618,D00575) |
'''Activity''' Estrogen | '''Activity''' Estrogen | ||
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|Oyo Yakuri. Pharmacometrics. Vol. 4, Pg. 217, 1970. | |Oyo Yakuri. Pharmacometrics. Vol. 4, Pg. 217, 1970. | ||
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| + | ==References== | ||
| + | {{reflist}} | ||
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| + | {{Sex hormones}} | ||
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| + | [[Category:Hormonal contraception]] | ||
| + | [[Category:Synthetic estrogens]] | ||
| + | [[Category:Prodrugs]] | ||
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| + | [[de:Mestranol]] | ||
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| + | {{pharma-stub}} | ||
Revision as of 06:53, 31 October 2008
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
| 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 |
| 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. |
