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Mestranol


Mestranol
Systematic (IUPAC) name
(8S,9S,13S,14S,17S)-17-ethynyl-3-methoxy- 13-methyl-7,8,9,11,12,14,15,16-octahydro-6H- cyclopenta[a]phenanthren-17-ol
Identifiers
CAS number	72-33-3
ATC code	?
PubChem	6291
Chemical data
Formula	C₂₁H₂₆O₂
Mol. mass	310.43 g/mol
Pharmacokinetic data
Bioavailability	?
Metabolism	?
Half life	?
Excretion	?
Therapeutic considerations
Pregnancy cat.	?
Legal status
Routes	?

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

Additional recommended knowledge

Essential Laboratory Skills Guide

Weighing the right way

What is the Correct Way to Check Repeatability in Balances?

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).^[1]

References

^ Faigle, Johann W.; Schenkel, Lotte (1998). "Pharmacokinetics of estrogens and progestogens", in in Fraser, Ian S. (ed.): Estrogens and Progestogens in Clinical Practice. London: Churchill Livingstone, pp. 273-294. ISBN 0-443-04706-5.

v • d • e Sex hormones and related agents (primarily G03, also L02, H01C) - human endogenous in CAPS
Progestogens: (receptor)	PROGESTERONE, Desogestrel, Drospirenone, Dydrogesterone, Ethisterone, Etonogestrel, Ethynodiol diacetate, Gestodene, Gestonorone, Levonorgestrel, Lynestrenol, Medroxyprogesterone, Megestrol, Norelgestromin, Norethisterone, Norethynodrel, Norgestimate, Norgestrel, Norgestrienone, Tibolone Selective progesterone receptor modulator: Asoprisnil, CDB-4124 Antiprogestogen: Mifepristone
Androgens: (receptor)	TESTOSTERONE, Androstanolone, Fluoxymesterone, Mesterolone, Methyltestosterone, (see also anabolic steroids) Antiandrogens: Bicalutamide, Cyproterone, Flutamide, Nilutamide, Spironolactone
Estrogens: (receptor)	ESTRADIOL, ESTRIOL, ESTRONE, Chlorotrianisene, Dienestrol, Diethylstilbestrol, Ethinylestradiol, Fosfestrol, Mestranol, Polyestradiol phosphate Selective estrogen receptor modulator: Bazedoxifene, Clomifene, Fulvestrant, Lasofoxifene, Raloxifene, Tamoxifen, Toremifene Aromatase inhibitor: Aminogluthetimide, Anastrozole, Exemestane, Formestane, Letrozole, Vorozole
Gonadotropins: (FSHR/LHCGR)	ovulation stim.: Clomifene, Urofollitropin Antigonadotropins: Danazol, Gestrinone
GnRH: (receptor)	agonist: Buserelin, Goserelin, Histrelin, Leuprorelin, Nafarelin, Triptorelin antagonist: Abarelix, Cetrorelix, Ganirelix