Mestranol

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Mestranol
Mestranol.svg
Systematic (IUPAC) name
3-Methoxy-19-nor-17α-pregna-1,3,5(10)-trien-20-yn-17-ol
Clinical data
AHFS/Drugs.com International Drug Names
MedlinePlus a601050
Legal status
?
Identifiers
CAS number 72-33-3 YesY
ATC code None
PubChem CID 6291
DrugBank DB01357
ChemSpider 6054 YesY
UNII B2V233XGE7 YesY
KEGG D00575 YesY
ChEBI CHEBI:6784 YesY
ChEMBL CHEMBL1201151 N
Synonyms (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
Chemical data
Formula C21H26O2 
Mol. mass 310.43 g/mol
 N (what is this?)  (verify)

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).[1]

Synthesis[edit]

The reaction of 17-keto steroids with nucleophiles illustrates the high degree of stereospecifity that is maintained in many steroid reactions; approach of that carbonyl group from the b face is virtually forbidden by the presence of the adjacent 18 methyl. The reaction products consequently consist of almost pure isomers from attack at the a face.

Preparation of Mestranol

Reaction of estrone 3-methyl ether with lithium acetylide thus leads to mestranol.[2]

See also[edit]

References[edit]

  1. ^ 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. 
  2. ^ Colton, F. B.; Nysted, L. N.; Riegel, B.; Raymond, A. L. (1957). "17-Alkyl-19-nortestosterones". Journal of the American Chemical Society 79 (5): 1123. doi:10.1021/ja01562a028.  edit
  3. ^ Revesz, C.; Banik, U. K.; Lefebvre, Y. (1970). "Ay-11483, A New Type of Orally Active Oestrogen". Reproduction 22: 27. doi:10.1530/jrf.0.0220027.  edit