Norethisterone acetate

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Norethisterone acetate
Norethisterone acetate.svg
Acetato de noretisterona3D.png
Systematic (IUPAC) name
(8R,9S,10R,13S,14S,17S)-17-ethynyl-13-methyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl acetate
Clinical data
AHFS/Drugs.com International Drug Names
MedlinePlus a604034
Oral tablet
Identifiers
38673-38-0 YesY
PubChem CID 63021
ChemSpider 5627 N
ChEBI CHEBI:7628 N
ChEMBL CHEMBL1201146 N
Chemical data
Formula C22H28O3
340.456 g/mol
 N (what is this?)  (verify)

Norethisterone acetate (INN, BAN), also known as norethindrone acetate (USAN), sold under brand names including Aygestin, Gestakadin, Milligynon, Monogest, Norlutate (Canada, USA distributed by ERFA Canada 2012 Inc.[1]), Primolut (Fr., Ger., Swed.), Sovel, Styptin, and others, is a steroidal progestin with additional antigonadotropic (and hence antiandrogen and antiestrogen)[2] effects that is used as a hormonal contraceptive.[3][4] It is an acetate ester of norethisterone.[5] Norethindrone acetate is indicated for abnormal uterine bleedings.[6]

Synthesis[edit]

Riglovic progestational component:[7][8]

Reaction of norethindrone (1) with acetic anhydride in the presence of p-toluene sulfonic acid, affords norethindrone acetate (2).[7] This in turn affords, on reaction with exess cyclopentanol in the presence of excess phosphorus pentoxide, the 3-cyclopentyl enol ether (3),[8] the progestational component of Riglovic®.

See also[edit]

References[edit]

  1. ^ http://www.eci2012.net/
  2. ^ Garza-Flores J, Menjívar M, Cardenas M, Reynoso M, García GA, Pérez Palacios G (January 1991). "Further studies on the antigonadotropic mechanism of action of norethisterone". The Journal of Steroid Biochemistry and Molecular Biology 38 (1): 89–93. doi:10.1016/0960-0760(91)90406-U. PMID 1825472. 
  3. ^ F.. Macdonald (1997). Dictionary of Pharmacological Agents. CRC Press. p. 1450. ISBN 978-0-412-46630-4. Retrieved 12 May 2012. 
  4. ^ Index Nominum 2000: International Drug Directory. Taylor & Francis US. 2000. p. 750. ISBN 978-3-88763-075-1. Retrieved 30 May 2012. 
  5. ^ Norethisterone Acetate @ Drugs.com
  6. ^ http://www.drugs.com/ppa/norethindrone-acetate.html
  7. ^ a b Iriarte, J.; Djerassi, C.; Ringold, H. J. (1959). "Steroids. CVII.1Δ5(6)-19-Nor Steroids, a New Class of Potent Anabolic Agents2". Journal of the American Chemical Society 81 (2): 436. doi:10.1021/ja01511a042.  edit
  8. ^ a b Ercoli, A.; Gardi, R. (1960). "Δ4-3-Keto Steroidal Enol Ethers. Paradoxical Dependency of Their Effectiveness on the Administration Route". Journal of the American Chemical Society 82 (3): 746. doi:10.1021/ja01488a062.  edit