Nestorone

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Nestorone
Nestorone.svg
Systematic (IUPAC) name
(17α)-17-acetyl-16-methylene-3-oxoestr-4-en-17-yl acetate
Clinical data
Legal status
  • Prescription only
Routes Subcutaneous implant, vaginal ring, transdermal patch[1]
Pharmacokinetic data
Bioavailability 10% (oral)[1]
Half-life 1-2 hours (oral)[1]
Identifiers
CAS number 7759-35-5
ATC code None
PubChem CID 108059
ChemSpider 97161
Chemical data
Formula C23H30O4 
Mol. mass 370.482 g/mol

Nestorone (or nesteron), also known as elcometrine and ST-1435,[2] is a 19-norprogesterone derivative and steroidal progestin which is used as a hormonal contraceptive in several South American countries.[1]

Nestorone is only weakly active orally, and is instead given as a subcutaneous implant.[3] It is more than 100-fold times as potent when delivered subcutaneously relative to orally.[1]

Nestorone acts primarily as a high-affinity agonist of the progesterone receptor. It lacks significant affinity for the androgen receptor, and accordingly, does not produce any androgenic or anabolic effects. It does not bind to the estrogen receptor either. Nestorone does however have some affinity for the glucocorticoid receptor, where it appears to act as an agonist, but it does not appear to produce any glucocorticoid side effects unless used at high doses.[1][4] It does not bind to the mineralocorticoid receptor.[5]

Nestorone does not bind to sex hormone-binding globulin, and is instead bound to serum albumin.[1]

See also[edit]

References[edit]

  1. ^ a b c d e f g Thomas L. Lemke; David A. Williams; Victoria F. Roche; S. William Zito (24 January 2012). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. p. 1403. ISBN 978-1-60913-345-0. Retrieved 13 September 2012. 
  2. ^ Martin Negwer; Hans-Georg Scharnow (2001). Organic-chemical drugs and their synonyms: (an international survey). Wiley-VCH. ISBN 978-3-527-30247-5. Retrieved 13 September 2012. 
  3. ^ Sanjay Rajagopalan; Debabrata Mukherjee; Emile R. Mohler (31 August 2004). Manual of Vascular Diseases. Lippincott Williams & Wilkins. p. 803. ISBN 978-0-7817-4499-7. Retrieved 13 September 2012. 
  4. ^ Kumar N, Koide SS, Tsong Y, Sundaram K (2000). "Nestorone: a progestin with a unique pharmacological profile". Steroids 65 (10-11): 629–36. doi:10.1016/S0039-128X(00)00119-7. PMID 11108869. 
  5. ^ Hussain R, El-Etr M, Gaci O, et al. (October 2011). "Progesterone and Nestorone facilitate axon remyelination: a role for progesterone receptors". Endocrinology 152 (10): 3820–31. doi:10.1210/en.2011-1219. PMID 21828184.