Gestrinone

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Gestrinone
Gestrinone.svg
Systematic (IUPAC) name
13-ethyl-17alpha-hydroxy-18,19 dinorpregna-4,9,11-trien-20-yn-3-one
Clinical data
AHFS/Drugs.com International Drug Names
Pregnancy cat. X
Legal status ?
Routes Oral, Intravaginal
Pharmacokinetic data
Metabolism Hepatic
Excretion Renal, fecal
Identifiers
CAS number 16320-04-0
ATC code G03XA02
PubChem CID 27812
ChemSpider 25877 YesY
UNII 1421533RCM YesY
KEGG D04317 YesY
Chemical data
Formula C21H24O2 
Mol. mass 308.41 g/mol
 YesY (what is this?)  (verify)

Gestrinone is a synthetic steroid with mixed progestogen and antiprogestogen (i.e., partial agonist) effects, and also has some mild androgenic activity.[1] It is marketed under the names Dimetriose, Dimetrose, and Nemestran, as a treatment for endometriosis. Gestrinone is available in many countries, but not in the USA. As it has anabolic effects, its use in competition has been banned by the International Olympic Committee.[2]

Method of action[edit]

Its mechanism of action consists of suppression of the release of pituitary gonadotropins. Gestrinone also interacts with the endometrium, inhibiting its growth. The inhibition is the result of gestrinone's interaction with the androgen receptor; this is also the reason for androgenic side effects. Gestrinone has been shown to interact with the estrogen receptor, the androgen receptor, and the progesterone receptor.[3]

Metabolism[edit]

The drug is well absorbed via the oral route, passed through the liver, and has a half-life of about 24 hours. It is metabolized by the liver and excreted by urine and feces.

Contraindications and side effects[edit]

The drug is contraindicated in pregnancy, during lactation, and in patients with severe cardiac, renal or hepatic insufficiency. It is also contraindicated in patients who experienced metabolic and/or vascular disorders during previous estrogen or progestogen therapy, or who are allergic to the medication. The drug is contraindicated in children.

Side effects include vaginal spotting, and, in susceptible individuals, signs of increased androgen activity such as acne, oily skin, fluid retention, weight gain, hirsutism, voice change, or hair loss.

Other uses[edit]

The drug has also been investigated for use as a prospective contraceptive agent and as a postcoital contraceptive.[4] It also has been used to shrink uterine fibroids and to reduce menorrhagia[5][6]

Its androgenic properties are more exploited in a "designer steroid", the derivative tetrahydrogestrinone. THG was banned by the Food and Drug Administration (FDA) in 2003.

References[edit]

  1. ^ Bromham, D. R.; Booker, M. W.; Rose, Gillian; Wardle, P. G.; Newton, J. R. (1995). "A multicentre comparative study of gestrinone and danazol in the treatment of endometriosis". Journal of Obstetrics and Gynaecology 15 (3): 188–194. doi:10.3109/01443619509015498. ISSN 0144-3615. 
  2. ^ "Helping athletes compete drug-free" (PDF). Canadian Centre for Ethics in Sport. May 2000. p. 34. Archived from the original on 2006-05-17. Retrieved 2006-06-01. 
  3. ^ Tamaya, T.; Fujimoto J., Watanabe Y., Arahori K. & Okada H. (1986). "Gestrinone (R2323) binding to steroid receptors in human uterine endometrial cytosol". Acta obstetricia et gynecologica Scandinavica 65 (5): 439–41. doi:10.3109/00016348609157380. PMID 3490730. 
  4. ^ "Emergency Contraception Update" (RTF). International Consortium for Emergency Contraception. October 2006. p. 5. Archived from the original on 2006-06-20. Retrieved 2006-06-01. 
  5. ^ La Marca, A.; Giulini S., Vito G., Orvieto R., Volpe A. & Jasonni V.M. (December 2004). "Gestrinone in the treatment of uterine leiomyomata: effects on uterine blood supply". Fertility and Sterility 82 (6): 1694–6. doi:10.1016/j.fertnstert.2004.08.004. PMID 15589885. 
  6. ^ Roy, SN.; Bhattacharya S. (2004). "Benefits and risks of pharmacological agents used for the treatment of menorrhagia". Drug safety : an international journal of medical toxicology and drug experience 27 (2): 75–90. doi:10.2165/00002018-200427020-00001. PMID 14717620. 

External links[edit]