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{{Drugbox
| verifiedrevid = 447568158
| IUPAC_name = 13-ethyl-17alpha-hydroxy-18,19 dinorpregna-4,9,11-trien-20-yn-3-one
| image = Gestrinone.png
| width = 203


<!--Clinical data-->
| tradename = 
| Drugs.com = {{drugs.com|international|gestrinone}}
| pregnancy_category = X
| legal_status = 
| routes_of_administration = [[Mouth|Oral]], Intravaginal


 
<!--Pharmacokinetic data-->
{{Drugbox|
| bioavailability =
|IUPAC_name =13-ethyl-17alpha-hydroxy-18,19 dinorpregna-4,9,11-trien-20-yn-3-one
| image=Gestrinone.svg
| width = 203px
| CAS_number=16320-04-0
| ATC_prefix=G03
| ATC_suffix=XA02
| ATC_supplemental=
| PubChem=27812
| DrugBank=
| C = 21 | H = 24 | O = 2
| molecular_weight = 308.4 g/mol
| bioavailability=  
| metabolism = [[Liver|Hepatic]]
| metabolism = [[Liver|Hepatic]]
| elimination_half-life=
| excretion = 
| pregnancy_category = X
| legal_status =
| routes_of_administration=
| excretion = [[Kidney|Renal]], fecal
| excretion = [[Kidney|Renal]], fecal
<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 16320-04-0
| ATC_prefix = G03
| ATC_suffix = XA02
| PubChem = 27812
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 25877
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 1421533RCM
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D04317
<!--Chemical data-->
| C=21 | H=24 | O=2
| molecular_weight = 308.41 g/mol
| smiles = O=C4\C=C3/C(=C2/C=C\[C@]1([C@@H](CC[C@]1(C#C)O)[C@@H]2CC3)CC)CC4
| InChI = 1/C21H24O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,9,11,13,18-19,23H,3,5-8,10,12H2,1H3/t18-,19+,20+,21+/m1/s1
| InChIKey = BJJXHLWLUDYTGC-ANULTFPQBO
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C21H24O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,9,11,13,18-19,23H,3,5-8,10,12H2,1H3/t18-,19+,20+,21+/m1/s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = BJJXHLWLUDYTGC-ANULTFPQSA-N
}}
}}
__NOTOC__
{{SI}}
{{SI}}
'''Gestrinone''' is a synthetic [[steroid]] [[hormone]] that acts as an anti-[[progestin]] and also has some [[androgen]]ic activity. 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.<ref>{{cite web| year = 2000| month = May| url =http://sport-dc.com/medcom/CANADA-LIST.pdf| title =Helping athletes compete drug-free| format =PDF| pages =34| publisher =Canadian Centre for Ethics in Sport| accessdate =2006-06-01}}</ref>
{{CMG}}
==Overview==
'''Gestrinone''' is a synthetic [[steroid]] with mixed [[progestogen]] and [[antiprogestogen]] (i.e., [[partial agonist]]) effects, and also has some mild [[androgen]]ic activity.<ref name="BromhamBooker1995">{{cite journal | last1 = Bromham | first1 = D. R. | last2 = Booker | first2 = M. W. | last3 = Rose | first3 = Gillian | last4 = Wardle | first4 = P. G. | last5 = Newton | first5 = J. R. | title = A multicentre comparative study of gestrinone and danazol in the treatment of endometriosis | journal = Journal of Obstetrics and Gynaecology | volume = 15 | issue = 3 | year = 1995 | pages = 188–194 | issn = 0144-3615 | doi = 10.3109/01443619509015498}}</ref> 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]].<ref>{{cite web|date=May 2000| url =http://sport-dc.com/medcom/CANADA-LIST.pdf| title =Helping athletes compete drug-free| format =PDF| pages =34| publisher =Canadian Centre for Ethics in Sport| accessdate =2006-06-01 |archiveurl = http://web.archive.org/web/20060517045357/http://sport-dc.com/medcom/CANADA-LIST.pdf <!-- Bot retrieved archive --> |archivedate = 2006-05-17}}</ref>


==Method of action==
==Method of action==
Its mechanism of action consists of suppression of the release of [[pituitary]] [[gonadotropin]]s. 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]].<ref>{{cite journal | last = Tamaya | first = T. | coauthors = Fujimoto J., Watanabe Y., Arahori K. & Okada H. | year = 1986 | title = Gestrinone (R2323) binding to steroid receptors in human uterine endometrial cytosol | journal = Acta obstetricia et gynecologica Scandinavica | volume = 65 | issue = 5 | pages = 439-41 | id = PMID 3490730 | accessdate = 2006-06-01}}</ref>
Its mechanism of action consists of suppression of the release of [[pituitary]] [[gonadotropin]]s. 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]].<ref>{{cite journal | doi = 10.3109/00016348609157380 | last = Tamaya | first = T. | coauthors = Fujimoto J., Watanabe Y., Arahori K. & Okada H. | year = 1986 | title = Gestrinone (R2323) binding to steroid receptors in human uterine endometrial cytosol | journal = Acta obstetricia et gynecologica Scandinavica | volume = 65 | issue = 5 | pages = 439–41 | pmid = 3490730 | accessdate = 2006-06-01}}</ref>
==Metabolism==
==Metabolism==
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.
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.
Line 37: Line 59:


==Other uses==
==Other uses==
The drug has also been investigated for use as a prospective [[contraceptive]] agent and as a [[Emergency contraception|postcoital contraceptive]].<ref>{{cite web| year = 2006| month =October| url =http://www.cecinfo.org/files/ecupdate-9610.rtf| title =Emergency Contraception Update | format =RTF| pages =5| publisher =International Consortium for Emergency Contraception| accessdate =2006-06-01}}</ref>  It also has been used to shrink [[uterine fibroid]]s and to reduce [[menorrhagia]]<ref>{{cite journal | last = La Marca | first = A. | coauthors = Giulini S., Vito G., Orvieto R., Volpe A. & Jasonni V.M. | year = 2004 | month = December | title = Gestrinone in the treatment of uterine leiomyomata: effects on uterine blood supply | journal = Fertility and Sterility | volume = 82 | issue = 6 | pages = 1694-6 | id = PMID 15589885 | accessdate = 2006-06-01}}</ref><ref>{{cite journal | last = Roy | first = SN. | coauthors = Bhattacharya S. | year = 2004 | title = Benefits and risks of pharmacological agents used for the treatment of menorrhagia | journal = Drug safety : an international journal of medical toxicology and drug experience | volume = 27 | issue = 2 | pages = 75-90 | id = PMID 14717620 | accessdate = 2006-06-01}}</ref>
The drug has also been investigated for use as a prospective [[contraceptive]] agent and as a [[Emergency contraception|postcoital contraceptive]].<ref>{{cite web|date=October 2006| url =http://www.cecinfo.org/files/ecupdate-9610.rtf| title =Emergency Contraception Update | format =RTF| pages =5| publisher =International Consortium for Emergency Contraception| accessdate =2006-06-01 |archiveurl = http://web.archive.org/web/20060620192932/http://www.cecinfo.org/files/ecupdate-9610.rtf <!-- Bot retrieved archive --> |archivedate = 2006-06-20}}</ref>  It also has been used to shrink [[uterine fibroid]]s and to reduce [[menorrhagia]]<ref>{{cite journal | last = La Marca | first = A. | coauthors = Giulini S., Vito G., Orvieto R., Volpe A. & Jasonni V.M. |date=December 2004 | title = Gestrinone in the treatment of uterine leiomyomata: effects on uterine blood supply | journal = Fertility and Sterility | volume = 82 | issue = 6 | pages = 1694–6 | pmid = 15589885 | accessdate = 2006-06-01 | doi = 10.1016/j.fertnstert.2004.08.004}}</ref><ref>{{cite journal | last = Roy | first = SN. |author2=Bhattacharya S. | year = 2004 | title = Benefits and risks of pharmacological agents used for the treatment of menorrhagia | journal = Drug safety : an international journal of medical toxicology and drug experience | volume = 27 | issue = 2 | pages = 75–90 | pmid = 14717620 | accessdate = 2006-06-01 | doi=10.2165/00002018-200427020-00001}}</ref>


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.
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==
==References==
<div class="references-small">
{{Reflist|2}}
<references/>
</div>
 
==External links==
* [http://emc.medicines.org.uk/emc/assets/c/html/displaydoc.asp?DocumentID=674 Prescription information]


{{Sex hormones}}
[[Category:Alkynes]]
[[Category:Anabolic steroids]]
[[Category:Anabolic steroids]]
[[Category:Endocrinology]]
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Latest revision as of 15:07, 13 April 2015

Gestrinone
Clinical data
AHFS/Drugs.comInternational Drug Names
Pregnancy
category
  • X
Routes of
administration		Oral, Intravaginal
ATC code
Pharmacokinetic data
MetabolismHepatic
ExcretionRenal, fecal
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
E number{{#property:P628}}
ECHA InfoCard{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
FormulaC21H24O2
Molar mass308.41 g/mol
3D model (JSmol)
  (verify)

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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

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

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

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

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

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

  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 (PDF) on 2006-05-17. Retrieved 2006-06-01.
  3. ↑ Tamaya, T. (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. Unknown parameter |coauthors= ignored (help); |access-date= requires |url= (help)
  4. ↑ "Emergency Contraception Update". International Consortium for Emergency Contraception. October 2006. p. 5. Archived from the original (RTF) on 2006-06-20. Retrieved 2006-06-01.
  5. ↑ La Marca, A. (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. Unknown parameter |coauthors= ignored (help); |access-date= requires |url= (help)
  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. |access-date= requires |url= (help)
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