Gestrinone

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Gestrinone
Clinical data
AHFS/Drugs.com	International Drug Names
Pregnancy; category	X;
Routes of; administration	Oral, Intravaginal
ATC code	G03XA02 (WHO) ;
Pharmacokinetic data
Metabolism	Hepatic
Excretion	Renal, fecal
Identifiers
	IUPAC name 13-ethyl-17alpha-hydroxy-18,19 dinorpregna-4,9,11-trien-20-yn-3-one;
CAS Number	16320-04-0 ;
PubChem CID	27812;
ChemSpider	25877 ;
UNII	1421533RCM;
KEGG	D04317 ;
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
Formula	C21H24O2
Molar mass	308.41 g/mol
3D model (JSmol)	Interactive image;
	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 InChI=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 ; Key:BJJXHLWLUDYTGC-ANULTFPQSA-N ;
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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

↑ 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.
↑ "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.
↑ 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)
↑ "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.
↑ 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)
↑ 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)

[BromhamBooker1995-1] 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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Clinical data

AHFS/Drugs.com	International Drug Names
Pregnancy category	X
Routes of administration	Oral, Intravaginal
ATC code	G03XA02 (WHO)
Pharmacokinetic data
Metabolism	Hepatic
Excretion	Renal, fecal
Identifiers
IUPAC name 13-ethyl-17alpha-hydroxy-18,19 dinorpregna-4,9,11-trien-20-yn-3-one
CAS Number	16320-04-0^Y
PubChem CID	27812
ChemSpider	25877^Y
UNII	1421533RCM
KEGG	D04317^Y
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
Formula	C₂₁H₂₄O₂
Molar mass	308.41 g/mol
3D model (JSmol)	Interactive image
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 InChI=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^Y Key:BJJXHLWLUDYTGC-ANULTFPQSA-N^Y
(verify)