Regonyl

Regonyl
Clinical data
Other namesTX-380; NSC-69588; 17α-Ethynyl-5α-androst-2-en-17β-ol 17β-acetate; 17β-Acetoxy-5α,17α-pregn-2-en-20-yne
Identifiers
  • [(5S,8R,9S,10S,13S,14S,17R)-17-ethynyl-10,13-dimethyl-1,4,5,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl] acetate
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC23H32O2
Molar mass340.507 g·mol−1
3D model (JSmol)
  • CC(=O)O[C@]1(CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@@H]4[C@@]3(CC=CC4)C)C)C#C
  • InChI=1S/C23H32O2/c1-5-23(25-16(2)24)15-12-20-18-10-9-17-8-6-7-13-21(17,3)19(18)11-14-22(20,23)4/h1,6-7,17-20H,8-15H2,2-4H3/t17-,18-,19+,20+,21+,22+,23+/m1/s1
  • Key:SQRBBVVZRKZEPF-OWNQEUAMSA-N

Regonyl (developmental code name TX-380), also known as 17α-ethynyl-5α-androst-2-en-17β-ol 17β-acetate, is a steroidal drug described as an antiprogestogen and "antiprolactin" (prolactin inhibitor).[1][2][3][4][5] It was studied for lactation inhibition in bitches.[4][5] It has minimal to no androgenic, estrogenic, or progestogenic activity but is said to strongly inhibit the hypothalamic–pituitary–gonadal axis at central and peripheral levels and to markedly oppose the action of progesterone.[2][3][6] However, the antiprogestogenic effects of regonyl do not appear to be due to direct interaction with the progesterone receptor.[6] The actions of regonyl result in estrus cycle disturbances and impaired ovulation.[2] Regonyl was proposed for use in humans, for instance in the treatment of gynecological disorders like endometriosis and benign breast disease, and in hormonal contraception.[2]

References

  1. ^ Negwer M, Scharnow HJ (5 December 2001). Organic-Chemical Drugs and Their Synonyms (8 ed.). Wiley. ISBN 978-3-527-30247-5. OCLC 1076100373. 9663. C23H32O2. 124-85-6. 5α,17α-Pregn-2-en-20-yn-17-ol acetate = (5α,17α)-Pregn-2-en-20-yn-17-ol acetate (•). S Regonyl, TX-380. U Antiprolactin.
  2. ^ a b c d Paris J, Fournau P, Granero M, Lanquetin A, Thévenot R (July 1986). "Pharmacological profile of the new pituitary-gonadic suppressant 17 beta-acetoxy-5 alpha, 17 alpha-pregn-2-ene-20-yne". Arzneimittel-Forschung. 36 (7): 1069–1074. PMID 3768074.
  3. ^ a b Sureau C, ed. (1986). Control and Management of Parturition. John Libbey Eurotext. pp. 245–. ISBN 978-0-86196-096-5. OCLC 1065197209.
  4. ^ a b Boiteux P. Tarissement de la sécrétion lactée chez la chienne par l'acetoxy 17 beta ethinyl 17 alpha (5 alpha) androstène 2 (regonyl nd) [Drying up of milk secretion in female dogs by acetoxy 17 beta ethinyl 17 alpha (5 alpha) androstene 2 (regonyl nd)] (Ph.D. thesis).
  5. ^ a b Calvin C (1989). Secretion Lactee D'origine Nerveuse Chez La Chienne, Traitement: Regonyl [Milky Secretion of Nervous Origin in Dogs, Treatment: Regonyl] (Ph.D. thesis).
  6. ^ a b Agarwal MK, Raynaud JP (13 March 1989). "Steroid antagonists Satellite workshop of the 8th International Congress of Endocrinology, Kyodai Kaikan, Kyoto, Japan". FEBS Letters. 245 (1–2): 1–3. doi:10.1016/0014-5793(89)80178-4. ISSN 0014-5793. S2CID 83951303.

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