δ4-Tibolone

Δ4-Tibolone
Clinical data
Other namesIsotibolone; ORG-OM-38; Delta-4-Tibolone; 7α-Methylnorethisterone; 7α-Methyl-17α-ethynyl-19-nortestosterone; 17α-Ethynyl-17β-hydroxy-7α-methyl-4-estren-3-one
Identifiers
  • (7R,8R,9S,10R,13S,14S,17R)-17-Ethynyl-17-hydroxy-7,13-dimethyl-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC21H28O2
Molar mass312.453 g·mol−1
3D model (JSmol)
  • C[C@@H]1CC2=CC(=O)CC[C@@H]2[C@@H]3[C@@H]1[C@@H]4CC[C@]([C@]4(CC3)C)(C#C)O
  • InChI=1S/C21H28O2/c1-4-21(23)10-8-18-19-13(2)11-14-12-15(22)5-6-16(14)17(19)7-9-20(18,21)3/h1,12-13,16-19,23H,5-11H2,2-3H3/t13-,16+,17-,18+,19-,20+,21+/m1/s1
  • Key:WAOKMNBZWBGYIK-KIURNNQRSA-N

δ4-Tibolone (developmental code ORG-OM-38; also known as isotibolone, 7α-methylnorethisterone, or 7α-methyl-17α-ethynyl-19-nortestosterone) is a synthetic androgen and progestin which was never marketed.[1][2] The compound is a major active metabolite of tibolone, which itself is a prodrug of δ4-tibolone along with 3α-hydroxytibolone and 3β-hydroxytibolone (which, in contrast to δ4-tibolone, are estrogens).[1] Tibolone and δ4-tibolone are thought to be responsible for the androgenic and progestogenic activity of tibolone, while 3α-hydroxytibolone and 3β-hydroxytibolone are thought to be responsible for its estrogenic activity.[1]

Activity

Isotibolone exhibited both estrogenic and progestogenic properties in several biological test systems and was found to be 10 to 40 times as potent as norethindrone in comparative assays. Tested for androgenic activity, it stimulated growth of seminal vesicles and the levator ani but was relatively inactive in stimulating prostate gland growth.[3]

See also

References

  1. ^ a b c Kuhl H (2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration" (PDF). Climacteric. 8 (Suppl 1): 3–63. doi:10.1080/13697130500148875. PMID 16112947. S2CID 24616324.
  2. ^ Escande A, Servant N, Rabenoelina F, Auzou G, Kloosterboer H, Cavaillès V, Balaguer P, Maudelonde T (2009). "Regulation of activities of steroid hormone receptors by tibolone and its primary metabolites". J. Steroid Biochem. Mol. Biol. 116 (1–2): 8–14. doi:10.1016/j.jsbmb.2009.03.008. PMID 19464167. S2CID 18346113.
  3. ^ Pharriss, B. B. (February 1970). "Biological properties of 17-ethinyl-7α-methyl-19-nortestosterone (U-13,851)". Contraception. 1 (2): 87–100. doi:10.1016/0010-7824(70)90049-1.


allikas: https://en.wikipedia.org/wiki/%CE%944-Tibolone