Turosteride

Turosteride
Clinical data
Other names1-(4-methyl-3-oxo-4-aza-5-alpha-androstane-17-beta-carbonyl)-1,3- diisopropylurea
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
  • Never marketed
Identifiers
IUPAC name
  • (4aR,4bS,6aS,7S,9aS,9bS,11aR)-1,4a,6a-trimethyl-2-oxo-N-(propan-2-yl)-N-(propan-2-ylcarbamoyl)hexadecahydro-1H-indeno[5,4-f]quinoline-7-carboxamide
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC27H45N3O3
Molar mass459.675 g·mol−1
3D model (JSmol)
SMILES
  • O=C(NC(C)C)N(C(=O)[C@@H]2[C@]1(CC[C@H]3[C@H]([C@@H]1CC2)CC[C@H]4N(C(=O)CC[C@]34C)C)C)C(C)C
InChI
  • InChI=1S/C27H45N3O3/c1-16(2)28-25(33)30(17(3)4)24(32)21-10-9-19-18-8-11-22-27(6,15-13-23(31)29(22)7)20(18)12-14-26(19,21)5/h16-22H,8-15H2,1-7H3,(H,28,33)/t18-,19-,20-,21+,22+,26-,27+/m0/s1
  • Key:WMPQMBUXZHMEFZ-YJPJVVPASA-N

Turosteride (FCE-26,073) is a selective inhibitor of the enzyme 5α-reductase which was under investigation by GlaxoSmithKline for the treatment of benign prostatic hyperplasia (BPH), but was never marketed.[1][2][3] Similarly to finasteride, turosteride is selective for the type II isoform of 5α-redcutase, with about 15-fold selectivity for it over type I isoform of the enzyme.[4][5] In animal studies it has been shown to inhibit prostate size and retard tumor growth.[2][3][6][7] It may also be useful for the treatment of acne and hair loss.[8]

See also

References

  1. ↑ David J. Triggle (1996). Dictionary of Pharmacological Agents. Boca Raton: Chapman & Hall/CRC. ISBN 0-412-46630-9.
  2. 1 2 di Salle E, Giudici D, Briatico G, Ornati G, Panzeri A (November 1993). "Hormonal effects of turosteride, a 5 alpha-reductase inhibitor, in the rat". The Journal of Steroid Biochemistry and Molecular Biology. 46 (5): 549–55. doi:10.1016/0960-0760(93)90181-U. PMID 8240976. S2CID 54390410.
  3. 1 2 Di Salle E, Briatico G, Giudici D, Ornati G, Panzeri A (February 1994). "Endocrine properties of the testosterone 5 alpha-reductase inhibitor turosteride (FCE 26073)". The Journal of Steroid Biochemistry and Molecular Biology. 48 (2–3): 241–8. doi:10.1016/0960-0760(94)90151-1. PMID 8142301. S2CID 54315230.
  4. ↑ Iehlé C, Délos S, Guirou O, Tate R, Raynaud JP, Martin PM (September 1995). "Human prostatic steroid 5 alpha-reductase isoforms--a comparative study of selective inhibitors". The Journal of Steroid Biochemistry and Molecular Biology. 54 (5–6): 273–9. doi:10.1016/0960-0760(95)00134-L. PMID 7577710. S2CID 37075222.
  5. ↑ Seiffert K, Seltmann H, Fritsch M, Zouboulis CC (February 2007). "Inhibition of 5alpha-reductase activity in SZ95 sebocytes and HaCaT keratinocytes in vitro". Hormone and Metabolic Research = Hormon- und Stoffwechselforschung = Hormones et Métabolisme. 39 (2): 141–8. doi:10.1055/s-2007-961814. PMID 17326010.
  6. ↑ Zaccheo T, Giudici D, di Salle E (February 1997). "Effect of turosteride, a 5 alpha-reductase inhibitor, on the Dunning R3327 rat prostatic carcinoma". The Prostate. 30 (2): 85–91. doi:10.1002/(SICI)1097-0045(19970201)30:2<85::AID-PROS3>3.0.CO;2-J. PMID 9051146.
  7. ↑ Zaccheo T, Giudici D, di Salle E (June 1998). "Effect of early treatment of prostate cancer with the 5alpha-reductase inhibitor turosteride in Dunning R3327 prostatic carcinoma in rats". The Prostate. 35 (4): 237–42. doi:10.1002/(SICI)1097-0045(19980601)35:4<237::AID-PROS1>3.0.CO;2-D. PMID 9609545.
  8. ↑ Rawlings, Anthony V.; Webster, Guy F. (2007). Acne and its therapy. New York: Informa Healthcare USA. ISBN 978-0-8247-2971-4.
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