Turosteride Explained

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
Legal Status:Never marketed
Routes Of Administration:Oral
Cas Number:137099-09-3
Atc Prefix:none
Pubchem:65986
Chemspiderid:59380
Unii:LU1LTK666W
Synonyms:1-(4-methyl-3-oxo-4-aza-5-alpha-androstane-17-beta-carbonyl)-1,3- diisopropylurea
C:27
H:45
N:3
O:3
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
Stdinchi: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
Stdinchikey: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

Notes and References

  1. Book: Triggle DJ . Dictionary of Pharmacological Agents . Chapman & Hall/CRC . Boca Raton . 1996 . 0-412-46630-9 .
  2. di Salle E, Giudici D, Briatico G, Ornati G, Panzeri A . Hormonal effects of turosteride, a 5 alpha-reductase inhibitor, in the rat . The Journal of Steroid Biochemistry and Molecular Biology . 46 . 5 . 549–555 . November 1993 . 8240976 . 10.1016/0960-0760(93)90181-U . 54390410 .
  3. Di Salle E, Briatico G, Giudici D, Ornati G, Panzeri A . Endocrine properties of the testosterone 5 alpha-reductase inhibitor turosteride (FCE 26073) . The Journal of Steroid Biochemistry and Molecular Biology . 48 . 2–3 . 241–248 . February 1994 . 8142301 . 10.1016/0960-0760(94)90151-1 . 54315230 .
  4. Iehlé C, Délos S, Guirou O, Tate R, Raynaud JP, Martin PM . Human prostatic steroid 5 alpha-reductase isoforms--a comparative study of selective inhibitors . The Journal of Steroid Biochemistry and Molecular Biology . 54 . 5–6 . 273–279 . September 1995 . 7577710 . 10.1016/0960-0760(95)00134-L . 37075222 .
  5. Seiffert K, Seltmann H, Fritsch M, Zouboulis CC . 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 . 141–148 . February 2007 . 17326010 . 10.1055/s-2007-961814 .
  6. Zaccheo T, Giudici D, di Salle E . Effect of turosteride, a 5 alpha-reductase inhibitor, on the Dunning R3327 rat prostatic carcinoma . The Prostate . 30 . 2 . 85–91 . February 1997 . 9051146 . 10.1002/(SICI)1097-0045(19970201)30:2<85::AID-PROS3>3.0.CO;2-J . 58856896 .
  7. Zaccheo T, Giudici D, di Salle E . Effect of early treatment of prostate cancer with the 5alpha-reductase inhibitor turosteride in Dunning R3327 prostatic carcinoma in rats . The Prostate . 35 . 4 . 237–242 . June 1998 . 9609545 . 10.1002/(SICI)1097-0045(19980601)35:4<237::AID-PROS1>3.0.CO;2-D . 28001980 .
  8. Book: Rawlings AV, Webster GF . Acne and its therapy . Informa Healthcare USA . New York . 2007 . 978-0-8247-2971-4 .

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