turosteride

{{Short description|Chemical compound}}

{{Infobox drug

| 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

| image = Turosteride_structure.png

| tradename =

| pregnancy_category =

| legal_status = Never marketed

| routes_of_administration = Oral

| bioavailability =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number = 137099-09-3

| ATC_prefix = none

| ATC_suffix =

| PubChem = 65986

| ChemSpiderID = 59380

| UNII_Ref = {{fdacite|correct|FDA}}

| 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.{{cite book | vauthors = Triggle DJ | title = Dictionary of Pharmacological Agents | publisher = Chapman & Hall/CRC | location = Boca Raton | year = 1996 | isbn = 0-412-46630-9 | url = https://books.google.com/books?id=Z_mfTTIApVEC}}{{cite journal | vauthors = di Salle E, Giudici D, Briatico G, Ornati G, Panzeri A | title = Hormonal effects of turosteride, a 5 alpha-reductase inhibitor, in the rat | journal = The Journal of Steroid Biochemistry and Molecular Biology | volume = 46 | issue = 5 | pages = 549–555 | date = November 1993 | pmid = 8240976 | doi = 10.1016/0960-0760(93)90181-U | s2cid = 54390410 }}{{cite journal | vauthors = Di Salle E, Briatico G, Giudici D, Ornati G, Panzeri A | title = Endocrine properties of the testosterone 5 alpha-reductase inhibitor turosteride (FCE 26073) | journal = The Journal of Steroid Biochemistry and Molecular Biology | volume = 48 | issue = 2–3 | pages = 241–248 | date = February 1994 | pmid = 8142301 | doi = 10.1016/0960-0760(94)90151-1 | s2cid = 54315230 }} 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.{{cite journal | vauthors = Iehlé C, Délos S, Guirou O, Tate R, Raynaud JP, Martin PM | title = Human prostatic steroid 5 alpha-reductase isoforms--a comparative study of selective inhibitors | journal = The Journal of Steroid Biochemistry and Molecular Biology | volume = 54 | issue = 5–6 | pages = 273–279 | date = September 1995 | pmid = 7577710 | doi = 10.1016/0960-0760(95)00134-L | s2cid = 37075222 }}{{cite journal | vauthors = Seiffert K, Seltmann H, Fritsch M, Zouboulis CC | title = Inhibition of 5alpha-reductase activity in SZ95 sebocytes and HaCaT keratinocytes in vitro | journal = Hormone and Metabolic Research = Hormon- und Stoffwechselforschung = Hormones et Métabolisme | volume = 39 | issue = 2 | pages = 141–148 | date = February 2007 | pmid = 17326010 | doi = 10.1055/s-2007-961814 }} In animal studies it has been shown to inhibit prostate size and retard tumor growth.{{cite journal | vauthors = Zaccheo T, Giudici D, di Salle E | title = Effect of turosteride, a 5 alpha-reductase inhibitor, on the Dunning R3327 rat prostatic carcinoma | journal = The Prostate | volume = 30 | issue = 2 | pages = 85–91 | date = February 1997 | pmid = 9051146 | doi = 10.1002/(SICI)1097-0045(19970201)30:2<85::AID-PROS3>3.0.CO;2-J | s2cid = 58856896 }}{{cite journal | vauthors = Zaccheo T, Giudici D, di Salle E | title = Effect of early treatment of prostate cancer with the 5alpha-reductase inhibitor turosteride in Dunning R3327 prostatic carcinoma in rats | journal = The Prostate | volume = 35 | issue = 4 | pages = 237–242 | date = June 1998 | pmid = 9609545 | doi = 10.1002/(SICI)1097-0045(19980601)35:4<237::AID-PROS1>3.0.CO;2-D | s2cid = 28001980 }} It may also be useful for the treatment of acne and hair loss.{{cite book | vauthors = Rawlings AV, Webster GF | title = Acne and its therapy | publisher = Informa Healthcare USA | location = New York | year = 2007 | isbn = 978-0-8247-2971-4 }}