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Details

Stereochemistry ABSOLUTE
Molecular Formula C27H45N3O3
Molecular Weight 459.6645
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TUROSTERIDE

SMILES

[H][C@@]12CC[C@H](C(=O)N(C(C)C)C(=O)NC(C)C)[C@@]1(C)CC[C@@]3([H])[C@@]2([H])CC[C@@]4([H])N(C)C(=O)CC[C@]34C

InChI

InChIKey=WMPQMBUXZHMEFZ-YJPJVVPASA-N
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

HIDE SMILES / InChI

Molecular Formula C27H45N3O3
Molecular Weight 459.6645
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 7 / 7
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Turosteride [FCE 26073] is a selective 5α-reductase inhibitor being developed by Pharmacia Corporation. Turosteride inhibits human and rat prostatic 5 alpha-reductases with IC50 values of 55 and 53 nM, respectively. It was in phase II clinical trials in Italy for the treatment of benign prostatic hyperplasia.

Originator

Approval Year

PubMed

Sample Use Guides

In Vivo Use Guide
The endocrine effects of turosteride were evaluated in adult male rats, treated orally at daily doses of 3, 10 and 30 mg/kg for 20 days. At these doses, the compound reduced the ventral prostate weight by 10, 33 and 42% and the intraprostatic total DHT content by 61, 74 and 78%, respectively, whereas no change in the intraprostatic content of T was observed.
Route of Administration: Oral
In Vitro Use Guide
Turosteride inhibits human and rat prostatic 5 alpha-reductases with IC50 values of 55 and 53 nM, respectively, whereas it caused a less marked inhibition of the dog enzyme (IC50 2.2 uM). Turosteride showed no relevant effect on rat adrenal C20,22-desmolase (IC50 254 uM) and human placental aromatase (IC50 > 100 uM), and only at relatively high concentrations it caused inhibition of human placental 5-ene-3 beta-hydroxysteroid dehydrogenase-isomerase (3 beta-HSD-I) (IC50 2.5 uM).
Substance Class Chemical
Record UNII
LU1LTK666W
Record Status Validated (UNII)
Record Version