TUROSTERIDE

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 Search

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

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	7 / 7
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://adisinsight.springer.com/drugs/800002567 | https://www.ncbi.nlm.nih.gov/pubmed/8142301

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

Title	Date	PubMed
Inhibition of 5alpha-reductase activity in SZ95 sebocytes and HaCaT keratinocytes in vitro.	2007 Feb	17326010

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 Created by `admin` on `Fri Dec 15 15:48:37 GMT 2023` Edited by `admin` on `Fri Dec 15 15:48:37 GMT 2023`
Record UNII	LU1LTK666W
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TUROSTERIDE

Official Name

English

1,3-DIISOPROPYL-1-((4-METHYL-3-OXO-4-AZA-5.ALPHA.-ANDROSTAN-17.BETA.-YL)CARBONYL)UREA

Common Name

English

turosteride [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C2319