RU-58841

Details

Stereochemistry	ACHIRAL
Molecular Formula	C17H18F3N3O3
Molecular Weight	369.3383
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1(C)N(CCCCO)C(=O)N(C1=O)C2=CC(=C(C=C2)C#N)C(F)(F)F

InChI

InChIKey=ARBYGDBJECGMGA-UHFFFAOYSA-N

InChI=1S/C17H18F3N3O3/c1-16(2)14(25)23(15(26)22(16)7-3-4-8-24)12-6-5-11(10-21)13(9-12)17(18,19)20/h5-6,9,24H,3-4,7-8H2,1-2H3

HIDE SMILES / InChI

Molecular Formula	C17H18F3N3O3
Molecular Weight	369.3383
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8136306
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/9415227 | https://www.ncbi.nlm.nih.gov/pubmed/9798729 | https://www.ncbi.nlm.nih.gov/pubmed/7625751 | https://www.ncbi.nlm.nih.gov/pubmed/9449168 | http://adisinsight.springer.com/drugs/800005990

RU58841 is a topically active non-steroidal antiandrogen. It demonstrated efficacy in animal models of androgen-dependent skin disorders such as acne and androgenetic alopecia. Under name of PSK 3841 was being developed by ProStrakan. It underwent clinical evaluation for the treatment of androgen-dependent conditions, such as acne and alopecia. Following the conclusion of phase II trials, no further development was reported. Based on this and the fact the compound is not listed on the companies pipeline, development is presumed discontinued.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Androgen Receptor 167 Target ID: CHEMBL1871 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9798729 \| https://www.ncbi.nlm.nih.gov/pubmed/8136306	Antagonist 2778

Conditions

Condition	Modality	Targets	Highest Phase	Product
Androgenic alopecia 8 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9798729 https://www.ncbi.nlm.nih.gov/pubmed/9415227 https://www.ncbi.nlm.nih.gov/pubmed/8136306	Primary		Phase II 1132	Unknown Approved Use Unknown
Acne 98 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7625751 https://www.ncbi.nlm.nih.gov/pubmed/9449168	Primary		Phase II 1132	Unknown Approved Use Unknown

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P001NZD	https://www.1pchem.com/search?query=1P001NZD
A2B Chem	AA76937	http://a2bchem.com/prod/AA76937
AChemBlock	10534	http://www.achemblock.com/catalogsearch/result/?q=10534
AK Scientific	Y0231	https://aksci.com/item_detail.php?cat=Y0231
Achemo Scientific Limited	AC-91862	http://www.achemo.com/search/?Keyword=AC-91862
Ambeed	A108339	http://www.ambeed.com/search/Search.html?keyword=A108339
ApexBio Technology	A3780	https://www.apexbt.com/catalogsearch/result/?q=A3780
AstaTech	40805	http://astatechinc.com/CPSResult.php?CRNO=40805
Axon MedChem	1680	https://www.axonmedchem.com/product/1680
BOC Sciences	154992-24-2	http://www.bocsci.com/description.asp?cas=154992-24-2
Capot Chemical	22486	https://www.capotchem.com/search.do?q=22486
Chem Scene	CS-0420	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0420
ChemShuttle	169571	https://www.chemshuttle.com/catalogsearch/result/?q=169571
Excenen	EX-A825	http://www.excenen.com/searchresultlist.php?id=EX-A825
Fluorochem	228200	http://www.fluorochem.co.uk/Products/Product?code=228200
Fluorochem	311291	http://www.fluorochem.co.uk/Products/Product?code=311291
Hairui	HR121849	http://www.hairuichem.com/en/product/search.do?q=HR121849
KeyOrganics	AS-74645	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-74645
Lab Network	LN01343319	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01343319
MedChem Express	HY-10561	https://www.medchemexpress.com/search.html?q=HY-10561&ft=&fa=&fp=
MolPort	MolPort-021-805-000	https://www.molport.com/shop/molecule-link/MolPort-021-805-000
Molnova	M12197	https://www.molnova.com/en/serch-list.html?keywords=M12197
MuseChem	I001957	https://www.musechem.com/product/I001957.html
Ryan Scientific	RU_58841	https://ryansci.com/products?q=RU_58841&list_q=&search_type=exact
Selleck Chemicals	S5285	http://www.selleckchem.com/search.html?searchDTO.searchParam=S5285
ShangHai Biochempartner	BCP000328	http://www.biochempartner.com/search_BCP000328
ShangHai Biochempartner	BCP02369	http://www.biochempartner.com/search_BCP02369
TargetMol	T2236	https://www.targetmol.com/search?keyword=T2236
Toronto Research Chemicals	R701505	https://www.trc-canada.com/product-detail/?CatNum=R701505
eMolecules	36745712	https://orderbb.emolecules.com/search/#?query=36745712
mcule	MCULE-5591296242	https://mcule.com/MCULE-5591296242/

PubMed

Title	Date	PubMed
RU 58841, a new specific topical antiandrogen: a candidate of choice for the treatment of acne, androgenetic alopecia and hirsutism.	1994 Jan	8136306
Preliminary pharmacokinetics and metabolism of novel non-steroidal antiandrogens in the rat: relation of their systemic activity to the formation of a common metabolite.	1994 Oct	7947350
Local inhibition of sebaceous gland growth by topically applied RU 58841.	1995 Jun 12	7625751
Effects of topical antiandrogen and 5-alpha-reductase inhibitors on sebaceous glands in male fuzzy rats.	1997	9449168
Importance of sebaceous glands in cutaneous penetration of an antiandrogen: target effect of liposomes.	1997 May	9145381
A controlled study of the effects of RU58841, a non-steroidal antiandrogen, on human hair production by balding scalp grafts maintained on testosterone-conditioned nude mice.	1997 Nov	9415227
Evaluation of RU58841 as an anti-androgen in prostate PC3 cells and a topical anti-alopecia agent in the bald scalp of stumptailed macaques.	1998 Aug	9798729
RU 58841-myristate--prodrug development for topical treatment of acne and androgenetic alopecia.	2005 Jan	15700772

Patents

Sample Use Guides

In Vivo Use Guide

Mice: topically (5 days/week) with RU58841 1% in ethanol. Stumptailed macaques: the topical application of RU58841 (a 5% solution in a propyleneglycol and isopropanol mixture).

Route of Administration: Transdermal

In Vitro Use Guide

RU58841 do not enhance androgen receptor transcriptional activity at 10 pM - 0.1 uM in PC3 cells.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:32:24 UTC 2023` Edited by `admin` on `Fri Dec 15 15:32:24 UTC 2023`
Record UNII	0D8FJQ0ADW
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

RU-58841

Code

English

4-(3-(4-HYDROXYBUTYL)-4,4-DIMETHYL-2,5-DIOXO-1-IMIDAZOLINDYL)-2-(TRIFLUOROMETHYL)-BENZONITRILE

Common Name

English

4-(4,4-DIMETHYL-2,5-DIOXO-3-(4-HYDROXYBUTYL)1-IMIDAZOLIDINYL)-2-(TRIFLUOROMETHYL)BENZONITRILE

Systematic Name

English

BENZONITRILE, 4-(3-(4-HYDROXYBUTYL)-4,4-DIMETHYL-2,5-DIOXO-1-IMIDAZOLIDINYL)-2-(TRIFLUOROMETHYL)-

Systematic Name

English

4-(3-(4-HYDROXYBUTYL)-4,4-DIMETHYL-2,5-DIOXO-1-IMIDAZOLIDINYL)-2-TRIFLUOROMETHYLBENZONITRILE

Systematic Name

English

Code System Code Type Description

PUBCHEM

132981