RU 58841

Iupac Name：4-[3-(4-hydroxybutyl)-4,4-dimethyl-2,5-dioxoimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile

Molecular Weight：369.344

Modify Date.: 2022-11-22 15:45

Introduction: RU-58841 is a non-steroidal antiandrogen that binds to the androgen receptor (Kd = 1.8, 1.1, 5.6, 1.3, and 1.4 nM for human, rat, mouse, hamster prostate, and hamster flank organ receptors, respectively). In vivo, topical administration of RU-58841 (1-100 μg per animal) reduces size of the flank organ withoutaffecting sex organs in a dose-dependent manner in hamsters. It has no effect on sex organ weight in intact rats when administered percutaneously, subcutaneously, or orally at doses up to 1 mg per animal. RU-58841 (5% v/v) also induces hair regrowth in the bald frontal scalps of postpubertal stumptailed macaques, a model for male pattern baldness. View more+

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1. Names and Identifiers

1.1 Name: RU 58841
1.2 Synonyms: 4-(4,4-Dimethyl-2,5-dioxo-3-(4-hydroxybutyl)1-imidazolidinyl)-2-(trifluoromethyl)benzonitrile 4-[3-(4-Hydroxybutyl)-4,4-dimethyl-2,5-dioxo-1-imidazolidinyl]-2-(trifluoromethyl)benzonitrile 4-[3-(4-Hydroxybutyl)-4,4-dimethyl-2,5-dioxo-1-imidazolidinyl]-2-trifluoromethylbenzonitrile 4-[3-(4-Hydroxybutyl)-4,4-diMethyl-2,5-dioxoiMidazolidin-1-yl]-2-(trifluoroMethyl)benzonitrile Benzonitrile, 4-[3-(4-hydroxybutyl)-4,4-dimethyl-2,5-dioxo-1-imidazolidinyl]-2-(trifluoromethyl)- CS-637 RU 58841 RU 588841 RU58841 RU-58841 RU-58841 E:candyli(at)speedgainpharma(dot)com

1.3 CAS No.: 154992-24-2

1.4 CID: 132981

1.5 EINECS(EC#): 1592732-453-0

1.6 Molecular Formula: C17H18F3N3O3 (isomer)

1.7 Inchi: 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

1.8 InChkey: ARBYGDBJECGMGA-UHFFFAOYSA-N

1.9 Canonical Smiles: CC1(C(=O)N(C(=O)N1CCCCO)C2=CC(=C(C=C2)C#N)C(F)(F)F)C

1.10 Isomers Smiles: CC1(C(=O)N(C(=O)N1CCCCO)C2=CC(=C(C=C2)C#N)C(F)(F)F)C

2. Properties

2.1 Density: 1.39

2.1 Boiling point: 493.6°C at 760 mmHg

2.1 Refractive index: 1.559

2.1 Flash Point: 252.3°C

2.1 Precise Quality: 369.13000

2.1 PSA: 84.64000

2.1 logP: 2.89968

2.1 pKa: 15.09±0.10(Predicted)

3. Use and Manufacturing

3.1 Usage: RU58841 (Roussel Uclaf) is a nonsteroidal topical antiandrogen without significant systemic effects apparently due to its metabolism in the skin. This appears to be a promising new hair growth agent that promotes hair growth on the scalp as well as retards hair growth of both beard and body hair follicles. RU58841 has produced highly efficacious results in stumptailed macaques.The synergistic effects of RU58841 and minoxidil topical solution (2% and 5%) have also been reported in stumptailed macaques. The effect of combined treatment was most remarkable early on, but by 1 year no significant benefit of combined treatment was apparent relative to either treatment alone.

4. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

no data available

2.2 GHS label elements, including precautionary statements

Pictogram(s)	no data available
Signal word	no data available
Hazard statement(s)	no data available
Precautionary statement(s)
Prevention	no data available
Response	no data available
Storage	no data available
Disposal	no data available

2.3 Other hazards which do not result in classification

no data available

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5. Synthesis Route

154992-24-2Total: 3 Synthesis Route

654-70-6 336 Suppliers

154992-24-2 131 Suppliers

Literatures:
RSC Advances, , vol. 4, # 27 p. 14143 - 14148
Yield: null

1259327-69-9

154992-24-2 131 Suppliers

Literatures:
RSC Advances, , vol. 4, # 27 p. 14143 - 14148
Yield: null

4753-59-7 46 Suppliers

143782-20-1 4 Suppliers

154992-24-2 131 Suppliers

Literatures:
Leonard, Matthew J.; Lingham, Anthony R.; Niere, Julie O.; Jackson, Neale R. C.; McKay, Peter G.; Huegel, Helmut M. RSC Advances, 2014 , vol. 4, # 27 p. 14143 - 14148
Yield: ~77%

6. Precursor and Product

precursor:

4753-59-7

654-70-6

1259327-69-9

143782-20-1

7. Other Information

7.0 Uses: Avoid hair loss

7.1 Mesh Entry Terms: 4-(4,4-dimethyl-2,5-dioxo-3-(4-hydroxybutyl)-1-imidazolidinyl)-2-(trifluoromethyl)benzonitrile

8. Computational chemical data

Molecular Weight: 369.344g/mol
Molecular Formula: C₁₇H₁₈F₃N₃O₃
Compound Is Canonicalized: True
XLogP3-AA: 2.1
Exact Mass: 369.13002593
Monoisotopic Mass: 369.13002593
Complexity: 611
Rotatable Bond Count: 5
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 7
Topological Polar Surface Area: 84.6
Heavy Atom Count: 26
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADceB7MYAAAAAAAAAAAAAAAAAAAWAAAAAwAAAAAAAAAAABAAAAHwAACAAADIjhmBYzwIMAAgCYBiVSUACiAAAhAgAIiAGIZIiI8CLAkbGUYAhshyLIyC8wgIAOiAAAQAAQAAAQAACAACAAAAAAAAAAAA==

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