RU 58841
[CAS# 154992-24-2]

Identification

• Classification: Organic raw materials >> Organic fluorine compound >> Fluorobenzonitrile series
• Name: RU 58841
• 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
• Molecular Formula: C₁₇H₁₈F₃N₃O₃
• Molecular Weight: 369.34
• CAS Registry Number: 154992-24-2
• SMILES: CC1(C(=O)N(C(=O)N1CCCCO)C2=CC(=C(C=C2)C#N)C(F)(F)F)C

Properties

• Solubilkity: 10 mM (DMSO)
• Density: 1.39

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H332-H335
• Safety Statements: P261-P280-P305+P351+P338

Discovery and Applications

RU 58841, a compound with the molecular formula C₁₇H₁₈F₃N₃O₃, has generated a great deal of interest for its potential in treating androgen-related conditions, particularly androgenic alopecia. Since its discovery, RU 58841 has been extensively studied for its effectiveness as a topical anti-androgen treatment.

The discovery of RU 58841 dates back to the 1990s, when researchers were investigating potential treatments for androgen-related conditions. The compound is a nonsteroidal anti-androgen, meaning it blocks androgen receptors without having steroidal properties. This property makes it particularly suitable for treating conditions such as acne, hirsutism, and most notably androgenic alopecia, without the systemic side effects that are often associated with steroidal anti-androgens.

RU 58841 works by binding to androgen receptors in the scalp, preventing dihydrotestosterone (DHT) from attaching to these receptors. DHT, a potent derivative of testosterone, is known to contribute significantly to hair follicle miniaturization, a key process in androgenetic alopecia. By blocking DHT, RU 58841 helps maintain the health and size of hair follicles, potentially slowing or even reversing hair loss.

One of the main advantages of RU 58841 is its topical action. When applied topically, it acts directly on the hair follicles without entering the bloodstream in large quantities, minimizing systemic side effects. This topical action distinguishes it from oral anti-androgens, which can affect the entire body and cause adverse side effects, such as decreased libido and changes in hormone levels.

Multiple studies have demonstrated the efficacy of RU 58841 in promoting hair regrowth and reducing hair loss. Animal studies, particularly those on short-tailed macaques, have shown promising results, with significant hair regrowth observed in the treated areas. Early human trials have also shown that RU 58841 is effective in increasing hair density and improving the overall appearance of hair in patients with androgenetic alopecia.

Despite these encouraging results, RU 58841 has not received regulatory approval for hair loss treatment. The lack of long-term clinical data and comprehensive safety studies has hampered its progress toward becoming a widely accepted treatment option. However, the compound remains available for research purposes, and some have sought it out through unofficial channels, although this is not recommended due to potential risks and lack of quality control.

In addition to hair loss, RU 58841 has been used to treat other androgen-related conditions. Its ability to block androgen receptors suggests it could be used to treat acne, which is often caused by androgen activity. Additionally, conditions such as hirsutism (excessive hair growth in women) may benefit from topical anti-androgen treatments such as RU 58841, which is a targeted approach with fewer systemic effects.

References

1994. RU 58841, a new specific topical antiandrogen: a candidate of choice for the treatment of acne, androgenetic alopecia and hirsutism. The Journal of Steroid Biochemistry and Molecular Biology, 48, 1.
DOI: 10.1016/0960-0760(94)90250-x

2008. Novel vesicular and particulate drug delivery systems for topical treatment of acne. Expert Opinion on Drug Delivery, 5, 6.
DOI: 10.1517/17425247.5.6.665

2010. Development of an in silico model for human skin permeation based on a Franz cell skin permeability assay. Bioorganic & Medicinal Chemistry Letters, 20, 1.
DOI: 10.1016/j.bmcl.2009.11.039