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RU58841 powder is a specific androgen receptor antagonist or anti-androgen, also known as PSK3841 or HMR3841. It belongs to the category of non-steroidal anti-androgens and is primarily used as a topical treatment for acne, androgenetic alopecia (male pattern baldness), and hirsutism (excessive hair growth in women). This compound was initially developed in the 1980s by researchers exploring androgen-blocking therapies. It has a chemical name of 4-(1-(4-hydroxybutyl)-5,5-dimethyl-2,4-dioxopyrrolidin-3-yl)-2-(trifluoromethyl)benzonitrile. It is typically available with a purity level of over 98% to 99%, making it suitable for research and certain therapeutic applications. Recommended storage conditions are at -20°C for long-term preservation (as powder) or at 2-4°C for shorter durations. Dissolved solutions should be stored at -20°C for up to six months. It is soluble in DMSO (dimethyl sulfoxide) at a concentration of 10 mM.
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Chemical Formula |
C17H18F3N3O3 |
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Exact Mass |
369.13 |
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Molecular Weight |
369.34 |
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m/z |
369.13 (100.0%), 370.13 (18.4%), 371.14 (1.6%), 370.13 (1.1%) |
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Elemental Analysis |
C, 55.28; H, 4.91; F, 15.43; N, 11.38; O, 13.00 |
RU58841 powder (chemical name: 4- [3- (4-hydroxybutyl) -4,4-dimethyl-2,5-dioxo-1-imidazolyl] -2- (trifluoromethyl) benzonitrile, CAS number: 154992-24-2) is a nonsteroidal anti androgenic compound that has attracted attention for its potential therapeutic effect on androgenic alopecia (AGA). Androgenic alopecia is a common hair disease that seriously affects the appearance and mental health of patients. Traditional treatment methods have certain limitations, but its emergence brings new hope for the treatment of this disease.
Molecular mechanism: Blocking the androgen signaling pathway
1. Competitive binding of androgen receptor (AR)
The core mechanism of action is to competitively bind AR in hair follicles with dihydrotestosterone (DHT), thereby blocking androgen signaling. In the human body, testosterone is converted into the more active DHT by the action of 5 α - reductase. The affinity between DHT and AR is 2-3 times that of testosterone, which allows DHT to bind more efficiently to AR and trigger a series of reactions that lead to hair follicle miniaturization, becoming a key factor in androgenic alopecia.
The molecular structure is unique and contains trifluoromethylphenylnitrile groups. This unique structure enables it to form stable complexes with the ligand binding domain (LBD) of AR. Its binding constant (Ki value) is much lower than that of DHT, which means that it has a significant advantage in the competition for binding with AR. It can preferentially occupy the receptor site, prevent the binding of DHT to AR, and effectively block the transmission of androgen signals.
Experimental evidence:
The experiments conducted in the prostate cancer cell line (PC3) have important reference value. The growth of prostate cancer cells is closely related to androgen signaling. In this experiment, the addition of 100 nM RU 58841 completely inhibited DHT induced AR nuclear translocation and downstream gene expression (such as PSA and NKX3.1). AR nuclear translocation is a key step in androgen signaling, and the expression of downstream genes is related to physiological processes such as cell proliferation and differentiation. This experimental result fully demonstrates the effective blocking effect of RU 58841 on androgen signaling at the cellular level.
Transplanting a human hair loss scalp model into nude mice is an important tool for studying hair loss treatment drugs. In this model, the proportion of hair follicle growth period in the treatment group increased by 40% compared to the control group, and hair length increased by 35%. This indicates that RU 58841 can improve the growth status of hair follicles at the overall tissue level, promote hair growth, and further validate its therapeutic potential for androgenic alopecia.
2. Inhibit the process of hair follicle miniaturization
After binding with AR, DHT activates a series of signaling pathways, leading to the differentiation of hair follicle stem cells into keratinocytes, ultimately resulting in adverse consequences such as hair follicle atrophy and shortened growth period. And by blocking AR signals, it can reverse this unfavorable process, which is manifested in the following aspects:
Extended growth period: The growth cycle of hair follicles includes growth period, regression period, and resting period. In patients with androgenetic alopecia, the growth period of hair follicles is shortened, leading to gradual thinning and shortening of hair. It can promote the transformation of hair follicles from the resting phase (Telogen) to the growth phase (Anagen), increase the proportion of hair follicles in the growth phase, and give hair follicles more time to grow and develop, thereby improving hair loss.
Animal experiments:
The short tailed macaque model has certain similarities with humans in terms of hair structure and growth cycle, making it an ideal animal model for studying hair loss treatment. In this model, after 6 months of local application of 5% RU 58841 solution, hair density increased by 103% and hair diameter increased by 26%, and the effect was better than finasteride (88% density increase, 12% diameter increase). This result not only demonstrates the effectiveness of RU 58841 in promoting hair growth and increasing hair diameter, but also demonstrates its advantages over the traditional drug finasteride.
The hamster ear skin model is also a commonly used animal model for studying hair loss related mechanisms. In this model, RU 58841 can significantly inhibit DHT induced hair follicle atrophy at a dose of 1 μ g, and the effect is limited to the application site without systemic side effects. This indicates that it has high local activity and good safety, which can effectively treat hair loss while reducing the impact on other organs throughout the body.
Preclinical studies: Safety and efficacy validation
The original design intention of RU 58841 is to avoid the systemic side effects of 5 α - reductase inhibitors such as finasteride (such as sexual dysfunction, depression, etc.). Finasteride reduces DHT production by inhibiting the activity of 5 α - reductase, but due to its wide range of effects, it can affect the levels of testosterone throughout the body, leading to a series of adverse reactions. And it has unique pharmacological properties, with a small molecular weight (345.34 g/mol) and high lipid solubility, which allows it to quickly penetrate the skin barrier and accumulate in hair follicles, while the systemic absorption rate is extremely low.
Monkey experiment: Monkeys are closely related to humans in terms of physiological structure and metabolism, and are an important animal model for studying drug safety. In the monkey experiment, after continuous local application of 5% RU 58841 for 6 months, only 2 cases detected trace amounts of the drug (10-20 ng/mL) in the plasma, which were completely cleared after 6 months. This result indicates that there is very little systemic absorption in the monkey's body, and it can be cleared in a timely manner without accumulating toxicity in the body.
Human trial: The Phase II clinical trial conducted by ProStrakan (120 AGA patients) has significant clinical significance. In this experiment, after 6 months of local application, there was no significant change in serum testosterone and DHT levels, and the incidence of sexual function related adverse events was not different from that of the placebo group. This further demonstrates its safety in human applications, as it can exert a therapeutic effect on androgenic alopecia without affecting systemic androgen levels and sexual function.
Synthesis Methods
Raw material preparation: The raw materials for synthesizing RU58841 include phenol, chloroacetic acid, sodium hydroxide, etc. These raw materials need to be prepared in a certain proportion and ensure that their purity meets the requirements.
Reaction conditions: Synthetic reactions are usually carried out in organic solvents such as methanol, ethanol, etc. The reaction temperature and time are optimized according to specific conditions to ensure the smooth progress of the reaction.
Synthesis process: Firstly, phenol and chloroacetic acid undergo esterification reaction under alkaline conditions to generate phenol acetate. Then, under the action of a catalyst, phenol acetate is condensed with another active intermediate to generate the precursor of RU58841. Finally, the precursor is converted to the target product RU58841 through a reduction reaction.
Post processing: After the synthesis is completed, the product needs to be purified and crystallized to remove impurities and improve the purity of the product. Common purification methods include recrystallization, chromatographic separation, etc.
The synthesis typically begins with 4-amino-2-(trifluoromethyl)benzonitrile as the starting material. From this compound, a series of reactions are carried out to form the desired product.
The first step involves converting the starting material, 4-amino-2-(trifluoromethyl)benzonitrile, into its corresponding isocyanate using triphosgene (a common reagent for this purpose). This reaction involves displacement of the amino group to form an isocyanate group.
The isocyanate product from the previous step undergoes a [3+2] cycloaddition reaction with an appropriate dipolarophile (a compound capable of undergoing this type of reaction). This reaction results in the formation of a heterocyclic intermediate, which is a crucial step in constructing the imidazolidine ring system found in it.
The heterocyclic intermediate is then subjected to an N-alkylation reaction, typically with a 4-hydroxybutyl halide (e.g., 4-bromobutan-1-ol) under basic conditions. This reaction introduces the desired alkyl chain into the heterocyclic ring, further advancing the structure towards the final product.
The final step involves deprotecting any remaining protecting groups (if present) and finalizing the structure to yield RU58841 Powder. This may involve oxidation or other transformations to ensure the correct functional groups are in place.
adverse reaction
RU58841 Powder is a non steroidal anti androgen drug originally developed for the treatment of androgen related diseases such as acne, androgenic alopecia (AGA), and hirsutism. Its mechanism of action is to block the interaction between androgens such as dihydrotestosterone (DHT) and the androgen receptor (AR) by binding with high affinity, thereby inhibiting the physiological effects mediated by androgens. Although RU 58841 has shown some efficacy in animal experiments and some clinical trials, its adverse reactions and long-term safety are not fully understood.
Local stimulus response
RU 58841 is usually prepared as an external solution using solvents such as ethanol or propylene glycol, and applied directly to the scalp. Due to the irritant nature of solvents and the physicochemical properties of the drug itself, some users may experience local skin irritation symptoms, including:
Redness And Itching
Drug solutions may disrupt the skin barrier function, causing contact dermatitis, manifested as local redness, itching, and even a burning sensation. This reaction is more common in the early stages of medication and may be related to the irritancy of the solvent or high drug concentration.
Peeling And Drying
Long term use may cause damage to the scalp's stratum corneum, resulting in flaking, dryness, or tightness. This may be related to the dehydration effect of solvents or the impact of drugs on skin metabolism.
Systemic side effects
Although RU 58841 is designed for topical use, the drug may still be absorbed into the bloodstream through the scalp, leading to systemic side effects. At present, research on its systemic side effects is not sufficient, but based on its anti androgenic effects, it may include the following aspects:
Sexual dysfunction
Unlike 5-alpha-reductase inhibitors such as finasteride, RU 58841 does not directly reduce DHT levels in the body, but may interfere with the physiological function of androgens by blocking androgen receptors in various tissues throughout the body. In theory, this may lead to sexual dysfunction such as decreased libido, erectile dysfunction, or reduced ejaculation volume. However, there are currently no large-scale clinical trials to confirm the incidence of this side effect.
Hormonal level disorders
Long term use may affect the function of the hypothalamic pituitary gonadal axis, leading to fluctuations in testosterone levels or relative increases in estrogen levels. This may cause non-specific symptoms such as emotional changes, fatigue, decreased muscle mass, or changes in body fat distribution.
Metabolic effects
Androgens play an important role in lipid metabolism, glucose metabolism, and bone health. RU 58841 may affect these metabolic processes by interfering with the androgen signaling pathway, but the specific mechanism is not yet clear.
Animal experimental evidence: In long-term toxicity experiments on primates such as macaques, no significant systemic side effects were observed with high-dose RU 58841 applied topically. However, the sample size of these experiments is small, and there are differences in drug metabolism and physiological responses between animals and humans.
Allergic reactions
As an external medication, RU 58841 may cause allergic reactions, especially in individuals who are sensitive to drug ingredients or solvents. The manifestations of allergic reactions include:
Contact dermatitis
Manifested as erythema, edema, papules, and blisters at the site of medication, accompanied by severe itching. This reaction usually occurs within hours to days after medication and is related to type I or IV hypersensitivity reactions.
Systemic allergic reactions
In rare cases, drugs may cause systemic allergic reactions such as urticaria, angioedema, respiratory distress, or anaphylactic shock by absorption into the bloodstream. Although this reaction is rare, it may be life-threatening.
Risk factors: A history of drug allergies, impaired skin barrier function, or simultaneous use of other potentially allergenic drugs or cosmetics may increase the risk of allergic reactions.
FAQ
What is RU58841 powder?
Product Description. About This Item Powerful Hair Loss Solution: RU58841 is a potent synthetic anti-androgen compound designed to combat hair loss, particularly male pattern baldness.
Is RU58841 better than Minoxidil?
The effectiveness and safety of RU 58841 remain unproven, making licensed treatments like finasteride, minoxidil, and hair transplants the recommended options for hair thinning and recession. RU 58841 is not recommended for use by most well-respected hair transplant clinics.
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