154992-24-2 Usage
Description
Different sources of media describe the Description of 154992-24-2 differently. You can refer to the following data:
1. 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.
2. 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 without affecting 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.
Androgen receptor
RU 58841 (PSK-3841) is a specific androgen receptor antagonist or anti-androgen. RU 58841 (PSK-3841) has a dramatic effect on hair regrowth.
Androgen receptor (AR) is a type of nuclear receptor that is activated by binding of either of the androgenic hormones testosterone or dihydrotestosterone in the cytoplasm and then translocating into the nucleus. Upon binding the hormone ligand, the receptor dissociates from accessory proteins, translocates into the nucleus, dimerizes, and then stimulates transcription of androgen responsive genes. The androgen receptor is most closely related to the progesterone receptor, and progestins in higher dosages can block the androgen receptor. The main function of the androgen receptor is as a DNA-binding transcription factor that regulates gene expression. Androgen regulated genes are critical for the development and maintenance of the male sexual phenotype. Mutations in this gene are also associated with complete androgen insensitivity (CAIS).
Uses
Different sources of media describe the Uses of 154992-24-2 differently. You can refer to the following data:
1. 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.
2. Avoid hair loss: RU58841 is a non-steroidal antiandrogenic medication that was initially developed in the 1980s as a topical treatment remedy for acne and male pattern baldness – androgenetic alopecia.
3. RU 58841, is a specific androgen receptor antagonist or anti-androgen, that has shown to have effect on hair growth.
Laboratory Procedures
RU-58841 is supplied as a crystalline solid. A stock solution may be made by dissolving the RU-58841 in the solvent of choice. RU-58841 is soluble in organic solvents such as ethanol, DMSO, and dimethyl formamide (DMF), which should be purged with an inert gas. The solubility of RU-58841 is approximately33 mg/ml in ethanol and DMF and approximately 25 mg/ml in DMSO.
RU-58841 is sparingly soluble in aqueous buffers. For maximum solubility in aqueous buffers, RU-58841 should first be dissolved in ethanol and then diluted with the aqueous buffer of choice. RU-58841 has a solubility of approximately 0.16 mg/ml in a 1:5 solution of ethanol:PBS (pH 7.2) using this method. We do not recommend storing the aqueous solution for more than one day.
Side effects
Since RU58841 has not passed into phase two of drug development, there are literally no studies that have highlighted the side effects of this medication specifically.
Pharmacologically speaking, there are absolutely no pharmacologic products that are 100% free of side effects. Like with every medication, RU58841 also affects each individual differently.
But based on the physiologic processes it undergoes, we can hypothesize on some of its potential side effects. For instance, you should be aware that RU58841 does not only block DHT but all other androgens including testosterone.
References
Battmann, T., Bonfils, A., Branche, C., et al. RU 58841, a new specific topical antiandrogen: A candidate of choice for the treatment of acne, androgenetic alopecia and hirsutism. J. Steroid Biochem. Mol. Biol. 48(1), 55-60 (1994).
Obana, N., Chang, C., and Uno, H. Inhibition of hair growth by testosterone in the presence of dermal papilla cells from the frontal bald scalp of the postpubertal stumptailed macaque. Endocrinology138(1), 356-361 (1997).
Preparation
RU58841 is active against baldness and is commercially available. The previously reported synthesis uses phosgene, three discrete inert atmosphere steps and three steps that require flash chromatography. Our synthesis uses no phosgene, only one inert atmosphere step and does not require flash chromatography. Alternative synthesis of the anti-baldness compound RU58841
Synthesis Reference(s)
A bromine–nitro substitution at tertiary carbon and using 2-nitropropane as leaving group enable a short phosgene-free synthesis of RU58841.pubs.rsc.org
Check Digit Verification of cas no
The CAS Registry Mumber 154992-24-2 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,5,4,9,9 and 2 respectively; the second part has 2 digits, 2 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 154992-24:
(8*1)+(7*5)+(6*4)+(5*9)+(4*9)+(3*2)+(2*2)+(1*4)=162
162 % 10 = 2
So 154992-24-2 is a valid CAS Registry Number.
InChI:InChI=1/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
154992-24-2Relevant articles and documents
Alternative synthesis of the anti-baldness compound RU58841
Leonard, Matthew J.,Lingham, Anthony R.,Niere, Julie O.,Jackson, Neale R. C.,McKay, Peter G.,Huegel, Helmut M.
, p. 14143 - 14148 (2014/04/17)
RU58841 is active against baldness and is commercially available. The previously reported synthesis uses phosgene, three discrete inert atmosphere steps and three steps that require flash chromatography. Our synthesis uses no phosgene, only one inert atmosphere step and does not require flash chromatography. This is achieved by stepwise construction of the hydantoin moiety around the amino group of 3-trifluoromethyl-4-cyanoaniline and ring closure to give a 2-nitropropane leaving group. On a small scale we achieved an overall yield of 33%.
Phenylimidazolidine preparation process
-
, (2008/06/13)
A subject of the invention is a preparation process for the products of formula (I): STR1 in which R1 and R2 represent in particular hydrogen, cyano, halogen or amino,R3 represents in particular hydrogen or hydroxyl alkyl, R4 and R5 represent in particular optionally substituted alkyl, X and y represent oxygen or sulphur, characterized in that a product of formula (A): STR2 is prepared in which W represents a halogen atom or a hydantoin derivative, which is subjected to various reactions in order to obtain the products of formula (I), all their isomers and their salts.
