RU 58841
- CAS NO.:154992-24-2
- Empirical Formula: C17H18F3N3O3
- Molecular Weight: 369.34
- MDL number: MFCD00925776
- EINECS: 1592732-453-0
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-11-26 17:46:08
What is RU 58841?
Description
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.
The Uses of RU 58841
RU 58841, is a specific androgen receptor antagonist or anti-androgen, that has shown to have effect on hair growth.
The Uses of RU 58841
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.
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
Biological Activity
Androgens are mainly produced in the adrenal glands and testes. They are male hormones responsible for sex-related development. The well-known androgen is testosterone. Dihydrotestosterone (DHT) is also an androgen, which is a byproduct of testosterone. Although DHT is important for male development and physical health, it can cause hair loss. RU58841 is a topical anti-androgen drug that counteracts the effects of dihydrotestosterone (DHT) by binding to the androgen receptors of the hair follicles, preventing DHT from interacting with the androgen receptors of the hair follicles. Therefore, the hair shrinkage process does not begin, ensuring that the hair undergoes a normal growth cycle.
Properties of RU 58841
Boiling point: | 493.6±55.0 °C(Predicted) |
Density | 1.39 |
storage temp. | Sealed in dry,Store in freezer, under -20°C |
solubility | DMF: 33 mg/ml; DMSO: 25 mg/ml; Ethanol: 33 mg/ml; Ethanol:PBS(pH 7.2) (1:5): 0.16 mg/ml |
form | Powder |
pka | 15.09±0.10(Predicted) |
color | White to off-white |
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 |
Safety information for RU 58841
Signal word | Danger |
Pictogram(s) |
Corrosion Corrosives GHS05 |
GHS Hazard Statements |
H290:Corrosive to Metals H314:Skin corrosion/irritation |
Precautionary Statement Codes |
P234:Keep only in original container. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P280:Wear protective gloves/protective clothing/eye protection/face protection. P363:Wash contaminated clothing before reuse. P390:Absorb spillage to prevent material damage. P301+P330+P331:IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. P303+P361+P353:IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. P405:Store locked up. P406:Store in corrosive resistant/… container with a resistant inner liner. |
Computed Descriptors for RU 58841
InChIKey | ARBYGDBJECGMGA-UHFFFAOYSA-N |
SMILES | C(#N)C1=CC=C(N2C(=O)N(CCCCO)C(C)(C)C2=O)C=C1C(F)(F)F |
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