841205-47-8

Basic information

• Product Name: (S)-N-(4-cyano-3-(trifluoromethyl)phenyl)-3-(4-cyanophenoxy)-2-hydroxy-2-methylpropanamide
• Synonyms: GTx-024;Ostarine NOT FOR SALE-PATENTED;EnobosarM;PropanaMide, 3-(4-cyanophenoxy)-N-[4-cyano-3-(trifluoroMethyl)phenyl]-2-hydroxy-2-Methyl-, (2S)-;MK-2866 (GTx-024);(S)-N-(4-Cyano-3-(trifluoromethyl)phenyl)-3-(4-cyanophenoxy)-2-hydroxy-2-methylpropanamide MK-2866, Ostarine;(S)-3-(4-Cyanophenoxy)-N-[4-cyano-3-(trifluoromethyl)phenyl]-2-hydroxy-2-methylpropionamide;Ostarine(MK2286)
• CAS NO: 841205-47-8
• Molecular Formula: C19H14F3N3O3
• Molecular Weight: 389.3279696
• EINECS: 803-892-7
• Product Categories: Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;Hormone Drugs;SARMs(Selective androgen receptor modulator);Inhibitors
• Mol File: 841205-47-8.mol

Chemical Properties

• Boiling Point: 632.3±55.0 °C(Predicted)
• Appearance: /
• Density: 1.41±0.1 g/cm3(Predicted)
• PKA: 12.13±0.29(Predicted)
• CAS DataBase Reference: (S)-N-(4-cyano-3-(trifluoromethyl)phenyl)-3-(4-cyanophenoxy)-2-hydroxy-2-methylpropanamide(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-N-(4-cyano-3-(trifluoromethyl)phenyl)-3-(4-cyanophenoxy)-2-hydroxy-2-methylpropanamide(841205-47-8)
• EPA Substance Registry System: (S)-N-(4-cyano-3-(trifluoromethyl)phenyl)-3-(4-cyanophenoxy)-2-hydroxy-2-methylpropanamide(841205-47-8)

Safety Data

• Hazardous Substances Data: 841205-47-8(Hazardous Substances Data)

Usage

description

Ostarine, also known as MK-2866, is a selective androgen receptor modulator (SARM) that has been shown to be effective in helping people lose weight and build muscle mass. Ostarine works by binding to the androgen receptors in the body, which can help reduce body fat and increase muscle mass. It is non-toxic and has few side effects, making it a safe choice for those looking for an edge in the gym.

Application

Ostarine is a non-steroidal agent with anabolic activity. Selective androgen receptor modulator (SARM) GTx-024 is designed to work like testosterone, thus promoting and/or maintaining libido, fertility, prostate growth, and muscle growth and strength. Mimicking testosterone's action, this agent may increase lean body mass, thereby ameliorating muscle wasting in the hypermetabolic state of cancer cachexia. Ostarine has been used in trials studying the treatment of Stress Urinary Incontinence and Triple Negative Breast Cancer.

Physiological action

Ostarine is a selective androgen receptor modulator (SARM) with Ki of 3.8 nM. Plasma concentration of ostarine declines in a biexponential manner after intravenous administration with terminal half-live of 6.0 hours. In vivo, ostarine significantly stimulates the growth of prostate, seminal vesicles, and levator ani muscle in castrated rats. Ostarine restores the weights of the prostate to 39.2%, of that observed in the intact control. The weight of seminal vesicle is also restored by ostarine to 78.8%, respectively, of that observed in the intact control. Ostarine stimulates the growth of levator ani muscle to a greater extent than androgenic organs, to 141.9%.

Uses

Ostarine is nonsteroidal selective androgen receptor modulator (SARM) used in the treatment of osteoporosis and muscle wasting in animal models. A potential compound for the treatment of hypoactive sexual desire disorder.

InChI:InChI=1/C19H14F3N3O3/c1-18(27,11-28-15-6-2-12(9-23)3-7-15)17(26)25-14-5-4-13(10-24)16(8-14)19(20,21)22/h2-8,27H,11H2,1H3,(H,25,26)/t18-/m1/s1

Upstream product

• 767-00-0 4-cyanophenol 
• 206193-17-1 (2R)-3-bromo-N-[4-cyano-3-(trifluoromethyl)phenyl]-2-hydroxy-2-methylpropanamide 
• 60-29-7 diethyl ether 
• 344-25-2 D-Prolin 
• 920-46-7 Methacryloyl chloride 
• 654-70-6 4-amino-2-trifluoromethylbenzonitrile 
• 113181-02-5 (S)-(-)-3-bromo-2-hydroxy-2-methyl-N-[(4-cyano-3-(trifluoromethyl)phenyl)]propanamide 

Relevant articles and documents

Synthesis method of nicotinate

The invention belongs to the technical field of compound preparation, and in particular, relates to (S)-1-((4-cyano-3-(trifluoromethyl)phenyl)amino)-3-(4-cyanophenoxy)-2-methyl-1-oxopropan-2-yl nicotinate and a synthesis method thereof. The method compris

Synthetic method of alpha-hydroxypropanamide derivatives with optical activity

The invention discloses a synthetic method of alpha-hydroxypropanamide derivatives with optical activity and belongs to the field of organic synthesis. Proline taken as a chiral auxiliary, as well asmethacryloyl chloride, is subjected to acylation, bromination and chiral auxiliary removal, a product and 4-cyano-3-trifluoromethylaniline are subjected to nucleophilic substitution, and 3-bromo-2-hydroxy-2-methyl-N-[(4-cyano-3-trifluoromethyl)phenyl]propanamide is obtained and subjected to nucleophilic substitution with 4-cyanophenol, and the compound 3-(4-cyanophenoxy)-N-[4-cyano-3-(trifluoromethylphenyl]-2-hydroxy-2-methylpropanamide with optical activity is prepared. 3-bromo-2-hydroxy-2-methyl propionic acid and 4-nitro-3-trifluoromethylaniline are subjected to aminolysis, a product is subjected to nucleophilic substitution with paracetamol, and the compound 3-(4-acetoxyphenoxy)-N-[4-nitro-3-(trifluoromethylphenyl]-2-hydroxy-2-methylpropanamide with optical activity is prepared. The efficient synthetic method of the alpha-hydroxypropanamide derivatives with optical activity is provided.

Design and synthesis of novel bicalutamide and enzalutamide derivatives as antiproliferative agents for the treatment of prostate cancer

Prostate cancer (PC) is one of the major causes of male death worldwide and the development of new and more potent anti-PC compounds is a constant requirement. Among the current treatments, (R)-bicalutamide and enzalutamide are non-steroidal androgen receptor antagonist drugs approved also in the case of castration-resistant forms. Both these drugs present a moderate antiproliferative activity and their use is limited due to the development of resistant mutants of their biological target. Insertion of fluorinated and perfluorinated groups in biologically active compounds is a current trend in medicinal chemistry, applied to improve their efficacy and stability profiles. As a means to obtain such effects, different modifications with perfluoro groups were rationally designed on the bicalutamide and enzalutamide structures, leading to the synthesis of a series of new antiproliferative compounds. Several new analogues displayed improved in vitro activity towards four different prostate cancer cell lines, while maintaining full AR antagonism and therefore representing promising leads for further development. Furthermore, a series of molecular modelling studies were performed on the AR antagonist conformation, providing useful insights on potential protein-ligand interactions.

METHODS OF TREATING UROLOGICAL DISORDERS USING SARMs

The present invention is directed to methods of treating, preventing, suppressing and/or inhibiting urological disorders such as urinary incontinence including stress urinary incontinence and pelvic-floor disorders by administering a SARM compound of the invention.

A METHOD OF TREATING ANDROGEN RECEPTOR (AR)-POSITIVE BREAST CANCERS WITH SELECTIVE ANDROGEN RECEPTOR MODULATOR (SARMS)

This invention relates to the treatment of androgen receptor-positive breast cancer in a subject, for example a female subject. Accordingly, this invention provides methods of: a) treating a subject suffering from breast cancer; b) treating a subject suffering from metastatic breast cancer; c) treating a subject suffering from refractory breast cancer; d) treating a subject suffering from AR-positive breast cancer; e) treating a subject suffering from AR-positive refractory breast cancer; f) treating a subject suffering from AR-positive metastatic breast cancer; g) treating a subject suffering from AR-positive and ER-positive breast cancer; h) treating a subject suffering from triple negative breast cancer; i) treating a subject suffering from advanced breast cancer; j) treating a subject suffering from breast cancer that has failed SERM (tamoxifen, toremifene), aromatase inhibitor, trastuzumab (Herceptin, ado-trastuzumab emtansine), pertuzumab (Perjeta), lapatinib, exemestane (Aromasin), bevacizumab (Avastin), and/or fulvestrant treatments; k) treating, preventing, suppressing or inhibiting metastasis in a subject suffering from breast cancer; 1) prolonging survival of a subject with breast cancer, and/or m) prolonging the progression-free survival of a subject with breast cancer; comprising administering to the subject a therapeutically effective amount of a selective androgen receptor modulator (SARM) compound, comprising administering to the subject a therapeutically effective amount of a SARM compound of this invention.

PHARMACEUTICAL COMPOSITIONS OF SELECTIVE ANDROGEN RECEPTOR MODULATORS AND METHODS OF USE THEREOF

This invention provides a pharmaceutical composition comprising Compound I-V, including inter alia solid dosage forms of powder-filled capsule formulations, liquid-filled softgel capsules (softgels), tablets, and sustained release dosage forms, and uses thereof in treating a variety of diseases or conditions in a subject, for example, treating a muscle wasting disease and/or disorder, a bone related disease and/or disorder, metabolic syndrome, diabetes and associated diseases, and others.

METHODS OF TREATING MEIBOMIAN GLAND DYSFUNCTION

The present invention includes methods for treating Meibomian gland dysfunctions. The invention also includes methods for improving tear lipid composition, for treating abnormal Meibomian gland secretion and for normalizing Meibomian gland secretions.

SOLID FORMS OF SELECTIVE ANDROGEN RECEPTOR MODULATORS

The present invention relates to solid forms of (S)-N-(4-cyano-3-(trifluoromethyl)phenyl)- 3-(4-cyanophenoxy)-2-hydroxy-2-methylpropanamide and process for producing the same.

METABOLITES OF SELECTIVE ANDROGEN RECEPTOR MODULATORS AND METHODS OF USE THEREOF

This invention provides metabolites of SARM compounds including inter alia glucuronidated metabolites and uses thereof in treating a variety of diseases or conditions in a subject, including, inter alia, muscle wasting disease and/or disorder, a bone related disease and/or disorder, metabolic syndrome, diabetes and associated diseases, and others.

TREATING RENAL DISEASE, BURNS, WOUNDS AND SPINAL CORD INJURY WITH SELECTIVE ANDROGEN RECEPTOR MODULATORS

This invention provides: 1) a method of treating a subject suffering from, or predisposed to a kidney disease or disorder; 2) a method of treating a subject suffering from a wound, or reducing the incidence of, or mitigating the severity of a wound in a subject; 3) a method of treating a subject suffering from a burn, or reducing the incidence of, or mitigating the severity of a burn in a subject, comprising the step of administering to said subject a selective androgen receptor modulator (SARM) compound; 4) a method of treating a subject suffering from a spinal cord injury, by administering to the subject a selective androgen receptor modulator (SARM) and/or an analog, derivative, isomer, metabolite, pharmaceutically acceptable salt, pharmaceutical product, hydrate, N-oxide, prodrug, polymorph, impurity or crystal of said SARM compound, or any combination thereof.