GLPG-0492 | DT-200 | CAS#1215085-92-9 | Selective Androgen Receptor Modulator

GLPG-0492
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 527902

CAS#: 1215085-92-9

Description: GLPG-0492, also known as DT-200, is a non-steroidal selective androgen receptor modulator potentially for the treatment of Duchenne muscular dystrophy. GLPG0492 treatment partially prevents immobilization-induced muscle atrophy with a trend to promote muscle fiber hypertrophy in a dose-dependent manner. Gene expression studies performed on tibialis samples revealed that both GLPG0492 was slowing down muscle loss by negatively interfering with major signaling pathways controlling muscle mass homeostasis.

Chemical Structure

GLPG-0492

CAS# 1215085-92-9

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 527902
Name: GLPG-0492
CAS#: 1215085-92-9
Chemical Formula: C19H14F3N3O3
Exact Mass: 389.10
Molecular Weight: 389.334
Elemental Analysis: C, 58.62; H, 3.62; F, 14.64; N, 10.79; O, 12.33

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 495	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: GLPG-0492; GLPG 0492; GLPG0492; DT-200; DT 200; DT200

IUPAC/Chemical Name: (S)-4-(4-(hydroxymethyl)-3-methyl-2,5-dioxo-4-phenylimidazolidin-1-yl)-2-(trifluoromethyl)benzonitrile

InChi Key: VAJGULUVTFDTAS-GOSISDBHSA-N

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

SMILES Code: N#CC1=CC=C(N(C(N(C)[C@]2(CO)C3=CC=CC=C3)=O)C2=O)C=C1C(F)(F)F

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

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Product Data:

Product Data

Instruction:

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Biological target:	GLPG0492 is a non-steroidal selective androgen receptor modulator (potency 12 nM).
In vitro activity:	Molecular modeling of the binding to the androgen receptor ligand binding domain suggests slight differences in the binding modes of RAD-140, GSK-2881078 and GLPG0492. In conclusion, androgenic activity of the three non-steroidal compounds in the two different in vitro test systems confirmed the results of the in silico modeling of the androgen receptor binding. Reference: J Steroid Biochem Mol Biol. 2019 May;189:81-86. https://pubmed.ncbi.nlm.nih.gov/30825507/
In vivo activity:	Sciatic nerve blood flow (SNBF) was markedly lower (about 43.4%) in untreated diabetic (DC) rats than in non-diabetic controls (NC). A significant delay in caudal motor nerve conduction velocity (MNCV) and significantly higher glucose, sorbitol and fructose values were observed in the sciatic nerve, accompanied by a markedly higher sorbitol concentration in erythrocytes. In contrast, TAT-treated diabetic groups (DT-10, DT-40 and DT-200) had significantly higher SNBF, MNCV and sciatic nerve myo-inositol values and lower sciatic nerve sorbitol and fructose levels and erythrocyte sorbitol concentration than the DC group. Reference: Diabetes Res Clin Pract. 1995 Feb;27(2):107-17. https://pubmed.ncbi.nlm.nih.gov/7607048/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	50.0	128.42

Preparing Stock Solutions

The following data is based on the product molecular weight 389.33 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:	1. Zierau O, Kolodziejczyk A, Vollmer G, Machalz D, Wolber G, Thieme D, Keiler AM. Comparison of the three SARMs RAD-140, GLPG0492 and GSK-2881078 in two different in vitro bioassays, and in an in silico androgen receptor binding assay. J Steroid Biochem Mol Biol. 2019 May;189:81-86. doi: 10.1016/j.jsbmb.2019.02.014. Epub 2019 Feb 27. PMID: 30825507. 2. Nique F, Hebbe S, Triballeau N, Peixoto C, Lefrançois JM, Jary H, Alvey L, Manioc M, Housseman C, Klaassen H, Van Beeck K, Guédin D, Namour F, Minet D, Van der Aar E, Feyen J, Fletcher S, Blanqué R, Robin-Jagerschmidt C, Deprez P. Identification of a 4-(hydroxymethyl)diarylhydantoin as a selective androgen receptor modulator. J Med Chem. 2012 Oct 11;55(19):8236-47. doi: 10.1021/jm300281x. Epub 2012 Sep 25. PMID: 22957947. 3. Hotta N, Kakuta H, Fukasawa H, Koh N, Sakakibara F, Nakamura J, Hamada Y, Wakao T, Hara T, Mori K, et al. Effect of a potent new aldose reductase inhibitor, (5-(3-thienyltetrazol-1-yl)acetic acid (TAT), on diabetic neuropathy in rats. Diabetes Res Clin Pract. 1995 Feb;27(2):107-17. doi: 10.1016/0168-8227(95)01033-a. PMID: 7607048.
In vitro protocol:	1. Zierau O, Kolodziejczyk A, Vollmer G, Machalz D, Wolber G, Thieme D, Keiler AM. Comparison of the three SARMs RAD-140, GLPG0492 and GSK-2881078 in two different in vitro bioassays, and in an in silico androgen receptor binding assay. J Steroid Biochem Mol Biol. 2019 May;189:81-86. doi: 10.1016/j.jsbmb.2019.02.014. Epub 2019 Feb 27. PMID: 30825507.
In vivo protocol:	1. Nique F, Hebbe S, Triballeau N, Peixoto C, Lefrançois JM, Jary H, Alvey L, Manioc M, Housseman C, Klaassen H, Van Beeck K, Guédin D, Namour F, Minet D, Van der Aar E, Feyen J, Fletcher S, Blanqué R, Robin-Jagerschmidt C, Deprez P. Identification of a 4-(hydroxymethyl)diarylhydantoin as a selective androgen receptor modulator. J Med Chem. 2012 Oct 11;55(19):8236-47. doi: 10.1021/jm300281x. Epub 2012 Sep 25. PMID: 22957947. 2. Hotta N, Kakuta H, Fukasawa H, Koh N, Sakakibara F, Nakamura J, Hamada Y, Wakao T, Hara T, Mori K, et al. Effect of a potent new aldose reductase inhibitor, (5-(3-thienyltetrazol-1-yl)acetic acid (TAT), on diabetic neuropathy in rats. Diabetes Res Clin Pract. 1995 Feb;27(2):107-17. doi: 10.1016/0168-8227(95)01033-a. PMID: 7607048.

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1: Blanqué R, Lepescheux L, Auberval M, Minet D, Merciris D, Cottereaux C, Clément-Lacroix P, Delerive P, Namour F. Characterization of GLPG0492, a selective androgen receptor modulator, in a mouse model of hindlimb immobilization. BMC Musculoskelet Disord. 2014 Sep 3;15:291. doi: 10.1186/1471-2474-15-291. PubMed PMID: 25185887; PubMed Central PMCID: PMC4167280.

2: Cozzoli A, Capogrosso RF, Sblendorio VT, Dinardo MM, Jagerschmidt C, Namour F, Camerino GM, De Luca A. GLPG0492, a novel selective androgen receptor modulator, improves muscle performance in the exercised-mdx mouse model of muscular dystrophy. Pharmacol Res. 2013 Jun;72:9-24. doi: 10.1016/j.phrs.2013.03.003. PubMed PMID: 23523664.

3: Nique F, Hebbe S, Triballeau N, Peixoto C, Lefrançois JM, Jary H, Alvey L, Manioc M, Housseman C, Klaassen H, Van Beeck K, Guédin D, Namour F, Minet D, Van der Aar E, Feyen J, Fletcher S, Blanqué R, Robin-Jagerschmidt C, Deprez P. Identification of a 4-(hydroxymethyl)diarylhydantoin as a selective androgen receptor modulator. J Med Chem. 2012 Oct 11;55(19):8236-47. doi: 10.1021/jm300281x. PubMed PMID: 22957947.

4: Thevis M, Schänzer W. Detection of SARMs in doping control analysis. Mol Cell Endocrinol. 2017 Jan 27. pii: S0303-7207(17)30053-9. doi: 10.1016/j.mce.2017.01.040. [Epub ahead of print] PubMed PMID: 28137616.

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GLPG-0492 featured