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| Chemical & Physical Properties | |
|---|---|
| CAS Number | 328947-93-9 |
| Catalog No. | 2A-1197870 |
| Chinese Name | LGD-2226 |
| Synonyms | LGD-2226; 6-[Bis(2,2,2-trifluoroethyl)amino]-4-(trifluoromethyl)-2(1H)-quinolinone |
| Molecular Formula | C14H9F9N2O |
| Molecular Weight | 392.22 |
| Purity | ≥98.0 (HPLC) |
| Melting Point | 187-190 °C |
| Application | LGD-2226 is a selective and orally active androgen receptor (AR) modulator with an EC50 of 0.2 nM and Ki of 1.5 nM for human AR. LGD-2226 has shown tissue selectivity in animal models, with lower effe |
| PubChem ID | 329748506 |
| MDL Number | MFCD15146764 |
| SMILES | FC(F)(F)CN(CC(F)(F)F)c1ccc2NC(=O)C=C(c2c1)C(F)(F)F |
| InChI | 1S/C14H9F9N2O/c15-12(16,17)5-25(6-13(18,19)20)7-1-2-10-8(3-7)9(14(21,22)23)4-11(26)24-10/h1-4H,5-6H2,(H,24,26) |
| InChI Key | ULBPQWIGZUGPHU-UHFFFAOYSA-N |
| Beilstein/REAXYS | 10716241 |
| NACRES Code | NA.24 |
| UNSPSC | 41116107 |
| Hazard Symbols | transportation |
| MSDS | msds/199733_1_328947_93_9.pdf |
| Bioactivity | LGD-2226 is a selective and orally active androgen receptor modulator with an EC50 of 0.2 nM and a Ki of 1.5 nM for human androgen receptor. LGD-2226 shows tissue selectivity in animal models, with reduced effects on prostate compared to muscle. LGD-2226 can be used for muscle wasting, osteoporosis and sexual dysfunction[1][2]. Related Catalog Research Areas >> Endocrinology Research Areas >> Metabolic Disease Signaling Pathways >> Others >> Androgen Receptor Target EC50: 0.2 nM (Androgen receptor)[1]; Ki: 1.5 nM (Androgen receptor)[1] In Vitro LGD-2226 (Compound 4m) occupies the same binding pocket as dihydrotestosterone (DHT), and in general, the protein backbone is superposable to that observed with DHT. Just like the carbonyl group of DHT, the quinolone carbonyl forms hydrogen bond interactions with GLN711 and ARG752. GLN711 forms an additional hydrogen bond with the quinolone NH of LGD-2226. The trifluoroethyl groups of LGD-2226 occupy the same space in the receptor as the C and D rings of the steroid[1]. In Vivo LGD-2226 (Compound 4m; 1-100 mg/kg; oral administration; daily; for 2 weeks; adult oORDX rats) has a pronounced effect on the levator ani muscle, maintaining the muscle weight at the eugonadal levels at an approximate 3 mg/kg dose. LGD-2226 has weak trophic effects on the prostate. An amount of 100 mg/kg LGD-2226 is required to maintain prostate weight at intact levels. These data clearly show the tissue selectivity of LGD-2226[1]. Animal Model: Adult orchidectomized (ORDX) rats[1] Dosage: 1-100 mg/kg Administration: Oral administration; daily; for 2 weeks Result: Had a pronounced effect on the levator ani muscle, maintaining the muscle weight at the eugonadal levels at an approximate 3 mg/kg dose. References [1]. van Oeveren A, et al. Discovery of 6-N,N-bis(2,2,2-trifluoroethyl)amino- 4-trifluoromethylquinolin-2(1H)-one as a novel selective androgen receptor modulator. J Med Chem. 2006 Oct 19;49(21):6143-6. [2]. Miner JN, et al. An orally active selective androgen receptor modulator is efficacious on bone, muscle, and sex function with reduced impact on prostate. Endocrinology. 2007 Jan;148(1):363-73. Chemical & Physical Properties Molecular Formula C14H9F9N2O Molecular Weight 392.22000 Exact Mass 392.05700 PSA 36.36000 LogP 4.89020 InChIKey ULBPQWIGZUGPHU-UHFFFAOYSA-N SMILES O=c1cc(C(F)(F)F)c2cc(N(CC(F)(F)F)CC(F)(F)F)ccc2[nH]1 |
| Use of | Properties Name 6-[bis(2,2,2-trifluoroethyl)amino]-4-(trifluoromethyl)-1H-quinolin-2-one Synonym More Synonyms LGD-2226 Biological Activity Related Catalog Research Areas >> Endocrinology Research Areas >> Metabolic Disease Signaling Pathways >> Others >> Androgen Receptor EC50: 0.2 nM (Androgen receptor)[1]; Ki: 1.5 nM (Androgen receptor)[1] References [1]. van Oeveren A, et al. Discovery of 6-N,N-bis(2,2,2-trifluoroethyl)amino- 4-trifluoromethylquinolin-2(1H)-one as a novel selective androgen receptor modulator. J Med Chem. 2006 Oct 19;49(21):6143-6. [2]. Miner JN, et al. An orally active selective androgen receptor modulator is efficacious on bone, muscle, and sex function with reduced impact on prostate. Endocrinology. 2007 Jan;148(1):363-73. Chemical & Physical Properties Molecular Formula C14H9F9N2O Exact Mass 392.05700 PSA 36.36000 LogP 4.89020 InChIKey ULBPQWIGZUGPHU-UHFFFAOYSA-N |
| Transport Info | Shipping Name: UN |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 United Nations shipping name European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Danger Regulations: No International Maritime Danger Regulations International Air Transport Danger Regulations: No Marine pollutants (yes/no): No 14.6 Special reminder to users No data available |
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