| Identification | Back Directory | [Name]
LGD-2226 | [CAS]
328947-93-9 | [Synonyms]
LGD-2226
LGD-2226
(LGD2226)
6-[Bis(2,2,2-trifluoroethyl)amino]-4-(trifluoromethyl)-2(1H)-quinolinone
2(1H)-Quinolinone, 6-[bis(2,2,2-trifluoroethyl)amino]-4-(trifluoromethyl)- | [EINECS(EC#)]
251-228-4 | [Molecular Formula]
C14H9F9N2O | [MDL Number]
MFCD15146764 | [MOL File]
328947-93-9.mol | [Molecular Weight]
392.22 |
| Chemical Properties | Back Directory | [Melting point ]
187-190°C | [Boiling point ]
364.4±42.0 °C(Predicted) | [density ]
1.526±0.06 g/cm3(Predicted) | [storage temp. ]
-20°C Freezer, Under inert atmosphere | [solubility ]
DMSO (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
9.88±0.70(Predicted) | [color ]
Pale Yellow to Light Yellow | [BRN ]
10716241 | [InChI]
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) | [InChIKey]
ULBPQWIGZUGPHU-UHFFFAOYSA-N | [SMILES]
N1C2=C(C=C(N(CC(F)(F)F)CC(F)(F)F)C=C2)C(C(F)(F)F)=CC1=O |
| Hazard Information | Back Directory | [Uses]
LGD-2226 is an orally active potent and selective androgen receptor modulator used in the treatment of muscle wasting and osteoporosis. Show to have an anabolic effect on muscle and bone tissue. | [Synthesis]
A 2 L round flask, under argon, was charged with a solution of the 14.00 g amine( 6-Amino-4-trifluoromethylquinolin-2(1H)-one )in 350 ml trifluoroacetic acid. 5.80 g NaBH4 was added within 1 h. The mixture was stirred at room temperature for 16 h. After that 4.50 g NaBH4 was added and then heated to 70°C for 5 h. The heating bath was removed and it was stirred at room temperature over 2 d. In several portions water was carefully added. In total 1500 ml water was slowly added. The yellow-greenish precipitate was filtered and rinsed with water. After drying, the crude product was purified by column chromatography on silica gel by using hexane-ethyl acetate (1:4), followed by a recrystallization in chloroform. 18.1 g of LGD-2226 was obtained as a bright yellow solid (76%). | [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. |
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