| Identification | Back Directory | [Name]
ML-180 | [CAS]
863588-32-3 | [Synonyms]
SR1848
ML-180
ML-180 (SR1848)
SR1848 >=98% (HPLC)
6-[4-(3-chlorophenyl)piperazin-1-yl]-3-cyclohexyl-1H-pyrimidine-2,4-dione
6-(4-(3-chlorophenyl)piperazin-1-yl)-3-cyclohexylpyrimidine-2,4(1H,3H)-dione
2,4(1H,3H)-Pyrimidinedione, 6-[4-(3-chlorophenyl)-1-piperazinyl]-3-cyclohexyl- | [Molecular Formula]
C20H25ClN4O2 | [MDL Number]
MFCD05894342 | [MOL File]
863588-32-3.mol | [Molecular Weight]
388.89 |
| Chemical Properties | Back Directory | [density ]
1.312±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,2-8°C | [solubility ]
DMSO: 10 mg/ml | [form ]
A crystalline solid | [pka]
9.37±0.40(Predicted) | [color ]
Off-white to light yellow | [InChI]
InChI=1S/C20H25ClN4O2/c21-15-5-4-8-17(13-15)23-9-11-24(12-10-23)18-14-19(26)25(20(27)22-18)16-6-2-1-3-7-16/h4-5,8,13-14,16H,1-3,6-7,9-12H2,(H,22,27) | [InChIKey]
CHMQQIFPOIZPIJ-UHFFFAOYSA-N | [SMILES]
C1(=O)NC(N2CCN(C3=CC=CC(Cl)=C3)CC2)=CC(=O)N1C1CCCCC1 |
| Hazard Information | Back Directory | [Description]
ML-180 is an inverse agonist of liver receptor homolog-1 (LRH-1, IC50 = 3.7 μM) with maximum efficacy of 64% repression.1 It is inactive at the related steroidogenic factor-1 transcriptional activator.1 Through LRH-1, ML-180 alters the expression of haptoglobin and serum amyloid proteins A1 and A4, induces the death of estrogen-receptor negative MDA-MB-231 breast cancer cells, and inhibits the steroidogenic acute regulatory promoter (IC50 = 2.05 μM).1 | [Uses]
ML-180 (SR1848) is a potent orphan nuclear receptor liver receptor homolog 1 (LRH-1; NR5A2) inverse agonist with an IC50 of 3.7 μM. ML-180 is inactive for steroidogenic factor-1 (SF-1; NR5A1; IC50>10 μM). ML-180 has the potential for LRH-1-dependent cancers[1][2]. | [Definition]
ChEBI: 6-[4-(3-chlorophenyl)-1-piperazinyl]-3-cyclohexyl-1H-pyrimidine-2,4-dione is a member of piperazines. | [in vivo]
ML-180 (SR1848; 30 mg/kg; i.p.; daily; for 10 days) has a statistically significant decrease of both LRH-1 and SHP mRNA in adrenal glands and pancreatic tissue[2].
| Animal Model: | 8-week-old C57Bl/6J mice[2] | | Dosage: | 30 mg/kg | | Administration: | IP; daily; for 10 days | | Result: | Had a statistically significant decrease of both LRH-1 and SHP mRNA in adrenal glands and pancreatic tissue.
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| [References]
[1] Busby S, et al. Discovery of Inverse Agonists for the Liver Receptor Homologue-1 (LRH1; NR5A2). PMID:23166964
[2] Corzo CA, et al. Antiproliferation activity of a small molecule repressor of liver receptor homolog 1. Mol Pharmacol. 2015 Feb;87(2):296-304. DOI:10.1124/mol.114.095554 |
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