RO4917838 (R enantioMer)
- Product Name
- RO4917838 (R enantioMer)
- CAS No.
- 845614-12-2
- Chemical Name
- RO4917838 (R enantioMer)
- Synonyms
- RG1678 (R enantioMer);RG 1678 (R enantioMer);RG-1678 (R enantioMer);RO4917838 (R enantioMer);Bitopertin (R enantioMer);RG1678 (R ENANTIOMER); RG 1678 (R ENANTIOMER); RG-1678 (R ENANTIOMER); RO4917838 (R ENANTIOMER);[4-(3-Fluoro-5-trifluoromethylpyridin-2-yl)piperazin-1-yl][5-Methylsulfonyl-2-[((R)-2,2,2-trifluoro-1-methylethyl)oxy]phenyl]methanone;Methanone, [4-[3-fluoro-5-(trifluoromethyl)-2-pyridinyl]-1-piperazinyl][5-(methylsulfonyl)-2-[(1R)-2,2,2-trifluoro-1-methylethoxy]phenyl]-
- CBNumber
- CB22666598
- Molecular Formula
- C21H20F7N3O4S
- Formula Weight
- 543.46
- MOL File
- 845614-12-2.mol
RO4917838 (R enantioMer) Property
- Boiling point:
- 635.1±55.0 °C(Predicted)
- Density
- 1.444±0.06 g/cm3(Predicted)
- storage temp.
- Store at -20°C
- solubility
- Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
- form
- Powder
- pka
- 3.57±0.39(Predicted)
- color
- White to off-white
N-Bromosuccinimide Price
- Product number
- CS-1261
- Product name
- BitopertinRenantiomer
- Purity
- 95.68%
- Packaging
- 5mg
- Price
- $220
- Updated
- 2021/12/16
RO4917838 (R enantioMer) Chemical Properties,Usage,Production
Uses
Bitopertin R enantiomer (RG1678 R enantiomer; RO4917838 R enantiomer) is the R-enantiomer of Bitopertin. Bitopertin is a potent, noncompetitive glycine reuptake inhibitor, inhibits glycine uptake at human GlyT1 with a concentration exhibiting IC50 of 25 nM.
in vivo
Bitopertin (RG1678) dose-dependently increases cerebrospinal fluid and striatal levels of glycine measured bymicrodialysis in rats. Additionally Bitopertin attenuates hyperlocomotion induced by the psychostimulant D-amphetamine or the NMDA receptor glycine site antagonist L-687,414 in mice. Bitopertin also prevents the hyper-response to D-amphetamine challenge in rats treated chronically with phencyclidine, an NMDA receptor open-channel blocker. Administration of vehicle has no effect on extracellular levels of striatal glycine, which remained constant throughout the experiment. In contrast, p.o. administration of Bitopertin (1-30 mg/kg) produced a dose-dependent increase in extracellular glycine levels. Bitopertin 30 mg/kg produces glycine levels 2.5 times higher than pretreatment levels. A similar dose-dependent increase in glycine concentration is observed in the CSF of rats treated p.o. with Bitopertin (1-10 mg/kg) compared with vehicle-treated animals, 3 h after drug administration. Interestingly, the level of CSF glycine increase 3 h after Bitopertin dosing is very similar to the increase in the microdialysis experiment at the same time point[1]. In vivo pharmacokinetic studies in rat and monkey reveals that Bitopertin (RG1678) has, in both species, a low plasma clearance, an intermediate volume of distribution, a good oral bioavailability (78% for rat, 56% for monkey), and a favorable terminal half-life (5.8 h for rat, 6.4 h for monkey). The plasma protein binding is high in the two preclinical species (97%) and in human (98%). The CNS penetration of Bitopertin in rat (brain/plasma=0.7) is better than that in mouse (brain/plasma=0.5)[2].
References
[1] Alberati D, et al. Glycine reuptake inhibitor RG1678: A pharmacologic characterization of an investigational agent for the treatment of schizophrenia. Neuropharmacology. 2012 Feb;62(2):1152-61. DOI:10.1016/j.neuropharm.2011.11.008
[2] Pinard E, et al. Selective GlyT1 Inhibitors: Discovery of [4-(3-Fluoro-5-trifluoromethylpyridin-2-yl)piperazin-1-yl][5-methanesulfonyl-2-((S)-2,2,2-trifluoro-1-methylethoxy)phenyl]methanone (RG1678), a Promising Novel Medicine To Treat Schizophrenia. J Me DOI:10.1021/jm100210p
[3] Alberati, Daniela; Moreau, Jean-Luc; Lengyel, Judith et al. Glycine reuptake inhibitor RG1678: A pharmacologic characterization of an investigational agent for the treatment of schizophrenia. Neuropharmacology (2012), 62(2), 1152-1161. DOI:10.1016/j.neuropharm.2011.11.008
[4] Hofmann C, Banken L, Hahn M et al. Evaluation of the Effects of Bitopertin (RG1678) on Cardiac Repolarization: A Thorough Corrected QT Study in Healthy Male Volunteers. Clin Ther. 2012 Oct;34(10):2061-71. DOI:10.1016/j.clinthera.2012.08.010
[5] Martin-Facklam M, Pizzagalli F, Zhou Y et al. Glycine Transporter Type 1 Occupancy by Bitopertin: a Positron Emission Tomography Study in Healthy Volunteers. Neuropsychopharmacology. 2012 Nov 7. doi: 10.1038/npp.2012.212. [Epub ahead of print] DOI:10.1038/npp.2012.212
RO4917838 (R enantioMer) Preparation Products And Raw materials
Raw materials
Preparation Products
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