Bitopertin

• CAT Number: I005056
• CAS Number: 845614-11-1
• Molecular Formula: C21H20F7N3O4S
• Molecular Weight: 543.5
• Purity: ≥95%
• Target: GlyT1
• Solubility: 10 mM in DMSO
• Storage: Store at -20°C
• IUPAC Name: [4-[3-fluoro-5-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl]-[5-methylsulfonyl-2-[(2S)-1,1,1-trifluoropropan-2-yl]oxyphenyl]methanone
• InChI: InChI=1S/C21H20F7N3O4S/c1-12(20(23,24)25)35-17-4-3-14(36(2,33)34)10-15(17)19(32)31-7-5-30(6-8-31)18-16(22)9-13(11-29-18)21(26,27)28/h3-4,9-12H,5-8H2,1-2H3/t12-/m0/s1
• InChIKey: YUUGYIUSCYNSQR-UHFFFAOYSA-N
• SMILES: C[C@@H](C(F)(F)F)OC1=C(C=C(C=C1)S(=O)(=O)C)C(=O)N2CCN(CC2)C3=C(C=C(C=N3)C(F)(F)F)F

Bitopertin (Cat.No:I005056), also known as RG1678, is a glycine reuptake inhibitor used in the treatment of schizophrenia. It acts by inhibiting the glycine transporter 1, which increases the availability of glycine in the synapses and enhances the NMDA receptor-mediated neurotransmission. Bitopertin has been shown to improve the symptoms of negative and cognitive symptoms of schizophrenia in clinical trials.

Reference

1:Bitopertin in Negative Symptoms of Schizophrenia-Results From the Phase III FlashLyte and DayLyte Studies. Bugarski-Kirola D, Blaettler T, Arango C, Fleischhacker WW, Garibaldi G, Wang A, Dixon M, Bressan RA, Nasrallah H, Lawrie S, Napieralski J, Ochi-Lohmann T, Reid C, Marder SR.Biol Psychiatry. 2016 Dec 15. pii: S0006-3223(16)33109-2. doi: 10.1016/j.biopsych.2016.11.014. [Epub ahead of print] PMID: 28117049 2:Efficacy and Safety of Bitopertin in Patients with Schizophrenia and Predominant Negative Symptoms: Subgroup Analysis of Japanese Patients from the Global Randomized Phase 2 Trial. Hirayasu Y, Sato SI, Shuto N, Nakano M, Higuchi T.Psychiatry Investig. 2017 Jan;14(1):63-73. doi: 10.4306/pi.2017.14.1.63. Epub 2016 Dec 29. PMID: 28096877 Free PMC Article3:Bitopertin in schizophrenia: glass half full? Javitt DC.Lancet Psychiatry. 2016 Dec;3(12):1092-1093. doi: 10.1016/S2215-0366(16)30354-6. Epub 2016 Nov 2. No abstract available. PMID: 27816569 4:Efficacy and safety of adjunctive bitopertin versus placebo in patients with suboptimally controlled symptoms of schizophrenia treated with antipsychotics: results from three phase 3, randomised, double-blind, parallel-group, placebo-controlled, multicentre studies in the SearchLyte clinical trial programme. Bugarski-Kirola D, Iwata N, Sameljak S, Reid C, Blaettler T, Millar L, Marques TR, Garibaldi G, Kapur S.Lancet Psychiatry. 2016 Dec;3(12):1115-1128. doi: 10.1016/S2215-0366(16)30344-3. Epub 2016 Nov 2. PMID: 27816567 5:Effects of the glycine reuptake inhibitors bitopertin and RG7118 on glycine in cerebrospinal fluid: results of two proofs of mechanism studies in healthy volunteers. Hofmann C, Pizzagalli F, Boetsch C, Alberati D, Ereshefsky L, Jhee S, Patat A, Boutouyrie-Dumont B, Martin-Facklam M.Psychopharmacology (Berl). 2016 Jul;233(13):2429-39. doi: 10.1007/s00213-016-4317-7. Epub 2016 May 14. PMID: 27178435 6:A double-blind randomized study assessing safety and efficacy following one-year adjunctive treatment with bitopertin, a glycine reuptake inhibitor, in Japanese patients with schizophrenia. Hirayasu Y, Sato S, Takahashi H, Iida S, Shuto N, Yoshida S, Funatogawa T, Yamada T, Higuchi T.BMC Psychiatry. 2016 Mar 15;16:66. doi: 10.1186/s12888-016-0778-9. PMID: 26980460 Free PMC Article7:Combining /’Bottom-Up/’ and /’Top-Down/’ Methods to Assess Ethnic Difference in Clearance: Bitopertin as an Example. Feng S, Shi J, Parrott N, Hu P, Weber C, Martin-Facklam M, Saito T, Peck R.Clin Pharmacokinet. 2016 Jul;55(7):823-32. doi: 10.1007/s40262-015-0356-1. PMID: 26715215 Free PMC Article8:Effects of Cytochrome P450 3A4 Inhibitors-Ketoconazole and Erythromycin-on Bitopertin Pharmacokinetics and Comparison with Physiologically Based Modelling Predictions. Boetsch C, Parrott N, Fowler S, Poirier A, Hainzl D, Banken L, Martin-Facklam M, Hofmann C.Clin Pharmacokinet. 2016 Feb;55(2):237-47. doi: 10.1007/s40262-015-0312-0. PMID: 26341813 9:Health-related quality of life in patients with prominent negative symptoms: results from a multicenter randomized Phase II trial on bitopertin. Rofail D, Regnault A, le Scouiller S, Berardo CG, Umbricht D, Fitzpatrick R.Qual Life Res. 2016 Jan;25(1):201-11. doi: 10.1007/s11136-015-1057-9. Epub 2015 Jul 5. PMID: 26143058 10:Physiologically based absorption modelling to predict the impact of drug properties on pharmacokinetics of bitopertin. Parrott N, Hainzl D, Scheubel E, Krimmer S, Boetsch C, Guerini E, Martin-Facklam M.AAPS J. 2014 Sep;16(5):1077-84. doi: 10.1208/s12248-014-9639-y. Epub 2014 Jun 27. PMID: 24970349 Free PMC Article