Iclepertin | CAS#1421936-85-7 | Glycine transporter inhibitor

MedKoo Cat#: 465391 | Name: Iclepertin

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Iclepertin, also known as BI 425809, is an antipsychotic glycine transporter inhibitor. iclepertin reversed sensory processing deficits and neural network dysfunction evoked by inhibition of N-methyl-D-aspartate receptors and enhanced working memory performance and social recognition in rodents. Iclepertin can be used for Alzheimer disease and schizophrenia research.

Chemical Structure

Iclepertin

CAS#1421936-85-7

Theoretical Analysis

MedKoo Cat#: 465391

Name: Iclepertin

CAS#: 1421936-85-7

Chemical Formula: C20H18F6N2O5S

Exact Mass: 512.0841

Molecular Weight: 512.42

Elemental Analysis: C, 46.88; H, 3.54; F, 22.25; N, 5.47; O, 15.61; S, 6.26

Price and Availability

Size	Price	Availability
25mg	USD 250.00	2 Weeks
50mg	USD 450.00	2 Weeks
100mg	USD 750.00	2 Weeks
200mg	USD 1,250.00	2 Weeks
500mg	USD 2,650.00	2 Weeks
1g	USD 3,850.00	2 Weeks
2g	USD 6,450.00	2 Weeks

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Related CAS #

1421936-85-7

Synonym

Iclepertin; BI 425809; BI-425809; BI425809;

IUPAC/Chemical Name

(5-(methylsulfonyl)-2-(((S)-1,1,1-trifluoropropan-2-yl)oxy)phenyl)((1R,5R)-1-(5-(trifluoromethyl)isoxazol-3-yl)-3-azabicyclo[3.1.0]hexan-3-yl)methanone

InChi Key

MYHDQTVHHMSLEF-FHGNATFXSA-N

InChi Code

InChI=1S/C20H18F6N2O5S/c1-10(19(21,22)23)32-14-4-3-12(34(2,30)31)5-13(14)17(29)28-8-11-7-18(11,9-28)15-6-16(33-27-15)20(24,25)26/h3-6,10-11H,7-9H2,1-2H3/t10-,11-,18-/m0/s1

SMILES Code

O=C(C1=CC(S(=O)(C)=O)=CC=C1O[C@@H](C)C(F)(F)F)N2C[C@@]3(C4=NOC(C(F)(F)F)=C4)C[C@@]3([H])C2

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Increased glycine availability at the synaptic cleft may enhance N-methyl-D-aspartate receptor signalling and provide a promising therapeutic strategy for cognitive impairment associated with schizophrenia.

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 512.42 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Latli B, Hrapchak MJ, Chevliakov M, Samankumara LP, Frutos RP, Lee H. Stable isotope synthesis of glycine transporter 1 inhibitor Iclepertin (BI 425809) and its major metabolites. J Labelled Comp Radiopharm. 2023 Nov;66(13):414-427. doi: 10.1002/jlcr.4063. Epub 2023 Sep 20. PMID: 37727936. 2: Latli B, Hrapchak MJ, Frutos RP, Lee H, Song JJ. Carbon 14 synthesis of glycine transporter 1 inhibitor Iclepertin (BI 425809) and its major metabolites. J Labelled Comp Radiopharm. 2023 Sep;66(11):336-344. doi: 10.1002/jlcr.4051. Epub 2023 Jun 29. PMID: 37382087. 3: Chan TS, Byer-Alcorace AJ, Latli B, Liu P, Maw HH, Raymond KG, Scaringella YS, Teitelbaum AM, Wang T, Whitcher-Johnstone A, Taub ME. Characterization of Divergent Metabolic Pathways in Elucidating an Unexpected, Slow-Forming, and Long Half-Life Major Metabolite of Iclepertin. Pharm Res. 2023 Aug;40(8):1901-1913. doi: 10.1007/s11095-023-03530-z. Epub 2023 Jun 6. PMID: 37280472. 4: Rosenbrock H, Desch M, Wunderlich G. Development of the novel GlyT1 inhibitor, iclepertin (BI 425809), for the treatment of cognitive impairment associated with schizophrenia. Eur Arch Psychiatry Clin Neurosci. 2023 Oct;273(7):1557-1566. doi: 10.1007/s00406-023-01576-z. Epub 2023 Mar 27. PMID: 36971864; PMCID: PMC10465677. 5: Wunderlich G, Blahova Z, Garcia M, Jessen F. Efficacy and safety of the novel GlyT1 inhibitor BI 425809 in Alzheimer's dementia: a randomized controlled trial. Alzheimers Res Ther. 2023 Jan 28;15(1):24. doi: 10.1186/s13195-023-01163-3. PMID: 36709275; PMCID: PMC9883916. 6: Desch M, Schlecker C, Hohl K, Liesenfeld KH, Chan T, Müller F, Wunderlich G, Keller S, Ishiguro N, Wind S. Pharmacokinetic-Interactions of BI 425809, a Novel Glycine Transporter 1 Inhibitor, With Cytochrome P450 and P-Glycoprotein Substrates: Findings From In Vitro Analyses and an Open-Label, Single-Sequence Phase I Study. J Clin Psychopharmacol. 2023 Mar-Apr 01;43(2):113-121. doi: 10.1097/JCP.0000000000001656. Epub 2023 Jan 26. PMID: 36700734; PMCID: PMC9988221. 7: Schultheis C, Rosenbrock H, Mack SR, Vinisko R, Schuelert N, Plano A, Süssmuth SD. Quantitative electroencephalography parameters as neurophysiological biomarkers of schizophrenia-related deficits: A Phase II substudy of patients treated with iclepertin (BI 425809). Transl Psychiatry. 2022 Aug 11;12(1):329. doi: 10.1038/s41398-022-02096-5. PMID: 35953474; PMCID: PMC9372178. 8: Rosenbrock H, Dorner-Ciossek C, Giovannini R, Schmid B, Schuelert N. Effects of the Glycine Transporter-1 Inhibitor Iclepertin (BI 425809) on Sensory Processing, Neural Network Function, and Cognition in Animal Models Related to Schizophrenia. J Pharmacol Exp Ther. 2022 Aug;382(2):223-232. doi: 10.1124/jpet.121.001071. Epub 2022 Jun 5. PMID: 35661632. 9: Burkard U, Desch M, Shatillo Y, Wunderlich G, Mack SR, Schlecker C, Teitelbaum AM, Liu P, Chan TS. Correction to: The Absolute Bioavailability, Absorption, Distribution, Metabolism, and Excretion of BI 425809 Administered as an Oral Dose or an Oral Dose with an Intravenous Microtracer Dose of [14C]‑BI 425809 in Healthy Males. Clin Drug Investig. 2022 Apr;42(4):375. doi: 10.1007/s40261-022-01134-w. Erratum for: Clin Drug Investig. 2022 Jan;42(1):87-99. PMID: 35286627; PMCID: PMC8989795. 10: Burkard U, Desch M, Shatillo Y, Wunderlich G, Mack SR, Schlecker C, Teitelbaum AM, Liu P, Chan TS. The Absolute Bioavailability, Absorption, Distribution, Metabolism, and Excretion of BI 425809 Administered as an Oral Dose or an Oral Dose with an Intravenous Microtracer Dose of [14C]-BI 425809 in Healthy Males. Clin Drug Investig. 2022 Jan;42(1):87-99. doi: 10.1007/s40261-021-01111-9. Epub 2021 Dec 22. Erratum in: Clin Drug Investig. 2022 Apr;42(4):375. PMID: 34936055; PMCID: PMC8901509. 11: Lobo MC, Whitehurst TS, Kaar SJ, Howes OD. New and emerging treatments for schizophrenia: a narrative review of their pharmacology, efficacy and side effect profile relative to established antipsychotics. Neurosci Biobehav Rev. 2022 Jan;132:324-361. doi: 10.1016/j.neubiorev.2021.11.032. Epub 2021 Nov 24. PMID: 34838528. 12: Desch M, Wunderlich G, Goettel M, Goetz S, Liesenfeld KH, Chan TS, Rosenbrock H, Sennewald R, Link J, Keller S, Wind S. Effects of Cytochrome P450 3A4 Induction and Inhibition on the Pharmacokinetics of BI 425809, a Novel Glycine Transporter 1 Inhibitor. Eur J Drug Metab Pharmacokinet. 2022 Jan;47(1):91-103. doi: 10.1007/s13318-021-00723-y. Epub 2021 Oct 29. PMID: 34716565; PMCID: PMC8752533. 13: Fleischhacker WW, Podhorna J, Gröschl M, Hake S, Zhao Y, Huang S, Keefe RSE, Desch M, Brenner R, Walling DP, Mantero-Atienza E, Nakagome K, Pollentier S. Efficacy and safety of the novel glycine transporter inhibitor BI 425809 once daily in patients with schizophrenia: a double-blind, randomised, placebo- controlled phase 2 study. Lancet Psychiatry. 2021 Mar;8(3):191-201. doi: 10.1016/S2215-0366(20)30513-7. PMID: 33610228. 14: Harvey PD, Bowie CR, McDonald S, Podhorna J. Evaluation of the Efficacy of BI 425809 Pharmacotherapy in Patients with Schizophrenia Receiving Computerized Cognitive Training: Methodology for a Double-blind, Randomized, Parallel-group Trial. Clin Drug Investig. 2020 Apr;40(4):377-385. doi: 10.1007/s40261-020-00893-8. PMID: 32036587; PMCID: PMC7105423. 15: Krogmann A, Peters L, von Hardenberg L, Bödeker K, Nöhles VB, Correll CU. Keeping up with the therapeutic advances in schizophrenia: a review of novel and emerging pharmacological entities. CNS Spectr. 2019 Aug;24(S1):38-69. doi: 10.1017/S109285291900124X. PMID: 31482779. 16: Tsuda Y, Ugai H, Wunderlich G, Shin JG. Pharmacokinetics of Single Doses of BI 425809 in Healthy Chinese and Japanese Subjects: A Randomized Study. Clin Ther. 2019 May;41(5):961-971. doi: 10.1016/j.clinthera.2019.03.014. Epub 2019 Apr 17. PMID: 31005336. 17: Rosenbrock H, Desch M, Kleiner O, Dorner-Ciossek C, Schmid B, Keller S, Schlecker C, Moschetti V, Goetz S, Liesenfeld KH, Fillon G, Giovannini R, Ramael S, Wunderlich G, Wind S. Evaluation of Pharmacokinetics and Pharmacodynamics of BI 425809, a Novel GlyT1 Inhibitor: Translational Studies. Clin Transl Sci. 2018 Nov;11(6):616-623. doi: 10.1111/cts.12578. Epub 2018 Aug 23. PMID: 30136756; PMCID: PMC6226115. 18: Moschetti V, Schlecker C, Wind S, Goetz S, Schmitt H, Schultz A, Liesenfeld KH, Wunderlich G, Desch M. Multiple Rising Doses of Oral BI 425809, a GlyT1 Inhibitor, in Young and Elderly Healthy Volunteers: A Randomised, Double-Blind, Phase I Study Investigating Safety and Pharmacokinetics. Clin Drug Investig. 2018 Aug;38(8):737-750. doi: 10.1007/s40261-018-0660-2. PMID: 29846887; PMCID: PMC6061410. 19: Moschetti V, Desch M, Goetz S, Liesenfeld KH, Rosenbrock H, Kammerer KP, Wunderlich G, Wind S. Safety, Tolerability and Pharmacokinetics of Oral BI 425809, a Glycine Transporter 1 Inhibitor, in Healthy Male Volunteers: A Partially Randomised, Single-Blind, Placebo-Controlled, First-in-Human Study. Eur J Drug Metab Pharmacokinet. 2018 Apr;43(2):239-249. doi: 10.1007/s13318-017-0440-z. PMID: 29076028; PMCID: PMC5854750.