MedKoo Cat#: 527495 | Name: SSR504734

Description:

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

SSR504734 is a novel potent inhibitor of glycine transporter 1 (GlyT1).

Chemical Structure

SSR504734
CAS#742693-38-5

Theoretical Analysis

MedKoo Cat#: 527495

Name: SSR504734

CAS#: 742693-38-5

Chemical Formula: C20H20ClF3N2O

Exact Mass: 396.1216

Molecular Weight: 396.84

Elemental Analysis: C, 60.53; H, 5.08; Cl, 8.93; F, 14.36; N, 7.06; O, 4.03

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
SSR 504734; SSR-504734; SSR504734
IUPAC/Chemical Name
2-Chloro-N-[(S)-phenyl[(2S)-piperidin-2-yl] methyl]-3-trifluoromethyl benzamide
InChi Key
VWBQBABOBQJMJH-HNNXBMFYSA-N
InChi Code
InChI=1S/C20H20ClF3N2O/c21-18-16(10-6-11-17(18)20(22,23)24)19(27)25-13-15-9-4-5-12-26(15)14-7-2-1-3-8-14/h1-3,6-8,10-11,15H,4-5,9,12-13H2,(H,25,27)/t15-/m0/s1
SMILES Code
O=C(NC[C@H]1N(C2=CC=CC=C2)CCCC1)C3=CC=CC(C(F)(F)F)=C3Cl
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
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
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

Preparing Stock Solutions

The following data is based on the product molecular weight 396.84 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.

Recalculate based on batch purity %
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: Yamamoto S, Shibata T, Abe K, Oda K, Aoki T, Kawakita Y, Kawamoto H. Discovery of 3-Chloro-N-{(S)-[3-(1-ethyl-1H-pyrazol-4-yl)phenyl][(2S)-piperidine-2-yl]methyl}- 4-(trifluoromethyl)pyridine-2-carboxamide as a Potent Glycine Transporter 1 Inhibitor. Chem Pharm Bull (Tokyo). 2016;64(9):1321-37. doi: 10.1248/cpb.c16-00314. PubMed PMID: 27581637. 2: Komatsu H, Furuya Y, Sawada K, Asada T. Involvement of the strychnine-sensitive glycine receptor in the anxiolytic effects of GlyT1 inhibitors on maternal separation-induced ultrasonic vocalization in rat pups. Eur J Pharmacol. 2015 Jan 5;746:252-7. doi: 10.1016/j.ejphar.2014.11.024. Epub 2014 Nov 27. PubMed PMID: 25435080. 3: Singer P, Zhang W, Yee BK. SSR504734 enhances basal expression of prepulse inhibition but exacerbates the disruption of prepulse inhibition by apomorphine. Psychopharmacology (Berl). 2013 Nov;230(2):309-17. doi: 10.1007/s00213-013-3160-3. Epub 2013 Jun 5. PubMed PMID: 23736281; PubMed Central PMCID: PMC3809335. 4: Cervo L, Di Clemente A, Orrù A, Moro F, Cassina C, Pich EM, Corsi M, Gozzi A, Bifone A. Inhibition of glycine transporter-1 reduces cue-induced nicotine-seeking, but does not promote extinction of conditioned nicotine cue responding in the rat. Addict Biol. 2013 Sep;18(5):800-11. doi: 10.1111/adb.12049. Epub 2013 Mar 14. PubMed PMID: 23490434. 5: Trinh MA, Kaphzan H, Wek RC, Pierre P, Cavener DR, Klann E. Brain-specific disruption of the eIF2α kinase PERK decreases ATF4 expression and impairs behavioral flexibility. Cell Rep. 2012 Jun 28;1(6):676-88. doi: 10.1016/j.celrep.2012.04.010. Epub 2012 May 24. PubMed PMID: 22813743; PubMed Central PMCID: PMC3401382. 6: Fuchigami T, Takano A, Gulyás B, Jia Z, Finnema SJ, Andersson JD, Nakao R, Magata Y, Haratake M, Nakayama M, Halldin C. Synthesis and evaluation of 2-chloro N-[(S)-{(S)-1-[11 C]methylpiperidin-2-yl} (phenyl)methyl]3-trifluoromethyl-benzamide ([11 C]N-methyl-SSR504734) as a PET radioligand for glycine transporter 1. EJNMMI Res. 2012 Jul 9;2(1):37. doi: 10.1186/2191-219X-2-37. PubMed PMID: 22776065; PubMed Central PMCID: PMC3531252. 7: Shan L. [(125)I]2-Iodo-N-[(S)-{(S)-1-methylpiperidin-2-yl}(phenyl)methyl]3-trifluoromethy l-benzamide. 2012 Apr 10 [updated 2012 May 30]. Molecular Imaging and Contrast Agent Database (MICAD) [Internet]. Bethesda (MD): National Center for Biotechnology Information (US); 2004-2013. Available from http://www.ncbi.nlm.nih.gov/books/NBK97276/ PubMed PMID: 22675745. 8: Zhang J, Wu J, Toyohara J, Fujita Y, Chen H, Hashimoto K. Pharmacological characterization of [³H]CHIBA-3007 binding to glycine transporter 1 in the rat brain. PLoS One. 2011;6(6):e21322. doi: 10.1371/journal.pone.0021322. Epub 2011 Jun 23. PubMed PMID: 21731704; PubMed Central PMCID: PMC3121759. 9: Toyohara J, Ishiwata K, Sakata M, Wu J, Nishiyama S, Tsukada H, Hashimoto K. In vivo evaluation of carbon-11-labelled non-sarcosine-based glycine transporter 1 inhibitors in mice and conscious monkeys. Nucl Med Biol. 2011 May;38(4):517-27. doi: 10.1016/j.nucmedbio.2010.11.009. Epub 2011 Feb 4. PubMed PMID: 21531289. 10: Nikiforuk A, Kos T, Rafa D, Behl B, Bespalov A, Popik P. Blockade of glycine transporter 1 by SSR-504734 promotes cognitive flexibility in glycine/NMDA receptor-dependent manner. Neuropharmacology. 2011 Jul-Aug;61(1-2):262-7. doi: 10.1016/j.neuropharm.2011.04.010. Epub 2011 Apr 21. PubMed PMID: 21530555. 11: Flood DG, Zuvich E, Marino MJ, Gasior M. Prepulse inhibition of the startle reflex and response to antipsychotic treatments in two outbred mouse strains in comparison to the inbred DBA/2 mouse. Psychopharmacology (Berl). 2011 Jun;215(3):441-54. doi: 10.1007/s00213-011-2196-5. Epub 2011 Feb 8. PubMed PMID: 21301810. 12: Durkin JT, Spais CM, Schreiber J, Kopec K, Meyer SL. Amino-terminal isoforms of the human glycine transporter GlyT1 exhibit similar pharmacology. Brain Res. 2011 Feb 16;1374:1-7. doi: 10.1016/j.brainres.2010.11.083. Epub 2010 Dec 4. PubMed PMID: 21138739. 13: Nishikawa H, Inoue T, Izumi T, Nakagawa S, Koyama T. SSR504734, a glycine transporter-1 inhibitor, attenuates acquisition and expression of contextual conditioned fear in rats. Behav Pharmacol. 2010 Sep;21(5-6):576-9. doi: 10.1097/FBP.0b013e32833d419d. PubMed PMID: 20613495. 14: Singer P, Feldon J, Yee BK. Interactions between the glycine transporter 1(GlyT1) inhibitor SSR504734 and psychoactive drugs in mouse motor behaviour. Eur Neuropsychopharmacol. 2009 Aug;19(8):571-80. doi: 10.1016/j.euroneuro.2009.02.004. Epub 2009 Mar 17. PubMed PMID: 19282154. 15: Mezler M, Hornberger W, Mueller R, Schmidt M, Amberg W, Braje W, Ochse M, Schoemaker H, Behl B. Inhibitors of GlyT1 affect glycine transport via discrete binding sites. Mol Pharmacol. 2008 Dec;74(6):1705-15. doi: 10.1124/mol.108.049312. Epub 2008 Sep 24. Erratum in: Mol Pharmacol. 2009 Jan;75(1):258.. Amberg, Martin Schmidt Willi [corrected to Schmidt, Martin]; Amberg, Martin Schmidt Willi [corrected to Amberg, Willi]. PubMed PMID: 18815213. 16: Singer P, Feldon J, Yee BK. The glycine transporter 1 inhibitor SSR504734 enhances working memory performance in a continuous delayed alternation task in C57BL/6 mice. Psychopharmacology (Berl). 2009 Jan;202(1-3):371-84. doi: 10.1007/s00213-008-1286-5. Epub 2008 Aug 29. PubMed PMID: 18758757. 17: Black MD, Varty GB, Arad M, Barak S, De Levie A, Boulay D, Pichat P, Griebel G, Weiner I. Procognitive and antipsychotic efficacy of glycine transport 1 inhibitors (GlyT1) in acute and neurodevelopmental models of schizophrenia: latent inhibition studies in the rat. Psychopharmacology (Berl). 2009 Jan;202(1-3):385-96. doi: 10.1007/s00213-008-1289-2. Epub 2008 Aug 16. PubMed PMID: 18709358. 18: Gozzi A, Herdon H, Schwarz A, Bertani S, Crestan V, Turrini G, Bifone A. Pharmacological stimulation of NMDA receptors via co-agonist site suppresses fMRI response to phencyclidine in the rat. Psychopharmacology (Berl). 2008 Dec;201(2):273-84. doi: 10.1007/s00213-008-1271-z. Epub 2008 Aug 15. PubMed PMID: 18704372. 19: Hashimoto K. Glycine transporter inhibitors as therapeutic agents for schizophrenia. Recent Pat CNS Drug Discov. 2006 Jan;1(1):43-53. Review. PubMed PMID: 18221190. 20: Harich S, Gross G, Bespalov A. Stimulation of the metabotropic glutamate 2/3 receptor attenuates social novelty discrimination deficits induced by neonatal phencyclidine treatment. Psychopharmacology (Berl). 2007 Jul;192(4):511-9. Epub 2007 Feb 23. PubMed PMID: 17318501.