LY-404187 | CAS#211311-95-4 | AMPA receptor potentiator

LY-404187
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 525586

CAS#: 211311-95-4

Description: LY-404187 is an ampakine, AMPA receptor potentiator. LY-404187 has been demonstrated to enhance cognitive function in animal studies, and has also shown effects suggesting antidepressant action as well as having possible application in the treatment of schizophrenia, Parkinson's disease and ADHD. These effects appear to be mediated through multiple mechanisms of action secondary to AMPA receptor potentiation, with a prominent effect seen in research being increased levels of BDNF in the brain.

Chemical Structure

LY-404187

CAS# 211311-95-4

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 525586
Name: LY-404187
CAS#: 211311-95-4
Chemical Formula: C19H22N2O2S
Exact Mass: 342.14
Molecular Weight: 342.457
Elemental Analysis: C, 66.64; H, 6.48; N, 8.18; O, 9.34; S, 9.36

Price and Availability

Size	Price	Availability
50mg	USD 450	2 weeks
100mg	USD 750	2 weeks
200mg	USD 1250	2 weeks
500mg	USD 2250	2 weeks
1g	USD 3450	2 weeks
2g	USD 5450	2 weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: LY-404187; LY 404187; LY404187.

IUPAC/Chemical Name: 2-Propanesulfonamide, N-(2-(4'-cyano(1,1'-biphenyl)-4-yl)propyl)-

InChi Key: HOQAVGZLYRYHSO-UHFFFAOYSA-N

InChi Code: InChI=1S/C19H22N2O2S/c1-14(2)24(22,23)21-13-15(3)17-8-10-19(11-9-17)18-6-4-16(12-20)5-7-18/h4-11,14-15,21H,13H2,1-3H3

SMILES Code: CC(S(=O)(NCC(C1=CC=C(C2=CC=C(C#N)C=C2)C=C1)C)=O)C

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:

Product Data:

Product Data

Instruction:

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Biological target:	LY-404187 is a potent, selective and centrally active positive allosteric modulator of AMPA receptors, with the EC50s of 5.65, 0.15, 1.44, 1.66 and 0.21 µM for GluR1i, GluR2i, GluR2o, GluR3i and GluR4i.
In vitro activity:	Using a strategy of combined morphological and biochemical analyses, this study investigated the effect of the AMPA receptor potentiator LY404187 on neurite growth in the SH-SY5Y human neuroblastoma cell line. LY404187 (0.1-10 microM) increased average neurite length and neurofilament expression when co-administered with s-AMPA. Antibody sequestration of BDNF attenuated neurite growth following AMPA receptor potentiator administration, suggesting that LY404187 increases neurite length in vitro by a BDNF mediated mechanism. Reference: Neuropharmacology. 2007 Feb;52(2):590-7. https://pubmed.ncbi.nlm.nih.gov/17101156/
In vivo activity:	The present study reports that the potent and selective AMPA receptor potentiator, R,S-N-2-(4-(4-Cyanophenyl)phenyl)propyl 2-propanesulfonamide (LY404187), provides both functional, neurochemical and histological protection against unilateral infusion of 6-hydroxydopamine into the substantia nigra or striatum of rats. In addition, LY404187 provided a dose-dependent increase in growth-associated protein-43 expression in the striatum. Reference: Eur J Pharmacol. 2004 Feb 20;486(2):163-74. https://pubmed.ncbi.nlm.nih.gov/14975705/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	67.1	196.01
	Ethanol	17.1	49.99

Preparing Stock Solutions

The following data is based on the product molecular weight 342.46 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

Formulation protocol:	1. Voss OP, Milne S, Sharkey J, O'Neill MJ, McCulloch J. Molecular mechanisms of neurite growth with AMPA receptor potentiation. Neuropharmacology. 2007 Feb;52(2):590-7. doi: 10.1016/j.neuropharm.2006.09.001. Epub 2006 Nov 13. PMID: 17101156. 2. Baumbarger PJ, Muhlhauser M, Zhai J, Yang CR, Nisenbaum ES. Positive modulation of alpha-amino-3-hydroxy-5-methyl-4-isoxazole propionic acid (AMPA) receptors in prefrontal cortical pyramidal neurons by a novel allosteric potentiator. J Pharmacol Exp Ther. 2001 Jul;298(1):86-102. PMID: 11408529. 3. Song B, Lee S, Choi S. LY404187, a potentiator of AMPARs, enhances both the amplitude and 1/CV2 of AMPA EPSCs but not NMDA EPSCs at CA3-CA1 synapses in the hippocampus of neonatal rats. Neurosci Lett. 2012 Dec 7;531(2):193-7. doi: 10.1016/j.neulet.2012.10.020. Epub 2012 Oct 26. PMID: 23103715. 4. O'Neill MJ, Murray TK, Whalley K, Ward MA, Hicks CA, Woodhouse S, Osborne DJ, Skolnick P. Neurotrophic actions of the novel AMPA receptor potentiator, LY404187, in rodent models of Parkinson's disease. Eur J Pharmacol. 2004 Feb 20;486(2):163-74. doi: 10.1016/j.ejphar.2003.12.023. PMID: 14975705.
In vitro protocol:	1. Voss OP, Milne S, Sharkey J, O'Neill MJ, McCulloch J. Molecular mechanisms of neurite growth with AMPA receptor potentiation. Neuropharmacology. 2007 Feb;52(2):590-7. doi: 10.1016/j.neuropharm.2006.09.001. Epub 2006 Nov 13. PMID: 17101156. 2. Baumbarger PJ, Muhlhauser M, Zhai J, Yang CR, Nisenbaum ES. Positive modulation of alpha-amino-3-hydroxy-5-methyl-4-isoxazole propionic acid (AMPA) receptors in prefrontal cortical pyramidal neurons by a novel allosteric potentiator. J Pharmacol Exp Ther. 2001 Jul;298(1):86-102. PMID: 11408529.
In vivo protocol:	1. Song B, Lee S, Choi S. LY404187, a potentiator of AMPARs, enhances both the amplitude and 1/CV2 of AMPA EPSCs but not NMDA EPSCs at CA3-CA1 synapses in the hippocampus of neonatal rats. Neurosci Lett. 2012 Dec 7;531(2):193-7. doi: 10.1016/j.neulet.2012.10.020. Epub 2012 Oct 26. PMID: 23103715. 2. O'Neill MJ, Murray TK, Whalley K, Ward MA, Hicks CA, Woodhouse S, Osborne DJ, Skolnick P. Neurotrophic actions of the novel AMPA receptor potentiator, LY404187, in rodent models of Parkinson's disease. Eur J Pharmacol. 2004 Feb 20;486(2):163-74. doi: 10.1016/j.ejphar.2003.12.023. PMID: 14975705.

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1: Andreasen JT, Fitzpatrick CM, Larsen M, Skovgaard L, Nielsen SD, Clausen RP, Troelsen K, Pickering DS. Differential role of AMPA receptors in mouse tests of antidepressant and anxiolytic action. Brain Res. 2015 Mar 19;1601:117-26. doi: 10.1016/j.brainres.2015.01.001. Epub 2015 Jan 8. PubMed PMID: 25578259.

2: Song B, Lee S, Choi S. LY404187, a potentiator of AMPARs, enhances both the amplitude and 1/CV2 of AMPA EPSCs but not NMDA EPSCs at CA3-CA1 synapses in the hippocampus of neonatal rats. Neurosci Lett. 2012 Dec 7;531(2):193-7. doi: 10.1016/j.neulet.2012.10.020. Epub 2012 Oct 26. PubMed PMID: 23103715.

3: Lindholm JS, Autio H, Vesa L, Antila H, Lindemann L, Hoener MC, Skolnick P, Rantamäki T, Castrén E. The antidepressant-like effects of glutamatergic drugs ketamine and AMPA receptor potentiator LY 451646 are preserved in bdnf⁺/⁻ heterozygous null mice. Neuropharmacology. 2012 Jan;62(1):391-7. doi: 10.1016/j.neuropharm.2011.08.015. Epub 2011 Aug 16. PubMed PMID: 21867718.

4: Schmidt MV, Trümbach D, Weber P, Wagner K, Scharf SH, Liebl C, Datson N, Namendorf C, Gerlach T, Kühne C, Uhr M, Deussing JM, Wurst W, Binder EB, Holsboer F, Müller MB. Individual stress vulnerability is predicted by short-term memory and AMPA receptor subunit ratio in the hippocampus. J Neurosci. 2010 Dec 15;30(50):16949-58. doi: 10.1523/JNEUROSCI.4668-10.2010. PubMed PMID: 21159965.

5: Roberts BM, Holden DE, Shaffer CL, Seymour PA, Menniti FS, Schmidt CJ, Williams GV, Castner SA. Prevention of ketamine-induced working memory impairments by AMPA potentiators in a nonhuman primate model of cognitive dysfunction. Behav Brain Res. 2010 Sep 1;212(1):41-8. doi: 10.1016/j.bbr.2010.03.039. Epub 2010 Mar 27. PubMed PMID: 20347881.

6: Jones N, Messenger MJ, O'Neill MJ, Oldershaw A, Gilmour G, Simmons RM, Iyengar S, Libri V, Tricklebank M, Williams SC. AMPA receptor potentiation can prevent ethanol-induced intoxication. Neuropsychopharmacology. 2008 Jun;33(7):1713-23. Epub 2007 Sep 12. PubMed PMID: 17851540.

7: Voss OP, Milne S, Sharkey J, O'Neill MJ, McCulloch J. Molecular mechanisms of neurite growth with AMPA receptor potentiation. Neuropharmacology. 2007 Feb;52(2):590-7. Epub 2006 Nov 13. PubMed PMID: 17101156.

8: Ryder JW, Falcone JF, Manro JR, Svensson KA, Merchant KM. Pharmacological characterization of cGMP regulation by the biarylpropylsulfonamide class of positive, allosteric modulators of alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptors. J Pharmacol Exp Ther. 2006 Oct;319(1):293-8. Epub 2006 Jun 27. PubMed PMID: 16803862.

9: Shah S, Tear S. Targeting neurological receptors. IDrugs. 2005 Dec;8(12):962-3. PubMed PMID: 16320121.

10: Jones N, O'Neill MJ, Tricklebank M, Libri V, Williams SC. Examining the neural targets of the AMPA receptor potentiator LY404187 in the rat brain using pharmacological magnetic resonance imaging. Psychopharmacology (Berl). 2005 Aug;180(4):743-51. Epub 2005 Sep 14. PubMed PMID: 15864556.

11: Fowler JH, Whalley K, Murray T, O'neill MJ, McCulloch J. The AMPA receptor potentiator LY404187 increases cerebral glucose utilization and c-fos expression in the rat. J Cereb Blood Flow Metab. 2004 Oct;24(10):1098-109. PubMed PMID: 15529010.

12: O'Neill MJ, Murray TK, Whalley K, Ward MA, Hicks CA, Woodhouse S, Osborne DJ, Skolnick P. Neurotrophic actions of the novel AMPA receptor potentiator, LY404187, in rodent models of Parkinson's disease. Eur J Pharmacol. 2004 Feb 20;486(2):163-74. PubMed PMID: 14975705.

13: Quirk JC, Nisenbaum ES. Multiple molecular determinants for allosteric modulation of alternatively spliced AMPA receptors. J Neurosci. 2003 Nov 26;23(34):10953-62. PubMed PMID: 14645491.

14: Bai F, Bergeron M, Nelson DL. Chronic AMPA receptor potentiator (LY451646) treatment increases cell proliferation in adult rat hippocampus. Neuropharmacology. 2003 Jun;44(8):1013-21. PubMed PMID: 12763094.

15: Quirk JC, Nisenbaum ES. LY404187: a novel positive allosteric modulator of AMPA receptors. CNS Drug Rev. 2002 Fall;8(3):255-82. Review. PubMed PMID: 12353058.

16: Mackowiak M, O'Neill MJ, Hicks CA, Bleakman D, Skolnick P. An AMPA receptor potentiator modulates hippocampal expression of BDNF: an in vivo study. Neuropharmacology. 2002 Jul;43(1):1-10. PubMed PMID: 12213254.

17: Bai F, Li X, Clay M, Lindstrom T, Skolnick P. Intra- and interstrain differences in models of "behavioral despair". Pharmacol Biochem Behav. 2001 Oct-Nov;70(2-3):187-92. PubMed PMID: 11701187.

18: Vandergriff J, Huff K, Bond A, Lodge D. Potentiation of responses to AMPA on central neurones by LY392098 and LY404187 in vivo. Neuropharmacology. 2001 Jun;40(8):1003-9. PubMed PMID: 11406191.

19: Gates M, Ogden A, Bleakman D. Pharmacological effects of AMPA receptor potentiators LY392098 and LY404187 on rat neuronal AMPA receptors in vitro. Neuropharmacology. 2001 Jun;40(8):984-91. PubMed PMID: 11406189.

20: Miu P, Jarvie KR, Radhakrishnan V, Gates MR, Ogden A, Ornstein PL, Zarrinmayeh H, Ho K, Peters D, Grabell J, Gupta A, Zimmerman DM, Bleakman D. Novel AMPA receptor potentiators LY392098 and LY404187: effects on recombinant human AMPA receptors in vitro. Neuropharmacology. 2001 Jun;40(8):976-83. PubMed PMID: 11406188.

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