S18986
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MedKoo CAT#: 526937

CAS#: 175340-20-2

Description: S18986, also known as S18986-1 and S189861, is a positive allosteric modulator of AMPA receptor. S18986 in the prelimbic cortex enhances acquisition and retention of an odor-reward association. S18986 enhances (S)-AMPA-mediated BDNF mRNA and protein expression in rat primary cortical neuronal cultures.


Price and Availability

Size
Price

5mg
USD 260
Size
Price

10mg
USD 425
Size
Price

25mg
USD 825

S18986 is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 526937
Name: S18986
CAS#: 175340-20-2
Chemical Formula: C10H12N2O2S
Exact Mass: 224.0619
Molecular Weight: 224.278
Elemental Analysis: C, 53.55; H, 5.39; N, 12.49; O, 14.27; S, 14.29


Synonym: S18986; S-18986; S 18986; S18986-1; S-18986-1; S 18986-1.

IUPAC/Chemical Name: (3aS)-2,3,3a,4-Tetrahydro-1H-pyrrolo[2,1-c][1,2,4]benzothiadiazine-5,5-dioxide

InChi Key: MNTIJYGEITVWHU-SNVBAGLBSA-N

InChi Code: InChI=1S/C10H12N2O2S/c13-15(14)9-5-2-1-4-8(9)12-7-3-6-10(12)11-15/h1-2,4-5,10-11H,3,6-7H2/t10-/m1/s1

SMILES Code: O=S1(N[C@](CCC2)([H])N2C3=CC=CC=C31)=O


Technical Data

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).

Harmonized System Code:
293490


References

1: Ball K, Bouzom F, Scherrmann JM, Walther B, Declèves X. A physiologically based modeling strategy during preclinical CNS drug development. Mol Pharm. 2014 Mar 3;11(3):836-48. doi: 10.1021/mp400533q. PubMed PMID: 24446829.

2: Yefimenko N, Portero-Tresserra M, Martí-Nicolovius M, Guillazo-Blanch G, Vale-Martínez A. The AMPA receptor modulator S18986 in the prelimbic cortex enhances acquisition and retention of an odor-reward association. Neurosci Lett. 2013 Aug 26;548:105-9. doi: 10.1016/j.neulet.2013.05.032. PubMed PMID: 23707650.

3: Vandesquille M, Carrié I, Louis C, Beracochea D, Lestage P. Effects of positive modulators of α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA)-type glutamate receptors in a benzodiazepine-induced deficit of spatial discrimination in mice. J Psychopharmacol. 2012 Jun;26(6):845-56. doi: 10.1177/0269881111416692. PubMed PMID: 21890586.

4: Vandesquille M, Krazem A, Louis C, Lestage P, Béracochéa D. S 18986 reverses spatial working memory impairments in aged mice: comparison with memantine. Psychopharmacology (Berl). 2011 Jun;215(4):709-20. doi: 10.1007/s00213-011-2168-9. PubMed PMID: 21274701.

5: Bernard K, Danober L, Thomas JY, Lebrun C, Muñoz C, Cordi A, Desos P, Lestage P, Morain P. DRUG FOCUS: S 18986: A positive allosteric modulator of AMPA-type glutamate receptors pharmacological profile of a novel cognitive enhancer. CNS Neurosci Ther. 2010 Oct;16(5):e193-212. doi: 10.1111/j.1755-5949.2009.00088.x. PubMed PMID: 21050420.

6: Destot-Wong KD, Liang K, Gupta SK, Favrais G, Schwendimann L, Pansiot J, Baud O, Spedding M, Lelièvre V, Mani S, Gressens P. The AMPA receptor positive allosteric modulator, S18986, is neuroprotective against neonatal excitotoxic and inflammatory brain damage through BDNF synthesis. Neuropharmacology. 2009 Sep;57(3):277-86. doi: 10.1016/j.neuropharm.2009.05.010. PubMed PMID: 19501111.

7: Gupta SK, Mishra R, Kusum S, Spedding M, Meiri KF, Gressens P, Mani S. GAP-43 is essential for the neurotrophic effects of BDNF and positive AMPA receptor modulator S18986. Cell Death Differ. 2009 Apr;16(4):624-37. doi: 10.1038/cdd.2008.188. PubMed PMID: 19136940.

8: Kelly SJ, Bernard K, Muñoz C, Lawrence RC, Thacker J, Grillo CA, Piroli GG, Reagan LP. Effects of the AMPA receptor modulator S 18986 on measures of cognition and oxidative stress in aged rats. Psychopharmacology (Berl). 2009 Jan;202(1-3):225-35. doi: 10.1007/s00213-008-1301-x. PubMed PMID: 18762915.

9: Cannazza G, Carrozzo MM, Braghiroli D, Parenti C. Enantiomerization of chiral 2,3,3a,4-tetrahydro-1H-pyrrolo[2,1-c][1,2,4] benzothiadiazine 5,5-dioxide by stopped-flow multidimensional HPLC. J Chromatogr B Analyt Technol Biomed Life Sci. 2008 Nov 1;875(1):192-9. doi: 10.1016/j.jchromb.2008.05.009. PubMed PMID: 18515197.

10: Marighetto A, Valerio S, Jaffard R, Mormede C, Muñoz C, Bernard K, Morain P. The AMPA modulator S 18986 improves declarative and working memory performances in aged mice. Behav Pharmacol. 2008 May;19(3):235-44. doi: 10.1097/FBP.0b013e3282feb0c1. PubMed PMID: 18469541.

11: Bloss EB, Hunter RG, Waters EM, Munoz C, Bernard K, McEwen BS. Behavioral and biological effects of chronic S18986, a positive AMPA receptor modulator, during aging. Exp Neurol. 2008 Mar;210(1):109-17. PubMed PMID: 18035355.

12: Bertaina-Anglade V, la Rochelle CD, Muñoz C, Morain P, Bernard K. Comparison of single vs. multiple administrations of the AMPA receptors modulator S 18986 in the object recognition task in rats. Fundam Clin Pharmacol. 2007 Aug;21(4):349-54. PubMed PMID: 17635172.

13: Béracochéa D, Philippin JN, Meunier S, Morain P, Bernard K. Improvement of episodic contextual memory by S 18986 in middle-aged mice: comparison with donepezil. Psychopharmacology (Berl). 2007 Jul;193(1):63-73. PubMed PMID: 17384936.

14: Lockhart BP, Rodriguez M, Mourlevat S, Peron P, Catesson S, Villain N, Galizzi JP, Boutin JA, Lestage P. S18986: a positive modulator of AMPA-receptors enhances (S)-AMPA-mediated BDNF mRNA and protein expression in rat primary cortical neuronal cultures. Eur J Pharmacol. 2007 Apr 30;561(1-3):23-31. PubMed PMID: 17331496.

15: Bourasset F, Bernard K, Muñoz C, Genissel P, Scherrmann JM. Neuropharmacokinetics of a new alpha-amino-3-hydroxy-5-methyl-4-isoxazole propionic acid (AMPA) modulator, S18986 [(S)-2,3-dihydro-[3,4]cyclopentano-1,2,4-benzothiadiazine-1,1-dioxide], in the rat. Drug Metab Dispos. 2005 Aug;33(8):1137-43. PubMed PMID: 15860654.

16: Rosi S, Giovannini MG, Lestage PJ, Muñoz C, Corte LD, Pepeu G. S 18986, a positive modulator of AMPA receptors with cognition-enhancing properties, increases ACh release in the hippocampus of young and aged rat. Neurosci Lett. 2004 May 6;361(1-3):120-3. PubMed PMID: 15135908.

17: Dicou E, Rangon CM, Guimiot F, Spedding M, Gressens P. Positive allosteric modulators of AMPA receptors are neuroprotective against lesions induced by an NMDA agonist in neonatal mouse brain. Brain Res. 2003 Apr 25;970(1-2):221-5. PubMed PMID: 12706264.

18: Lebrun C, Pillière E, Lestage P. Effects of S 18986-1, a novel cognitive enhancer, on memory performances in an object recognition task in rats. Eur J Pharmacol. 2000 Aug 4;401(2):205-12. PubMed PMID: 10924928.

19: Lockhart B, Iop F, Closier M, Lestage P. (S)-2,3-dihydro-[3,4]cyclopentano-1,2,4-benzothiadiazine-1,1-dioxide: (S18986-1) a positive modulator of AMPA receptors enhances (S)-AMPA-mediated [3H]noradrenaline release from rat hippocampal and frontal cortex slices. Eur J Pharmacol. 2000 Aug 4;401(2):145-53. PubMed PMID: 10924919.