S-18986

S-18986 is a positive allosteric modulator of the AMPA receptor related to cyclothiazide. It has nootropic and neuroprotective effects in animal studies, and induces both production of BDNF and AMPA-mediated release of noradrenaline and acetylcholine in the hippocampus and frontal cortex of the brain.^[1]^[2]^[3]^[4]^[5]^[6]^[7]^[8]^[9]^[10]

Legal status

US: Investigational New Drug

CAS Number

175340-20-2^Y

PubChem CID

637863

IUPHAR/BPS

4304

Quick facts Legal status, Identifiers ...

S-18986
Legal status

Legal status	US: Investigational New Drug
Identifiers
IUPAC name (S)-2,3-dihydro-[3,4]cyclopentano-1,2,4-benzothiadiazine-1,1-dioxide
CAS Number	175340-20-2^Y
PubChem CID	637863
IUPHAR/BPS	4304
ChemSpider	553445^N
UNII	IA262432Y9
CompTox Dashboard (EPA)	DTXSID40938656
Chemical and physical data
Formula	C₁₀H₁₂N₂O₂S
Molar mass	224.28 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C1C[C@@H]2NS(=O)(=O)C3=CC=CC=C3N2C1
InChI 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^N Key:MNTIJYGEITVWHU-SNVBAGLBSA-N^N
^NY (what is this?) (verify)

References

[1]
Lockhart B, Iop F, Closier M, Lestage P (August 2000). "(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". European Journal of Pharmacology. 401 (2): 145–53. doi:10.1016/S0014-2999(00)00433-7. PMID 10924919.
[2]
Lebrun C, Pillière E, Lestage P (August 2000). "Effects of S 18986-1, a novel cognitive enhancer, on memory performances in an object recognition task in rats". European Journal of Pharmacology. 401 (2): 205–12. doi:10.1016/S0014-2999(00)00429-5. PMID 10924928.
[3]
Dicou E, Rangon CM, Guimiot F, Spedding M, Gressens P (April 2003). "Positive allosteric modulators of AMPA receptors are neuroprotective against lesions induced by an NMDA agonist in neonatal mouse brain". Brain Research. 970 (1–2): 221–5. doi:10.1016/S0006-8993(03)02357-6. PMID 12706264. S2CID 22186254.
[4]
Rosi S, Giovannini MG, Lestage PJ, Muñoz C, Corte LD, Pepeu G (May 2004). "S 18986, a positive modulator of AMPA receptors with cognition-enhancing properties, increases ACh release in the hippocampus of young and aged rat". Neuroscience Letters. 361 (1–3): 120–3. doi:10.1016/j.neulet.2003.12.061. PMID 15135908. S2CID 12800129.
[5]
Bourasset F, Bernard K, Muñoz C, Genissel P, Scherrmann JM (August 2005). "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 Metabolism and Disposition. 33 (8): 1137–43. doi:10.1124/dmd.105.004424. PMID 15860654. S2CID 14891912.
[6]
Béracochéa D, Philippin JN, Meunier S, Morain P, Bernard K (July 2007). "Improvement of episodic contextual memory by S 18986 in middle-aged mice: comparison with donepezil". Psychopharmacology. 193 (1): 63–73. doi:10.1007/s00213-007-0765-4. PMID 17384936. S2CID 39655878.
[7]
Marighetto A, Valerio S, Jaffard R, Mormede C, Muñoz C, Bernard K, Morain P (May 2008). "The AMPA modulator S 18986 improves declarative and working memory performances in aged mice". Behavioural Pharmacology. 19 (3): 235–44. doi:10.1097/FBP.0b013e3282feb0c1. PMID 18469541. S2CID 20415746.
[8]
Kelly SJ, Bernard K, Muñoz C, Lawrence RC, Thacker J, Grillo CA, Piroli GG, Reagan LP (January 2009). "Effects of the AMPA receptor modulator S 18986 on measures of cognition and oxidative stress in aged rats". Psychopharmacology. 202 (1–3): 225–35. doi:10.1007/s00213-008-1301-x. PMID 18762915. S2CID 35139538.
[9]
Gupta SK, Mishra R, Kusum S, Spedding M, Meiri KF, Gressens P, Mani S (April 2009). "GAP-43 is essential for the neurotrophic effects of BDNF and positive AMPA receptor modulator S18986". Cell Death and Differentiation. 16 (4): 624–37. doi:10.1038/cdd.2008.188. PMID 19136940.
[10]
Destot-Wong KD, Liang K, Gupta SK, Favrais G, Schwendimann L, Pansiot J, Baud O, Spedding M, Lelièvre V, Mani S, Gressens P (September 2009). "The AMPA receptor positive allosteric modulator, S18986, is neuroprotective against neonatal excitotoxic and inflammatory brain damage through BDNF synthesis". Neuropharmacology. 57 (3): 277–86. doi:10.1016/j.neuropharm.2009.05.010. PMID 19501111. S2CID 1400467.

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