Capeserod

{{Short description|Chemical compound}}

{{cs1 config|name-list-style=vanc}}

{{Drugbox

| IUPAC_name = 5-(5-Amino-6-chloro-2,3-dihydro-1,4-benzodioxin-8-yl)-3-[1-(2-phenylethyl)piperidin-4-yl]-1,3,4-oxadiazol-2-one

| image = Capeserod.svg

| width = 175

| tradename =

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| CAS_number = 769901-96-4

| CAS_supplemental =
191023-43-5 (HCl)

| ATC_prefix = None

| ATC_suffix =

| PubChem = 9805719

| ChemSpiderID = 7981479

| UNII = 8163770L8P

| IUPHAR_ligand = 29

| ChEMBL = 2027925

| C=23 | H=25 | Cl=1 | N=4 | O=4

| smiles = C1CN(CCC1N2C(=O)OC(=N2)C3=CC(=C(C4=C3OCCO4)N)Cl)CCC5=CC=CC=C5

| StdInChI = 1S/C23H25ClN4O4/c24-18-14-17(20-21(19(18)25)31-13-12-30-20)22-26-28(23(29)32-22)16-7-10-27(11-8-16)9-6-15-4-2-1-3-5-15/h1-5,14,16H,6-13,25H2

| StdInChIKey = MDBNTXARNGRHEV-UHFFFAOYSA-N

}}

Capeserod (INN;{{cite web|title=WHO Drug Information. Vol. 20, No. 3, 2006. International Nonproprietary Names for Pharmaceutical Substances (INN). Recommended International Nonproprietary Names: List 56|url=http://apps.who.int/medicinedocs/documents/s14181e/s14181e.pdf|archive-url=https://web.archive.org/web/20110705092935/http://apps.who.int/medicinedocs/documents/s14181e/s14181e.pdf|url-status=dead|archive-date=July 5, 2011|publisher=World Health Organization|access-date=25 April 2016|page=208}} development code SL65.0155) is a selective 5-HT₄ receptor partial agonist with K_i = 0.6 nM and IA = 40–50% (relative to serotonin).{{cite journal |vauthors=Moser PC, Bergis OE, Jegham S, etal | title = SL65.0155, a novel 5-hydroxytryptamine(4) receptor partial agonist with potent cognition-enhancing properties | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 302 | issue = 2 | pages = 731–41 |date=August 2002 | pmid = 12130738 | doi = 10.1124/jpet.102.034249 | s2cid = 18256582 | url = https://hal.archives-ouvertes.fr/hal-03161682/file/Version%20HAL.pdf }} It potently enhances cognition, learning, and memory,{{cite journal |vauthors=Spencer JP, Brown JT, Richardson JC, etal | title = Modulation of hippocampal excitability by 5-HT4 receptor agonists persists in a transgenic model of Alzheimer's disease | journal = Neuroscience | volume = 129 | issue = 1 | pages = 49–54 | year = 2004 | pmid = 15489027 | doi = 10.1016/j.neuroscience.2004.06.070 | s2cid = 41720408 }}{{cite journal | vauthors = Micale V, Leggio GM, Mazzola C, Drago F | title = Cognitive effects of SL65.0155, a serotonin 5-HT4 receptor partial agonist, in animal models of amnesia | journal = Brain Research | volume = 1121 | issue = 1 | pages = 207–15 |date=November 2006 | pmid = 17011531 | doi = 10.1016/j.brainres.2006.08.108 | s2cid = 25494253 }}{{cite journal | vauthors = Restivo L, Roman F, Dumuis A, Bockaert J, Marchetti E, Ammassari-Teule M | title = The promnesic effect of G-protein-coupled 5-HT4 receptors activation is mediated by a potentiation of learning-induced spine growth in the mouse hippocampus | journal = Neuropsychopharmacology | volume = 33 | issue = 10 | pages = 2427–34 |date=September 2008 | pmid = 18075492 | doi = 10.1038/sj.npp.1301644 | doi-access = free }}{{cite journal |vauthors=Marchetti E, Jacquet M, Jeltsch H, etal | title = Complete recovery of olfactory associative learning by activation of 5-HT4 receptors after dentate granule cell damage in rats | journal = Neurobiology of Learning and Memory | volume = 90 | issue = 1 | pages = 185–91 |date=July 2008 | pmid = 18485752 | doi = 10.1016/j.nlm.2008.03.010 | s2cid = 38967009 | url = https://univoak.eu/islandora/object/islandora%3A84565 | url-access = subscription }}{{cite journal | vauthors = Hille C, Bate S, Davis J, Gonzalez MI | title = 5-HT4 receptor agonism in the five-choice serial reaction time task | journal = Behavioural Brain Research | volume = 195 | issue = 1 | pages = 180–6 |date=December 2008 | pmid = 18765258 | doi = 10.1016/j.bbr.2008.08.007 | s2cid = 1063310 }} and also possesses antidepressant effects.{{cite journal | vauthors = Tamburella A, Micale V, Navarria A, Drago F | title = Antidepressant properties of the 5-HT4 receptor partial agonist, SL65.0155: behavioral and neurochemical studies in rats | journal = Progress in Neuro-psychopharmacology & Biological Psychiatry | volume = 33 | issue = 7 | pages = 1205–10 |date=October 2009 | pmid = 19596038 | doi = 10.1016/j.pnpbp.2009.07.001 | s2cid = 207408833 }} Capeserod was in phase II clinical trials around 2004–2006 for the treatment of memory deficits and dementia but no new information has surfaced since and it appears to have been abandoned.{{cite journal | vauthors = Bockaert J, Claeysen S, Compan V, Dumuis A | title = 5-HT4 receptors | journal = Current Drug Targets. CNS and Neurological Disorders | volume = 3 | issue = 1 | pages = 39–51 |date=February 2004 | pmid = 14965243 | doi = 10.2174/1568007043482615| s2cid = 19243201 | url = https://hal.archives-ouvertes.fr/hal-01667891/file/2004%20CDT%20Bockaert.pdf}}{{cite book | author = Roth, Bryan L. | title = The Serotonin Receptors: From Molecular Pharmacology to Human Therapeutics (The Receptors) | publisher = Humana Press | location = Totowa, NJ | year = 2006 | isbn = 1-58829-568-0 | url = https://books.google.com/books?id=J6i6YpvCQfIC&q=SL65.0155%20phase%20II&pg=PA472}}