Zacopride: Difference between revisions
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{{Short description|Chemical compound}} |
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{{Drugbox |
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| IUPAC_name = 4-​amino-​''N''-​1-​azabicyclo[2.2.2]oct-​3-​yl-​5-​chloro-​2-​methoxybenzamide |
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| verifiedrevid = 396760537 |
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| IUPAC_name = 4-amino-5-chloro-2-methoxy-''N''-(quinuclidin-3-yl)benzamide |
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<!--Clinical data--> |
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| tradename = |
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<!--Pharmacokinetic data--> |
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| excretion = |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 97262 |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 1S/C15H20ClN3O2/c1-21-14-7-12(17)11(16)6-10(14)15(20)18-13-8-19-4-2-9(13)3-5-19/h6-7,9,13H,2-5,8,17H2,1H3,(H,18,20) |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = FEROPKNOYKURCJ-UHFFFAOYSA-N |
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| IUPHAR_ligand = 245 |
| IUPHAR_ligand = 245 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank |
| DrugBank = |
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| C = 15 | H = 20 | Cl = 1 | N = 3 | O = 2 |
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| UNII_Ref = {{fdacite|changed|FDA}} |
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| molecular_weight = 309.791 g/mol |
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| UNII = 9GN3OT4156 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = 18041 |
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<!--Chemical data--> |
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| C=15 | H=20 | Cl=1 | N=3 | O=2 |
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'''Zacopride''' is a potent [[Antagonist (pharmacology)|antagonist]] at the [[5-HT3 receptor| |
'''Zacopride''' is a potent [[Antagonist (pharmacology)|antagonist]] at the [[5-HT3 receptor|5-HT<sub>3</sub>]] [[Receptor (biochemistry)|receptor]]<ref>{{cite journal | vauthors = Smith WW, Sancilio LF, Owera-Atepo JB, Naylor RJ, Lambert L | title = Zacopride, a potent 5-HT3 antagonist | journal = The Journal of Pharmacy and Pharmacology | volume = 40 | issue = 4 | pages = 301–2 | date = April 1988 | pmid = 2900319 | doi = 10.1111/j.2042-7158.1988.tb05253.x | s2cid = 32862252 }}</ref> and an [[agonist]] at the [[5-HT4 receptor|5-HT<sub>4</sub>]] receptor.<ref name="Lefebvre1993">{{cite journal | vauthors = Lefebvre H, Contesse V, Delarue C, Soubrane C, Legrand A, Kuhn JM, Wolf LM, Vaudry H | display-authors = 6 | title = Effect of the serotonin-4 receptor agonist zacopride on aldosterone secretion from the human adrenal cortex: in vivo and in vitro studies | journal = The Journal of Clinical Endocrinology and Metabolism | volume = 77 | issue = 6 | pages = 1662–6 | date = December 1993 | doi = 10.1210/jcem.77.6.8263156 | pmid = 8263156 }}</ref> It has [[anxiolytic]]<ref>{{cite journal | vauthors = Costall B, Domeney AM, Gerrard PA, Kelly ME, Naylor RJ | title = Zacopride: anxiolytic profile in rodent and primate models of anxiety | journal = The Journal of Pharmacy and Pharmacology | volume = 40 | issue = 4 | pages = 302–5 | date = April 1988 | pmid = 2900320 | doi = 10.1111/j.2042-7158.1988.tb05254.x | s2cid = 1083706 }}</ref> and [[nootropic]] effects in animal models,<ref>{{cite journal | vauthors = Fontana DJ, Daniels SE, Eglen RM, Wong EH | title = Stereoselective effects of (R)- and (S)-zacopride on cognitive performance in a spatial navigation task in rats | journal = Neuropharmacology | volume = 35 | issue = 3 | pages = 321–7 | date = March 1996 | pmid = 8783207 | doi = 10.1016/0028-3908(96)00191-8 | s2cid = 12818436 }}</ref> with the (''R'')-(+)-enantiomer being the more active form.<ref>{{cite journal | vauthors = Young R, Johnson DN | title = Anxiolytic-like activity of R(+)- and S(-)-zacopride in mice | journal = European Journal of Pharmacology | volume = 201 | issue = 2–3 | pages = 151–5 | date = August 1991 | pmid = 1686755 | doi = 10.1016/0014-2999(91)90338-Q }}</ref> It also has [[antiemetic]]<ref>{{cite journal | vauthors = Yamakuni H, Nakayama H, Matsui S, Imazumi K, Matsuo M, Mutoh S | title = Inhibitory effect of zacopride on Cisplatin-induced delayed emesis in ferrets | journal = Journal of Pharmacological Sciences | volume = 101 | issue = 1 | pages = 99–102 | date = May 2006 | pmid = 16651699 | doi = 10.1254/jphs.SCJ05007X | doi-access = free }}</ref> and pro-respiratory effects, both reducing [[sleep apnea]]<ref>{{cite journal | vauthors = Carley DW, Depoortere H, Radulovacki M | title = R-zacopride, a 5-HT3 antagonist/5-HT4 agonist, reduces sleep apneas in rats | journal = Pharmacology, Biochemistry, and Behavior | volume = 69 | issue = 1–2 | pages = 283–9 | year = 2001 | pmid = 11420096 | doi = 10.1016/S0091-3057(01)00535-4 | s2cid = 11848748 }}</ref> and reversing [[opioid]]-induced [[respiratory depression]] in animal studies.<ref>{{cite journal | vauthors = Meyer LC, Fuller A, Mitchell D | title = Zacopride and 8-OH-DPAT reverse opioid-induced respiratory depression and hypoxia but not catatonic immobilization in goats | journal = American Journal of Physiology. Regulatory, Integrative and Comparative Physiology | volume = 290 | issue = 2 | pages = R405-13 | date = February 2006 | pmid = 16166206 | doi = 10.1152/ajpregu.00440.2005 | s2cid = 224414 }}</ref> Early animal trials have also revealed that administration of zacopride can reduce preference for and consumption of ethanol.<ref name="KnappPohorecky1992">{{cite journal | vauthors = Knapp DJ, Pohorecky LA | title = Zacopride, a 5-HT3 receptor antagonist, reduces voluntary ethanol consumption in rats | journal = Pharmacology, Biochemistry, and Behavior | volume = 41 | issue = 4 | pages = 847–50 | date = April 1992 | pmid = 1594653 | doi = 10.1016/0091-3057(92)90237-A | s2cid = 45436887 }}</ref> |
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Zacopride was found to significantly increase [[aldosterone]] levels in human subjects for 180 minutes at a dose of 400 micrograms. It is thought to do this by stimulating the 5- |
Zacopride was found to significantly increase [[aldosterone]] levels in human subjects for 180 minutes at a dose of 400 micrograms. It is thought to do this by stimulating the 5-HT<sub>4</sub> receptors on the adrenal glands. Zacopride also stimulated aldosterone secretion when applied to human adrenal glands ''in vitro''. No significant changes were observed in [[renin]], [[ACTH]], or [[cortisol]] levels.<ref name="Lefebvre1993" /> |
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Zacopride has been tested in clinical trials for the treatment of [[schizophrenia]], but was found unsuccessful.<ref name="Faustman1992">{{cite journal | vauthors = Newcomer JW, Faustman WO, Zipursky RB, Csernansky JG | title = Zacopride in schizophrenia: a single-blind serotonin type 3 antagonist trial | journal = Archives of General Psychiatry | volume = 49 | issue = 9 | pages = 751–2 | date = September 1992 | pmid = 1514881 | doi = 10.1001/archpsyc.1992.01820090079013 }}</ref> |
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== References == |
== References == |
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{{Reflist|2}} |
{{Reflist|2}} |
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{{Other respiratory system products}} |
{{Other respiratory system products}} |
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{{Serotonergics}} |
{{Serotonergics}} |
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[[Category:5-HT3 antagonists]] |
[[Category:5-HT3 antagonists]] |
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[[Category: |
[[Category:Anilines]] |
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[[Category:Benzamides]] |
[[Category:Benzamides]] |
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[[Category:Phenol ethers]] |
[[Category:Phenol ethers]] |
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[[Category: |
[[Category:Quinuclidines]] |
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{{nervous-system-drug-stub}} |
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{{respiratory-system-drug-stub}} |
{{respiratory-system-drug-stub}} |