Substance that mimics stimulation of cholinergic receptors
This article is about drugs stimulating parasympathetic system. For drugs inhibiting parasympathetic system, see
parasympatholytics .
Aparasympathomimetic drug , sometimes called acholinomimetic drug [ 1] cholinergic receptor stimulating agent [ 2] parasympathetic nervous system (PSNS).[ 3] [ 2] cholinergic drugsacetylcholine (ACh) is theneurotransmitter used by the PSNS.[ 1] [ 4] nicotinic ormuscarinic receptors (thus mimicking acetylcholine), or indirectly by inhibitingcholinesterase , promoting acetylcholine release, or other mechanisms.[ 5] glaucoma ,Sjögren syndrome andunderactive bladder .[ 6]
Somechemical weapons such assarin orVX , non-lethalriot control agents such astear gas , andinsecticides such asdiazinon fall into this category.[citation needed
Structure activity relationships for parasympathomimetic drugs [ edit ] For a cholinergic agent, the following criteria describe the structure activity relationship:[ 7]
Ing's Rule of 5: there should be no more than five atoms between the nitrogen and the terminal hydrogen for muscarinic (or cholinergic) activity; the molecule must possess a nitrogen atom capable of bearing a positive charge, preferably a quaternary ammonium salt; for maximum potency, the size of the alkyl groups substituted on the nitrogen should not exceed the size of a methyl group; the molecule should have an oxygen atom, preferably an ester-like oxygen capable of participating in a hydrogen bond; there should be a two-carbon unit between the oxygen atom and the nitrogen atom. [ edit ] These act by stimulating thenicotinic ormuscarinic receptors.
Choline esters Plant alkaloids Indirect acting parasympathomimetic substances may be either reversible cholinesterase inhibitors, irreversible cholinesterase inhibitors or substances that promote ACh release oranti-adrenergics . The latter inhibits the antagonistic system, thesympathetic nervous system .
^a b Dowd, Frank (2017).Pharmacology and therapeutics for dentistry: Chapter 6 - Cholinergic Agonists and Muscarinic Receptor Antagonists . St. Louis, Missouri: Elsevier. pp. 82– 97.ISBN 978-0-323-39307-2 OCLC 958121223 . ^a b Forrester, John V.; Dick, Andrew D.; McMenamin, Paul G.; Roberts, Fiona; Pearlman, Eric (2016). "General and ocular pharmacology".The Eye . Elsevier. pp. 338–369.e1.doi :10.1016/b978-0-7020-5554-6.00006-x .ISBN 978-0-7020-5554-6 Parasympathomimetics are a group of drugs that act either by directly stimulating the muscarinic receptor, for example pilocarpine, or by inhibiting the enzyme acetylcholinesterase, which hydrolyses the acetylcholine in the synapse. ^ "Dorlands Medical Dictionary:parasympathomimetic" . Archived fromthe original on 2009-07-26.^ Parasympathomimetics ^ Brenner, G. M. (2000).Pharmacology. Philadelphia, PA: W.B. Saunders Company.ISBN 0-7216-7757-6 ^ Moro, Christian; Phelps, Charlotte; Veer, Vineesha; Clark, Justin; Glasziou, Paul; Tikkinen, Kari A. O.; Scott, Anna M. (2021-11-24). "The effectiveness of parasympathomimetics for treating underactive bladder: A systematic review and meta-analysis".Neurourology and Urodynamics .41 (1):127– 139.doi :10.1002/nau.24839 .ISSN 1520-6777 .PMID 34816481 .S2CID 244530010 . ^ "Medicinal Chemistry of Adrenergics and Cholinergics" . Archived fromthe original on 2010-11-04. Retrieved2010-10-23 .^ Karadsheh, N; Kussie, P; Linthicum, DS (1991). "Inhibition of acetylcholinesterase by caffeine, anabasine, methyl pyrrolidine and their derivatives".Toxicology Letters .55 (3):335– 42.doi :10.1016/0378-4274(91)90015-X .PMID 2003276 .
mAChRs Tooltip Muscarinic acetylcholine receptors
Agonists Antagonists 3-Quinuclidinyl benzilate 4-DAMP Aclidinium bromide (+formoterol )Abediterol AF-DX 250 AF-DX 384 Ambutonium bromide Anisodamine Anisodine Antihistamines (first-generation) (e.g.,brompheniramine ,buclizine ,captodiame ,chlorphenamine (chlorpheniramine) ,cinnarizine ,clemastine ,cyproheptadine ,dimenhydrinate ,dimetindene ,diphenhydramine ,doxylamine ,meclizine ,mequitazine ,perlapine ,phenindamine ,pheniramine ,phenyltoloxamine ,promethazine ,propiomazine ,triprolidine )AQ-RA 741 Atropine Atropine methonitrate Atypical antipsychotics (e.g.,clozapine ,fluperlapine ,olanzapine (+fluoxetine ),rilapine ,quetiapine ,tenilapine ,zotepine )Benactyzine Benzatropine (benztropine) Benzilone Benzilylcholine mustard Benzydamine Bevonium BIBN 99 Biperiden Bornaprine Camylofin CAR-226,086 CAR-301,060 CAR-302,196 CAR-302,282 CAR-302,368 CAR-302,537 CAR-302,668 Caramiphen Cimetropium bromide Clidinium bromide Cloperastine CS-27349 Cyclobenzaprine Cyclopentolate Darifenacin DAU-5884 Desfesoterodine Dexetimide DIBD Dicycloverine (dicyclomine) Dihexyverine Difemerine Diphemanil metilsulfate Ditran Drofenine EA-3167 EA-3443 EA-3580 EA-3834 Emepronium bromide Etanautine Etybenzatropine (ethybenztropine) Fenpiverinium Fentonium bromide Fesoterodine Flavoxate Glycopyrronium bromide (+beclometasone/formoterol ,+indacaterol ,+neostigmine )Hexahydrodifenidol Hexahydrosiladifenidol Hexbutinol Hexocyclium Himbacine HL-031,120 Homatropine Imidafenacin Ipratropium bromide (+salbutamol )Isopropamide J-104,129 Hyoscyamine Mamba toxin 3 Mamba toxin 7 Mazaticol Mebeverine Meladrazine Mepenzolate Methantheline Methoctramine Methylatropine Methylhomatropine Methylscopolamine Metixene Muscarinic toxin 7 N-Ethyl-3-piperidyl benzilate N-Methyl-3-piperidyl benzilate Nefopam Octatropine methylbromide (anisotropine methylbromide) Orphenadrine Otenzepad (AF-DX 116) Otilonium bromide Oxapium iodide Oxitropium bromide Oxybutynin Oxyphencyclimine Oxyphenonium bromide PBID PD-102,807 PD-0298029 Penthienate Pethidine pFHHSiD Phenglutarimide Phenyltoloxamine Pipenzolate bromide Piperidolate Pirenzepine Piroheptine Pizotifen Poldine Pridinol Prifinium bromide Procyclidine Profenamine (ethopropazine) Propantheline bromide Propiverine Quinidine 3-Quinuclidinyl thiochromane-4-carboxylate Revefenacin Rociverine RU-47,213 SCH-57,790 SCH-72,788 SCH-217,443 Scopolamine (hyoscine) Scopolamine butylbromide (hyoscine butylbromide) Silahexacyclium Sofpironium bromide Solifenacin SSRIs Tooltip Selective serotonin reuptake inhibitors (e.g.,femoxetine ,paroxetine )Telenzepine Terodiline Tetracyclic antidepressants (e.g.,amoxapine ,maprotiline ,mianserin ,mirtazapine )Tiemonium iodide Timepidium bromide Tiotropium bromide Tiquizium bromide Tofenacin Tolterodine Tricyclic antidepressants (e.g.,amitriptyline (+perphenazine ),amitriptylinoxide ,butriptyline ,cidoxepin ,clomipramine ,desipramine ,desmethyldesipramine ,dibenzepin ,dosulepin (dothiepin) ,doxepin ,imipramine ,lofepramine ,nitroxazepine ,northiaden (desmethyldosulepin) ,nortriptyline ,protriptyline ,quinupramine ,trimipramine )Tridihexethyl Trihexyphenidyl Trimebutine Tripitamine (tripitramine) Tropacine Tropatepine Tropicamide Tropine benzilate Trospium chloride Typical antipsychotics (e.g.,chlorpromazine ,chlorprothixene ,cyamemazine (cyamepromazine) ,loxapine ,mesoridazine ,thioridazine )Umeclidinium bromide (+vilanterol )WIN-2299 Xanomeline Zamifenacin
Precursors (andprodrugs )
nAChRs Tooltip Nicotinic acetylcholine receptors
Agonists PAMs Tooltip positive allosteric modulators )5-HIAA 6-Chloronicotine A-84,543 A-366,833 A-582,941 A-867,744 ABT-202 ABT-418 ABT-560 ABT-894 Acetylcholine Altinicline Anabasine Anatabine Anatoxin-a AR-R17779 Bephenium hydroxynaphthoate Butinoline Butyrylcholine Carbachol Choline Choline m-bromophenyl ether Cotinine Cytisine Decamethonium Desformylflustrabromine Dianicline Dimethylphenylpiperazinium Epibatidine Epiboxidine Ethanol (alcohol) Ethoxysebacylcholine EVP-4473 EVP-6124 Galantamine GTS-21 Ispronicline Ivermectin JNJ-39393406 Levamisole Lobeline MEM-63,908 (RG-3487) Morantel Nicotine (tobacco )NS-1738 PHA-543,613 PHA-709,829 PNU-120,596 PNU-282,987 Pozanicline Pyrantel Rivanicline RJR-2429 Sazetidine A SB-206553 Sebacylcholine SIB-1508Y SIB-1553A SSR-180,711 Suberyldicholine Suxamethonium (succinylcholine) Suxethonium (succinyldicholine) TC-1698 TC-1734 TC-1827 TC-2216 TC-5214 TC-5619 TC-6683 Tebanicline Tribendimidine Tropisetron UB-165 Varenicline WAY-317,538 XY-4083 Antagonists NAMs Tooltip negative allosteric modulators )
Precursors (andprodrugs )
