From Wikipedia, the free encyclopedia
Substance that mimics stimulation of cholinergic receptors
A parasympathomimetic drug , sometimes called a cholinomimetic drug
[1] or
cholinergic receptor
stimulating agent ,
[2] is a substance that stimulates the
parasympathetic nervous system (PSNS).
[3]
[2] These chemicals are also called
cholinergic drugs because
acetylcholine (ACh) is the
neurotransmitter used by the PSNS.
[1]
[4] Chemicals in this family can act either directly by stimulating the
nicotinic or
muscarinic receptors (thus mimicking acetylcholine), or indirectly by inhibiting
cholinesterase , promoting acetylcholine release, or other mechanisms.
[5] Common uses of parasympathomimetics include
glaucoma ,
Sjögren syndrome and
underactive bladder .
[6]
Some
chemical weapons such as
sarin or
VX , non-lethal
riot control agents such as
tear gas , and insecticides such as
diazinon fall into this category.
Structure activity relationships for parasympathomimetic drugs
[7]
For a cholinergic agent, the following criteria describe the structure activity relationship:
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.
Pharmaceuticals/Supplements
Direct-acting
These act by stimulating the
nicotinic or
muscarinic receptors.
Choline esters
Plant alkaloids
Indirect-acting
Indirect acting parasympathomimetic substances may be either reversible cholinesterase inhibitors, irreversible cholinesterase inhibitors or substances that promote ACh release or
anti-adrenergics . The latter inhibits the antagonistic system, the
sympathetic nervous system .
See also
References
^
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 from
the 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 from
the original on 2010-11-04. Retrieved 2010-10-23 .
^ 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 .
External links
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
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
Trospium chloride
Typical antipsychotics (e.g.,
chlorpromazine ,
chlorprothixene ,
cyamemazine (cyamepromazine) ,
loxapine ,
mesoridazine ,
thioridazine )
Umeclidinium bromide (
+vilanterol )
WIN-2299
Xanomeline
Zamifenacin
Precursors (and
prodrugs )
nAChRs Tooltip Nicotinic acetylcholine receptors
Agonists (and
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
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 (and
NAMs Tooltip negative allosteric modulators )
Precursors (and
prodrugs )