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Chemical compound
Pharmaceutical compound
Bethanechol Trade names Urecholine, others Other names 2-[(aminocarbonyl)oxy]- N ,N ,N -trimethyl- 1-propanaminium AHFS /Drugs.com Monograph MedlinePlus a682849 Routes of By mouth , subcutaneous ATC code Legal status
2-(Carbamoyloxy)-N ,N ,N -trimethylpropan-1-aminium
CAS Number PubChem CID IUPHAR/BPS DrugBank ChemSpider UNII KEGG ChEBI ChEMBL CompTox Dashboard (EPA ) Formula C 7 H 17 N 2 O 2 Molar mass −1 3D model (JSmol )
InChI=1S/C7H16N2O2/c1-6(11-7(8)10)5-9(2,3)4/h6H,5H2,1-4H3,(H-,8,10)/p+1
Y Key:NZUPCNDJBJXXRF-UHFFFAOYSA-O
Y (verify)
Bethanechol is a parasympathomimetic choline carbamate that selectively stimulates muscarinic receptors without any effect on nicotinic receptors . Unlike acetylcholine , bethanechol is not hydrolyzed by cholinesterase and will therefore have a long duration of action. Bethanechol is sold under the brand names Duvoid (Roberts), Myotonachol (Glenwood), Urecholine (Merck Frosst), and Urocarb (Hamilton). The name bethanechol refers to its structure as the urethane of b eta-methylchol ine.
Bethanechol alleviates dry mouth[ 2] orally or subcutaneously to treat urinary retention [ 3] general anesthetic , diabetic neuropathy of the bladder, or a side effect of antidepressants ; or to treat gastrointestinal lack of muscular tone . The muscarinic receptors in the bladder and gastrointestinal tract stimulate contraction of the bladder and expulsion of urine , and increased gastrointestinal motility, respectively. Bethanechol should be used to treat these disorders only after mechanical obstruction is ruled out as a possible cause.
Its potential benefit in the treatment of cerebral palsy has been investigated.[ 4]
Atropine is given preoperatively to prevent voiding of the bowel/bladder during surgery; then, bethanechol is given postoperatively to revert this action.[ 5]
Use of bethanechol, as well as all other muscarinic receptor agonists, is contraindicated in patients with asthma , coronary insufficiency , peptic ulcers , intestinal obstruction and hyperthyroidism . The parasympathomimetic action of this drug will exacerbate the symptoms of these disorders.
^ "Active substance: bethanechol" (PDF) . List of nationally authorised medicinal products, Human Medicines Evaluation Division . European Medicines Agency. 11 February 2021.^ Gorsky M, Epstein JB, Parry J, Epstein MS, Le ND, Silverman S (February 2004). "The efficacy of pilocarpine and bethanechol upon saliva production in cancer patients with hyposalivation following radiation therapy". Oral Surgery, Oral Medicine, Oral Pathology, Oral Radiology, and Endodontics . 97 (2): 190– 195. doi :10.1016/j.tripleo.2003.08.031 . PMID 14970777 . ^ Moro C, Phelps C, Veer V, Clark J, Glasziou P, Tikkinen KA, Scott AM (January 2022). "The effectiveness of parasympathomimetics for treating underactive bladder: A systematic review and meta-analysis" (PDF) . Neurourology and Urodynamics . 41 (1): 127– 139. doi :10.1002/nau.24839 . PMID 34816481 . S2CID 244530010 . ^ Carter WJ (September 2008). "Unexpected benefits of bethanechol in adults with cerebral palsy". The Medical Journal of Australia . 189 (5): 293. doi :10.5694/j.1326-5377.2008.tb02034.x . PMID 18759732 . S2CID 29048832 . ^ Obied H (2011). Cholinergic Pharmacology . CSU.
"Bethanechol" . Drug Information Portal . U.S. National Library of Medicine.
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 Trospium chloride Typical antipsychotics (e.g., chlorpromazine , chlorprothixene , cyamemazine (cyamepromazine) , loxapine , mesoridazine , thioridazine )Umeclidinium bromide (+vilanterol )WIN-2299 Xanomeline Zamifenacin
Precursors (and prodrugs )
