DT-Web

DB01019 - Bethanechol


Identification
Name Bethanechol
Accession Number DB01019 (APRD00051)
Type small molecule
Description Bethanechol is a synthetic ester structurally and pharmacologically related to acetylcholine. A slowly hydrolyzed muscarinic agonist with no nicotinic effects, bethanechol is generally used to increase smooth muscle tone, as in the GI tract following abdominal surgery or in urinary retention in the absence of obstruction. It may cause hypotension, cardiac rate changes, and bronchial spasms. [PubChem]
Structure
MOL SDF PDB SMILES InChI
Categories (*)
Molecular Weight 161.2221
Groups approved
Monoisotopic Weight 161.129002798
Pharmacology
Indication For the treatment of acute postoperative and postpartum nonobstructive (functional) urinary retention and for neurogenic atony of the urinary bladder with retention.
Mechanism of action Bethanechol directly stimulates cholinergic receptors in the parasympathetic nervous system while stimulating the ganglia to a lesser extent. Its effects are predominantly muscarinic, inducing little effect on nicotinic receptors and negligible effects on the cardiovascular system.
Absorption Not Available
Protein binding Not Available
Biotransformation Not Available
Route of elimination Not Available
Toxicity Not Available
Affected organisms
  • Humans and other mammals
Interactions
Drug Interactions
Drug Mechanism of interaction
Tacrine The acetylcholinesterase inhibitor, Tacrine, may increase the cholinergic effects of Bethanecol, a cholinergic agonist. Monitor for increased cholinergic effects.
Food Interactions
  • Take on empty stomach: 1 hour before or 2 hours after meals to avoid nausea.

Targets


Muscarinic acetylcholine receptor M2
Name Muscarinic acetylcholine receptor M2
Gene Name CHRM2
Pharmacological action yes
Actions agonist
References
  • Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. - Pubmed
  • Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. - Pubmed
  • Agrawal A, Hila A, Tutuian R, Mainie I, Castell DO: Bethanechol improves smooth muscle function in patients with severe ineffective esophageal motility. J Clin Gastroenterol. 2007 Apr;41(4):366-70. - Pubmed
  • Buranakarl C, Kijtawornrat A, Angkanaporn K, Komolvanich S, Bovee KC: Effects of bethanechol on canine urinary bladder smooth muscle function. Res Vet Sci. 2001 Dec;71(3):175-81. - Pubmed
  • Cruzblanca H: An M2-like muscarinic receptor enhances a delayed rectifier K+ current in rat sympathetic neurones. Br J Pharmacol. 2006 Oct;149(4):441-9. Epub 2006 Sep 4. - Pubmed
DTHybrid score 0.2688

Predictions


Id Partner name Gene Name Score
103 Muscarinic acetylcholine receptor M1 CHRM1 0.1448
51 Muscarinic acetylcholine receptor M3 CHRM3 0.1374
450 Muscarinic acetylcholine receptor M4 CHRM4 0.0829
274 Muscarinic acetylcholine receptor M5 CHRM5 0.0649
813 Neuronal acetylcholine receptor subunit alpha-2 CHRNA2 0.051
3923 Cholinesterase BCHE 0.0312
492 Histamine H1 receptor HRH1 0.0286
4512 Cytochrome P450 3A4 CYP3A4 0.0214
4119 Cytochrome P450 2D6 CYP2D6 0.0212
502 5-hydroxytryptamine 2A receptor HTR2A 0.0158
1588 Multidrug resistance protein 1 ABCB1 0.013
556 Alpha-1A adrenergic receptor ADRA1A 0.0123
590 5-hydroxytryptamine 2C receptor HTR2C 0.0119
831 D(2) dopamine receptor DRD2 0.0117
23 D(1A) dopamine receptor DRD1 0.0105
6145 Solute carrier family 22 member 1 SLC22A1 0.0094
4757 Cytochrome P450 2C9 CYP2C9 0.009
4200 Cytochrome P450 1A2 CYP1A2 0.0087
789 Alpha-1D adrenergic receptor ADRA1D 0.0086
341 5-hydroxytryptamine 3 receptor HTR3A 0.0082
540 Sodium-dependent noradrenaline transporter SLC6A2 0.008
632 Alpha-1B adrenergic receptor ADRA1B 0.008
6013 Cytochrome P450 2E1 CYP2E1 0.0079
6016 Cytochrome P450 2C19 CYP2C19 0.0079
1181 Alpha-1-acid glycoprotein 1 ORM1 0.0078
833 Organic cation/carnitine transporter 1 SLC22A4 0.0075
6144 Solute carrier family 22 member 2 SLC22A2 0.0073
432 D(4) dopamine receptor DRD4 0.0072
723 Cytosolic phospholipase A2 PLA2G4A 0.0067
4924 Cytochrome P450 2C8 CYP2C8 0.0067
824 Sodium-dependent serotonin transporter SLC6A4 0.0064
4118 Cytochrome P450 3A5 CYP3A5 0.0063
474 Acetylcholinesterase ACHE 0.0063
6024 Cytochrome P450 1A1 CYP1A1 0.006
436 5-hydroxytryptamine 2B receptor HTR2B 0.0059
118 Organic cation/carnitine transporter 2 SLC22A5 0.0059
638 D(3) dopamine receptor DRD3 0.0059
6030 Cytochrome P450 2B6 CYP2B6 0.0058
706 Glutamate [NMDA] receptor subunit 3A GRIN3A 0.0058
6098 Potassium voltage-gated channel subfamily D member 2 KCND2 0.0054
6099 Potassium voltage-gated channel subfamily D member 3 KCND3 0.0054
5878 Alpha-7 nicotinic cholinergic receptor subunit CHRFAM7A 0.0052
320 5-hydroxytryptamine 1A receptor HTR1A 0.0051
2129 Sucrase-isomaltase, intestinal SI 0.0051
378 Alpha-2C adrenergic receptor ADRA2C 0.005
318 Alpha-2A adrenergic receptor ADRA2A 0.0049
629 Alpha-2B adrenergic receptor ADRA2B 0.0049
458 Neuronal acetylcholine receptor subunit alpha-10 CHRNA10 0.0047
528 5-hydroxytryptamine 1E receptor HTR1E 0.0045
1256 5-hydroxytryptamine 6 receptor HTR6 0.0041
163 D(1B) dopamine receptor DRD5 0.0041
5718 Cytochrome P450 2A6 CYP2A6 0.004
716 5-hydroxytryptamine 7 receptor HTR7 0.0038
6139 Solute carrier organic anion transporter family member 1A2 SLCO1A2 0.0036
220 Sodium channel protein type 5 subunit alpha SCN5A 0.0035
725 5-hydroxytryptamine 1D receptor HTR1D 0.0034
885 5-hydroxytryptamine 1B receptor HTR1B 0.0033
6176 UDP-glucuronosyltransferase 1-3 UGT1A3 0.0032
6107 Cytochrome P450 3A7 CYP3A7 0.0032
465 Calmodulin CALM1 0.0025
215 Sodium channel protein type 11 subunit alpha SCN11A 0.0024
6432 Transporter snf 0.0021
587 Serum albumin ALB 0.0016
198 Sodium channel protein type 10 subunit alpha SCN10A 0.0016
6106 Cytochrome P450 2C18 CYP2C18 0.0015
1360 Sphingomyelin phosphodiesterase SMPD1 0.0015
6147 Solute carrier family 22 member 3 SLC22A3 0.0015
6101 Dimethylaniline monooxygenase [N-oxide-forming] 3 FMO3 0.0015
713 Sodium-dependent dopamine transporter SLC6A3 0.0014
6047 Calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1A PDE1A 0.0014
6100 BDNF/NT-3 growth factors receptor NTRK2 0.0013
5692 Calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1B PDE1B 0.0013
762 Voltage-dependent calcium channel subunit alpha-2/delta-1 CACNA2D1 0.001
4110 Voltage-dependent L-type calcium channel subunit beta-2 CACNB2 0.001
4115 Voltage-dependent L-type calcium channel subunit alpha-1D CACNA1D 0.001
1618 High affinity nerve growth factor receptor NTRK1 0.001
478 Voltage-dependent L-type calcium channel subunit alpha-1C CACNA1C 0.001
1086 Potassium voltage-gated channel subfamily KQT member 2 KCNQ2 0.001
124 Histamine H2 receptor HRH2 0.0009
164 Histamine H4 receptor HRH4 0.0009
734 D1 dopamine receptor-interacting protein calcyon CALY 0.0009
858 Potassium voltage-gated channel subfamily A member 1 KCNA1 0.0008
20 Prostaglandin G/H synthase 1 PTGS1 0.0008
193 Beta-1 adrenergic receptor ADRB1 0.0007
766 Beta-2 adrenergic receptor ADRB2 0.0007
6025 UDP-glucuronosyltransferase 1-4 UGT1A4 0.0007
467 Delta-type opioid receptor OPRD1 0.0006
696 Kappa-type opioid receptor OPRK1 0.0006
1898 Cytochrome P450 1B1 CYP1B1 0.0005
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