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Bethanechol

Bethanechol structure

CAS No:
674-38-4
Formula:
C7H17N2O2
Chemical Name:
Bethanechol
Synonyms:
1-Propanaminium,2-[(aminocarbonyl)oxy]-N,N,N-trimethyl-;Ammonium,(2-hydroxypropyl)trimethyl-,carbamate (ester);2-[(Aminocarbonyl)oxy]-N,N,N-trimethyl-1-propanaminium;Bethanechol;Carbamoyl-β-methylcholine;Carbamyl-β-methylcholine;Liberan;2-Carbamoyloxypropyl(trimethyl)azanium;111318-31-1;91609-06-2
Categories:
Organic Chemistry > Amides

Description

Bethanechol is a parasympathomimetic choline carbamate that selectively stimulates muscarinic receptors without any effect on nicotinic receptors.Target: muscarinic receptorHyoscine butylbromide concentration dependently reduced muscle contractions, calcium mobilization, and epithelial secretion induced by the muscarinic agonist bethanechol with IC50 values of 429, 121, and 224 nmol L(-1), respectively.[2] Bethanechol presentes significantly improve of salivary parameters. Bethanechol is

Solid

Bethanechol is the carbamic acid ester of 2-methylcholine. A slowly hydrolysed muscarinic agonist with no nicotinic effects, it is used as its chloride salt to increase smooth muscle tone, as in the gastrointestinal tract following abdominal surgery, treatment of gastro-oesophageal reflux disease, and as an alternative to catheterisation in the treatment of non-obstructive urinary retention. It has a role as a muscarinic agonist. It is a quaternary ammonium ion and a carbamate ester.|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.|A slowly hydrolyzing 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, HEART RATE changes, and BRONCHIAL SPASM.

Bethanechol Basic Attributes

Molecular Weight：

161.22

Exact Mass：

161.12900

EC Number：

209-686-8

DSSTox ID：

DTXSID5048398

ATC Code：

N07AB02|N - Nervous system

HScode：

2924199090

Characteristics

PSA：

52.3

XLogP3：

0.87670

Appearance：

Solid

Melting Point：

217 - 221 °C (chloride salt)

Water Solubility：

3.11e-01 g/L

Drug Information

Drug Indication：

For the treatment of acute postoperative and postpartum nonobstructive (functional) urinary retention and for neurogenic atony of the urinary bladder with retention.

Pharmacology：

Bethanechol is a parasympathomimetic (cholinergic) used for the treatment of acute postoperative and postpartum nonobstructive (functional) urinary retention and for neurogenic atony of the urinary bladder with retention. Bethanechol, a cholinergic agent, is a synthetic ester which is structurally and pharmacologically related to acetylcholine. It increases the tone of the detrusor urinae muscle, usually producing a contraction sufficiently strong to initiate micturition and empty the bladder. It stimulates gastric motility, increases gastric tone, and often restores impaired rhythmic peristalsis. Bethanechol chloride is not destroyed by cholinesterase and its effects are more prolonged than those of acetytcholine.

MeSH：

Drugs that mimic the effects of parasympathetic nervous system activity. Included here are drugs that directly stimulate muscarinic receptors and drugs that potentiate cholinergic activity, usually by slowing the breakdown of acetylcholine (CHOLINESTERASE INHIBITORS). Drugs that stimulate both sympathetic and parasympathetic postganglionic neurons (GANGLIONIC STIMULANTS) are not included here. (See all compounds classified as Parasympathomimetics.)|Drugs that bind to and activate muscarinic cholinergic receptors (RECEPTORS, MUSCARINIC). Muscarinic agonists are most commonly used when it is desirable to increase smooth muscle tone, especially in the GI tract, urinary bladder and the eye. They may also be used to reduce heart rate. (See all compounds classified as Muscarinic Agonists.)

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.

MeSH Entry Terms：

Bethanechol

Bethanechol Use and Manufacturing

Uses

Cholinergic.

Use Classification：

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients|Pharmaceuticals -> Animal Drugs -> Approved in Taiwan

Computed Properties

Molecular Weight:161.22
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:4
Exact Mass:161.129002789
Monoisotopic Mass:161.129002789
Topological Polar Surface Area:52.3
Heavy Atom Count:11
Formal Charge:1
Complexity:140
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes