| Identification | ||||||||||||||||||||||||||||||||||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Name | Anisotropine Methylbromide | |||||||||||||||||||||||||||||||||||||||
| Accession Number | DB00517 (APRD00800) | |||||||||||||||||||||||||||||||||||||||
| Type | small molecule | |||||||||||||||||||||||||||||||||||||||
| Groups | approved | |||||||||||||||||||||||||||||||||||||||
| Description | Anisotropine methylbromide is a quaternary ammonium compound. Its use as treatment adjunct in peptic ulcer has been replaced by the use of more effective agents. Depending on the dose, anisotropine methylbromide may reduce the motility and secretory activity of the gastrointestinal system, and the tone of the ureter and urinary bladder and may have a slight relaxant action on the bile ducts and gallbladder. In general, smaller doses of anisotropine methylbromide inhibit salivary and bronchial secretions, sweating, and accommodation; cause dilatation of the pupil; and increase the heart rate. Larger doses are required to decrease motility of the gastrointestinal and urinary tracts and to inhibit gastric acid secretion. |
|||||||||||||||||||||||||||||||||||||||
| Structure |
Download: MOL | SDF | SMILES | InChI Display: 2D Structure | 3D Structure |
|||||||||||||||||||||||||||||||||||||||
| Synonyms | Not Available | |||||||||||||||||||||||||||||||||||||||
| Salts | Not Available | |||||||||||||||||||||||||||||||||||||||
| Brand names |
|
|||||||||||||||||||||||||||||||||||||||
| Brand mixtures | Not Available | |||||||||||||||||||||||||||||||||||||||
| Categories |
|
|||||||||||||||||||||||||||||||||||||||
| CAS number | 80-50-2 | |||||||||||||||||||||||||||||||||||||||
| Weight |
Average: 362.345 Monoisotopic: 361.16164192 |
|||||||||||||||||||||||||||||||||||||||
| Chemical Formula | C17H32BrNO2 | |||||||||||||||||||||||||||||||||||||||
| InChI Key | InChIKey=QSFKGMJOKUZAJM-UHFFFAOYSA-M | |||||||||||||||||||||||||||||||||||||||
| InChI |
InChI=1S/C17H32NO2.BrH/c1-5-7-13(8-6-2)17(19)20-16-11-14-9-10-15(12-16)18(14,3)4;/h13-16H,5-12H2,1-4H3;1H/q+1;/p-1
Plain Text
|
|||||||||||||||||||||||||||||||||||||||
| IUPAC Name |
(3S)-8,8-dimethyl-3-[(2-propylpentanoyl)oxy]-8-azabicyclo[3.2.1]octan-8-ium bromide
|
|||||||||||||||||||||||||||||||||||||||
| SMILES |
[Br-].CCCC(CCC)C(=O)O[C@H]1CC2CCC(C1)[N+]2(C)C
Plain Text
|
|||||||||||||||||||||||||||||||||||||||
| Mass Spec | Not Available | |||||||||||||||||||||||||||||||||||||||
| Taxonomy | ||||||||||||||||||||||||||||||||||||||||
| Kingdom | Not Available | |||||||||||||||||||||||||||||||||||||||
| Classes | Not Available | |||||||||||||||||||||||||||||||||||||||
| Substructures | Not Available | |||||||||||||||||||||||||||||||||||||||
| Pharmacology | ||||||||||||||||||||||||||||||||||||||||
| Indication | For use in conjunction with antacids or histamine H2-receptor antagonists in the treatment of peptic ulcer, to reduce further gastric acid secretion and delay gastric emptying. | |||||||||||||||||||||||||||||||||||||||
| Pharmacodynamics | Anisotropine methylbromide is a quaternary ammonium compound. Its use as treatment adjunct in peptic ulcer has been replaced by the use of more effective agents. Depending on the dose, anisotropine methylbromide may reduce the motility and secretory activity of the gastrointestinal system, and the tone of the ureter and urinary bladder and may have a slight relaxant action on the bile ducts and gallbladder. In general, smaller doses of anisotropine methylbromide inhibit salivary and bronchial secretions, sweating, and accommodation; cause dilatation of the pupil; and increase the heart rate. Larger doses are required to decrease motility of the gastrointestinal and urinary tracts and to inhibit gastric acid secretion. | |||||||||||||||||||||||||||||||||||||||
| Mechanism of action | Quaternary ammonium compounds such as anisotropine methylbromide inhibit the muscarinic actions of acetylcholine on structures innervated by postganglionic cholinergic nerves as well as on smooth muscles that respond to acetylcholine but lack cholinergic innervation. These postganglionic receptor sites are present in the autonomic effector cells of the smooth muscle, cardiac muscle, sinoatrial and atrioventricular nodes, and exocrine glands. | |||||||||||||||||||||||||||||||||||||||
| Absorption | Gastrointestinal absorption is poor and irregular. Total absorption after an oral dose is about 10 to 25%. | |||||||||||||||||||||||||||||||||||||||
| Volume of distribution | Not Available | |||||||||||||||||||||||||||||||||||||||
| Protein binding | Not Known | |||||||||||||||||||||||||||||||||||||||
| Metabolism | Hepatic, by enzymatic hydrolysis. | |||||||||||||||||||||||||||||||||||||||
| Route of elimination | Not Available | |||||||||||||||||||||||||||||||||||||||
| Half life | Not Known | |||||||||||||||||||||||||||||||||||||||
| Clearance | Not Available | |||||||||||||||||||||||||||||||||||||||
| Toxicity | Not Available | |||||||||||||||||||||||||||||||||||||||
| Affected organisms |
|
|||||||||||||||||||||||||||||||||||||||
| Pathways | Not Available | |||||||||||||||||||||||||||||||||||||||
| Pharmacoeconomics | ||||||||||||||||||||||||||||||||||||||||
| Manufacturers |
|
|||||||||||||||||||||||||||||||||||||||
| Packagers | Not Available | |||||||||||||||||||||||||||||||||||||||
| Dosage forms | Not Available | |||||||||||||||||||||||||||||||||||||||
| Prices | Not Available | |||||||||||||||||||||||||||||||||||||||
| Patents | Not Available | |||||||||||||||||||||||||||||||||||||||
| Properties | ||||||||||||||||||||||||||||||||||||||||
| State | solid | |||||||||||||||||||||||||||||||||||||||
| Experimental Properties |
|
|||||||||||||||||||||||||||||||||||||||
| Predicted Properties |
|
|||||||||||||||||||||||||||||||||||||||
| References | ||||||||||||||||||||||||||||||||||||||||
| Synthesis Reference | Not Available | |||||||||||||||||||||||||||||||||||||||
| General Reference | Not Available | |||||||||||||||||||||||||||||||||||||||
| External Links |
|
|||||||||||||||||||||||||||||||||||||||
| ATC Codes | Not Available | |||||||||||||||||||||||||||||||||||||||
| AHFS Codes | Not Available | |||||||||||||||||||||||||||||||||||||||
| PDB Entries | Not Available | |||||||||||||||||||||||||||||||||||||||
| FDA label | Not Available | |||||||||||||||||||||||||||||||||||||||
| MSDS | Not Available | |||||||||||||||||||||||||||||||||||||||
| Interactions | ||||||||||||||||||||||||||||||||||||||||
| Drug Interactions |
|
|||||||||||||||||||||||||||||||||||||||
| Food Interactions | Not Available | |||||||||||||||||||||||||||||||||||||||
| Targets |
|---|
|
1. Muscarinic acetylcholine receptor M1 Pharmacological action: yesActions: antagonist The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover Organism class: humanUniProt ID: P11229 ![]() Gene: CHRM1 ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
2. Muscarinic acetylcholine receptor M2 Pharmacological action: yesActions: antagonist The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is adenylate cyclase inhibition Organism class: humanUniProt ID: P08172 ![]() Gene: CHRM2 ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
3. Muscarinic acetylcholine receptor M3 Pharmacological action: yesActions: antagonist The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover Organism class: humanUniProt ID: P20309 ![]() Gene: CHRM3 ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
|
| Comments |
|---|