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Identification
Name Propantheline
Accession Number DB00782 (APRD00177)
Type small molecule
Groups approved
Description

A muscarinic antagonist used as an antispasmodic, in rhinitis, in urinary incontinence, and in the treatment of ulcers. At high doses it has nicotinic effects resulting in neuromuscular blocking. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • Propantheline Bromide
  • Propanthelinium
  • Propanthelinum
Synonyms
Propantheline Bromide
Propanthelinium
Propanthelinum
Salts Not Available
Brand names
Name Company
Pro-Banthine
Propanthel
Brand mixtures Not Available
Categories
  • Anti-Ulcer Agents
  • Muscarinic Antagonists
  • Antispasmodics
  • Antimuscarinics
CAS number 298-50-0
Weight Average: 368.4892
Monoisotopic: 368.222568831
Chemical Formula C23H30NO3
InChI Key InChIKey=VVWYOYDLCMFIEM-UHFFFAOYSA-N
InChI
InChI=1S/C23H30NO3/c1-16(2)24(5,17(3)4)14-15-26-23(25)22-18-10-6-8-12-20(18)27-21-13-9-7-11-19(21)22/h6-13,16-17,22H,14-15H2,1-5H3/q+1
Plain Text
IUPAC Name
methylbis(propan-2-yl){2-[(9H-xanthen-9-yl)carbonyloxy]ethyl}azanium
SMILES
CC(C)[N+](C)(CCOC(=O)C1C2=CC=CC=C2OC2=CC=CC=C12)C(C)C
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Xanthenes
Substructures
  • Xanthenes
  • Carboxylic Acids and Derivatives
  • Pyrans
  • Acetates
  • Phenols and Derivatives
  • Phenylacetates
  • Ethers
  • Benzene and Derivatives
  • Quaternary Ammonium Salts
  • Benzopyrans
  • Heterocyclic compounds
  • Aromatic compounds
  • Anisoles
  • Phenyl Esters
  • Cations
Pharmacology
Indication For the treatment of enuresis. It has also been used for hyperhidrosis, and cramps or spasms of the stomach, intestines or bladder.
Pharmacodynamics Propantheline is an anticholinergic drug, a medication that reduces the effect of acetylcholine, a chemical released from nerves that stimulates muscles, by blocking the receptors for acetylcholine on smooth muscle (a type of muscle). It also has a direct relaxing effect on smooth muscle. Propantheline is used to treat or prevent spasm in the muscles of the gastrointestinal tract in the irritable bowel syndrome. In addition, Propantheline inhibits gastrointestinal propulsive motility and decreases gastric acid secretion and controls excessive pharyngeal, tracheal and bronchial secretions.
Mechanism of action Action is achieved via a dual mechanism: (1) a specific anticholinergic effect (antimuscarinic) at the acetylcholine-receptor sites and (2) a direct effect upon smooth muscle (musculotropic).
Absorption Not Available
Volume of distribution Not Available
Protein binding Not Available
Metabolism Not Available
Route of elimination Approximately 70% of the dose is excreted in the urine, mostly as metabolites.
Half life Not Available
Clearance Not Available
Toxicity Not Available
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Gd searle llc
  • Shire development inc
  • Ascot hosp pharmaceuticals inc div travenol laboratories inc
  • Heather drug co inc
  • Impax laboratories inc
  • Mylan pharmaceuticals inc
  • Par pharmaceutical inc
  • Private formulations inc
  • Roxane laboratories inc
  • Sandoz inc
  • Tablicaps inc
  • Watson laboratories inc
Packagers
Dosage forms
Form Route Strength
Tablet Oral
Prices
Unit description Cost Unit
Propantheline bromide powder 7.77 USD g
Propantheline Bromide 15 mg tablet 0.76 USD tablet
Propantheline 15 mg tablet 0.6 USD tablet
Patents Not Available
Properties
State solid
Melting point Not Available
Experimental Properties Not Available
Predicted Properties
Property Value Source
water solubility 7.22e-05 g/l ALOGPS
logP 2.66 ALOGPS
logP 0.36 ChemAxon Molconvert
logS -6.8 ALOGPS
pKa 0 ChemAxon Molconvert
hydrogen acceptor count 1 ChemAxon Molconvert
hydrogen donor count 0 ChemAxon Molconvert
polar surface area 35.53 ChemAxon Molconvert
rotatable bond count 7 ChemAxon Molconvert
refractivity 119.25 ChemAxon Molconvert
polarizability 40.87 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Compound C07506 Link_out
PubChem Compound 4934 Link_out
PubChem Substance 46507187 Link_out
ChemSpider 4765 Link_out
Therapeutic Targets Database DAP001123 Link_out
PharmGKB PA451133 Link_out
IUPHAR 329 Link_out
Guide to Pharmacology 329 Link_out
Drug Product Database 2030837 Link_out
Drugs.com http://www.drugs.com/cdi/propantheline.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Propantheline Link_out
ATC Codes
  • A03AB05
AHFS Codes
  • 12:08.08
PDB Entries Not Available
FDA label Not Available
MSDS show (73.8 KB)
Interactions
Drug Interactions
Drug Interaction
Donepezil Possible antagonism of action
Galantamine Possible antagonism of action
Haloperidol The anticholinergic increases the risk of psychosis and tardive dyskinesia
Tacrine The therapeutic effects of the central acetylcholinesterase inhibitor, Tacrine, and/or the anticholinergic, Propantheline, may be reduced due to antagonism. The interaction may be beneficial when the anticholinergic action is a side effect. Monitor for decreased efficacy of both agents.
Trimethobenzamide Trimethobenzamide and Propantheline, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Monitor for enhanced anticholinergic effects.
Triprolidine Triprolidine and Propantheline, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Monitor for enhanced anticholinergic effects.
Trospium Trospium and Propantheline, two anticholinergics, may cause additive anticholinergic effects and enhanced adverse/toxic effects. Monitor for enhanced anticholinergic effects.
Food Interactions Not Available
Targets

1. Muscarinic acetylcholine receptor M1

Pharmacological action: yes
Actions: 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: human
UniProt ID: P11229 Link_out
Gene: CHRM1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. 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
  2. Lukacs VA, Korting HC: [Antiperspirants and deodorants—ingredients and evaluation] Derm Beruf Umwelt. 1989 Mar-Apr;37(2):53-7. Pubmed
  3. Saitoh H, Hasegawa N, Kawai S, Miyazaki K, Arita T: Interaction of tertiary amines and quaternary ammonium compounds with gastrointestinal mucin. J Pharmacobiodyn. 1986 Dec;9(12):1008-14. Pubmed
  4. Trkulja V, Crljen-Manestar V, Banfic H, Lackovic Z: Involvement of the peripheral cholinergic muscarinic system in the compensatory ovarian hypertrophy in the rat. Exp Biol Med (Maywood). 2004 Sep;229(8):793-805. Pubmed
  5. Mokry J, Nosalova G, Jakubesova M: Propantheline and in vitro reactivity of urinary bladder smooth muscle in guinea pigs. Bratisl Lek Listy. 2005;106(4-5):151-4. Pubmed
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 14, 2012 11:43