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Details

Stereochemistry ACHIRAL
Molecular Formula C23H30NO3
Molecular Weight 368.4892
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 1

SHOW SMILES / InChI
Structure of PROPANTHELINE

SMILES

CC(C)[N+](C)(CCOC(=O)C1C2=CC=CC=C2OC3=CC=CC=C13)C(C)C

InChI

InChIKey=VVWYOYDLCMFIEM-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Description

Propantheline is an antimuscarinic agent used for the treatment of excessive sweating (hyperhidrosis), cramps or spasms of the stomach, intestines (gut) or bladder, and involuntary urination (enuresis). It can also be used to control the symptoms of irritable bowel syndrome and similar conditions. Propantheline is one of a group of antispasmodic medications which work by blocking the action of the chemical messenger acetylcholine, which is produced by nerve cells, to muscarinic receptors present in various smooth muscular tissues, in places such as the gut, bladder, and eye. Normally, the binding of acetylcholine induces involuntary smooth muscular contractions. Varying degrees of drying of salivary secretions may occur as well as decreased sweating. Ophthalmic side effects include blurred vision, mydriasis, cycloplegia, and increased ocular tension. Other reported adverse reactions include urinary hesitancy and retention, tachycardia, palpitations, loss of the sense of taste, headache, nervousness, mental confusion, drowsiness, weakness, dizziness, insomnia, nausea, vomiting, constipation, bloated feeling, impotence, suppression of lactation, and allergic reactions or drug idiosyncrasies including anaphylaxis, urticaria and other dermal manifestations.

CNS Activity

Approval Year

PubMed

PubMed

TitleDatePubMed
Stoichiometric and microenvironmental effects on hydrolysis of propantheline and oxyphenonium bromides in cyclodextrin solutions.
2001 Jun
Variable effects of previously untested muscarinic receptor antagonists on experimental myopia.
2003 Mar
Methyl 9H-xanthene-9-carboxyl-ate.
2008 Apr 16
Patient perspectives in the management of overactive bladder, focus on transdermal oxybutynin.
2008 Feb 2
Locked-in Syndrome in a Nigerian male with Multiple Sclerosis: a case report and literature review.
2008 Oct 30
Response to "Suspected differential interactions of digoxin with imidafenacin and propantheline; some thoughts for introspection".
2009
Anticholinergics for urinary symptoms in multiple sclerosis.
2009 Jan 21
A meta-analysis of the placebo response in antimuscarinic drug trials for overactive bladder.
2009 Jul 22
Oxybutynin extended release for the management of overactive bladder: a clinical review.
2009 Sep 21
Comparison of risk of neurovascular and cardiovascular side effects between tiotropium and other anticholinergic agents.
2010
Inappropriate prescribing in the hospitalized elderly patient: defining the problem, evaluation tools, and possible solutions.
2010 Apr 7
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.
2010 Dec
Simultaneous spectrophotometric estimation of haloperidol and trihexyphenidyl in tablets.
2010 Mar
New approaches in the management of multiple sclerosis.
2010 Nov 24
New insights into molecular targets for urinary incontinence.
2010 Oct
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.
2011 Jul 14
Patents

Patents

Sample Use Guides

In Vivo Use Guide
The usual initial adult dose of Propantheline bromide tablets is 15 mg taken 30 minutes before each meal and 30 mg at bedtime (a total of 75 mg daily). Subsequent dosage adjustment should be made according to the patient’s individual response and tolerance.
Route of Administration: Oral
In Vitro Use Guide
Binding studies were performed with [3 H]NMS following the protocol from RBI. The binding buffer, pH 7.4, consisted of 0.15 M NaCl, 1.5 mM KH2 PO4 , and 2.7 mM Na2 HPO4 . NaF 10 mM was added to the buffer as an esterase inhibitor. The assay mixture (1 mL) contained 100 μL diluted membranes (receptor proteins, final concentration: m1 25 μg/mL, m2 42 μg/mL, m3 15.9 μg/mL, m4 20 μg/mL). Final concentrations of [3 H]NMS for the m2-m4 binding studies were 0.5 nM and 1 nM for m1. Specific binding was defined as the difference between the [3 H]NMS binding in the absence and presence of 1 μM atropine. Incubation was carried out at room temperature for 60 minutes. The assay was terminated by filtration through a Whatman GF/B filter (presoaked with 0.5% polyethyleneimine). The filter was then washed 3 times with 10 mL ice-cold binding buffer, transferred to vials, and added with 10 mL of Scintiverse liquid. Finally, detection was performed on a Packard 31800 liquid scintillation analyzer
Name Type Language
PROPANTHELINE
HSDB   VANDF   WHO-DD  
Common Name English
PROPANTHELINE [WHO-DD]
Common Name English
PROPANTHELINE [HSDB]
Common Name English
PROPANTHELINE CATION
Common Name English
PROPANTHELINE [VANDF]
Common Name English
2-PROPANAMINIUM, N-METHYL-N-(1-METHYLETHYL)-N-(2-((9H-XANTHEN-9- YLCARBONYL)OXY)ETHYL)
Common Name English
PROPANTHELINE ION
Common Name English
Classification Tree Code System Code
WHO-ATC A03AB05
Created by admin on Tue Mar 06 10:38:20 UTC 2018 , Edited by admin on Tue Mar 06 10:38:20 UTC 2018
WHO-VATC QA03CA34
Created by admin on Tue Mar 06 10:38:20 UTC 2018 , Edited by admin on Tue Mar 06 10:38:20 UTC 2018
WHO-VATC QA03AB05
Created by admin on Tue Mar 06 10:38:20 UTC 2018 , Edited by admin on Tue Mar 06 10:38:20 UTC 2018
WHO-ATC A03CA34
Created by admin on Tue Mar 06 10:38:20 UTC 2018 , Edited by admin on Tue Mar 06 10:38:20 UTC 2018
LIVERTOX 807
Created by admin on Tue Mar 06 10:38:20 UTC 2018 , Edited by admin on Tue Mar 06 10:38:20 UTC 2018
NDF-RT N0000175574
Created by admin on Tue Mar 06 10:38:20 UTC 2018 , Edited by admin on Tue Mar 06 10:38:20 UTC 2018
NDF-RT N0000175370
Created by admin on Tue Mar 06 10:38:20 UTC 2018 , Edited by admin on Tue Mar 06 10:38:20 UTC 2018
Code System Code Type Description
MESH
D011413
Created by admin on Tue Mar 06 10:38:20 UTC 2018 , Edited by admin on Tue Mar 06 10:38:20 UTC 2018
PRIMARY
WIKIPEDIA
Propantheline
Created by admin on Tue Mar 06 10:38:20 UTC 2018 , Edited by admin on Tue Mar 06 10:38:20 UTC 2018
PRIMARY
HSDB
298-50-0
Created by admin on Tue Mar 06 10:38:20 UTC 2018 , Edited by admin on Tue Mar 06 10:38:20 UTC 2018
PRIMARY
PUBCHEM
4934
Created by admin on Tue Mar 06 10:38:20 UTC 2018 , Edited by admin on Tue Mar 06 10:38:20 UTC 2018
PRIMARY SWITZERF
CAS
298-50-0
Created by admin on Tue Mar 06 10:38:20 UTC 2018 , Edited by admin on Tue Mar 06 10:38:20 UTC 2018
PRIMARY
DRUG BANK
DB00782
Created by admin on Tue Mar 06 10:38:20 UTC 2018 , Edited by admin on Tue Mar 06 10:38:20 UTC 2018
PRIMARY
EPA CompTox
298-50-0
Created by admin on Tue Mar 06 10:38:20 UTC 2018 , Edited by admin on Tue Mar 06 10:38:20 UTC 2018
PRIMARY
RXCUI
8761
Created by admin on Tue Mar 06 10:38:20 UTC 2018 , Edited by admin on Tue Mar 06 10:38:20 UTC 2018
PRIMARY RxNorm
IUPHAR
329
Created by admin on Tue Mar 06 10:38:20 UTC 2018 , Edited by admin on Tue Mar 06 10:38:20 UTC 2018
PRIMARY
EVMPD
SUB04081MIG
Created by admin on Tue Mar 06 10:38:20 UTC 2018 , Edited by admin on Tue Mar 06 10:38:20 UTC 2018
PRIMARY
LactMed
298-50-0
Created by admin on Tue Mar 06 10:38:20 UTC 2018 , Edited by admin on Tue Mar 06 10:38:20 UTC 2018
PRIMARY
NCI_THESAURUS
C78077
Created by admin on Tue Mar 06 10:38:20 UTC 2018 , Edited by admin on Tue Mar 06 10:38:20 UTC 2018
PRIMARY
ECHA (EC/EINECS)
206-063-2
Created by admin on Tue Mar 06 10:38:20 UTC 2018 , Edited by admin on Tue Mar 06 10:38:20 UTC 2018
PRIMARY