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Details

Stereochemistry ACHIRAL
Molecular Formula C23H30NO3
Molecular Weight 368.4901
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 1

SHOW SMILES / InChI
Structure of PROPANTHELINE

SMILES

CC(C)[N+](C)(CCOC(=O)C1c2ccccc2Oc3ccccc31)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
Curator's Comment:: description was created based on several sources, including https://www.drugbank.ca/drugs/DB00782 | http://reference.medscape.com/drug/pro-banthine-propantheline-342000 | https://www.ncbi.nlm.nih.gov/pubmed/12049493

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

Curator's Comment:: propantheline has very little capacity for penetration across the blood-brain barrier

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PRO-BANTHINE

Approved Use

Propantheline bromide is effective as adjunctive therapy in the treatment of peptic ulcer.

Launch Date

-5.2859519E11
Primary
PRO-BANTHINE

Approved Use

Propantheline bromide is effective as adjunctive therapy in the treatment of peptic ulcer.

Launch Date

-5.2859519E11
Primary
PRO-BANTHINE

Approved Use

Propantheline bromide is effective as adjunctive therapy in the treatment of peptic ulcer.

Launch Date

-5.2859519E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
51.5 ng/mL
45 mg single, oral
dose: 45 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PROPANTHELINE BROMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
53.1 ng/mL
60 mg single, oral
dose: 60 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PROPANTHELINE BROMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
20.6 ng/mL
30 mg single, oral
dose: 30 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PROPANTHELINE BROMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
186.9 ng × h/mL
45 mg single, oral
dose: 45 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PROPANTHELINE BROMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
159 ng × h/mL
60 mg single, oral
dose: 60 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PROPANTHELINE BROMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
62.2 ng × h/mL
30 mg single, oral
dose: 30 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PROPANTHELINE BROMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1.56 h
60 mg single, oral
dose: 60 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PROPANTHELINE BROMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
1.57 h
30 mg single, oral
dose: 30 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PROPANTHELINE BROMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
PubMed

PubMed

TitleDatePubMed
Receptor binding studies of soft anticholinergic agents.
2001
Effects of YM905, a novel muscarinic M3-receptor antagonist, on experimental models of bowel dysfunction in vivo.
2001 Jul
Stoichiometric and microenvironmental effects on hydrolysis of propantheline and oxyphenonium bromides in cyclodextrin solutions.
2001 Jun
Anticholinergic drugs versus placebo for overactive bladder syndrome in adults.
2002
Taurine in submandibular gland of the rat: effect of muscarinic drugs.
2002 Apr
Influence of prokinetics on the gastrointestinal transit and residence times of activated charcoal.
2002 Aug
An improved method of evaluation of drug-evoked changes in gastric emptying in mice.
2002 Mar-Apr
Clinical pharmacokinetics of drugs used to treat urge incontinence.
2003
Interventions for preventing oral mucositis for patients with cancer receiving treatment.
2003
Variable effects of previously untested muscarinic receptor antagonists on experimental myopia.
2003 Mar
Interleukin-1 (IL-1) system gene expression in granulosa cells: kinetics during terminal preovulatory follicle maturation in the mare.
2003 May 16
Cumulus expansion, nuclear maturation and connexin 43, cyclooxygenase-2 and FSH receptor mRNA expression in equine cumulus-oocyte complexes cultured in vitro in the presence of FSH and precursors for hyaluronic acid synthesis.
2004 Jun 22
Propantheline and in vitro reactivity of urinary bladder smooth muscle in guinea pigs.
2005
Clinical observations of the effect of antidiuretic hormone on nocturia in elderly men.
2005 Dec
Ocular complications of neurological therapy.
2005 Jul
Trospium chloride: an update on a quaternary anticholinergic for treatment of urge urinary incontinence.
2005 Jun
In vivo effect of interleukin-1beta and interleukin-1RA on oocyte cytoplasmic maturation, ovulation, and early embryonic development in the mare.
2005 Jun 22
Evaluation of antimotility effect of Lantana camara L. var. acuelata constituents on neostigmine induced gastrointestinal transit in mice.
2005 Sep 17
Interventions for preventing oral mucositis for patients with cancer receiving treatment.
2006 Apr 19
Masking mechanisms of bitter taste of drugs studied with ion selective electrodes.
2006 Aug
Prophylaxis of mucosal toxicity by oral propantheline and cryotherapy in children with malignancies undergoing myeloablative chemo-radiotherapy.
2006 Dec
Anticholinergic drugs versus placebo for overactive bladder syndrome in adults.
2006 Oct 18
Application of the convection-dispersion equation to modelling oral drug absorption.
2007 Jan
Clomipramine-induced mood and perceived performance changes in selected healthy individuals.
2007 Jun
Interventions for preventing oral mucositis for patients with cancer receiving treatment.
2007 Oct 17
The effectiveness of intravesical oxybutynin, propantheline, and capsaicin in the management of neuropathic bladder following spinal cord injury.
2007 Oct 22
Choice of antimuscarinic agents for overactive bladder in the older patient: focus on darifenacin.
2008
No effect of imidafenacin, a novel antimuscarinic drug, on digoxin pharmacokinetics in healthy subjects.
2008
Persistence, adherence, and switch rates among extended-release and immediate-release overactive bladder medications in a regional managed care plan.
2008 Apr
Methyl 9H-xanthene-9-carboxyl-ate.
2008 Apr 16
Patient perspectives in the management of overactive bladder, focus on transdermal oxybutynin.
2008 Feb 2
Pharmacological interventions for clozapine-induced hypersalivation.
2008 Jul
Pharmacological interventions for clozapine-induced hypersalivation.
2008 Jul 16
Using the zebrafish lateral line to screen for ototoxicity.
2008 Jun
Cycloheximide and disulfoton are positive in the photoclastogencity assay but do not absorb UV irradiation: another example of pseudophotoclastogenicity?
2008 Mar
Pharmacokinetics of meloxicam administered as regular and fast dissolving formulations to the rat: influence of gastrointestinal dysfunction on the relative bioavailability of two formulations.
2008 Nov
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
Desirable pharmacokinetic properties of (13)C-uracil as a breath test probe of gastric emptying in comparison with (13)C-acetate and (13)C-octanoate in rats.
2009
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

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
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 Sat Jun 26 01:16:50 UTC 2021 , Edited by admin on Sat Jun 26 01:16:50 UTC 2021
NCI_THESAURUS C29704
Created by admin on Sat Jun 26 01:16:50 UTC 2021 , Edited by admin on Sat Jun 26 01:16:50 UTC 2021
WHO-VATC QA03CA34
Created by admin on Sat Jun 26 01:16:50 UTC 2021 , Edited by admin on Sat Jun 26 01:16:50 UTC 2021
WHO-VATC QA03AB05
Created by admin on Sat Jun 26 01:16:50 UTC 2021 , Edited by admin on Sat Jun 26 01:16:50 UTC 2021
WHO-ATC A03CA34
Created by admin on Sat Jun 26 01:16:50 UTC 2021 , Edited by admin on Sat Jun 26 01:16:50 UTC 2021
LIVERTOX 807
Created by admin on Sat Jun 26 01:16:50 UTC 2021 , Edited by admin on Sat Jun 26 01:16:50 UTC 2021
NDF-RT N0000175574
Created by admin on Sat Jun 26 01:16:50 UTC 2021 , Edited by admin on Sat Jun 26 01:16:50 UTC 2021
NDF-RT N0000175370
Created by admin on Sat Jun 26 01:16:50 UTC 2021 , Edited by admin on Sat Jun 26 01:16:50 UTC 2021
Code System Code Type Description
MESH
D011413
Created by admin on Sat Jun 26 01:16:50 UTC 2021 , Edited by admin on Sat Jun 26 01:16:50 UTC 2021
PRIMARY
WIKIPEDIA
Propantheline
Created by admin on Sat Jun 26 01:16:50 UTC 2021 , Edited by admin on Sat Jun 26 01:16:50 UTC 2021
PRIMARY
FDA UNII
1306V2B0Q8
Created by admin on Sat Jun 26 01:16:50 UTC 2021 , Edited by admin on Sat Jun 26 01:16:50 UTC 2021
PRIMARY
HSDB
3174
Created by admin on Sat Jun 26 01:16:50 UTC 2021 , Edited by admin on Sat Jun 26 01:16:50 UTC 2021
PRIMARY
PUBCHEM
4934
Created by admin on Sat Jun 26 01:16:50 UTC 2021 , Edited by admin on Sat Jun 26 01:16:50 UTC 2021
PRIMARY
CAS
298-50-0
Created by admin on Sat Jun 26 01:16:50 UTC 2021 , Edited by admin on Sat Jun 26 01:16:50 UTC 2021
PRIMARY
DRUG BANK
DB00782
Created by admin on Sat Jun 26 01:16:50 UTC 2021 , Edited by admin on Sat Jun 26 01:16:50 UTC 2021
PRIMARY
EPA CompTox
298-50-0
Created by admin on Sat Jun 26 01:16:50 UTC 2021 , Edited by admin on Sat Jun 26 01:16:50 UTC 2021
PRIMARY
LACTMED
Propantheline
Created by admin on Sat Jun 26 01:16:50 UTC 2021 , Edited by admin on Sat Jun 26 01:16:50 UTC 2021
PRIMARY
DRUG CENTRAL
2293
Created by admin on Sat Jun 26 01:16:50 UTC 2021 , Edited by admin on Sat Jun 26 01:16:50 UTC 2021
PRIMARY
RXCUI
8761
Created by admin on Sat Jun 26 01:16:50 UTC 2021 , Edited by admin on Sat Jun 26 01:16:50 UTC 2021
PRIMARY RxNorm
IUPHAR
329
Created by admin on Sat Jun 26 01:16:50 UTC 2021 , Edited by admin on Sat Jun 26 01:16:50 UTC 2021
PRIMARY
EVMPD
SUB04081MIG
Created by admin on Sat Jun 26 01:16:50 UTC 2021 , Edited by admin on Sat Jun 26 01:16:50 UTC 2021
PRIMARY
NCI_THESAURUS
C78077
Created by admin on Sat Jun 26 01:16:50 UTC 2021 , Edited by admin on Sat Jun 26 01:16:50 UTC 2021
PRIMARY
ECHA (EC/EINECS)
206-063-2
Created by admin on Sat Jun 26 01:16:50 UTC 2021 , Edited by admin on Sat Jun 26 01:16:50 UTC 2021
PRIMARY