U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C23H30NO3.Br
Molecular Weight 448.393
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PROPANTHELINE BROMIDE

SMILES

[Br-].CC(C)[N+](C)(CCOC(=O)C1C2=C(OC3=C1C=CC=C3)C=CC=C2)C(C)C

InChI

InChIKey=XLBIBBZXLMYSFF-UHFFFAOYSA-M
InChI=1S/C23H30NO3.BrH/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;1H/q+1;/p-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

1953
Primary
PRO-BANTHINE

Approved Use

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

Launch Date

1953
Primary
PRO-BANTHINE

Approved Use

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

Launch Date

1953
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
Sick sinus syndrome in nine West Highland white terriers.
2001 Feb 3
[Protein-losing syndrome of the gastrointestinal tract].
2001 Oct 26
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
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
Propantheline and in vitro reactivity of urinary bladder smooth muscle in guinea pigs.
2005
Trospium chloride: an update on a quaternary anticholinergic for treatment of urge urinary incontinence.
2005 Jun
Masking mechanisms of bitter taste of drugs studied with ion selective electrodes.
2006 Aug
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
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
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.
2010 Dec
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 BROMIDE
EP   INN   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
INN  
Official Name English
PROPANTHELINE BROMIDE [MART.]
Common Name English
PROPANTHELINE BROMIDE [USP IMPURITY]
Common Name English
PROPANTHELINE BROMIDE [USP-RS]
Common Name English
PROPANTHELINE BROMIDE [USP MONOGRAPH]
Common Name English
NSC-757294
Code English
PROPANTHELINE BROMIDE [MI]
Common Name English
N-ISOPROPYL-N-METHYL-N-(2-((9H-XANTHEN-9-YLCARBONYL)OXY)ETHYL)PROPAN-2-AMINIUM BROMIDE
Systematic Name English
propantheline bromide [INN]
Common Name English
2-PROPANAMINIUM, N-METHYL-N-(1-METHYLETHYL)-N-(2-((9H-XANTHEN-9-YLCARBONYL)OXY)ETHYL)-, BROMIDE
Systematic Name English
PROPANTHELINE BROMIDE [EP IMPURITY]
Common Name English
PRO-BANTHINE
Brand Name English
PROPANTHELINE BROMIDE [ORANGE BOOK]
Common Name English
PROPANTHELINE BROMIDE [JAN]
Common Name English
Propantheline bromide [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29704
Created by admin on Fri Dec 15 15:13:24 GMT 2023 , Edited by admin on Fri Dec 15 15:13:24 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C29383
Created by admin on Fri Dec 15 15:13:24 GMT 2023 , Edited by admin on Fri Dec 15 15:13:24 GMT 2023
PRIMARY
SMS_ID
100000081151
Created by admin on Fri Dec 15 15:13:24 GMT 2023 , Edited by admin on Fri Dec 15 15:13:24 GMT 2023
PRIMARY
EVMPD
SUB10098MIG
Created by admin on Fri Dec 15 15:13:24 GMT 2023 , Edited by admin on Fri Dec 15 15:13:24 GMT 2023
PRIMARY
FDA UNII
UX9Z118X9F
Created by admin on Fri Dec 15 15:13:24 GMT 2023 , Edited by admin on Fri Dec 15 15:13:24 GMT 2023
PRIMARY
MERCK INDEX
m9189
Created by admin on Fri Dec 15 15:13:24 GMT 2023 , Edited by admin on Fri Dec 15 15:13:24 GMT 2023
PRIMARY Merck Index
DAILYMED
UX9Z118X9F
Created by admin on Fri Dec 15 15:13:24 GMT 2023 , Edited by admin on Fri Dec 15 15:13:24 GMT 2023
PRIMARY
INN
226
Created by admin on Fri Dec 15 15:13:24 GMT 2023 , Edited by admin on Fri Dec 15 15:13:24 GMT 2023
PRIMARY
RXCUI
8762
Created by admin on Fri Dec 15 15:13:24 GMT 2023 , Edited by admin on Fri Dec 15 15:13:24 GMT 2023
PRIMARY RxNorm
ChEMBL
CHEMBL1180725
Created by admin on Fri Dec 15 15:13:24 GMT 2023 , Edited by admin on Fri Dec 15 15:13:24 GMT 2023
PRIMARY
NSC
757294
Created by admin on Fri Dec 15 15:13:24 GMT 2023 , Edited by admin on Fri Dec 15 15:13:24 GMT 2023
PRIMARY
PUBCHEM
9279
Created by admin on Fri Dec 15 15:13:24 GMT 2023 , Edited by admin on Fri Dec 15 15:13:24 GMT 2023
PRIMARY
ECHA (EC/EINECS)
200-030-6
Created by admin on Fri Dec 15 15:13:24 GMT 2023 , Edited by admin on Fri Dec 15 15:13:24 GMT 2023
PRIMARY
DRUG BANK
DBSALT000225
Created by admin on Fri Dec 15 15:13:24 GMT 2023 , Edited by admin on Fri Dec 15 15:13:24 GMT 2023
PRIMARY
EPA CompTox
DTXSID2023519
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PRIMARY
RS_ITEM_NUM
1570508
Created by admin on Fri Dec 15 15:13:24 GMT 2023 , Edited by admin on Fri Dec 15 15:13:24 GMT 2023
PRIMARY
WIKIPEDIA
PROPANTHELINE BROMIDE
Created by admin on Fri Dec 15 15:13:24 GMT 2023 , Edited by admin on Fri Dec 15 15:13:24 GMT 2023
PRIMARY
CAS
50-34-0
Created by admin on Fri Dec 15 15:13:24 GMT 2023 , Edited by admin on Fri Dec 15 15:13:24 GMT 2023
PRIMARY