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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

Molecular Formula C23H30NO3
Molecular Weight 368.4892
Charge 1
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula BrH
Molecular Weight 80.912
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Sick sinus syndrome in nine West Highland white terriers.
2001 Feb 3
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
[Protein-losing syndrome of the gastrointestinal tract].
2001 Oct 26
A stability-indicating proton nuclear magnetic resonance spectroscopic method for the analysis of propantheline bromide in pharmaceutical samples.
2001 Sep
Anticholinergic drugs versus placebo for overactive bladder syndrome in adults.
2002
Taurine in submandibular gland of the rat: effect of muscarinic drugs.
2002 Apr
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
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
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
Locked-in Syndrome in a Nigerian male with Multiple Sclerosis: a case report and literature review.
2008 Oct 30
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
Anticholinergics for urinary symptoms in multiple sclerosis.
2009 Jan 21
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
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:13:24 UTC 2023
Edited
by admin
on Fri Dec 15 15:13:24 UTC 2023
Record UNII
UX9Z118X9F
Record Status Validated (UNII)
Record Version
  • Download
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 UTC 2023 , Edited by admin on Fri Dec 15 15:13:24 UTC 2023
Code System Code Type Description
NCI_THESAURUS
C29383
Created by admin on Fri Dec 15 15:13:24 UTC 2023 , Edited by admin on Fri Dec 15 15:13:24 UTC 2023
PRIMARY
SMS_ID
100000081151
Created by admin on Fri Dec 15 15:13:24 UTC 2023 , Edited by admin on Fri Dec 15 15:13:24 UTC 2023
PRIMARY
EVMPD
SUB10098MIG
Created by admin on Fri Dec 15 15:13:24 UTC 2023 , Edited by admin on Fri Dec 15 15:13:24 UTC 2023
PRIMARY
FDA UNII
UX9Z118X9F
Created by admin on Fri Dec 15 15:13:24 UTC 2023 , Edited by admin on Fri Dec 15 15:13:24 UTC 2023
PRIMARY
MERCK INDEX
m9189
Created by admin on Fri Dec 15 15:13:24 UTC 2023 , Edited by admin on Fri Dec 15 15:13:24 UTC 2023
PRIMARY Merck Index
DAILYMED
UX9Z118X9F
Created by admin on Fri Dec 15 15:13:24 UTC 2023 , Edited by admin on Fri Dec 15 15:13:24 UTC 2023
PRIMARY
INN
226
Created by admin on Fri Dec 15 15:13:24 UTC 2023 , Edited by admin on Fri Dec 15 15:13:24 UTC 2023
PRIMARY
RXCUI
8762
Created by admin on Fri Dec 15 15:13:24 UTC 2023 , Edited by admin on Fri Dec 15 15:13:24 UTC 2023
PRIMARY RxNorm
ChEMBL
CHEMBL1180725
Created by admin on Fri Dec 15 15:13:24 UTC 2023 , Edited by admin on Fri Dec 15 15:13:24 UTC 2023
PRIMARY
NSC
757294
Created by admin on Fri Dec 15 15:13:24 UTC 2023 , Edited by admin on Fri Dec 15 15:13:24 UTC 2023
PRIMARY
PUBCHEM
9279
Created by admin on Fri Dec 15 15:13:24 UTC 2023 , Edited by admin on Fri Dec 15 15:13:24 UTC 2023
PRIMARY
ECHA (EC/EINECS)
200-030-6
Created by admin on Fri Dec 15 15:13:24 UTC 2023 , Edited by admin on Fri Dec 15 15:13:24 UTC 2023
PRIMARY
DRUG BANK
DBSALT000225
Created by admin on Fri Dec 15 15:13:24 UTC 2023 , Edited by admin on Fri Dec 15 15:13:24 UTC 2023
PRIMARY
EPA CompTox
DTXSID2023519
Created by admin on Fri Dec 15 15:13:24 UTC 2023 , Edited by admin on Fri Dec 15 15:13:24 UTC 2023
PRIMARY
RS_ITEM_NUM
1570508
Created by admin on Fri Dec 15 15:13:24 UTC 2023 , Edited by admin on Fri Dec 15 15:13:24 UTC 2023
PRIMARY
WIKIPEDIA
PROPANTHELINE BROMIDE
Created by admin on Fri Dec 15 15:13:24 UTC 2023 , Edited by admin on Fri Dec 15 15:13:24 UTC 2023
PRIMARY
CAS
50-34-0
Created by admin on Fri Dec 15 15:13:24 UTC 2023 , Edited by admin on Fri Dec 15 15:13:24 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY