PROPANTHELINE BROMIDE

US Previously Marketed

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 Search

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
Sources: https://www.drugs.com/pro/propantheline.html
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

Approval Year

Targets

Primary Target	Pharmacology	Potency
Muscarinic acetylcholine receptor M2 121 Target ID: CHEMBL211 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12049493	Antagonist 2778	9.48 null [pKi]
Muscarinic acetylcholine receptor M1 169 Target ID: CHEMBL216 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12049493	Antagonist 2778	9.66 null [pKi]
Muscarinic acetylcholine receptor M3 159 Target ID: CHEMBL245 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12049493	Antagonist 2778	10.04 null [pKi]
Muscarinic acetylcholine receptor M4 86 Target ID: CHEMBL1821 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12049493	Antagonist 2778	10.24 null [pKi]

Conditions

Condition	Modality	Highest Phase	Product
Peptic ulcer 72 Sources: https://www.drugs.com/pro/propantheline.html	Primary	Approved 8429	PRO-BANTHINE Approved Use Propantheline bromide is effective as adjunctive therapy in the treatment of peptic ulcer. Launch Date 1953
Overactive bladder 38 Sources: https://clinicaltrials.gov/ct2/show/NCT01640002	Primary	Approved 8429	PRO-BANTHINE Approved Use Propantheline bromide is effective as adjunctive therapy in the treatment of peptic ulcer. Launch Date 1953
Urinary calculus 3 Sources: https://clinicaltrials.gov/ct2/show/NCT01010048	Primary	Phase IV 63	PRO-BANTHINE Approved Use Propantheline bromide is effective as adjunctive therapy in the treatment of peptic ulcer. Launch Date 1953

C_max

Value	Dose	Analyte	Population
51.5 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6689152	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7389749	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7389749	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

Value	Dose	Analyte	Population
186.9 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6689152	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7389749	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7389749	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.56 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7389749	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7389749	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

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	P-gp 1537

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 1537	substrate 3367 Sources: https://link.springer.com/article/10.1023/A:1016217505990	yes

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY547023	https://www.001chemical.com/chem/298-50-0
AK Scientific, Inc. (AKSCI)	X6652	http://www.aksci.com/item_detail.php?cat=X6652
BOC Sciences	298-50-0	https://www.bocsci.com/propantheline-cas-298-50-0-item-65424.html
Debye Scientific	DB-047660	http://www.debyesci.com/cas_298-50-0.html
Finetech	FT-0603371	http://www.finetechnology-ind.com/prod/detail/pub/298-50-0.html
Hairui	HR104087	http://www.hairuichem.com/en/product/298-50-0.html
Molcore	MC547023	https://www.molcore.com/product/298-50-0
Smolecule	S585496	https://www.smolecule.com/products/s585496
THE BioTek	bt-301960	https://www.thebiotek.com/product/others/bt-301960
iChemical	EBD53149	http://www.ichemical.com/chemicals/cas-298-50-0

PubMed

Title	Date	PubMed
Sick sinus syndrome in nine West Highland white terriers.	2001 Feb 3	11271916
Stoichiometric and microenvironmental effects on hydrolysis of propantheline and oxyphenonium bromides in cyclodextrin solutions.	2001 Jun	11357177
Clinical pharmacokinetics of drugs used to treat urge incontinence.	2003	14606931
Variable effects of previously untested muscarinic receptor antagonists on experimental myopia.	2003 Mar	12601066
Interventions for preventing oral mucositis for patients with cancer receiving treatment.	2006 Apr 19	16625538
Prophylaxis of mucosal toxicity by oral propantheline and cryotherapy in children with malignancies undergoing myeloablative chemo-radiotherapy.	2006 Dec	17146197
Anticholinergic drugs versus placebo for overactive bladder syndrome in adults.	2006 Oct 18	17054185
Clomipramine-induced mood and perceived performance changes in selected healthy individuals.	2007 Jun	17502789
Choice of antimuscarinic agents for overactive bladder in the older patient: focus on darifenacin.	2008	18982920
Persistence, adherence, and switch rates among extended-release and immediate-release overactive bladder medications in a regional managed care plan.	2008 Apr	18439051
Using the zebrafish lateral line to screen for ototoxicity.	2008 Jun	18408970
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	19585373
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.	2010 Dec	21818443
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.	2011 Jul 14	21599003

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

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:13:24 GMT 2023` Edited by `admin` on `Fri Dec 15 15:13:24 GMT 2023`
Record UNII	UX9Z118X9F
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PROPANTHELINE BROMIDE

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