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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
MOL RATIO 1 MOL RATIO (average)
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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

Targets

Primary TargetPharmacologyConditionPotency
9.48 null [pKi]
9.66 null [pKi]
10.04 null [pKi]
10.24 null [pKi]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PRO-BANTHINE
Primary
PRO-BANTHINE
Primary
PRO-BANTHINE

Cmax

ValueDoseCo-administeredAnalytePopulation
51.5 ng/mL
45 mg single, oral
PROPANTHELINE BROMIDE plasma
Homo sapiens
53.1 ng/mL
60 mg single, oral
PROPANTHELINE BROMIDE plasma
Homo sapiens
20.6 ng/mL
30 mg single, oral
PROPANTHELINE BROMIDE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
186.9 ng × h/mL
45 mg single, oral
PROPANTHELINE BROMIDE plasma
Homo sapiens
159 ng × h/mL
60 mg single, oral
PROPANTHELINE BROMIDE plasma
Homo sapiens
62.2 ng × h/mL
30 mg single, oral
PROPANTHELINE BROMIDE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
1.56 h
60 mg single, oral
PROPANTHELINE BROMIDE plasma
Homo sapiens
1.57 h
30 mg single, oral
PROPANTHELINE BROMIDE plasma
Homo sapiens

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victim

PubMed

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
Record UNII
UX9Z118X9F
Record Status Validated (UNII)
Record Version