Details
Stereochemistry | ACHIRAL |
Molecular Formula | C23H30NO3 |
Molecular Weight | 368.4892 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 1 |
SHOW SMILES / InChI
SMILES
CC(C)[N+](C)(CCOC(=O)C1C2=C(OC3=C1C=CC=C3)C=CC=C2)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
DescriptionSources: https://www.drugs.com/pro/propantheline.htmlCurator'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
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.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL211 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12049493 |
9.48 null [pKi] | ||
Target ID: CHEMBL216 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12049493 |
9.66 null [pKi] | ||
Target ID: CHEMBL245 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12049493 |
10.04 null [pKi] | ||
Target ID: CHEMBL1821 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12049493 |
10.24 null [pKi] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | PRO-BANTHINE Approved UsePropantheline bromide is effective as adjunctive therapy in the treatment of peptic ulcer. Launch Date-5.2859519E11 |
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Primary | PRO-BANTHINE Approved UsePropantheline bromide is effective as adjunctive therapy in the treatment of peptic ulcer. Launch Date-5.2859519E11 |
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Primary | PRO-BANTHINE Approved UsePropantheline bromide is effective as adjunctive therapy in the treatment of peptic ulcer. Launch Date-5.2859519E11 |
Cmax
Value | Dose | Co-administered | 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 | Co-administered | 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 |
T1/2
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 |
PubMed
Title | Date | PubMed |
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Receptor binding studies of soft anticholinergic agents. | 2001 |
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Sick sinus syndrome in nine West Highland white terriers. | 2001 Feb 3 |
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Effects of YM905, a novel muscarinic M3-receptor antagonist, on experimental models of bowel dysfunction in vivo. | 2001 Jul |
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Stoichiometric and microenvironmental effects on hydrolysis of propantheline and oxyphenonium bromides in cyclodextrin solutions. | 2001 Jun |
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[Protein-losing syndrome of the gastrointestinal tract]. | 2001 Oct 26 |
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A stability-indicating proton nuclear magnetic resonance spectroscopic method for the analysis of propantheline bromide in pharmaceutical samples. | 2001 Sep |
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Anticholinergic drugs versus placebo for overactive bladder syndrome in adults. | 2002 |
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Taurine in submandibular gland of the rat: effect of muscarinic drugs. | 2002 Apr |
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Influence of prokinetics on the gastrointestinal transit and residence times of activated charcoal. | 2002 Aug |
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An improved method of evaluation of drug-evoked changes in gastric emptying in mice. | 2002 Mar-Apr |
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Clinical pharmacokinetics of drugs used to treat urge incontinence. | 2003 |
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Interventions for preventing oral mucositis for patients with cancer receiving treatment. | 2003 |
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Variable effects of previously untested muscarinic receptor antagonists on experimental myopia. | 2003 Mar |
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Interleukin-1 (IL-1) system gene expression in granulosa cells: kinetics during terminal preovulatory follicle maturation in the mare. | 2003 May 16 |
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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 |
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Propantheline and in vitro reactivity of urinary bladder smooth muscle in guinea pigs. | 2005 |
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Clinical observations of the effect of antidiuretic hormone on nocturia in elderly men. | 2005 Dec |
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Ocular complications of neurological therapy. | 2005 Jul |
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In vivo effect of interleukin-1beta and interleukin-1RA on oocyte cytoplasmic maturation, ovulation, and early embryonic development in the mare. | 2005 Jun 22 |
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Evaluation of antimotility effect of Lantana camara L. var. acuelata constituents on neostigmine induced gastrointestinal transit in mice. | 2005 Sep 17 |
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Interventions for preventing oral mucositis for patients with cancer receiving treatment. | 2006 Apr 19 |
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Masking mechanisms of bitter taste of drugs studied with ion selective electrodes. | 2006 Aug |
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Anticholinergic drugs versus placebo for overactive bladder syndrome in adults. | 2006 Oct 18 |
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Application of the convection-dispersion equation to modelling oral drug absorption. | 2007 Jan |
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Clomipramine-induced mood and perceived performance changes in selected healthy individuals. | 2007 Jun |
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The effectiveness of intravesical oxybutynin, propantheline, and capsaicin in the management of neuropathic bladder following spinal cord injury. | 2007 Oct 22 |
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Choice of antimuscarinic agents for overactive bladder in the older patient: focus on darifenacin. | 2008 |
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Methyl 9H-xanthene-9-carboxyl-ate. | 2008 Apr 16 |
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Patient perspectives in the management of overactive bladder, focus on transdermal oxybutynin. | 2008 Feb 2 |
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Pharmacological interventions for clozapine-induced hypersalivation. | 2008 Jul |
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Pharmacological interventions for clozapine-induced hypersalivation. | 2008 Jul 16 |
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Using the zebrafish lateral line to screen for ototoxicity. | 2008 Jun |
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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 |
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Locked-in Syndrome in a Nigerian male with Multiple Sclerosis: a case report and literature review. | 2008 Oct 30 |
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Response to "Suspected differential interactions of digoxin with imidafenacin and propantheline; some thoughts for introspection". | 2009 |
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Anticholinergics for urinary symptoms in multiple sclerosis. | 2009 Jan 21 |
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A meta-analysis of the placebo response in antimuscarinic drug trials for overactive bladder. | 2009 Jul 22 |
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Oxybutynin extended release for the management of overactive bladder: a clinical review. | 2009 Sep 21 |
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Comparison of risk of neurovascular and cardiovascular side effects between tiotropium and other anticholinergic agents. | 2010 |
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Inappropriate prescribing in the hospitalized elderly patient: defining the problem, evaluation tools, and possible solutions. | 2010 Apr 7 |
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Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method. | 2010 Dec |
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Simultaneous spectrophotometric estimation of haloperidol and trihexyphenidyl in tablets. | 2010 Mar |
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New approaches in the management of multiple sclerosis. | 2010 Nov 24 |
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New insights into molecular targets for urinary incontinence. | 2010 Oct |
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Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2. | 2011 Jul 14 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/pro/propantheline.html
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12049493
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
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A03AB05
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NCI_THESAURUS |
C29704
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QA03AB05
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A03CA34
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NBK548063
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N0000175574
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N0000175370
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Propantheline
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100000085090
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298-50-0
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DB00782
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)