Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C23H30NO3.Br |
| Molecular Weight | 448.393 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[Br-].CC(C)[N+](C)(CCOC(=O)C1C2=CC=CC=C2OC3=CC=CC=C13)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
| Molecular Formula | C23H30NO3 |
| Molecular Weight | 368.4892 |
| Charge | 1 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| 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 |
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 Date1953 |
|||
| Primary | PRO-BANTHINE Approved UsePropantheline bromide is effective as adjunctive therapy in the treatment of peptic ulcer. Launch Date1953 |
|||
| Primary | PRO-BANTHINE Approved UsePropantheline bromide is effective as adjunctive therapy in the treatment of peptic ulcer. Launch Date1953 |
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 |
|
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 |
|
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 |
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 |
|
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 |
|
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 |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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 |
|
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 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2. | 2011-07-14 |
|
| Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method. | 2010-12 |
|
| New approaches in the management of multiple sclerosis. | 2010-11-24 |
|
| New insights into molecular targets for urinary incontinence. | 2010-10 |
|
| Inappropriate prescribing in the hospitalized elderly patient: defining the problem, evaluation tools, and possible solutions. | 2010-04-07 |
|
| Simultaneous spectrophotometric estimation of haloperidol and trihexyphenidyl in tablets. | 2010-03 |
|
| Comparison of risk of neurovascular and cardiovascular side effects between tiotropium and other anticholinergic agents. | 2010 |
|
| Oxybutynin extended release for the management of overactive bladder: a clinical review. | 2009-09-21 |
|
| A meta-analysis of the placebo response in antimuscarinic drug trials for overactive bladder. | 2009-07-22 |
|
| Anticholinergics for urinary symptoms in multiple sclerosis. | 2009-01-21 |
|
| 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 |
|
| Pharmacokinetics of meloxicam administered as regular and fast dissolving formulations to the rat: influence of gastrointestinal dysfunction on the relative bioavailability of two formulations. | 2008-11 |
|
| Locked-in Syndrome in a Nigerian male with Multiple Sclerosis: a case report and literature review. | 2008-10-30 |
|
| Pharmacological interventions for clozapine-induced hypersalivation. | 2008-07-16 |
|
| Pharmacological interventions for clozapine-induced hypersalivation. | 2008-07 |
|
| Using the zebrafish lateral line to screen for ototoxicity. | 2008-06 |
|
| Methyl 9H-xanthene-9-carboxyl-ate. | 2008-04-16 |
|
| Persistence, adherence, and switch rates among extended-release and immediate-release overactive bladder medications in a regional managed care plan. | 2008-04 |
|
| Cycloheximide and disulfoton are positive in the photoclastogencity assay but do not absorb UV irradiation: another example of pseudophotoclastogenicity? | 2008-03 |
|
| Patient perspectives in the management of overactive bladder, focus on transdermal oxybutynin. | 2008-02-02 |
|
| 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 |
|
| The effectiveness of intravesical oxybutynin, propantheline, and capsaicin in the management of neuropathic bladder following spinal cord injury. | 2007-10-22 |
|
| Interventions for preventing oral mucositis for patients with cancer receiving treatment. | 2007-10-17 |
|
| Clomipramine-induced mood and perceived performance changes in selected healthy individuals. | 2007-06 |
|
| Application of the convection-dispersion equation to modelling oral drug absorption. | 2007-01 |
|
| Prophylaxis of mucosal toxicity by oral propantheline and cryotherapy in children with malignancies undergoing myeloablative chemo-radiotherapy. | 2006-12 |
|
| Anticholinergic drugs versus placebo for overactive bladder syndrome in adults. | 2006-10-18 |
|
| Masking mechanisms of bitter taste of drugs studied with ion selective electrodes. | 2006-08 |
|
| Interventions for preventing oral mucositis for patients with cancer receiving treatment. | 2006-04-19 |
|
| Clinical observations of the effect of antidiuretic hormone on nocturia in elderly men. | 2005-12 |
|
| Evaluation of antimotility effect of Lantana camara L. var. acuelata constituents on neostigmine induced gastrointestinal transit in mice. | 2005-09-17 |
|
| Ocular complications of neurological therapy. | 2005-07 |
|
| In vivo effect of interleukin-1beta and interleukin-1RA on oocyte cytoplasmic maturation, ovulation, and early embryonic development in the mare. | 2005-06-22 |
|
| Trospium chloride: an update on a quaternary anticholinergic for treatment of urge urinary incontinence. | 2005-06 |
|
| Propantheline and in vitro reactivity of urinary bladder smooth muscle in guinea pigs. | 2005 |
|
| 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. | 2004-06-22 |
|
| Interleukin-1 (IL-1) system gene expression in granulosa cells: kinetics during terminal preovulatory follicle maturation in the mare. | 2003-05-16 |
|
| Variable effects of previously untested muscarinic receptor antagonists on experimental myopia. | 2003-03 |
|
| Clinical pharmacokinetics of drugs used to treat urge incontinence. | 2003 |
|
| Interventions for preventing oral mucositis for patients with cancer receiving treatment. | 2003 |
|
| An improved method of evaluation of drug-evoked changes in gastric emptying in mice. | 2002-12-03 |
|
| Influence of prokinetics on the gastrointestinal transit and residence times of activated charcoal. | 2002-08 |
|
| Taurine in submandibular gland of the rat: effect of muscarinic drugs. | 2002-04 |
|
| Anticholinergic drugs versus placebo for overactive bladder syndrome in adults. | 2002 |
|
| [Protein-losing syndrome of the gastrointestinal tract]. | 2001-10-26 |
|
| A stability-indicating proton nuclear magnetic resonance spectroscopic method for the analysis of propantheline bromide in pharmaceutical samples. | 2001-09 |
|
| Receptor binding studies of soft anticholinergic agents. | 2001 |
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
| Substance Class |
Chemical
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UX9Z118X9F
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Validated (UNII)
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C29704
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m9189
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8762
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CHEMBL1180725
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PROPANTHELINE BROMIDE
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50-34-0
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PARENT -> SALT/SOLVATE |
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