Identification

Name
Propantheline
Accession Number
DB00782  (APRD00177)
Type
Small Molecule
Groups
Approved
Description

A muscarinic antagonist used as an antispasmodic, in rhinitis, in urinary incontinence, and in the treatment of ulcers. At high doses it has nicotinic effects resulting in neuromuscular blocking.

Structure
Thumb
Synonyms
  • Propantheline
External IDs
SC 3171
Product Ingredients
IngredientUNIICASInChI Key
Propantheline bromideUX9Z118X9F50-34-0XLBIBBZXLMYSFF-UHFFFAOYSA-M
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Pro-BanthineTablet7.5 mg/1OralShire1953-04-022012-01-10Us
Pro-BanthineTablet15 mg/1OralShire1953-04-022012-01-10Us
Pro-banthine Tablets 15mgTabletOralWell Spring Pharmaceutical Corporation1994-12-312009-02-23Canada
Pro-banthine Tablets 7.5 mgTabletOralWell Spring Pharmaceutical Corporation1994-12-312009-02-23Canada
Propanthel Tab 15mgTabletOralIcn Pharmaceuticals1974-12-312005-04-26Canada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Propantheline BromideTablet, film coated15 mg/1OralWest-Ward Pharmaceuticals Corp.1981-12-14Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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International/Other Brands
Ercoril (Medic) / Methaphyllin (Sannova) / Pro Banthine (Pfizer) / Prokind (Beacon) / Propanline (Chin Teng) / Propantheline (Shou Chan) / Spastheline (Sun)
Categories
UNII
1306V2B0Q8
CAS number
298-50-0
Weight
Average: 368.4892
Monoisotopic: 368.222568831
Chemical Formula
C23H30NO3
InChI Key
VVWYOYDLCMFIEM-UHFFFAOYSA-N
InChI
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
IUPAC Name
methylbis(propan-2-yl)[2-(9H-xanthene-9-carbonyloxy)ethyl]azanium
SMILES
CC(C)[N+](C)(CCOC(=O)C1C2=CC=CC=C2OC2=CC=CC=C12)C(C)C

Pharmacology

Indication

For the treatment of enuresis. It has also been used for hyperhidrosis, and cramps or spasms of the stomach, intestines or bladder.

Associated Conditions
Pharmacodynamics

Propantheline is an anticholinergic drug, a medication that reduces the effect of acetylcholine, a chemical released from nerves that stimulates muscles, by blocking the receptors for acetylcholine on smooth muscle (a type of muscle). It also has a direct relaxing effect on smooth muscle. Propantheline is used to treat or prevent spasm in the muscles of the gastrointestinal tract in the irritable bowel syndrome. In addition, Propantheline inhibits gastrointestinal propulsive motility and decreases gastric acid secretion and controls excessive pharyngeal, tracheal and bronchial secretions.

Mechanism of action

Action is achieved via a dual mechanism: (1) a specific anticholinergic effect (antimuscarinic) at the acetylcholine-receptor sites and (2) a direct effect upon smooth muscle (musculotropic).

TargetActionsOrganism
AMuscarinic acetylcholine receptor M1
antagonist
Humans
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination

Approximately 70% of the dose is excreted in the urine, mostly as metabolites.

Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1,10-PhenanthrolineThe therapeutic efficacy of Propantheline can be decreased when used in combination with 1,10-Phenanthroline.
2,5-Dimethoxy-4-ethylamphetamineThe risk or severity of Tachycardia can be increased when Propantheline is combined with 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamine2,5-Dimethoxy-4-ethylthioamphetamine may increase the central nervous system depressant (CNS depressant) activities of Propantheline.
4-Bromo-2,5-dimethoxyamphetamine4-Bromo-2,5-dimethoxyamphetamine may increase the central nervous system depressant (CNS depressant) activities of Propantheline.
4-Methoxyamphetamine4-Methoxyamphetamine may increase the central nervous system depressant (CNS depressant) activities of Propantheline.
5-methoxy-N,N-dimethyltryptamine5-methoxy-N,N-dimethyltryptamine may increase the central nervous system depressant (CNS depressant) activities of Propantheline.
7-Nitroindazole7-Nitroindazole may increase the central nervous system depressant (CNS depressant) activities of Propantheline.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline may increase the central nervous system depressant (CNS depressant) activities of Propantheline.
AbacavirPropantheline may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbediterolThe risk or severity of Tachycardia can be increased when Propantheline is combined with Abediterol.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
  • Take before a meal. Take before a meal. Propantheline bromide should be taken 15 to 30 minutes before meals.

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0014920
KEGG Compound
C07506
PubChem Compound
4934
PubChem Substance
46507187
ChemSpider
4765
RxNav
8761
ChEBI
8481
ChEMBL
CHEMBL1180725
ZINC
ZINC000001530761
Therapeutic Targets Database
DAP001123
PharmGKB
PA164746224
Guide to Pharmacology
GtP Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Propantheline
ATC Codes
A03AB05 — PropanthelineA03CA34 — Propantheline and psycholeptics
MSDS
Download (73.8 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1Unknown StatusTreatmentOveractive Bladder Associated With HTLV-11
4Unknown StatusTreatmentUrinary Tract Stones1

Pharmacoeconomics

Manufacturers
  • Gd searle llc
  • Shire development inc
  • Ascot hosp pharmaceuticals inc div travenol laboratories inc
  • Heather drug co inc
  • Impax laboratories inc
  • Mylan pharmaceuticals inc
  • Par pharmaceutical inc
  • Private formulations inc
  • Roxane laboratories inc
  • Sandoz inc
  • Tablicaps inc
  • Watson laboratories inc
Packagers
  • Dispensing Solutions
  • Gallipot
  • Kaiser Foundation Hospital
  • Major Pharmaceuticals
  • Roxane Labs
  • Shire Inc.
  • Southwood Pharmaceuticals
Dosage forms
FormRouteStrength
TabletOral15 mg/1
TabletOral7.5 mg/1
TabletOral
Tablet, film coatedOral15 mg/1
Prices
Unit descriptionCostUnit
Propantheline bromide powder7.77USD g
Propantheline Bromide 15 mg tablet0.76USD tablet
Propantheline 15 mg tablet0.6USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility7.22e-05 mg/mLALOGPS
logP2.66ALOGPS
logP0.36ChemAxon
logS-6.8ALOGPS
pKa (Strongest Acidic)18.1ChemAxon
pKa (Strongest Basic)-7.2ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area35.53 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity119.25 m3·mol-1ChemAxon
Polarizability40.87 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.9327
Blood Brain Barrier+0.9012
Caco-2 permeable+0.6808
P-glycoprotein substrateSubstrate0.7706
P-glycoprotein inhibitor INon-inhibitor0.8742
P-glycoprotein inhibitor IINon-inhibitor0.6149
Renal organic cation transporterInhibitor0.5354
CYP450 2C9 substrateNon-substrate0.7749
CYP450 2D6 substrateNon-substrate0.6028
CYP450 3A4 substrateSubstrate0.7332
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorInhibitor0.8931
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.867
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7234
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.8167
BiodegradationNot ready biodegradable0.6006
Rat acute toxicity2.7150 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9055
hERG inhibition (predictor II)Non-inhibitor0.5772
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as xanthenes. These are polycyclic aromatic compounds containing a xanthene moiety, which consists of two benzene rings joined to each other by a pyran ring.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzopyrans
Sub Class
1-benzopyrans
Direct Parent
Xanthenes
Alternative Parents
Diarylethers / Benzenoids / Tetraalkylammonium salts / Carboxylic acid esters / Oxacyclic compounds / Monocarboxylic acids and derivatives / Organopnictogen compounds / Organic salts / Organic oxides / Hydrocarbon derivatives
show 3 more
Substituents
Xanthene / Diaryl ether / Benzenoid / Quaternary ammonium salt / Tetraalkylammonium salt / Carboxylic acid ester / Carboxylic acid derivative / Ether / Monocarboxylic acid or derivatives / Oxacycle
show 12 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
xanthenes (CHEBI:8481)

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Phosphatidylinositol phospholipase c activity
Specific Function
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
Gene Name
CHRM1
Uniprot ID
P11229
Uniprot Name
Muscarinic acetylcholine receptor M1
Molecular Weight
51420.375 Da
References
  1. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  2. Lukacs VA, Korting HC: [Antiperspirants and deodorants--ingredients and evaluation]. Derm Beruf Umwelt. 1989 Mar-Apr;37(2):53-7. [PubMed:2656175]
  3. Saitoh H, Hasegawa N, Kawai S, Miyazaki K, Arita T: Interaction of tertiary amines and quaternary ammonium compounds with gastrointestinal mucin. J Pharmacobiodyn. 1986 Dec;9(12):1008-14. [PubMed:3572714]
  4. Trkulja V, Crljen-Manestar V, Banfic H, Lackovic Z: Involvement of the peripheral cholinergic muscarinic system in the compensatory ovarian hypertrophy in the rat. Exp Biol Med (Maywood). 2004 Sep;229(8):793-805. [PubMed:15337834]
  5. Mokry J, Nosalova G, Jakubesova M: Propantheline and in vitro reactivity of urinary bladder smooth muscle in guinea pigs. Bratisl Lek Listy. 2005;106(4-5):151-4. [PubMed:16080359]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]

Drug created on June 13, 2005 07:24 / Updated on June 02, 2020 01:05

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