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. [PubChem]

Structure
Thumb
Synonyms
  • Propantelina bromuro
  • Propantelina, bromuro de
  • Propanthelin bromid
  • Propantheline
  • Propanthéline, bromure de
  • Propanthelini Bromidum
External IDs
SC 3171 / UNII-UX9Z118X9F
Product Ingredients
IngredientUNIICASInChI Key
Propantheline BromideUX9Z118X9F50-34-0XLBIBBZXLMYSFF-UHFFFAOYSA-M
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Pro-BanthineTablet15 mg/1OralShire1953-04-022012-01-10Us
Pro-BanthineTablet7.5 mg/1OralShire1953-04-022012-01-10Us
Pro-banthine Tablets 15mgTablet15 mgOralWell Spring Pharmaceutical Corporation1994-12-312009-02-23Canada
Pro-banthine Tablets 7.5 mgTablet7.5 mgOralWell Spring Pharmaceutical Corporation1994-12-312009-02-23Canada
Propanthel Tab 15mgTablet15 mgOralIcn Pharmaceuticals1974-12-312005-04-26Canada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Propantheline BromideTablet, film coated15 mg/1OralWest-Ward Pharmaceuticals Corp.1981-12-14Not applicableUs
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
Human
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
DrugInteraction
1,10-PhenanthrolineThe therapeutic efficacy of Propantheline can be decreased when used in combination with 1,10-Phenanthroline.
AcetaminophenAcetaminophen may decrease the excretion rate of Propantheline which could result in a higher serum level.
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Propantheline which could result in a higher serum level.
AclidiniumPropantheline may increase the anticholinergic activities of Aclidinium.
AgmatineThe risk or severity of adverse effects can be increased when Propantheline is combined with Agmatine.
AlcuroniumThe risk or severity of adverse effects can be increased when Propantheline is combined with Alcuronium.
AlfentanilThe risk or severity of adverse effects can be increased when Propantheline is combined with Alfentanil.
AlphacetylmethadolThe risk or severity of adverse effects can be increased when Propantheline is combined with Alphacetylmethadol.
AlphaprodineThe risk or severity of adverse effects can be increased when Propantheline is combined with Alphaprodine.
AlprazolamAlprazolam may decrease the excretion rate of Propantheline which could result in a higher serum level.
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0014920
KEGG Compound
C07506
PubChem Compound
4934
PubChem Substance
46507187
ChemSpider
4765
ChEBI
8481
ChEMBL
CHEMBL1180725
Therapeutic Targets Database
DAP001123
PharmGKB
PA164746224
IUPHAR
329
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

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
TabletOral15 mg
TabletOral7.5 mg
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
Human
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 August 02, 2018 07:39