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Identification
NamePropantheline
Accession NumberDB00782  (APRD00177)
TypeSmall Molecule
GroupsApproved
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 Identifiers
  • SC 3171
  • UNII-UX9Z118X9F
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Pro-banthine Tablets 15mgtablet15 mgoralWellspring Pharmaceutical Canada Corp1994-12-312009-02-23Canada
Pro-banthine Tablets 7.5 mgtablet7.5 mgoralWellspring Pharmaceutical Canada Corp1994-12-312009-02-23Canada
Propanthel Tab 15mgtablet15 mgoralIcn Canada Ltd.1974-12-312005-04-26Canada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Propantheline Bromidetablet, film coated15 mg/1oralRoxane Laboratories, Inc.1981-12-14Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
ErcorilMedic
MethaphyllinSannova
Pro BanthinePfizer
ProkindBeacon
PropanlineChin Teng
PropanthelineShou Chan
SpasthelineSun
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Propantheline Bromide
Thumb
  • InChI Key: XLBIBBZXLMYSFF-UHFFFAOYSA-M
  • Monoisotopic Mass: 447.140906478
  • Average Mass: 448.393
DBSALT000225
Categories
UNII1306V2B0Q8
CAS number298-50-0
WeightAverage: 368.4892
Monoisotopic: 368.222568831
Chemical FormulaC23H30NO3
InChI KeyInChIKey=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
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzopyrans
Sub Class1-benzopyrans
Direct ParentXanthenes
Alternative Parents
Substituents
  • Xanthene
  • Diaryl ether
  • Acyl choline
  • Choline
  • Benzenoid
  • Quaternary ammonium salt
  • Carboxylic acid ester
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor the treatment of enuresis. It has also been used for hyperhidrosis, and cramps or spasms of the stomach, intestines or bladder.
PharmacodynamicsPropantheline 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 actionAction 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).
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationApproximately 70% of the dose is excreted in the urine, mostly as metabolites.
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
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
Dosage forms
FormRouteStrength
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.
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot 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
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesA03AB05A03CA34
AHFS Codes
  • 12:08.08
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (73.8 KB)
Interactions
Drug Interactions
Drug
AclidiniumAclidinium may increase the anticholinergic activities of Propantheline.
Botulinum Toxin Type APropantheline may increase the anticholinergic activities of Botulinum Toxin Type A.
Botulinum Toxin Type BPropantheline may increase the anticholinergic activities of Botulinum Toxin Type B.
CimetropiumPropantheline may increase the anticholinergic activities of Cimetropium Bromide.
DronabinolPropantheline may increase the tachycardic activities of Dronabinol.
EluxadolinePropantheline may increase the activities of Eluxadoline.
Glucagon recombinantThe risk or severity of adverse effects can be increased when Propantheline is combined with Glucagon recombinant.
Ipratropium bromideIpratropium bromide may increase the anticholinergic activities of Propantheline.
ItoprideThe therapeutic efficacy of Itopride can be decreased when used in combination with Propantheline.
MianserinMianserin may increase the anticholinergic activities of Propantheline.
MirabegronThe risk or severity of adverse effects can be increased when Propantheline is combined with Mirabegron.
MorphineThe risk or severity of adverse effects can be increased when Propantheline is combined with Morphine.
PhenelzinePhenelzine may increase the orthostatic hypotensive activities of Propantheline.
Potassium ChloridePropantheline may increase the ulcerogenic activities of Potassium Chloride.
PramlintidePramlintide may increase the anticholinergic activities of Propantheline.
ProcyclidineThe risk or severity of adverse effects can be increased when Procyclidine is combined with Propantheline.
RamosetronPropantheline may increase the activities of Ramosetron.
SecretinThe therapeutic efficacy of Secretin can be decreased when used in combination with Propantheline.
SulpirideThe therapeutic efficacy of Sulpiride can be decreased when used in combination with Propantheline.
TacrineThe therapeutic efficacy of Propantheline can be decreased when used in combination with Tacrine.
TiotropiumPropantheline may increase the anticholinergic activities of Tiotropium.
TopiramateThe risk or severity of adverse effects can be increased when Propantheline is combined with Topiramate.
TranylcypromineTranylcypromine may increase the orthostatic hypotensive activities of Propantheline.
TrichlormethiazideThe serum concentration of Trichlormethiazide can be increased when it is combined with Propantheline.
UmeclidiniumUmeclidinium may increase the anticholinergic activities of Propantheline.
Food InteractionsNot Available

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 action of G proteins. Primary transducing effect is Pi turnover.
Gene Name:
CHRM1
Uniprot ID:
P11229
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 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23