You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NamePropantheline
Accession NumberDB00782  (APRD00177)
TypeSmall Molecule
GroupsApproved
DescriptionA 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
1,10-PhenanthrolineThe therapeutic efficacy of Propantheline can be decreased when used in combination with 1,10-Phenanthroline.
AclidiniumAclidinium may increase the anticholinergic activities of Propantheline.
AclidiniumThe risk or severity of adverse effects can be increased when Propantheline is combined with Aclidinium.
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.
AmbenoniumThe therapeutic efficacy of Propantheline can be decreased when used in combination with Ambenonium.
Anisotropine MethylbromideThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Propantheline.
Atracurium besylateThe risk or severity of adverse effects can be increased when Atracurium besylate is combined with Propantheline.
AtropineThe risk or severity of adverse effects can be increased when Atropine is combined with Propantheline.
BenactyzineThe risk or severity of adverse effects can be increased when Propantheline is combined with Benactyzine.
BendroflumethiazideThe serum concentration of Bendroflumethiazide can be increased when it is combined with Propantheline.
BenzatropineThe risk or severity of adverse effects can be increased when Benzatropine is combined with Propantheline.
BezitramideThe risk or severity of adverse effects can be increased when Propantheline is combined with Bezitramide.
BiperidenThe risk or severity of adverse effects can be increased when Propantheline is combined with Biperiden.
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.
BuprenorphineThe risk or severity of adverse effects can be increased when Propantheline is combined with Buprenorphine.
ButorphanolThe risk or severity of adverse effects can be increased when Propantheline is combined with Butorphanol.
CarfentanilThe risk or severity of adverse effects can be increased when Propantheline is combined with Carfentanil.
ChlorothiazideThe serum concentration of Chlorothiazide can be increased when it is combined with Propantheline.
ChlorphenoxamineThe risk or severity of adverse effects can be increased when Propantheline is combined with Chlorphenoxamine.
ChlorthalidoneThe serum concentration of Chlorthalidone can be increased when it is combined with Propantheline.
CimetropiumPropantheline may increase the anticholinergic activities of Cimetropium.
CodeineThe risk or severity of adverse effects can be increased when Propantheline is combined with Codeine.
CoumaphosThe therapeutic efficacy of Propantheline can be decreased when used in combination with Coumaphos.
CyclopentolateThe risk or severity of adverse effects can be increased when Propantheline is combined with Cyclopentolate.
DarifenacinThe risk or severity of adverse effects can be increased when Darifenacin is combined with Propantheline.
DecamethoniumThe therapeutic efficacy of Propantheline can be decreased when used in combination with Decamethonium.
DemecariumThe therapeutic efficacy of Propantheline can be decreased when used in combination with Demecarium.
DesloratadineThe risk or severity of adverse effects can be increased when Propantheline is combined with Desloratadine.
DexetimideThe risk or severity of adverse effects can be increased when Propantheline is combined with Dexetimide.
DextromoramideThe risk or severity of adverse effects can be increased when Propantheline is combined with Dextromoramide.
DextropropoxypheneThe risk or severity of adverse effects can be increased when Propantheline is combined with Dextropropoxyphene.
DezocineThe risk or severity of adverse effects can be increased when Propantheline is combined with Dezocine.
DichlorvosThe therapeutic efficacy of Propantheline can be decreased when used in combination with Dichlorvos.
DicyclomineThe risk or severity of adverse effects can be increased when Propantheline is combined with Dicyclomine.
DihydrocodeineThe risk or severity of adverse effects can be increased when Propantheline is combined with Dihydrocodeine.
DihydroetorphineThe risk or severity of adverse effects can be increased when Propantheline is combined with Dihydroetorphine.
DihydromorphineThe risk or severity of adverse effects can be increased when Propantheline is combined with Dihydromorphine.
DiphenoxylateThe risk or severity of adverse effects can be increased when Propantheline is combined with Diphenoxylate.
DonepezilThe therapeutic efficacy of Propantheline can be decreased when used in combination with Donepezil.
DPDPEThe risk or severity of adverse effects can be increased when Propantheline is combined with DPDPE.
DronabinolPropantheline may increase the tachycardic activities of Dronabinol.
EchothiophateThe therapeutic efficacy of Propantheline can be decreased when used in combination with Echothiophate.
EdrophoniumThe therapeutic efficacy of Propantheline can be decreased when used in combination with Edrophonium.
EluxadolinePropantheline may increase the constipating activities of Eluxadoline.
EthopropazineThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Propantheline.
EthylmorphineThe risk or severity of adverse effects can be increased when Propantheline is combined with Ethylmorphine.
EtorphineThe risk or severity of adverse effects can be increased when Propantheline is combined with Etorphine.
FentanylThe risk or severity of adverse effects can be increased when Propantheline is combined with Fentanyl.
FenthionThe therapeutic efficacy of Propantheline can be decreased when used in combination with Fenthion.
FesoterodineThe risk or severity of adverse effects can be increased when Propantheline is combined with Fesoterodine.
GalantamineThe therapeutic efficacy of Propantheline can be decreased when used in combination with Galantamine.
Gallamine TriethiodideThe risk or severity of adverse effects can be increased when Gallamine Triethiodide is combined with Propantheline.
Ginkgo bilobaThe therapeutic efficacy of Propantheline can be decreased when used in combination with Ginkgo biloba.
Glucagon recombinantThe risk or severity of adverse effects can be increased when Propantheline is combined with Glucagon recombinant.
GlycopyrroniumThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Propantheline.
GlycopyrroniumPropantheline may increase the anticholinergic activities of Glycopyrronium.
HeroinThe risk or severity of adverse effects can be increased when Propantheline is combined with Heroin.
HexamethoniumThe risk or severity of adverse effects can be increased when Propantheline is combined with Hexamethonium.
HomatropineThe risk or severity of adverse effects can be increased when Propantheline is combined with Homatropine.
Huperzine AThe therapeutic efficacy of Propantheline can be decreased when used in combination with Huperzine A.
HydrochlorothiazideThe serum concentration of Hydrochlorothiazide can be increased when it is combined with Propantheline.
HydrocodoneThe risk or severity of adverse effects can be increased when Propantheline is combined with Hydrocodone.
HydroflumethiazideThe serum concentration of Hydroflumethiazide can be increased when it is combined with Propantheline.
HydromorphoneThe risk or severity of adverse effects can be increased when Propantheline is combined with Hydromorphone.
HyoscyamineThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Propantheline.
IndapamideThe serum concentration of Indapamide can be increased when it is combined with Propantheline.
Ipratropium bromideThe risk or severity of adverse effects can be increased when Ipratropium bromide is combined with Propantheline.
IsoflurophateThe therapeutic efficacy of Propantheline can be decreased when used in combination with Isoflurophate.
ItoprideThe therapeutic efficacy of Itopride can be decreased when used in combination with Propantheline.
KetobemidoneThe risk or severity of adverse effects can be increased when Propantheline is combined with Ketobemidone.
Levomethadyl AcetateThe risk or severity of adverse effects can be increased when Propantheline is combined with Levomethadyl Acetate.
LevorphanolThe risk or severity of adverse effects can be increased when Propantheline is combined with Levorphanol.
LofentanilThe risk or severity of adverse effects can be increased when Propantheline is combined with Lofentanil.
MalathionThe therapeutic efficacy of Propantheline can be decreased when used in combination with Malathion.
MecamylamineThe risk or severity of adverse effects can be increased when Mecamylamine is combined with Propantheline.
MefloquineThe therapeutic efficacy of Propantheline can be decreased when used in combination with Mefloquine.
MemantineThe therapeutic efficacy of Propantheline can be decreased when used in combination with Memantine.
MethadoneThe risk or severity of adverse effects can be increased when Propantheline is combined with Methadone.
Methadyl AcetateThe risk or severity of adverse effects can be increased when Propantheline is combined with Methadyl Acetate.
MethanthelineThe risk or severity of adverse effects can be increased when Propantheline is combined with Methantheline.
MethyclothiazideThe serum concentration of Methyclothiazide can be increased when it is combined with Propantheline.
MetixeneThe risk or severity of adverse effects can be increased when Propantheline is combined with Metixene.
MetolazoneThe serum concentration of Metolazone can be increased when it is combined with Propantheline.
MianserinMianserin may increase the anticholinergic activities of Propantheline.
MinaprineThe therapeutic efficacy of Propantheline can be decreased when used in combination with Minaprine.
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.
N-butylscopolammonium bromideThe risk or severity of adverse effects can be increased when Propantheline is combined with N-butylscopolammonium bromide.
NabilonePropantheline may increase the tachycardic activities of Nabilone.
NalbuphineThe risk or severity of adverse effects can be increased when Propantheline is combined with Nalbuphine.
NeostigmineThe therapeutic efficacy of Propantheline can be decreased when used in combination with Neostigmine.
NormethadoneThe risk or severity of adverse effects can be increased when Propantheline is combined with Normethadone.
NVA237The risk or severity of adverse effects can be increased when Propantheline is combined with NVA237.
OpiumThe risk or severity of adverse effects can be increased when Propantheline is combined with Opium.
OrphenadrineThe risk or severity of adverse effects can be increased when Propantheline is combined with Orphenadrine.
OxybutyninThe risk or severity of adverse effects can be increased when Propantheline is combined with Oxybutynin.
OxycodoneThe risk or severity of adverse effects can be increased when Propantheline is combined with Oxycodone.
OxymorphoneThe risk or severity of adverse effects can be increased when Propantheline is combined with Oxymorphone.
OxyphenoniumThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Propantheline.
PancuroniumThe risk or severity of adverse effects can be increased when Propantheline is combined with Pancuronium.
PentazocineThe risk or severity of adverse effects can be increased when Propantheline is combined with Pentazocine.
PentoliniumThe risk or severity of adverse effects can be increased when Propantheline is combined with Pentolinium.
PethidineThe risk or severity of adverse effects can be increased when Propantheline is combined with Pethidine.
PhysostigmineThe therapeutic efficacy of Propantheline can be decreased when used in combination with Physostigmine.
PipecuroniumThe risk or severity of adverse effects can be increased when Propantheline is combined with Pipecuronium.
PirenzepineThe risk or severity of adverse effects can be increased when Pirenzepine is combined with Propantheline.
PolythiazideThe serum concentration of Polythiazide can be increased when it is combined with 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.
PyridostigmineThe therapeutic efficacy of Propantheline can be decreased when used in combination with Pyridostigmine.
QuinethazoneThe serum concentration of Quinethazone can be increased when it is combined with Propantheline.
QuinidineThe risk or severity of adverse effects can be increased when Propantheline is combined with Quinidine.
RamosetronPropantheline may increase the constipating activities of Ramosetron.
RemifentanilThe risk or severity of adverse effects can be increased when Propantheline is combined with Remifentanil.
RivastigmineThe therapeutic efficacy of Propantheline can be decreased when used in combination with Rivastigmine.
ScopolamineThe risk or severity of adverse effects can be increased when Scopolamine is combined with Propantheline.
Scopolamine butylbromideThe risk or severity of adverse effects can be increased when Propantheline is combined with Scopolamine butylbromide.
SecretinThe therapeutic efficacy of Secretin can be decreased when used in combination with Propantheline.
SolifenacinThe risk or severity of adverse effects can be increased when Propantheline is combined with Solifenacin.
SufentanilThe risk or severity of adverse effects can be increased when Propantheline is combined with Sufentanil.
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.
TapentadolThe risk or severity of adverse effects can be increased when Propantheline is combined with Tapentadol.
TiotropiumPropantheline may increase the anticholinergic activities of Tiotropium.
TiotropiumThe risk or severity of adverse effects can be increased when Tiotropium is combined with Propantheline.
TolterodineThe risk or severity of adverse effects can be increased when Propantheline is combined with Tolterodine.
TopiramateThe risk or severity of adverse effects can be increased when Propantheline is combined with Topiramate.
TramadolThe risk or severity of adverse effects can be increased when Propantheline is combined with Tramadol.
TrichlorfonThe therapeutic efficacy of Propantheline can be decreased when used in combination with Trichlorfon.
TrichlormethiazideThe serum concentration of Trichlormethiazide can be increased when it is combined with Propantheline.
TrihexyphenidylThe risk or severity of adverse effects can be increased when Trihexyphenidyl is combined with Propantheline.
TrimethaphanThe risk or severity of adverse effects can be increased when Propantheline is combined with Trimethaphan.
TropicamideThe risk or severity of adverse effects can be increased when Propantheline is combined with Tropicamide.
TrospiumThe risk or severity of adverse effects can be increased when Trospium is combined with Propantheline.
TubocurarineThe risk or severity of adverse effects can be increased when Propantheline is combined with Tubocurarine.
UmeclidiniumUmeclidinium may increase the anticholinergic activities of Propantheline.
UmeclidiniumThe risk or severity of adverse effects can be increased when Propantheline is combined with Umeclidinium.
VecuroniumThe risk or severity of adverse effects can be increased when Propantheline is combined with Vecuronium.
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 ]
Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23