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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2021-09-14 14:57:38 UTC
HMDB IDHMDB0014920
Secondary Accession Numbers
  • HMDB14920
Metabolite Identification
Common NamePropantheline
DescriptionPropantheline 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. Propantheline is a drug. By giving this medication it becomes easier to do "dry" dentistryPropantheline 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. Propantheline is an extremely weak basic (essentially neutral) compound (based on its pKa). It can also be used to control the symptoms of irritable bowel syndrome and similar conditions. Side effects include tachycardia, constipation, hypersensitivity to light, dry mouth, and urinary retention. This can also be prescribed by dentists for certain patients who salivate excessively. This agent can also be used for patients who experience intense GI symptoms while tapering off of TCAs. Propantheline can also be used to treat excessive sweating because acetylcholine block also reduces secretions such as sweat and tears. Propantheline bromide (INN) 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). By relaxing the gut muscle, propantheline can relieve pain in conditions caused by spasm of the muscle in the gut.
Structure
Data?1582753235
Synonyms
ValueSource
Propantheline bromideHMDB
PropantheliniumHMDB
PropanthelinumHMDB
Bromide, propanthelineHMDB
ProbanthineHMDB
Pro banthineHMDB
Pro-banthineHMDB
Chemical FormulaC23H30NO3
Average Molecular Weight368.4892
Monoisotopic Molecular Weight368.222568831
IUPAC Namemethylbis(propan-2-yl)[2-(9H-xanthene-9-carbonyloxy)ethyl]azanium
Traditional Namepropantheline
CAS Registry Number298-50-0
SMILES
CC(C)[N+](C)(CCOC(=O)C1C2=CC=CC=C2OC2=CC=CC=C12)C(C)C
InChI Identifier
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
InChI KeyVVWYOYDLCMFIEM-UHFFFAOYSA-N
Chemical Taxonomy
Description 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
  • Benzenoid
  • Quaternary ammonium salt
  • Tetraalkylammonium salt
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Ether
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Organic nitrogen compound
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic salt
  • Organic oxygen compound
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility7.2e-05 g/LNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility7.2e-05 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity119.25 m³·mol⁻¹ChemAxon
Polarizability40.87 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004u-6911000000-12b0c3360d2453760c3a2017-08-28View Spectrum
MSMass Spectrum (Electron Ionization)splash10-004r-5900000000-258d85710309b3e372fc2021-09-05View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0339000000-88596dedd4ec0b9277302017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pxr-0797000000-d206aafcf67084b1149e2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-6930000000-57cb7302dad26c11faf72017-09-01View Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00782 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00782 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00782
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4765
KEGG Compound IDC07506
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPropantheline bromide
METLIN IDNot Available
PubChem Compound4934
PDB IDNot Available
ChEBI ID754675
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in G-protein coupled receptor protein signaling pathway
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:
51420.4
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 ]