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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2019-07-23 06:02:09 UTC
HMDB IDHMDB0015591
Secondary Accession Numbers
  • HMDB15591
Metabolite Identification
Common NameMepenzolate
DescriptionMepenzolate is a post-ganglionic parasympathetic inhibitor. It decreases gastric acid and pepsin secretion and suppresses spontaneous contractions of the colon. Mepenzolate diminishes gastric acid and pepsin secretion. Mepenzolate also suppresses spontaneous contractions of the colon. Pharmacologically, it is a post-ganglionic parasympathetic inhibitor. It has not been shown to be effective in contributing to the healing of peptic ulcer, decreasing the rate of recurrence, or preventing complications.
Structure
Data?1563861729
Synonyms
ValueSource
1-Methyl-3-piperidyl benzilate methyl bromideHMDB
Mepenzolate bromideHMDB
Mepenzolic acidHMDB
N-Methyl-3-piperidyl benzilate methyl bromideHMDB
N-Methyl-3-piperidyldiphenylglycolate methobromideHMDB
Mepenzolic acid, bromine saltMeSH
CantilMeSH
Mepenzolate bromide, (+-)-isomerMeSH
Aventis behring brand OF mepenzolate bromideMeSH
N-Methyl-3-piperidylbenzilate methyl bromideMeSH
Mepenzolate iodideMeSH
Mepenzolic acid, bromine salt, 1-(methyl-(14)C)-labeledMeSH
Chemical FormulaC21H26NO3
Average Molecular Weight340.436
Monoisotopic Molecular Weight340.191268703
IUPAC Name3-[(2-hydroxy-2,2-diphenylacetyl)oxy]-1,1-dimethylpiperidin-1-ium
Traditional Namemepenzolate
CAS Registry Number25990-43-6
SMILES
C[N+]1(C)CCCC(C1)OC(=O)C(O)(C1=CC=CC=C1)C1=CC=CC=C1
InChI Identifier
InChI=1S/C21H26NO3/c1-22(2)15-9-14-19(16-22)25-20(23)21(24,17-10-5-3-6-11-17)18-12-7-4-8-13-18/h3-8,10-13,19,24H,9,14-16H2,1-2H3/q+1
InChI KeyGKNPSSNBBWDAGH-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassDiphenylmethanes
Direct ParentDiphenylmethanes
Alternative Parents
Substituents
  • Diphenylmethane
  • Piperidine
  • Quaternary ammonium salt
  • Tertiary alcohol
  • Tetraalkylammonium salt
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Organopnictogen compound
  • Organic oxide
  • Aromatic alcohol
  • Amine
  • Alcohol
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organic salt
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic cation
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.00063 g/LNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00063 g/LALOGPS
logP-1.1ALOGPS
logP-0.97ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)11.05ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity109.4 m³·mol⁻¹ChemAxon
Polarizability37.76 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-053r-4900000000-bba2c7e06054ee5b9889JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0zfr-3090000000-75247afb1f7cc3799743JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03ec-0915000000-279c2f267ec9c60be8e5JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1932000000-3cc3ed2add9a9bcdc345JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01px-9500000000-8076c276b72604a21f0aJSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB04843 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB04843 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB04843
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3917
KEGG Compound IDC07818
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMepenzolate
METLIN IDNot Available
PubChem Compound4057
PDB IDNot Available
ChEBI ID569580
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:
CHRM3
Uniprot ID:
P20309
Molecular weight:
66127.4
References
  1. Tsai CS, Guede-Guina F, Smith MO, Vangah-Manda M, Ochillo RF: Isolation of cholinergic active ingredients in aqueous extracts of Mareya micrantha using the longitudinal muscle of isolated guinea-pig ileum as a pharmacological activity marker. J Ethnopharmacol. 1995 Mar;45(3):215-22. [PubMed:7623487 ]
  2. Tsai CS, Ochillo RF: Low temperature and muscarinic receptor activities. Cryobiology. 1989 Oct;26(5):485-95. [PubMed:2791613 ]
  3. Ochillo RF, Pugh DA: Atropine and mepenzolate mydriasis in rabbits: a comparative pupillographic analysis of two antimuscarinic agents. Res Commun Chem Pathol Pharmacol. 1982 Jun;36(3):503-6. [PubMed:7122991 ]
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. Tsai CS, Guede-Guina F, Smith MO, Vangah-Manda M, Ochillo RF: Isolation of cholinergic active ingredients in aqueous extracts of Mareya micrantha using the longitudinal muscle of isolated guinea-pig ileum as a pharmacological activity marker. J Ethnopharmacol. 1995 Mar;45(3):215-22. [PubMed:7623487 ]
  2. Tsai CS, Ochillo RF: Low temperature and muscarinic receptor activities. Cryobiology. 1989 Oct;26(5):485-95. [PubMed:2791613 ]
  3. Ochillo RF, Pugh DA: Atropine and mepenzolate mydriasis in rabbits: a comparative pupillographic analysis of two antimuscarinic agents. Res Commun Chem Pathol Pharmacol. 1982 Jun;36(3):503-6. [PubMed:7122991 ]