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Record Information
Version3.6
Creation Date2012-09-06 15:16:51 UTC
Update Date2016-02-11 01:32:35 UTC
HMDB IDHMDB15361
Secondary Accession NumbersNone
Metabolite Identification
Common NameDiphenidol
DescriptionDiphenidol is only found in individuals that have used or taken this drug. It is an antiemetic agent used in the treatment of vomiting and vertigo. Diphenidol overdose may result in serious toxicity in children.The mechanism by which diphenidol exerts its antiemetic and antivertigo effects is not precisely known. It is thought to diminish vestibular stimulation and depress labyrinthine function and as an antimuscarinic agent. An action on the medullary chemoreceptive trigger zone may also be involved in the antiemetic effect. Diphenidol has no significant sedative, tranquilizing, or antihistaminic action. It has a weak peripheral anticholinergic effect.
Structure
Thumb
Synonyms
ValueSource
alpha,alpha-Diphenyl-1-piperidinebutanolChEBI
DifenidolChEBI
DifenidolumChEBI
Diphenyl(3-(1-piperidyl)propyl)carbinolChEBI
a,a-Diphenyl-1-piperidinebutanolGenerator
α,α-diphenyl-1-piperidinebutanolGenerator
DifenidoloHMDB
Chemical FormulaC21H27NO
Average Molecular Weight309.4452
Monoisotopic Molecular Weight309.209264491
IUPAC Name1,1-diphenyl-4-(piperidin-1-yl)butan-1-ol
Traditional Namediphenidol
CAS Registry Number972-02-1
SMILES
OC(CCCN1CCCCC1)(C1=CC=CC=C1)C1=CC=CC=C1
InChI Identifier
InChI=1S/C21H27NO/c23-21(19-11-4-1-5-12-19,20-13-6-2-7-14-20)15-10-18-22-16-8-3-9-17-22/h1-2,4-7,11-14,23H,3,8-10,15-18H2
InChI KeyInChIKey=OGAKLTJNUQRZJU-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
  • Phenylbutylamine
  • Aralkylamine
  • Piperidine
  • Tertiary alcohol
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Antiemetics
  • Antivertigo Agents
Application
  • Pharmaceutical
Cellular locations
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility5.87e-03 g/LNot Available
LogP4.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0059 mg/mLALOGPS
logP4.08ALOGPS
logP4.22ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)13.4ChemAxon
pKa (Strongest Basic)9.23ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area23.47 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity96.92 m3·mol-1ChemAxon
Polarizability36.66 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01231
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01231
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01231
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2947
KEGG Compound IDC06961
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB15361
Metagene LinkHMDB15361
METLIN IDNot Available
PubChem Compound3055
PDB IDNot Available
ChEBI ID4638
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. MedicineNet [Link]

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. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
  2. 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. [17016423 ]
  3. Braverman AS, Tallarida RJ, Ruggieri MR Sr: Interaction between muscarinic receptor subtype signal transduction pathways mediating bladder contraction. Am J Physiol Regul Integr Comp Physiol. 2002 Sep;283(3):R663-8. [12185001 ]
  4. Varoli L, Angeli P, Burnelli S, Marucci G, Recanatini M: Synthesis and antagonistic activity at muscarinic receptor subtypes of some 2-carbonyl derivatives of diphenidol. Bioorg Med Chem. 1999 Sep;7(9):1837-44. [10530931 ]
  5. Waelbroeck M, Camus J, Tastenoy M, Mutschler E, Strohmann C, Tacke R, Lambrecht G, Christophe J: Stereoselectivity of (R)- and (S)-hexahydro-difenidol binding to neuroblastoma M1, cardiac M2, pancreatic M3, and striatum M4 muscarinic receptors. Chirality. 1991;3(2):118-23. [1863523 ]
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. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
  2. 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. [17016423 ]
  3. Waelbroeck M, Camus J, Tastenoy M, Mutschler E, Strohmann C, Tacke R, Lambrecht G, Christophe J: Stereoselectivity of (R)- and (S)-hexahydro-difenidol binding to neuroblastoma M1, cardiac M2, pancreatic M3, and striatum M4 muscarinic receptors. Chirality. 1991;3(2):118-23. [1863523 ]
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 adenylate cyclase inhibition
Gene Name:
CHRM2
Uniprot ID:
P08172
Molecular weight:
51714.6
References
  1. Pelat M, Lazartigues E, Tran MA, Gharib C, Montastruc JL, Montastruc P, Rascol O: Characterization of the central muscarinic cholinoceptors involved in the cholinergic pressor response in anesthetized dogs. Eur J Pharmacol. 1999 Aug 27;379(2-3):117-24. [10497897 ]
  2. Lazartigues E, Freslon JL, Tellioglu T, Brefel-Courbon C, Pelat M, Tran MA, Montastruc JL, Rascol O: Pressor and bradycardic effects of tacrine and other acetylcholinesterase inhibitors in the rat. Eur J Pharmacol. 1998 Nov 13;361(1):61-71. [9851542 ]
  3. Kovacs I, Yamamura HI, Waite SL, Varga EV, Roeske WR: Pharmacological comparison of the cloned human and rat M2 muscarinic receptor genes expressed in the murine fibroblast (B82) cell line. J Pharmacol Exp Ther. 1998 Feb;284(2):500-7. [9454790 ]
  4. Pavia J, Munoz M, Jimenez E, Martos F, Gonzalez-Correa JA, De la Cruz JP, Garcia V, Sanchez de la Cuesta F: Pharmacological characterization and distribution of muscarinic receptors in human placental syncytiotrophoblast brush-border and basal plasma membranes. Eur J Pharmacol. 1997 Feb 12;320(2-3):209-14. [9059856 ]
  5. Jovanovic A, Grbovic L, Tulic I: Endothelium-dependent relaxation in response to acetylcholine in the human uterine artery. Eur J Pharmacol. 1994 Apr 21;256(2):131-9. [8050463 ]
  6. Braverman AS, Tallarida RJ, Ruggieri MR Sr: Interaction between muscarinic receptor subtype signal transduction pathways mediating bladder contraction. Am J Physiol Regul Integr Comp Physiol. 2002 Sep;283(3):R663-8. [12185001 ]
  7. Varoli L, Angeli P, Burnelli S, Marucci G, Recanatini M: Synthesis and antagonistic activity at muscarinic receptor subtypes of some 2-carbonyl derivatives of diphenidol. Bioorg Med Chem. 1999 Sep;7(9):1837-44. [10530931 ]
  8. Waelbroeck M, Camus J, Tastenoy M, Mutschler E, Strohmann C, Tacke R, Lambrecht G, Christophe J: Stereoselectivity of (R)- and (S)-hexahydro-difenidol binding to neuroblastoma M1, cardiac M2, pancreatic M3, and striatum M4 muscarinic receptors. Chirality. 1991;3(2):118-23. [1863523 ]