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Identification
Name Diphenidol
Accession Number DB01231 (APRD00929)
Type small molecule
Groups approved
Description

Diphenidol is an antiemetic agent used in the treatment of vomiting and vertigo. Diphenidol overdose may result in serious toxicity in children.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
Difenidol
Difenidol HCl
Difenidol hydrochloride
Difenidolo [DCIT]
Difenidolum [INN-Latin]
Diphenidol HCl
Diphenidol hydrochloride
Salts Not Available
Brand names
Name Company
Ansmin
Avomol
Celmidol
Cephadol
Cerrosa
Maniol
Nometic
Satanolon
Verterge
Vontrol
Yesdol
First Prev Next Last
Brand mixtures Not Available
Categories
  • Antiemetics
  • Antivertigo Agents
CAS number 972-02-1
Weight Average: 309.4452
Monoisotopic: 309.209264491
Chemical Formula C21H27NO
InChI Key InChIKey=OGAKLTJNUQRZJU-UHFFFAOYSA-N
InChI
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
Plain Text
IUPAC Name
1,1-diphenyl-4-(piperidin-1-yl)butan-1-ol
SMILES
OC(CCCN1CCCCC1)(C1=CC=CC=C1)C1=CC=CC=C1
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Diphenylmethanes
Substructures
  • Hydroxy Compounds
  • Benzyl Alcohols and Derivatives
  • Benzene and Derivatives
  • Aliphatic and Aryl Amines
  • Alcohols and Polyols
  • Diphenylmethanes
  • Heterocyclic compounds
  • Aromatic compounds
  • Piperidines
Pharmacology
Indication For use in the prevention and symptomatic treatment of peripheral (labyrinthine) vertigo and associated nausea and vomiting that occur in such conditions as Meniere's disease and surgery of the middle and inner ear. Also for the control of nausea and vomiting associated with postoperative states, malignant neoplasms, labyrinthine disturbances, antineoplastic agent therapy, radiation sickness, and infectious diseases.
Pharmacodynamics Diphenidol is used for control of nausea and vomiting. It has an antivertigo effect on the vestibular apparatus, inhibiting the chemoreceptor trigger zone to control nausea and vomiting, thus preventing motion sickness.
Mechanism of action 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.
Absorption Well absorbed from gastrointestinal tract following oral administration.
Volume of distribution Not Available
Protein binding Not Available
Metabolism Not Available
Route of elimination Not Available
Half life 4 hours
Clearance Not Available
Toxicity Symptoms of overdose include drowsiness (severe); shortness of breath or troubled breathing; unusual tiredness or weakness (severe).
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Glaxosmithkline
Packagers
  • Professional Co.
Dosage forms
Form Route Strength
Tablet Oral
Prices
Unit description Cost Unit
Diphenidol hcl powder 32.4 USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
melting point 104.5 °C PhysProp
logP 4.3 Not Available
Predicted Properties
Property Value Source
water solubility 5.87e-03 g/l ALOGPS
logP 4.08 ALOGPS
logP 4.22 ChemAxon
logS -4.7 ALOGPS
pKa (strongest acidic) 13.4 ChemAxon
pKa (strongest basic) 9.23 ChemAxon
physiological charge 1 ChemAxon
hydrogen acceptor count 2 ChemAxon
hydrogen donor count 1 ChemAxon
polar surface area 23.47 ChemAxon
rotatable bond count 6 ChemAxon
refractivity 96.92 ChemAxon
polarizability 36.66 ChemAxon
References
Synthesis Reference Not Available
General Reference
  1. Link
External Links
Resource Link
KEGG Drug D03858 Link_out
KEGG Compound C06961 Link_out
PubChem Compound 3055 Link_out
PubChem Substance 46506486 Link_out
ChemSpider 2947 Link_out
ChEBI 4638 Link_out
ChEMBL 4638 Link_out
Therapeutic Targets Database DAP001133 Link_out
PharmGKB PA164746037 Link_out
Drugs.com http://www.drugs.com/cons/diphenidol.html Link_out
ATC Codes Not Available
AHFS Codes Not Available
PDB Entries Not Available
FDA label show (374 KB)
MSDS show (73.5 KB)
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. Muscarinic acetylcholine receptor M1

Pharmacological action: yes
Actions: antagonist

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

Organism class: human
UniProt ID: P11229 Link_out
Gene: CHRM1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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. Pubmed
  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. Pubmed
  3. Waelbroeck M, Camus J, Tastenoy M, Mutschler E, Strohmann C, Tacke R, Lambrecht G, Christophe J: Stereoselectivity of®- and (S)-hexahydro-difenidol binding to neuroblastoma M1, cardiac M2, pancreatic M3, and striatum M4 muscarinic receptors. Chirality. 1991;3(2):118-23. Pubmed

2. Muscarinic acetylcholine receptor M3

Pharmacological action: yes
Actions: antagonist

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

Organism class: human
UniProt ID: P20309 Link_out
Gene: CHRM3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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. Pubmed
  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. Pubmed
  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. Pubmed
  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. Pubmed
  5. Waelbroeck M, Camus J, Tastenoy M, Mutschler E, Strohmann C, Tacke R, Lambrecht G, Christophe J: Stereoselectivity of®- and (S)-hexahydro-difenidol binding to neuroblastoma M1, cardiac M2, pancreatic M3, and striatum M4 muscarinic receptors. Chirality. 1991;3(2):118-23. Pubmed

3. Muscarinic acetylcholine receptor M2

Pharmacological action: yes
Actions: antagonist

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

Organism class: human
UniProt ID: P08172 Link_out
Gene: CHRM2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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. Pubmed
  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. Pubmed
  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. Pubmed
  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. Pubmed
  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. Pubmed
  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. Pubmed
  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. Pubmed
  8. Waelbroeck M, Camus J, Tastenoy M, Mutschler E, Strohmann C, Tacke R, Lambrecht G, Christophe J: Stereoselectivity of®- and (S)-hexahydro-difenidol binding to neuroblastoma M1, cardiac M2, pancreatic M3, and striatum M4 muscarinic receptors. Chirality. 1991;3(2):118-23. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:20