Details
Stereochemistry | ACHIRAL |
Molecular Formula | C21H27NO |
Molecular Weight | 309.4452 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(CCCN1CCCCC1)(C2=CC=CC=C2)C3=CC=CC=C3
InChI
InChIKey=OGAKLTJNUQRZJU-UHFFFAOYSA-N
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
Molecular Formula | C21H27NO |
Molecular Weight | 309.4452 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Diphenidol, a nonphenothiazinic antiemetic agent used primarily in patients with Meniere disease and labyrinthopathies to treat vomiting and vertigo, is considered to be a relatively safe drug. Since it was first approved in the United States in 1967, this drug has been widely used in Latin America and Asia and has contributed to sporadic suicidal and accidental poisonings in mainland China and Taiwan. 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. Diphenidol is used to relieve or prevent nausea, vomiting, and dizziness caused by certain medical problems.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL216 Sources: https://www.drugbank.ca/drugs/DB01231 |
6.37 null [pKi] | ||
Target ID: CHEMBL211 Sources: https://www.drugbank.ca/drugs/DB01231 |
5.55 null [pKi] | ||
Target ID: CHEMBL245 Sources: https://www.drugbank.ca/drugs/DB01231 |
5.95 null [pKi] | ||
Target ID: CHEMBL1821 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18395442 |
6.04 null [pKi] | ||
Target ID: CHEMBL2035 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18395442 |
5.89 null [pKi] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | VONTROL Approved UseINDICATIONS
VERTIGO—‘Vontrol’ is indicated in peripheral (labyrinthine) vertigo and associated nausea and vomiting, as seen in such conditions as: Meniere’s disease, middle- and inner-ear surgery (labyrinthitis).
NAUSEA AND VOMITING—‘Vontrol’ is indicated in the control of nausea and vomiting, as seen in such conditions as: postoperative states, malignant neoplasms and labyrinthine disturbances. Launch Date1967 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
157.4 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18506741/ |
25 mg 2 times / day multiple, oral dose: 25 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
DIPHENIDOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
445.57 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18506741/ |
25 mg 2 times / day multiple, oral dose: 25 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
DIPHENIDOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3.23 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18506741/ |
25 mg 2 times / day multiple, oral dose: 25 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
DIPHENIDOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
Doses
Dose | Population | Adverse events |
---|---|---|
15 mg/kg single, intravenous Highest studied dose Dose: 15 mg/kg Route: intravenous Route: single Dose: 15 mg/kg Sources: |
unhealthy, adult n = 18 Health Status: unhealthy Condition: tachyarrhythmias Age Group: adult Sex: unknown Population Size: 18 Sources: |
Disc. AE: Central nervous system disorder NOS... AEs leading to discontinuation/dose reduction: Central nervous system disorder NOS (14 patients) Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Central nervous system disorder NOS | 14 patients Disc. AE |
15 mg/kg single, intravenous Highest studied dose Dose: 15 mg/kg Route: intravenous Route: single Dose: 15 mg/kg Sources: |
unhealthy, adult n = 18 Health Status: unhealthy Condition: tachyarrhythmias Age Group: adult Sex: unknown Population Size: 18 Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Neuropharmacological mechanisms of emesis. I. Effects of antiemetic drugs on motion- and apomorphine-induced pica in rats. | 1995 Nov |
|
Simultaneous determination of enantiomers of structurally related anticholinergic analogs in human serum by liquid chromatography-electrospray ionization mass spectrometry with on-line sample cleanup. | 2001 Oct 25 |
|
Synthesis and antagonistic activity at muscarinic receptor subtypes of some derivatives of diphenidol. | 2003 Sep |
|
Diphenidol has no actual broad antiemetic activity in dogs and ferrets. | 2004 Nov |
|
Development of an HPLC method for determination of diphenidol in plasma and its application in an oral multi-dose bioequivalence study in a healthy female Mexican population. | 2005 Jul 15 |
|
Oral administration of prednisone to control refractory vertigo in Ménière's disease: a pilot study. | 2005 Sep |
|
Determination of difenidol hydrochloride by capillary electrophoresis with electrochemiluminescence detection. | 2006 Feb 2 |
|
Capillary electrophoresis with end-column electrochemiluminescence for the analysis of chloroquine phosphate and the study on its interaction with human serum albumin. | 2007 Jun 22 |
|
A novel amperometric sensor for the detection of difenidol hydrochloride based on the modification of Ru(bpy)(3)(2+) on a glassy carbon electrode. | 2007 Oct 15 |
|
Enzymatic preparation of cefaclor with immobilized penicillin acylase. | 2008 |
|
Synthesis and pharmacological profile of a series of 1-substituted-2-carbonyl derivatives of Diphenidol: novel M4 muscarinic receptor antagonists. | 2008 Mar |
|
Effects of endolymphatic sac drainage with steroids for intractable Meniere's disease: a long-term follow-up and randomized controlled study. | 2008 May |
|
Diphenidol-related diamines as novel muscarinic M4 receptor antagonists. | 2008 May 1 |
|
Ultra-fast chromatographic micro-assay for quantification of diphenidol in plasma: application in an oral multi-dose switchability trial. | 2008 Oct |
|
[Clinical analysis on the cervical vertigo after operation of middle ear]. | 2009 May |
|
(2-Methyl-phen-yl)(phen-yl)methanol. | 2010 Jul 31 |
|
Diphenidol inhibited sodium currents and produced spinal anesthesia. | 2010 Jun |
|
Neuropharmacology of vestibular system disorders. | 2010 Mar |
|
Generation of gold nanostructures at the surface of platinum electrode by electrodeposition for ECL detection for CE. | 2010 Mar |
|
Evaluation of phenoxybenzamine in the CFA model of pain following gene expression studies and connectivity mapping. | 2010 Sep 16 |
|
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2. | 2011 Jul 14 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/cons/diphenidol.html
For oral dosage form (tablets):
Adults: 25 to 50 milligrams (mg) every four hours as needed.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22683869
In vitro binding assays demonstrated that difenidol at micromolar concentrations bound to the α(1A)-, α(1B)- and α(1D)-adrenoceptor subtypes. Difenidol inhibited the phenylephrine-induced increase in [Ca(2+)](i) in Chinese hamster ovary cells expressing human α(1A)-, α(1B)- or α(1D)-adrenoceptor subtypes with similar IC(50) values in the low micromolar range.
Substance Class |
Chemical
Created
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admin
on
Edited
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Record UNII |
NQO8R319LY
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Record Status |
Validated (UNII)
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N0000009034
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N0000178372
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NCI_THESAURUS |
C267
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m4611
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C65421
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313
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DB01231
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DTXSID3022950
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C004858
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3316
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DIPHENIDOL
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ACTIVE MOIETY |