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Details

Stereochemistry ACHIRAL
Molecular Formula C21H27NO.ClH
Molecular Weight 345.906
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIPHENIDOL HYDROCHLORIDE

SMILES

Cl.OC(CCCN1CCCCC1)(C2=CC=CC=C2)C3=CC=CC=C3

InChI

InChIKey=AVZIYZHXZAYGJS-UHFFFAOYSA-N
InChI=1S/C21H27NO.ClH/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;1H

HIDE SMILES / InChI

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

Molecular Formula ClH
Molecular Weight 36.461
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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
VONTROL

Approved Use

INDICATIONS 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 Date

-8.6572802E10
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
157.4 ng/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
445.57 ng × h/mL
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

T1/2

ValueDoseCo-administeredAnalytePopulation
3.23 h
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

Doses

DosePopulationAdverse 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

AEs

AESignificanceDosePopulation
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:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes [IC50 35 uM]
Drug as victim
PubMed

PubMed

TitleDatePubMed
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
Oral administration of prednisone to control refractory vertigo in Ménière's disease: a pilot study.
2005 Sep
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
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
[Clinical analysis on the cervical vertigo after operation of middle ear].
2009 May
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.
2011 Jul 14
Patents

Patents

Sample Use Guides

In Vivo Use Guide
For oral dosage form (tablets): Adults: 25 to 50 milligrams (mg) every four hours as needed.
Route of Administration: Oral
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
by admin
on Fri Dec 15 15:00:34 UTC 2023
Edited
by admin
on Fri Dec 15 15:00:34 UTC 2023
Record UNII
DG355XWQ4T
Record Status Validated (UNII)
Record Version
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Name Type Language
DIPHENIDOL HYDROCHLORIDE
MI   ORANGE BOOK   USAN   VANDF  
USAN  
Official Name English
VONTROL
Brand Name English
SK&F-478-A
Code English
DIPHENIDOL HYDROCHLORIDE [ORANGE BOOK]
Common Name English
DIFENIDOL HYDROCHLORIDE
JAN   MART.   WHO-DD  
Common Name English
SK&F 478-A
Code English
DIPHENIDOL HYDROCHLORIDE [MI]
Common Name English
DIPHENIDOL HCL
Common Name English
NSC-23012
Code English
DIPHENIDOL HYDROCHLORIDE [USAN]
Common Name English
Difenidol hydrochloride [WHO-DD]
Common Name English
α,α-Diphenyl-1-piperidinebutanol hydrochloride
Systematic Name English
CEPHADOL
Brand Name English
DIFENIDOL HYDROCHLORIDE [MART.]
Common Name English
DIFENIDOL HYDROCHLORIDE [JAN]
Common Name English
DIPHENIDOL HYDROCHLORIDE [VANDF]
Common Name English
1-PIPERIDINEBUTANOL, .ALPHA.,.ALPHA.-DIPHENYL-, HYDROCHLORIDE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C267
Created by admin on Fri Dec 15 15:00:34 UTC 2023 , Edited by admin on Fri Dec 15 15:00:34 UTC 2023
Code System Code Type Description
EVMPD
SUB01690MIG
Created by admin on Fri Dec 15 15:00:34 UTC 2023 , Edited by admin on Fri Dec 15 15:00:34 UTC 2023
PRIMARY
ChEMBL
CHEMBL936
Created by admin on Fri Dec 15 15:00:34 UTC 2023 , Edited by admin on Fri Dec 15 15:00:34 UTC 2023
PRIMARY
PUBCHEM
66266
Created by admin on Fri Dec 15 15:00:34 UTC 2023 , Edited by admin on Fri Dec 15 15:00:34 UTC 2023
PRIMARY
FDA UNII
DG355XWQ4T
Created by admin on Fri Dec 15 15:00:34 UTC 2023 , Edited by admin on Fri Dec 15 15:00:34 UTC 2023
PRIMARY
NCI_THESAURUS
C65422
Created by admin on Fri Dec 15 15:00:34 UTC 2023 , Edited by admin on Fri Dec 15 15:00:34 UTC 2023
PRIMARY
NSC
23012
Created by admin on Fri Dec 15 15:00:34 UTC 2023 , Edited by admin on Fri Dec 15 15:00:34 UTC 2023
PRIMARY
RXCUI
47877
Created by admin on Fri Dec 15 15:00:34 UTC 2023 , Edited by admin on Fri Dec 15 15:00:34 UTC 2023
PRIMARY RxNorm
ECHA (EC/EINECS)
221-850-0
Created by admin on Fri Dec 15 15:00:34 UTC 2023 , Edited by admin on Fri Dec 15 15:00:34 UTC 2023
PRIMARY
CAS
3254-89-5
Created by admin on Fri Dec 15 15:00:34 UTC 2023 , Edited by admin on Fri Dec 15 15:00:34 UTC 2023
PRIMARY
EPA CompTox
DTXSID10186248
Created by admin on Fri Dec 15 15:00:34 UTC 2023 , Edited by admin on Fri Dec 15 15:00:34 UTC 2023
PRIMARY
DRUG BANK
DBSALT000395
Created by admin on Fri Dec 15 15:00:34 UTC 2023 , Edited by admin on Fri Dec 15 15:00:34 UTC 2023
PRIMARY
SMS_ID
100000084777
Created by admin on Fri Dec 15 15:00:34 UTC 2023 , Edited by admin on Fri Dec 15 15:00:34 UTC 2023
PRIMARY
MERCK INDEX
m4611
Created by admin on Fri Dec 15 15:00:34 UTC 2023 , Edited by admin on Fri Dec 15 15:00:34 UTC 2023
PRIMARY Merck Index
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