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Details

Stereochemistry ACHIRAL
Molecular Formula C30H32N2O2
Molecular Weight 452.5873
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIPHENOXYLATE

SMILES

CCOC(=O)C1(CCN(CCC(C#N)(C2=CC=CC=C2)C3=CC=CC=C3)CC1)C4=CC=CC=C4

InChI

InChIKey=HYPPXZBJBPSRLK-UHFFFAOYSA-N
InChI=1S/C30H32N2O2/c1-2-34-28(33)29(25-12-6-3-7-13-25)18-21-32(22-19-29)23-20-30(24-31,26-14-8-4-9-15-26)27-16-10-5-11-17-27/h3-17H,2,18-23H2,1H3

HIDE SMILES / InChI

Molecular Formula C30H32N2O2
Molecular Weight 452.5873
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including ISBN-13: 978-0323055932

Diphenoxylate is an opioid drug used for the treatment of acute diarrhea. The drug is used in combination with atropine and marketed under names Lomotil and Diphenoxylate hydrochloride and atropine sulfate. Diphenoxylate is biotransformed in man by ester hydrolysis to diphenoxylic acid (difenoxine), which is biologically active and the major metabolite in the blood. The drug exerts its action by activating mu opioid receptors of intestinal mucosa.

CNS Activity

Curator's Comment: At high doses it exhibits codeine-like subjective effects.

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P35372|||G8XRH8|||Q5TDA1|||Q9UN57
Gene ID: 4988.0
Gene Symbol: OPRM1
Target Organism: Homo sapiens (Human)
Sources: ISBN-13: 978-0323055932
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
LOMOTIL

Approved Use

Lomotil is effective as adjunctive therapy in the management of diarrhea.

Launch Date

-2.93414404E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
622.68 ng/mL
10 mg/kg single, oral
dose: 10 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
DIPHENOXYLATE plasma
Rattus norvegicus
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
9.5 ng/mL
5 mg single, oral
dose: 5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DIPHENOXYLATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
7157.61 ng × h/mL
10 mg/kg single, oral
dose: 10 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
DIPHENOXYLATE plasma
Rattus norvegicus
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
10.68 h
10 mg/kg single, oral
dose: 10 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
DIPHENOXYLATE plasma
Rattus norvegicus
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
2.5 h
5 mg single, oral
dose: 5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DIPHENOXYLATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
15.5%
DIPHENOXYLATE unknown
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
20 mg 1 times / day steady, oral
Studied dose
Dose: 20 mg, 1 times / day
Route: oral
Route: steady
Dose: 20 mg, 1 times / day
Co-administed with::
atropine sulfate(0.025 mg)
Sources:
unhealthy
300 mg 1 times / day steady, oral (max)
Dose: 300 mg, 1 times / day
Route: oral
Route: steady
Dose: 300 mg, 1 times / day
Sources:
unhealthy
Other AEs: Drug dependence...
AEs

AEs

AESignificanceDosePopulation
Drug dependence
300 mg 1 times / day steady, oral (max)
Dose: 300 mg, 1 times / day
Route: oral
Route: steady
Dose: 300 mg, 1 times / day
Sources:
unhealthy
Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer






Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
minor
yes (co-administration study)
Comment: diphenoxylate decreased omeprazole AUC and Cmax
Page: abstract
no
no
no
no
no (co-administration study)
Comment: diphenoxylate had no effect on buproprion AUC and Cmax
Page: 18805.0
no
no (co-administration study)
Comment: diphenoxylate had no effect on metroprolol AUC and Cmax
Page: 18805.0
no
no (co-administration study)
Comment: diphenoxylate had no effect on testosterone AUC and Cmax
Page: 18805.0
unlikely
yes
yes (co-administration study)
Comment: diphenoxylate decreased phenacetin AUC and Cmax
Page: abstract
yes
yes (co-administration study)
Comment: diphenoxylate decreased tolbutamide AUC and Cmax
Page: abstract
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Evolutionary explanations in medical and health profession courses: are you answering your students' "why" questions?
2005 May 10
Guidelines for the diagnosis and management of carcinoid tumours. Part 1: the gastrointestinal tract. A statement from a Canadian National Carcinoid Expert Group.
2006 Apr
Prevention and management of chemotherapy-induced diarrhea in patients with colorectal cancer: a consensus statement by the Canadian Working Group on Chemotherapy-Induced Diarrhea.
2007 Feb
Drug-induced diarrhea.
2007 Oct
In vivo evaluation of antidiarrhoeal activity of Rhus semialata fruit extract in rats.
2007 Oct 27
Methylnaltrexone in the treatment of opioid-induced constipation.
2008
Are one or two dangerous? Diphenoxylate-atropine exposure in toddlers.
2008 Jan
Anticholinergic activity of 107 medications commonly used by older adults.
2008 Jul
Managing toxicities and optimal dosing of targeted drugs in advanced kidney cancer.
2009 May
An Open-Label, Noncomparative, Multicenter Study to Evaluate Efficacy and Safety of NASHA/Dx Gel as a Bulking Agent for the Treatment of Fecal Incontinence.
2010
Re: "Are one or two dangerous? Diphenoxylate-atropine exposure in toddlers".
2010 Apr
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.
2010 Dec
Antidiarrheal activity of extracts and compound from Trilepisium madagascariense stem bark.
2010 Jun
Effect of an antidiabetic polysaccharide from Inula japonica on constipation in normal and two models of experimental constipated mice.
2010 Nov
Patents

Sample Use Guides

Adults: The recommended initial dosage is two Lomotil tablets (each tablet contains 2,5 mg diphenoxylate hydrochloride) four times daily; Dosage schedule for children: The recommended initial total daily dosage of Lomotil liquid for children is 0.3 to 0.4 mg/kg, administered in four divided doses.
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Sat Dec 16 15:50:13 UTC 2023
Edited
by admin
on Sat Dec 16 15:50:13 UTC 2023
Record UNII
73312P173G
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIPHENOXYLATE
HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
diphenoxylate [INN]
Common Name English
ISONIPECOTIC ACID, 1-(3-CYANO-3,3-DIPHENYLPROPYL)-4-PHENYL-, ETHYL ESTER
Common Name English
DIPHENOXYLATE [MI]
Common Name English
DIPHENOXYLATE [VANDF]
Common Name English
DIPHENOXYLATE [HSDB]
Common Name English
1-(3-CYANO-3,3-DIPHENYLPROPYL)-4-PHENYLPIPERIDINE-4-CARBOXYLIC ACID ETHYL ESTER
Systematic Name English
Diphenoxylate [WHO-DD]
Common Name English
IDS-ND-016
Code English
4-PIPERIDINECARBOXYLIC ACID, 1-(3-CYANO-3,3-DIPHENYLPROPYL)-4-PHENYL-, ETHYL ESTER
Systematic Name English
Classification Tree Code System Code
NDF-RT N0000178374
Created by admin on Sat Dec 16 15:50:13 UTC 2023 , Edited by admin on Sat Dec 16 15:50:13 UTC 2023
NCI_THESAURUS C266
Created by admin on Sat Dec 16 15:50:13 UTC 2023 , Edited by admin on Sat Dec 16 15:50:13 UTC 2023
WHO-ATC A07DA01
Created by admin on Sat Dec 16 15:50:13 UTC 2023 , Edited by admin on Sat Dec 16 15:50:13 UTC 2023
LIVERTOX NBK548367
Created by admin on Sat Dec 16 15:50:13 UTC 2023 , Edited by admin on Sat Dec 16 15:50:13 UTC 2023
WHO-VATC QA07DA01
Created by admin on Sat Dec 16 15:50:13 UTC 2023 , Edited by admin on Sat Dec 16 15:50:13 UTC 2023
DEA NO. 9170
Created by admin on Sat Dec 16 15:50:13 UTC 2023 , Edited by admin on Sat Dec 16 15:50:13 UTC 2023
Code System Code Type Description
PUBCHEM
13505
Created by admin on Sat Dec 16 15:50:13 UTC 2023 , Edited by admin on Sat Dec 16 15:50:13 UTC 2023
PRIMARY
CAS
915-30-0
Created by admin on Sat Dec 16 15:50:13 UTC 2023 , Edited by admin on Sat Dec 16 15:50:13 UTC 2023
PRIMARY
DRUG CENTRAL
918
Created by admin on Sat Dec 16 15:50:13 UTC 2023 , Edited by admin on Sat Dec 16 15:50:13 UTC 2023
PRIMARY
NCI_THESAURUS
C62024
Created by admin on Sat Dec 16 15:50:13 UTC 2023 , Edited by admin on Sat Dec 16 15:50:13 UTC 2023
PRIMARY
DRUG BANK
DB01081
Created by admin on Sat Dec 16 15:50:13 UTC 2023 , Edited by admin on Sat Dec 16 15:50:13 UTC 2023
PRIMARY
MESH
D004157
Created by admin on Sat Dec 16 15:50:13 UTC 2023 , Edited by admin on Sat Dec 16 15:50:13 UTC 2023
PRIMARY
LACTMED
Diphenoxylate
Created by admin on Sat Dec 16 15:50:13 UTC 2023 , Edited by admin on Sat Dec 16 15:50:13 UTC 2023
PRIMARY
HSDB
3067
Created by admin on Sat Dec 16 15:50:13 UTC 2023 , Edited by admin on Sat Dec 16 15:50:13 UTC 2023
PRIMARY
ChEMBL
CHEMBL1201294
Created by admin on Sat Dec 16 15:50:13 UTC 2023 , Edited by admin on Sat Dec 16 15:50:13 UTC 2023
PRIMARY
DAILYMED
73312P173G
Created by admin on Sat Dec 16 15:50:13 UTC 2023 , Edited by admin on Sat Dec 16 15:50:13 UTC 2023
PRIMARY
IUPHAR
7164
Created by admin on Sat Dec 16 15:50:13 UTC 2023 , Edited by admin on Sat Dec 16 15:50:13 UTC 2023
PRIMARY
EPA CompTox
DTXSID8022951
Created by admin on Sat Dec 16 15:50:13 UTC 2023 , Edited by admin on Sat Dec 16 15:50:13 UTC 2023
PRIMARY
INN
850
Created by admin on Sat Dec 16 15:50:13 UTC 2023 , Edited by admin on Sat Dec 16 15:50:13 UTC 2023
PRIMARY
CHEBI
4639
Created by admin on Sat Dec 16 15:50:13 UTC 2023 , Edited by admin on Sat Dec 16 15:50:13 UTC 2023
PRIMARY
SMS_ID
100000082328
Created by admin on Sat Dec 16 15:50:13 UTC 2023 , Edited by admin on Sat Dec 16 15:50:13 UTC 2023
PRIMARY
MERCK INDEX
m4613
Created by admin on Sat Dec 16 15:50:13 UTC 2023 , Edited by admin on Sat Dec 16 15:50:13 UTC 2023
PRIMARY Merck Index
FDA UNII
73312P173G
Created by admin on Sat Dec 16 15:50:13 UTC 2023 , Edited by admin on Sat Dec 16 15:50:13 UTC 2023
PRIMARY
ECHA (EC/EINECS)
213-020-1
Created by admin on Sat Dec 16 15:50:13 UTC 2023 , Edited by admin on Sat Dec 16 15:50:13 UTC 2023
PRIMARY
EVMPD
SUB07212MIG
Created by admin on Sat Dec 16 15:50:13 UTC 2023 , Edited by admin on Sat Dec 16 15:50:13 UTC 2023
PRIMARY
RXCUI
3500
Created by admin on Sat Dec 16 15:50:13 UTC 2023 , Edited by admin on Sat Dec 16 15:50:13 UTC 2023
PRIMARY RxNorm
WIKIPEDIA
DIPHENOXYLATE
Created by admin on Sat Dec 16 15:50:13 UTC 2023 , Edited by admin on Sat Dec 16 15:50:13 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
Related Record Type Details
METABOLITE -> PARENT
Metabolite to parent drug ratio in non-uraemic human plasma.
URINE
Related Record Type Details
ACTIVE MOIETY