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Details

Stereochemistry ACHIRAL
Molecular Formula C30H32N2O2.ClH
Molecular Weight 489.048
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIPHENOXYLATE HYDROCHLORIDE

SMILES

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

InChI

InChIKey=SHTAFWKOISOCBI-UHFFFAOYSA-N
InChI=1S/C30H32N2O2.ClH/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;1H

HIDE SMILES / InChI

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

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
Therapeutic response to octreotide in patients with refractory CPT-11 induced diarrhea.
2001
Small amounts of some drugs can be toxic to young children: one pill or one swallow can require aggressive treatment.
2003 Jun
Medical management of fecal incontinence.
2004 Jan
Deadly pediatric poisons: nine common agents that kill at low doses.
2004 Nov
Comparison between prospective and retrospective evaluation of Crohn's disease activity index.
2005 May
Lomotil dependence: a note of caution.
2005 Nov-Dec
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
Long-acting octreotide in the treatment of diarrhea after pelvic pouch surgery.
2006 Dec
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
Diphenoxylate hydrochloride dependency.
2007 Jul
Myasthenia gravis.
2007 Nov 6
Drug-induced diarrhea.
2007 Oct
Toward achieving optimal response: understanding and managing antidepressant side effects.
2008
Anticholinergic activity of 107 medications commonly used by older adults.
2008 Jul
[Methodological study on quality evaluation of rhubarb based on purgative bioassay].
2008 Jun
[Topic: Treating travelers' diarrhea. When should medication be given?].
2008 Jun
Bowel management for the treatment of pediatric fecal incontinence.
2009 Dec
Pharmacokinetic drug interactions of synthetic opiate analgesics.
2009 Mar-Apr
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
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 Fri Dec 15 14:59:29 UTC 2023
Edited
by admin
on Fri Dec 15 14:59:29 UTC 2023
Record UNII
W24OD7YW48
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIPHENOXYLATE HYDROCHLORIDE
EP   MART.   MI   ORANGE BOOK   USP   VANDF   WHO-DD   WHO-IP  
Common Name English
COLONAID COMPONENT DIPHENOXYLATE HYDROCHLORIDE
Common Name English
DIPHENOXYLATE HYDROCHLORIDE CII
USP-RS  
Common Name English
DIPHENOXYLATE HYDROCHLORIDE COMPONENT OF LONOX
Common Name English
LOMOTIL COMPONENT DIPHENOXYLATE HYDROCHLORIDE
Common Name English
DIPHENOXYLATE HYDROCHLORIDE COMPONENT OF COLONAID
Common Name English
DIPHENOXYLATE HYDROCHLORIDE [ORANGE BOOK]
Common Name English
LOGEN COMPONENT DIPHENOXYLATE HYDROCHLORIDE
Common Name English
DIPHENOXYLATE HYDROCHLORIDE [MI]
Common Name English
DIPHENOXYLATE HYDROCHLORIDE COMPONENT OF LOMOTIL
Common Name English
DIPHENOXYLATE HYDROCHLORIDE COMPONENT OF LO-TROL
Common Name English
DIPHENOXYLATE HYDROCHLORIDE [EP MONOGRAPH]
Common Name English
R-1132 (ANTIPERISTALTIC)
Code English
LONOX COMPONENT DIPHENOXYLATE HYDROCHLORIDE
Common Name English
DIPHENOXYLATE HYDROCHLORIDE [VANDF]
Common Name English
LO-TROL COMPONENT DIPHENOXYLATE HYDROCHLORIDE
Common Name English
DIPHENOXYLATI HYDROCHLORIDUM [WHO-IP LATIN]
Common Name English
DIPHENOXYLATE HYDROCHLORIDE [USP-RS]
Common Name English
DIPHENOXYLATE HYDROCHLORIDE [WHO-IP]
Common Name English
DIPHENOXYLATE HCL
Common Name English
DI-ATRO COMPONENT DIPHENOXYLATE HYDROCHLORIDE
Common Name English
LOMANATE COMPONENT DIPHENOXYLATE HYDROCHLORIDE
Common Name English
ETHYL 1-(3-CYANO-3,3-DIPHENYLPROPYL)-4-PHENYLISONIPECOTATE MONOHYDROCHLORIDE
Systematic Name English
ISONIPECOTIC ACID, 1-(3-CYANO-3,3-DIPHENYLPROPYL)-4-PHENYL-, ETHYL ESTER, MONOHYDROCHLORIDE
Systematic Name English
DIPHENOXYLATE HYDROCHLORIDE COMPONENT OF LOMANATE
Common Name English
Diphenoxylate hydrochloride [WHO-DD]
Common Name English
DIPHENOXYLATE HYDROCHLORIDE COMPONENT OF LOW-QUEL
Common Name English
4-PIPERIDINECARBOXYLIC ACID, 1-(3-CYANO-3,3-DIPHENYLPROPYL)-4-PHENYL-, ETHYL ESTER, MONOHYDROCHLORIDE
Common Name English
DIPHENOXYLATE HYDROCHLORIDE COMPONENT OF LOGEN
Common Name English
DIPHENOXYLATE HYDROCHLORIDE [MART.]
Common Name English
DIPHENOXYLATE HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
LOW-QUEL COMPONENT DIPHENOXYLATE HYDROCHLORIDE
Common Name English
DIPHENOXYLATE HYDROCHLORIDE COMPONENT OF DI-ATRO
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C266
Created by admin on Fri Dec 15 14:59:29 UTC 2023 , Edited by admin on Fri Dec 15 14:59:29 UTC 2023
Code System Code Type Description
NCI_THESAURUS
C28995
Created by admin on Fri Dec 15 14:59:29 UTC 2023 , Edited by admin on Fri Dec 15 14:59:29 UTC 2023
PRIMARY
EPA CompTox
DTXSID3047843
Created by admin on Fri Dec 15 14:59:29 UTC 2023 , Edited by admin on Fri Dec 15 14:59:29 UTC 2023
PRIMARY
SMS_ID
100000089955
Created by admin on Fri Dec 15 14:59:29 UTC 2023 , Edited by admin on Fri Dec 15 14:59:29 UTC 2023
PRIMARY
RS_ITEM_NUM
1219008
Created by admin on Fri Dec 15 14:59:29 UTC 2023 , Edited by admin on Fri Dec 15 14:59:29 UTC 2023
PRIMARY
CAS
3810-80-8
Created by admin on Fri Dec 15 14:59:29 UTC 2023 , Edited by admin on Fri Dec 15 14:59:29 UTC 2023
PRIMARY
PUBCHEM
19650
Created by admin on Fri Dec 15 14:59:29 UTC 2023 , Edited by admin on Fri Dec 15 14:59:29 UTC 2023
PRIMARY
EVMPD
SUB01776MIG
Created by admin on Fri Dec 15 14:59:29 UTC 2023 , Edited by admin on Fri Dec 15 14:59:29 UTC 2023
PRIMARY
ECHA (EC/EINECS)
223-287-6
Created by admin on Fri Dec 15 14:59:29 UTC 2023 , Edited by admin on Fri Dec 15 14:59:29 UTC 2023
PRIMARY
CHEBI
59784
Created by admin on Fri Dec 15 14:59:29 UTC 2023 , Edited by admin on Fri Dec 15 14:59:29 UTC 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
DIPHENOXYLATE HYDROCHLORIDE
Created by admin on Fri Dec 15 14:59:29 UTC 2023 , Edited by admin on Fri Dec 15 14:59:29 UTC 2023
PRIMARY Description:A white or almost white, crystalline powder; odourless.Solubility: Sparingly soluble in water, acetone R and ethanol (~750 g/l) TS; practically insoluble in ether R.Category: Antidiarrhoeal drug.Storage: Diphenoxylate hydrochloride should be kept in a well-closed container.Requirements:Definition: Diphenoxylate hydrochloride contains not less than 98.0% and not more than 101.0% of C30H32N2O2,HCl, calculated with reference to the dried substance.
ChEMBL
CHEMBL1201294
Created by admin on Fri Dec 15 14:59:29 UTC 2023 , Edited by admin on Fri Dec 15 14:59:29 UTC 2023
PRIMARY
MERCK INDEX
m4613
Created by admin on Fri Dec 15 14:59:29 UTC 2023 , Edited by admin on Fri Dec 15 14:59:29 UTC 2023
PRIMARY Merck Index
DRUG BANK
DBSALT000809
Created by admin on Fri Dec 15 14:59:29 UTC 2023 , Edited by admin on Fri Dec 15 14:59:29 UTC 2023
PRIMARY
RXCUI
82005
Created by admin on Fri Dec 15 14:59:29 UTC 2023 , Edited by admin on Fri Dec 15 14:59:29 UTC 2023
PRIMARY RxNorm
DAILYMED
W24OD7YW48
Created by admin on Fri Dec 15 14:59:29 UTC 2023 , Edited by admin on Fri Dec 15 14:59:29 UTC 2023
PRIMARY
FDA UNII
W24OD7YW48
Created by admin on Fri Dec 15 14:59:29 UTC 2023 , Edited by admin on Fri Dec 15 14:59:29 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
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IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
ACTIVE MOIETY