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
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
DescriptionSources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=f170584a-1072-4fd7-b1dc-6756703483b9Curator's Comment: description was created based on several sources, including ISBN-13: 978-0323055932
Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=f170584a-1072-4fd7-b1dc-6756703483b9
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
Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=f170584a-1072-4fd7-b1dc-6756703483b9
Curator's Comment: At high doses it exhibits codeine-like subjective effects.
Originator
Sources: https://www.google.com/patents/US2898340
Curator's Comment: ISBN: 978-0-471-89980-8
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: P35372|||G8XRH8|||Q5TDA1|||Q9UN57 Gene ID: 4988.0 Gene Symbol: OPRM1 Target Organism: Homo sapiens (Human) Sources: ISBN-13: 978-0323055932 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | LOMOTIL Approved UseLomotil is effective as adjunctive therapy in the management of diarrhea. Launch Date-2.93414404E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/5026379 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/5026379 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
15.5% |
DIPHENOXYLATE unknown | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse 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 Health Status: unhealthy Sources: |
|
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 Health Status: unhealthy Sources: |
Other AEs: Drug dependence... Other AEs: Drug dependence Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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 Health Status: unhealthy Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: abstract |
minor | yes (co-administration study) Comment: diphenoxylate decreased omeprazole AUC and Cmax Page: abstract |
||
Page: 18805.0 |
no | |||
Page: 18805.0 |
no | |||
Page: 18805.0 |
no | |||
Page: 18805.0 |
no | no (co-administration study) Comment: diphenoxylate had no effect on buproprion AUC and Cmax Page: 18805.0 |
||
Page: 18805.0 |
no | no (co-administration study) Comment: diphenoxylate had no effect on metroprolol AUC and Cmax Page: 18805.0 |
||
Page: 18805.0 |
no | no (co-administration study) Comment: diphenoxylate had no effect on testosterone AUC and Cmax Page: 18805.0 |
||
Page: 136.0 |
unlikely | |||
Page: abstract |
yes | yes (co-administration study) Comment: diphenoxylate decreased phenacetin AUC and Cmax Page: abstract |
||
Page: abstract |
yes | yes (co-administration study) Comment: diphenoxylate decreased tolbutamide AUC and Cmax Page: abstract |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 135.0 |
no |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: abstract |
PubMed
Title | Date | PubMed |
---|---|---|
[Irritable colon]. | 2001 Aug 20 |
|
Irritable bowel syndrome: update on pathogenesis and management. | 2002 Jan-Mar |
|
The efficacy of octreotide in the therapy of acute radiation-induced diarrhea: a randomized controlled study. | 2002 Sep 1 |
|
Drug treatment for faecal incontinence in adults. | 2003 |
|
Antidiarrhoeal effects of methanolic root extract of Hemidesmus indicus (Indian sarsaparilla)--an in vitro and in vivo study. | 2003 Apr |
|
Protective effect of Arque-Ajeeb on acute experimental diarrhoea in rats. | 2004 Jul 6 |
|
Deadly pediatric poisons: nine common agents that kill at low doses. | 2004 Nov |
|
[Treatment of 64 cases with compound diphenoxylate poisoning with naloxone]. | 2004 Sep |
|
Evolutionary explanations in medical and health profession courses: are you answering your students' "why" questions? | 2005 May 10 |
|
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 |
|
Anticholinergic activity of 107 medications commonly used by older adults. | 2008 Jul |
|
Long-term outcome of in-patients with substance use disorders: A study from North India. | 2008 Oct |
|
Antimotility agents for chronic diarrhoea in people with HIV/AIDS. | 2008 Oct 8 |
|
Hashish body packing: a case report. | 2009 |
|
Bowel management for the treatment of pediatric fecal incontinence. | 2009 Dec |
|
Management of side effects associated with sunitinib therapy for patients with renal cell carcinoma. | 2009 Feb 18 |
|
[Roles of enteric nervous system neurotransmitters and interstitial cells of Cajal in the colon in slow transit constipation in rats]. | 2009 Jun |
|
Pretreatment with diphenoxylate hydrochloride/atropine sulfate (Lomotil) does not decrease physiologic bowel FDG activity on PET/CT scans of the abdomen and pelvis. | 2009 Mar-Apr |
|
Managing toxicities and optimal dosing of targeted drugs in advanced kidney cancer. | 2009 May |
|
Re: "Are one or two dangerous? Diphenoxylate-atropine exposure in toddlers". | 2010 Apr |
|
Inappropriate prescribing in the hospitalized elderly patient: defining the problem, evaluation tools, and possible solutions. | 2010 Apr 7 |
|
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method. | 2010 Dec |
|
Antidiarrhoeal activity of carbazole alkaloids from Murraya koenigii Spreng (Rutaceae) seeds. | 2010 Jan |
|
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
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Classification Tree | Code System | Code | ||
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NDF-RT |
N0000178374
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NCI_THESAURUS |
C266
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WHO-ATC |
A07DA01
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LIVERTOX |
NBK548367
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WHO-VATC |
QA07DA01
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DEA NO. |
9170
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D004157
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Diphenoxylate
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3067
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m4613
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73312P173G
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213-020-1
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SUB07212MIG
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3500
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DIPHENOXYLATE
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ACTIVE MOIETY
METABOLITE (PARENT)
SALT/SOLVATE (PARENT)