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
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
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 |
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 |
---|---|---|
Therapeutic response to octreotide in patients with refractory CPT-11 induced diarrhea. | 2001 |
|
Behind the counter: pharmacies and dispensing patterns of pharmacy attendants in Karachi. | 2001 Apr |
|
Treatment options for fecal incontinence. | 2001 Jan |
|
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 |
|
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 |
|
A randomized controlled trial of mycophenolate mofetil in patients with IgA nephropathy [ISRCTN62574616]. | 2004 Mar 25 |
|
Acute anticholinergic poisoning in children. | 2005 Dec |
|
Tissue distribution of loperamide and N-desmethylloperamide following a fatal overdose. | 2005 Oct |
|
Treatment of diarrhea in patients with inflammatory bowel disease: concepts and cautions. | 2007 |
|
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 |
|
Hashish body packing: a case report. | 2009 |
|
Inappropriate prescribing in the hospitalized elderly patient: defining the problem, evaluation tools, and possible solutions. | 2010 Apr 7 |
|
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
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 16 15:51:21 UTC 2022
by
admin
on
Fri Dec 16 15:51:21 UTC 2022
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Record UNII |
W24OD7YW48
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C266
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C28995
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DTXSID3047843
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1219008
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3810-80-8
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19650
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SUB01776MIG
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223-287-6
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59784
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DIPHENOXYLATE HYDROCHLORIDE
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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. | ||
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CHEMBL1201294
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M4613
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DBSALT000809
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82005
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W24OD7YW48
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W24OD7YW48
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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ACTIVE MOIETY |