ContaminantDB: Diphenoxylate

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (3)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:28:19 UTC

Update Date

2026-03-26 20:04:12 UTC

Accession Number

CHEM002340

Identification

Common Name

Diphenoxylate

Class

Small Molecule

Description

A meperidine congener used as an antidiarrheal, usually in combination with atropine. At high doses, it acts like morphine. Its unesterified metabolite difenoxin has similar properties and is used similarly. It has little or no analgesic activity. This medication is classified as a Schedule V under the Controlled Substances Act by the Food and Drug Administration (FDA) and the DEA in the United States when used in preparations. When diphenoxylate is used alone, it is classified as a Schedule II.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins

Contaminant Type

Amine
Analgesic, Opioid
Antidiarrheal
Antiperistaltic Agent
Drug
Ester
Ether
Food Toxin
Metabolite
Narcotic
Nitrile
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-(3-Cyano-3,3-diphenylpropyl)-4-phenyl-isonipecotic acid ethyl ester	ChEBI
2,2-Diphenyl-4-(4-carbethoxy-4-phenylpiperidino)butyronitrile	ChEBI
4-Ethoxycarbonyl-alpha,alpha,4-triphenyl-1-piperidinebutyronitrile	ChEBI
Difenoxilato	ChEBI
Diphenoxylatum	ChEBI
Ethyl 1-(3-cyano-3,3-diphenylpropyl)-4-phenyl-4-piperidinecarboxylate	ChEBI
Ethyl 1-(3-cyano-3,3-diphenylpropyl)-4-phenylisonipecotate	ChEBI
1-(3-Cyano-3,3-diphenylpropyl)-4-phenyl-isonipecotate ethyl ester	Generator
4-Ethoxycarbonyl-a,a,4-triphenyl-1-piperidinebutyronitrile	Generator
4-Ethoxycarbonyl-α,α,4-triphenyl-1-piperidinebutyronitrile	Generator
Ethyl 1-(3-cyano-3,3-diphenylpropyl)-4-phenyl-4-piperidinecarboxylic acid	Generator
Ethyl 1-(3-cyano-3,3-diphenylpropyl)-4-phenylisonipecotic acid	Generator
Diphenoxylic acid	Generator
Dea no. 9170	HMDB
Difenossilato	HMDB
Diphenoxalate	HMDB
Diphenoxylate monohydrochloride	HMDB
Monohydrochloride, diphenoxylate	HMDB
Hydrochloride, diphenoxylate	HMDB
Diphenoxylate hydrochloride	HMDB

Chemical Formula

C₃₀H₃₂N₂O₂

Average Molecular Mass

452.587 g/mol

Monoisotopic Mass

452.246 g/mol

CAS Registry Number

915-30-0

IUPAC Name

ethyl 1-(3-cyano-3,3-diphenylpropyl)-4-phenylpiperidine-4-carboxylate

Traditional Name

diphenoxylate

SMILES

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

InChI Identifier

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

InChI Key

HYPPXZBJBPSRLK-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as diphenylacetonitriles. These are cyclic aromatic compounds containing a diphenylacetonitrile moiety, which consists of a diphenylmethane linked to and acetonitrile to form 2,2-diphenylacetonitrile.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylacetonitriles

Direct Parent

Diphenylacetonitriles

Alternative Parents

Substituents

Diphenylacetonitrile
Diphenylmethane
Phenylpiperidine
Piperidinecarboxylic acid
Aralkylamine
Piperidine
Amino acid or derivatives
Carboxylic acid ester
Tertiary amine
Tertiary aliphatic amine
Nitrile
Carbonitrile
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Azacycle
Hydrocarbon derivative
Organic oxide
Amine
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Organopnictogen compound
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

ethyl ester (CHEBI:4639 )
tertiary amine (CHEBI:4639 )
nitrile (CHEBI:4639 )
piperidinecarboxylate ester (CHEBI:4639 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

antidiarrhoeal drug

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	220.5-222°C
Boiling Point	Not Available
Solubility	800 mg/L (at 25°C)

Predicted Properties

Property	Value	Source
Water Solubility	0.0015 g/L	ALOGPS
logP	5.74	ALOGPS
logP	5.88	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Basic)	8.5	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	53.33 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	146.76 m³·mol⁻¹	ChemAxon
Polarizability	51.58 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0002-6591000000-e04da61bbde263b104e3	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0002-6591000000-e04da61bbde263b104e3	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-1129000000-033454565afde0495c58	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0udi-0000900000-e2841fe11576faaa404e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0udi-0000900000-f16aa8a859221ed0173c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0udi-0220900000-38d21080081c6d144498	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0ap0-2920000000-ed4957b090e4b3a6f38d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0aor-2900000000-becb90ead622a0131fdb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0udi-0210900000-f33819852c9168d0f8a0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0ap0-2930000000-27b1d68dee5988eaa135	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0udi-0220900000-eb48236d047d8482c9db	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0000900000-e2841fe11576faaa404e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0000900000-f16aa8a859221ed0173c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0ufr-1222900000-c125937f2ff362112070	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-0aor-2900000000-b973c5ffabd9b4d287ca	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-0aor-2900000000-5fa40194a7aea2fbeaff	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0udi-0220900000-38d21080081c6d144498	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0ap0-2920000000-ed4957b090e4b3a6f38d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-0aor-2900000000-becb90ead622a0131fdb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0ap0-2930000000-315293eb975bc2a18e68	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0011900000-4f997e63c9c65b9c3cf3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05g0-0344900000-56fc8f46c973ef960e51	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-0971000000-b83c6e7e52cb3ee497b0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0000900000-ec078fed32982bfba96e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ufr-2343900000-eaa7ee09954f3184115d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-116u-3941000000-217be57f7c4a4f20f18a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0003900000-ed80455eb1b0d171468d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ugi-0009100000-945c8f0ee309cb0cc7df	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0002-2390000000-0d133bb29f340639db02	Spectrum

Toxicity Profile

Route of Exposure

Oral. 90%

Mechanism of Toxicity

Diphenoxylate is an opiate receptor agonists that stimulate mu receptors in GI to decrease the peristalsis and constrict the sphincters. Diphenoxylate has a direct effect on circular smooth muscle of the bowel, that conceivably results in segmentation and prolongation of gastrointestinal transit time. The clinical antidiarrheal action of diphenoxylate may thus be a consequence of enhanced segmentation that allows increased contact of the intraluminal contents with the intestinal mucosa.

Metabolism

Hepatic Half Life: 12-14 hours

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

For as adjunctive therapy in the management of diarrhea

Minimum Risk Level

Not Available

Health Effects

Medical problems can include congested lungs, liver disease, tetanus, infection of the heart valves, skin abscesses, anemia and pneumonia. Death can occur from overdose.

Symptoms

Coma, dry skin and mucous membranes, enlarged pupils of the eyes, extremely high body temperature, flushing, involuntary eyeball movement, lower than normal muscle tone, pinpoint pupils, rapid heartbeat, restlessness, sluggishness, suppressed breathing

Treatment

In the event of overdose, induction of vomiting, gastric lavage, establishment of a patent airway, and possibly mechanically assisted respiration are advised. in vitro and animal studies indicate that activated charcoal may significantly decrease the bioavailability of diphenoxylate. In noncomatose patients, a slurry of 100 g of activated charcoal can be administered immediately after the induction of vomiting or gastric lavage. A pure narcotic antagonist (eg, naloxone) should be used in the treatment of respiratory depression caused by Lomotil. When a narcotic antagonist is administered intravenously, the onset of action is generally apparent within two minutes. It may also be administered subcutaneously or intramuscularly, providing a slightly less rapid onset of action but a more prolonged effect. (2)

Concentrations

Not Available

External Links

DrugBank ID

DB01081

HMDB ID

HMDB0015213

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Janssen, P.A.J.; U.S.Patent 2,898,340; August 4,1959.
Dryden, H.L. Jr. and Erickson, R.A.; U.S. Patent 4,086,234; April 25,1978; assigned to
G.D.Searle & Co.

MSDS

Link

General References

Not Available

Diphenoxylate (CHEM002340)

Structure for CHEM002340: Diphenoxylate