Record Information |
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Version | 2.0 |
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Creation Date | 2009-07-21 20:28:19 UTC |
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Update Date | 2014-12-24 20:25:54 UTC |
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Accession Number | T3D2978 |
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Identification |
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Common Name | Diphenoxylate |
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Class | Small Molecule |
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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. |
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Compound Type | - Amine
- Analgesic, Opioid
- Antidiarrheal
- Antiperistaltic Agent
- Drug
- Ester
- Ether
- Food Toxin
- Metabolite
- Narcotic
- Nitrile
- Organic Compound
- Synthetic Compound
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Chemical Structure | |
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Synonyms | Synonym | 1-(3-Cyano-3,3-diphenylpropyl)-4-phenyl-isonipecotic acid ethyl ester | 2,2-Diphenyl-4-(4-carbethoxy-4-phenylpiperidino)butyronitrile | 4-Ethoxycarbonyl-alpha,alpha,4-triphenyl-1-piperidinebutyronitrile | Dea No. 9170 | Difenossilato | Difenoxilato | Diphenoxalate | Diphenoxylatum | Diphenoxylic acid | Ethyl 1-(3-cyano-3,3-diphenylpropyl)-4-phenyl-4-piperidinecarboxylate | Ethyl 1-(3-cyano-3,3-diphenylpropyl)-4-phenylisonipecotate | Lomotil |
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Chemical Formula | C30H32N2O2 |
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Average Molecular Mass | 452.587 g/mol |
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Monoisotopic Mass | 452.246 g/mol |
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CAS Registry Number | 915-30-0 |
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IUPAC Name | ethyl 1-(3-cyano-3,3-diphenylpropyl)-4-phenylpiperidine-4-carboxylate |
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Traditional Name | diphenoxylate |
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SMILES | CCOC(=O)C1(CCN(CCC(C#N)(C2=CC=CC=C2)C2=CC=CC=C2)CC1)C1=CC=CC=C1 |
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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 |
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InChI Key | InChIKey=HYPPXZBJBPSRLK-UHFFFAOYSA-N |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Benzene and substituted derivatives |
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Sub Class | Diphenylacetonitriles |
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Direct Parent | Diphenylacetonitriles |
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Alternative Parents | |
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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
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Molecular Framework | Aromatic heteromonocyclic compounds |
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External Descriptors | |
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Biological Properties |
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Status | Detected and Not Quantified |
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Origin | Exogenous |
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Cellular Locations | |
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Biofluid Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | Not Available |
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Applications | |
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Biological Roles | Not Available |
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Chemical Roles | Not Available |
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Physical Properties |
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State | Solid |
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Appearance | White powder. |
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Experimental Properties | Property | Value |
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Melting Point | 220.5-222°C | Boiling Point | Not Available | Solubility | 800 mg/L (at 25°C) | LogP | 6.3 |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | Deposition Date | View |
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GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0002-6591000000-e04da61bbde263b104e3 | 2017-09-12 | View Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0002-6591000000-e04da61bbde263b104e3 | 2018-05-18 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-004i-1129000000-033454565afde0495c58 | 2017-09-01 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0udi-0000900000-e2841fe11576faaa404e | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0udi-0000900000-f16aa8a859221ed0173c | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0udi-0220900000-38d21080081c6d144498 | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0ap0-2920000000-ed4957b090e4b3a6f38d | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0aor-2900000000-becb90ead622a0131fdb | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - , positive | splash10-0udi-0210900000-f33819852c9168d0f8a0 | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-0ap0-2930000000-27b1d68dee5988eaa135 | 2021-09-20 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - 30V, Positive | splash10-0udi-0220900000-eb48236d047d8482c9db | 2021-09-20 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-0000900000-e2841fe11576faaa404e | 2021-09-20 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-0udi-0000900000-f16aa8a859221ed0173c | 2021-09-20 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - 35V, Positive | splash10-0ufr-1222900000-c125937f2ff362112070 | 2021-09-20 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - 50V, Positive | splash10-0aor-2900000000-b973c5ffabd9b4d287ca | 2021-09-20 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - 50V, Positive | splash10-0aor-2900000000-5fa40194a7aea2fbeaff | 2021-09-20 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - 30V, Positive | splash10-0udi-0220900000-38d21080081c6d144498 | 2021-09-20 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-0ap0-2920000000-ed4957b090e4b3a6f38d | 2021-09-20 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - 50V, Positive | splash10-0aor-2900000000-becb90ead622a0131fdb | 2021-09-20 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-0ap0-2930000000-315293eb975bc2a18e68 | 2021-09-20 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-0011900000-4f997e63c9c65b9c3cf3 | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-05g0-0344900000-56fc8f46c973ef960e51 | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00di-0971000000-b83c6e7e52cb3ee497b0 | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-0000900000-ec078fed32982bfba96e | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0ufr-2343900000-eaa7ee09954f3184115d | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-116u-3941000000-217be57f7c4a4f20f18a | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-0003900000-ed80455eb1b0d171468d | 2021-10-11 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0ugi-0009100000-945c8f0ee309cb0cc7df | 2021-10-11 | View Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-0002-2390000000-0d133bb29f340639db02 | 2014-09-20 | View Spectrum |
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Toxicity Profile |
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Route of Exposure | Oral. 90% |
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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. |
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Metabolism | Hepatic
Half Life: 12-14 hours |
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Toxicity Values | Not Available |
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Lethal Dose | Not Available |
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Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
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Uses/Sources | For as adjunctive therapy in the management of diarrhea |
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Minimum Risk Level | Not Available |
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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. |
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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 |
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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) |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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External Links |
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DrugBank ID | DB01081 |
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HMDB ID | HMDB15213 |
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PubChem Compound ID | 13505 |
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ChEMBL ID | CHEMBL1201294 |
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ChemSpider ID | 12919 |
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KEGG ID | C07872 |
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UniProt ID | Not Available |
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OMIM ID | |
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ChEBI ID | 4639 |
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BioCyc ID | Not Available |
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CTD ID | Not Available |
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Stitch ID | Diphenoxylate |
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PDB ID | Not Available |
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ACToR ID | Not Available |
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Wikipedia Link | Diphenoxylate |
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References |
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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. |
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MSDS | Link |
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General References | - Wishart DS, Knox C, Guo AC, Cheng D, Shrivastava S, Tzur D, Gautam B, Hassanali M: DrugBank: a knowledgebase for drugs, drug actions and drug targets. Nucleic Acids Res. 2008 Jan;36(Database issue):D901-6. Epub 2007 Nov 29. [18048412 ]
- RxList: The Internet Drug Index (2009). [Link]
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Gene Regulation |
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Up-Regulated Genes | Not Available |
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Down-Regulated Genes | Not Available |
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