<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">3018</id>
  <title>T3D2976</title>
  <common-name>Diphenhydramine</common-name>
  <description>Diphenhydramine is a histamine H1 antagonist used as an antiemetic, antitussive, for dermatoses and pruritus, for hypersensitivity reactions, as a hypnotic, an antiparkinson, and as an ingredient in common cold preparations. It has some undesired antimuscarinic and sedative effects. -- Pubchem; Pseudoephedrine is a phenethylamine, and an isomer of ephedrine. Pseudoephedrine is the International Nonproprietary Name (INN) of the (1S,2S)- diastereomer of ephedrine (which has 1R,2S- configuration). Other names are (+)-pseudoephedrine and D-pseudoephedrine (Reynolds, 1989). The enantiomer (-)-(1R,2R)-Pseudoephedrine has fewer side-effects, fewer central nervous system (CNS) stimulatory effects, does not reduce to d-methamphetamine, yet retains its efficacy as a decongestant. However, the patent holder for (-)-Pseudoephedrine (Pfizer/Warner-Lambert) has not yet sought or received government approval for its sale to the public.(US Patent 6,495,529); Treatment for urinary incontinence is an unlabeled use for these medications. Unlabeled use means doctors can use the medication to treat a condition other than that for which it was first approved by the U.S. Food and Drug Administration (FDA). These medications are approved by the FDA for the treatment of nasal congestion caused by colds or allergies. However it has also been successful in treating stress incontinence by increasing the pressure (tension) exerted by the muscles of the bladder neck and the urethra, which helps retain the urine within the bladder. Despite being one of the oldest antihistamines on the market, it is by and large the most effective antihistamine available, either by prescription or over-the-counter, and has been shown to exceed the effectiveness of even the latest prescription drugs. Consequently, it is frequently used when an allergic reaction requires fast, effective reversal of the (often dangerous) effects of a massive histamine release. However, it is not always the drug of choice for treating allergies. Like many other first generation antihistamines, is also a potent anticholinergic agent. This leads to profound drowsiness as a very common side-effect, along with the possibilities of motor impairment (ataxia), dry mouth and throat, flushed skin, rapid or irregular heartbeat (tachycardia), blurred vision at near point due to lack of accommodation (cycloplegia), abnormal sensitivity to bright light (photophobia), pupil dilatation, urinary retention, constipation, difficulty concentrating, short-term memory loss, visual disturbances, hallucinations, confusion, erectile dysfunction, and delirium. -- Wikipedia;.</description>
  <cas>58-73-1</cas>
  <pubchem-id>3100</pubchem-id>
  <chemical-formula>C17H21NO</chemical-formula>
  <weight>255.162310</weight>
  <appearance>White powder.</appearance>
  <melting-point>161-162°C</melting-point>
  <boiling-point>150-165°C at 2.00E+00 mm Hg</boiling-point>
  <density nil="true"/>
  <solubility>3060 mg/L (at 37°C)</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Oral; topical ; parenteral(intramuscular or intravenous injection). Quickly absorbed with maximum activity occurring in approximately one hour.</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Diphenhydramine competes with free histamine for binding at HA-receptor sites. This antagonizes the effects of histamine on HA-receptors, leading to a reduction of the negative symptoms brought on by histamine HA-receptor binding.</mechanism-of-toxicity>
  <metabolism>Hepatic and renal
Route of Elimination: Little, if any, is excreted unchanged in the urine; most appears as the degradation products of metabolic transformation in the liver, which are almost completely excreted within 24 hours.
Half Life: 1-4 hours</metabolism>
  <toxicity>LD50: 500 mg/kg (Oral, Rat) (A308)</toxicity>
  <lethaldose></lethaldose>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>For the treatment of symptoms associated with Vertigo/Meniere's disease, nausea and vomiting, motion sickness and insect bite.</use-source>
  <min-risk-level></min-risk-level>
  <health-effects>They cause slurred speech, disorientation and "drunken" behavior. They are physically and psychologically addictive.</health-effects>
  <symptoms>Considerable overdosage can lead to myocardial infarction (heart attack), serious ventricular dysrhythmias, coma and death.</symptoms>
  <treatment>There is no specific antidote for diphenhydramine toxicity, but the anticholinergic syndrome has been treated with physostigmine for severe delirium or tachycardia. Benzodiazepines may be administered to decrease the likelihood of psychosis, agitation, and seizures in patients who are prone to these symptoms.</treatment>
  <created-at type="dateTime">2009-07-21T20:28:18Z</created-at>
  <updated-at type="dateTime">2026-03-31T19:08:39Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Diphenhydramine</wikipedia>
  <uniprot-id></uniprot-id>
  <kegg-compound-id>C06960</kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id>4636</chebi-id>
  <biocyc-id>CPD-10890</biocyc-id>
  <ctd-id></ctd-id>
  <stitch-id>Diphenylhydramine  </stitch-id>
  <drugbank-id>DB01075</drugbank-id>
  <pdb-id>2PM</pdb-id>
  <actor-id></actor-id>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>CN(C)CCOC(C1=CC=CC=C1)C1=CC=CC=C1</moldb-smiles>
  <moldb-formula>C17H21NO</moldb-formula>
  <moldb-inchi>InChI=1S/C17H21NO/c1-18(2)13-14-19-17(15-9-5-3-6-10-15)16-11-7-4-8-12-16/h3-12,17H,13-14H2,1-2H3</moldb-inchi>
  <moldb-inchikey>ZZVUWRFHKOJYTH-UHFFFAOYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">255.3547</moldb-average-mass>
  <moldb-mono-mass type="decimal">255.162314299</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>3.27</logp>
  <hmdb-id>HMDB01927</hmdb-id>
  <chembl-id>CHEMBL657</chembl-id>
  <chemspider-id>2989</chemspider-id>
  <structure-image-file-name nil="true"/>
  <structure-image-content-type nil="true"/>
  <structure-image-file-size type="integer" nil="true"/>
  <structure-image-updated-at type="dateTime" nil="true"/>
  <biodb-id nil="true"/>
  <synthesis-reference>&lt;p&gt;Alison B. Lukacsko, Joseph J. Piala, &amp;#8220;Effect of a combination of a terbutaline, diphenhydramine and ranitidine composition on gastrointestinal injury produced by nonsteroidal anti-inflammatory compositions.&amp;#8221; U.S. Patent US5260333, issued December, 1983.&lt;/p&gt;</synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM002338</chemdb-id>
  <dsstox-id>DTXSID4022949</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00010439</susdat-id>
  <iupac>[2-(diphenylmethoxy)ethyl]dimethylamine</iupac>
</compound>
