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QuickView for Diphenhydramine (compound)


PubChem
Name: Diphenhydramine
PubChem Compound ID: 174697
Description: 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.
Molecular formula: C23H29NO8
Molecular weight: 447.478 g/mol
Synonyms:
Diphenhydramine citrate; Diphenhydramine citrate (USP); Ethanamine, 2-(diphenylmethoxy)-N,N-dimethyl-, 2-hydroxy-1,2,3-propanetricarboxylate (1:1); 2-(Diphenylmethoxy)-N,N-dimethylethylamine citrate (1:1); Advil PM (TN); D03854; 58-73-1; Advil PM; 88637-37-0; (2-(Diphenylmethoxy)ethyl)dimethylammonium dihydrogen 2-hydroxypropane-1,2,3-tricarboxylate.
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DrugBank
Identification
Name: Diphenhydramine
Name (isomeric): DB01075
Drug Type: small molecule
Description: 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.
Synonyms:
Diphenhydramine Salicylate; Diphenhydramine Hcl; Diphenhydramine Base; Diphenylhydramine
Brand: Hydramine, Compoz, Benzhydraminum, Medidryl, Dormarex 2, Amidryl, Difenidramina, Sleep-Eze D, Benadryl Preservative Free, Bagodryl, Diabenyl, Vena, Benodin, Benapon, Twilite Caplets, Bena, Histaxin, Banophen, Syntedril, Difedryl, Nytol Quickgels, Allergeval, Ben-Allergin, Benzhydroamina, Benzantine, Allerdryl, Nausen, Sominex, Benzhydramine, Belix, Antistominum, Diphenhist, Benadrin, Ibiodral, Allergical, Silphen, Etanautine, Betramin, Dihidral, Baramine, Nervine Nighttime Sleep-Aid, Difenhydramin, Dimedryl, Dermistina, Desentol, Diphantine, Benodine, Benadryl Allergy, Torinal, Dibondrin, Siladryl, Unisom Sleepgels Maximum Strength, Aller-Med, Novamina, Benachlor, Automin, Hyrexin, Debendrin, Drylistan, Mephadryl, Benadryl, Dimedrol, Allermax Caplets, Allergan B, Dryistan, Benzhydryl, Benylin, Allergin, Diabylen, Vicks Formula 44, Allergina, Dibendrin, Alledryl, Ambodryl, Dermodrin, Genahist, Probedryl, Nytol Quickcaps, Allergival, Rigidyl, Soverin, Dabylen, Beldin, Diphen Cough, Dibenil, Diphenhist Captabs, Dylamon, Restamin, Sleep-Eze D Extra Strength, Aleryl, Banophen Caplets, Rigidil, Benzhydril, Diphen, Antitussive, Antomin, Benylan, Syntodril, Hyadrine
Brand name mixture:
Dm Syrup(Ammonium Chloride + Dextromethorphan Hydrobromide + Diphenhydramine Hydrochloride), Caladryl Lotion(Calamine + Diphenhydramine Hydrochloride), Sinutab N.T. Regular Strength Caplets(Acetaminophen + Diphenhydramine Hydrochloride + Pseudoephedrine Hydrochloride), Bye Bye Bite Lot(Benzocaine + Diphenhydramine Hydrochloride + Menthol), Salon...
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Category: Antidyskinetics, Ethanolamine Derivatives, Hypnotics and Sedatives, Histamine H1 Antagonists, Anesthetics, Antipruritics, Antiparkinson Agents, Antiemetics, Anti-Allergic Agents, Antitussives, Anesthetics, Local
CAS number: 58-73-1
Pharmacology
Indication: For the treatment of symptoms associated with Vertigo/Meniere's disease, nausea and vomiting, motion sickness and insect bite.
Pharmacology:
Diphenhydramine is an antihistamine of the ethanolamine class. Ethanolamine antihistamines have significant antimuscarinic activity and produce marked sedation in most patients. In addition to the usual allergic symptoms, the drug also treats irritant cough and nausea, vomiting, and vertigo associated with motion sickness. It also is used commonly ...
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Mechanism of Action: 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.
Absorption: Quickly absorbed with maximum activity occurring in approximately one hour.
Protein binding: 98 to 99%
Biotransformation: 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
Toxicity: LD50=500 mg/kg (orally in rats). Considerable overdosage can lead to myocardial infarction (heart attack), serious ventricular dysrhythmias, coma and death.
Affected organisms: Humans and other mammals
Interactions
Food interaction:
Avoid alcohol.
Take with food.
Drug interaction:
TamsulosinDiphenhydramine, a CYP2D6 inhibitor, may decrease the metabolism and clearance of Tamsulosin, a CYP2D6 substrate. Monitor for changes in therapeutic/adverse effects of Tamsulosin if Diphenhydramine is initiated, discontinued, or dose changed.
ThioridazineIncreased risk of cardiotoxicity and arrhythmias
TriprolidineTriprolidine and Diphenhydramine, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Additive CNS depressant effects may also occur. Monitor for enhanced anticholinergic and CNS depressant effects.
AtomoxetineDiphenhydramine, a moderate CYP2D6 inhibitor, may increase the therapeutic and adverse effects of atomoxetine by decreasing its metabolism.
TamoxifenDiphenhydramine may decrease the therapeutic effect of Tamoxifen by decreasing the production of active metabolites. Consider alternate therapy.
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