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QuickView for Diphenhydramine (compound)

Summary
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PubChem

PubChem Compound 174697

PubChem Compound 174697

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. show more » 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; EINECS 289-432-0 show less «

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... show more » 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), Salonpas Medicated Plaster(Borneol + Camphor + Diphenhydramine + Menthol + Methyl Salicylate + Olive Oil + Rosin + Thymol + Zinc Oxide), Benadryl Decongestant Tablets(Diphenhydramine Hydrochloride + Pseudoephedrine Hydrochloride), Children's Tylenol Allergy - D Chewable Tablets(Acetaminophen + Diphenhydramine Hydrochloride + Pseudoephedrine Hydrochloride), Dm Cough Syr(Ammonium Chloride + Dextromethorphan Hydrobromide + Diphenhydramine Hydrochloride), Contac-C Ext.Stren.Night Time Cough,Cold&Flu(Acetaminophen + Diphenhydramine Hydrochloride + Pseudoephedrine Hydrochloride), Dm Plus Cough Syrup(Ammonium Chloride + Dextromethorphan Hydrobromide + Diphenhydramine Hydrochloride), Calamine Lotion with Antih Lot(Calamine + Diphenhydramine Hydrochloride + Zinc Oxide), Calamine W Antihistamine Lotion(Calamine + Diphenhydramine Hydrochloride), Sting-Eze-Liq(Benzocaine + Camphor + Diphenhydramine Hydrochloride + Phenol), Children's Tylenol Allergy-D Suspension(Acetaminophen + Diphenhydramine Hydrochloride + Pseudoephedrine Hydrochloride), Caladryl Cream(Calamine + Diphenhydramine Hydrochloride), Contac Day & Night Sinus/Allergy Caplet(Acetaminophen + Diphenhydramine Hydrochloride + Pseudoephedrine Hydrochloride), Ambenyl Cough Syrup(Ammonium Chloride + Bromodiphenhydramine Hydrochloride + Codeine Phosphate + Diphenhydramine Hydrochloride + Potassium Guaiacol Sulphonate), Calmylin #4 Syr(Ammonium Chloride + Dextromethorphan Hydrobromide + Diphenhydramine Hydrochloride), Sting Kure - Liq(Benzocaine + Camphor + Diphenhydramine Hydrochloride + Phenol), Cough Syr W Codeine Diphenhyd Hcl & Ammon Cl(Ammonium Chloride + Codeine Phosphate + Diphenhydramine Hydrochloride), Pulmorex Expectorant Liq(Ammonium Chloride + Diphenhydramine Hydrochloride + Guaifenesin), Suppress Cough Syr W.Cod.Diphen.Hcl Amm.Chl.(Ammonium Chloride + Codeine Phosphate + Diphenhydramine Hydrochloride), Calamine Lotion W Antihistamine(Calamine + Diphenhydramine Hydrochloride) show less «
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 ... show more » 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 to treat drug-induced extrapyramidal symptoms as well as to treat mild cases of Parkinson's disease. Rather than preventing the release of histamine, as do cromolyn and nedocromil, diphenhydramine competes with free histamine for binding at HA-receptor sites. Diphenhydramine competitively antagonizes the effects of histamine on HA-receptors in the GI tract, uterus, large blood vessels, and bronchial muscle. Ethanolamine derivatives have greater anticholinergic activity than do other antihistamines, which probably accounts for the antidyskinetic action of diphenhydramine. This anticholinergic action appears to be due to a central antimuscarinic effect, which also may be responsible for its antiemetic effects, although the exact mechanism is unknown. show less «
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:

Tamsulosin	Diphenhydramine, 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.
Thioridazine	Increased risk of cardiotoxicity and arrhythmias
Triprolidine	Triprolidine 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.
Atomoxetine	Diphenhydramine, a moderate CYP2D6 inhibitor, may increase the therapeutic and adverse effects of atomoxetine by decreasing its metabolism.
Tamoxifen	Diphenhydramine may decrease the therapeutic effect of Tamoxifen by decreasing the production of active metabolites. Consider alternate therapy.

Targets

Histamine H1 receptor

Enzymes

Cytochrome P450 2D6

Cytochrome P450 1A2

Cytochrome P450 2C9

Cytochrome P450 2C19

Cytochrome P450 2C18

Cytochrome P450 2B6

Prostaglandin G/H synthase 1

Transporters

Solute carrier family 22 member 2

Solute carrier family 22 member 1

Organic cation/carnitine transporter 2