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QuickView for Doxylamine (compound)

Summary
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PubChem

PubChem Compound 3162

PubChem Compound 3162

Name:	Doxylamine
PubChem Compound ID:	3162
Description:	Histamine H1 antagonist with pronounced sedative properties. It is used in allergies and as an antitussive, antiemetic, and hypnotic. Doxylamine has also been administered in veterinary applications and was formerly used in PARKINSONISM.
Molecular formula:	C₁₇H₂₂N₂O
Molecular weight:	270.369 g/mol
Synonyms:	Pyridine, 2-(alpha-(2-(dimethylamino)ethoxy)-alpha-methylbenzyl)-; DivK1c_000841; 2-Dimethylaminoethoxyphenylmethyl-2-picoline; Spectrum2_000115; 5-21-03-00508 (Beilstein Handbook Reference); Doxylaminum [INN-Latin]; Doxylamine; NINDS_000841; KBio2_006630; Prestwick1_000027. show more » Pyridine, 2-(alpha-(2-(dimethylamino)ethoxy)-alpha-methylbenzyl)-; DivK1c_000841; 2-Dimethylaminoethoxyphenylmethyl-2-picoline; Spectrum2_000115; 5-21-03-00508 (Beilstein Handbook Reference); Doxylaminum [INN-Latin]; Doxylamine; NINDS_000841; KBio2_006630; Prestwick1_000027; Prestwick0_000027; 469-21-6; Ethanamine, N,N-dimethyl-2-(1-phenyl-1-(2-pyridinyl)ethoxy)- (9CI); Dossilamina [DCIT]; 2-(alpha-(2-(Dimethylamino)ethoxy)-alpha-methylbenzyl)pyridine; Spectrum3_000409; Ethanamine, N,N-dimethyl-2-(1-phenyl-1-(2-pyridinyl)ethoxy)-; KBio1_000841; BRN 0230379; NCI C60684; HSDB 5184; Doxilminio [INN-Spanish]; EINECS 207-414-2; Spectrum_001014; KBio3_001158; Phenyl-2-pyridylmethyl-beta-N,N-dimethylaminoethyl ether; KBio2_001494; SPBio_000130; Spectrum4_000528; Ethanamine, N,N-dimethyl-2-[1-phenyl-1-(2-pyridinyl)ethoxy]-; KBioSS_001494; N,N-Dimethyl-2-(1-phenyl-1-(2-pyridinyl)ethoxy)ethanamine; Pyridine, 2-[.alpha.-[2-(dimethylamino)ethoxy]-.alpha.-methylbenzyl]-; KBioGR_001135; SPBio_002014; KBio2_004062 show less «

DrugBank

Identification

Name:	Doxylamine
Name (isomeric):	DB00366
Drug Type:	small molecule
Description:	Histamine H1 antagonist with pronounced sedative properties. It is used in allergies and as an antitussive, antiemetic, and hypnotic. Doxylamine has also been administered in veterinary applications and was formerly used in PARKINSONISM.
Synonyms:	Doxilminio [INN-Spanish]; Dossilamina [DCIT]; Doxylaminum [INN-Latin]
Brand name mixture:	Neocitran Cold & Flu Syrup(Acetaminophen + Dextromethorphan Hydrobromide + Doxylamine Succinate + Pseudoephedrine Hydrochloride), Regular Strength Sinus Medication(Acetaminophen + Doxylamine Succinate + Pseudoephedrine Hydrochloride), Tylenol Cold & Flu Nighttime(Acetaminophen + Dextromethorphan Hydrobromide + Doxylamine Succinate + Pseudoephedr... show more » Neocitran Cold & Flu Syrup(Acetaminophen + Dextromethorphan Hydrobromide + Doxylamine Succinate + Pseudoephedrine Hydrochloride), Regular Strength Sinus Medication(Acetaminophen + Doxylamine Succinate + Pseudoephedrine Hydrochloride), Tylenol Cold & Flu Nighttime(Acetaminophen + Dextromethorphan Hydrobromide + Doxylamine Succinate + Pseudoephedrine Hydrochloride), Nitetime Cold Medicine(Acetaminophen + Dextromethorphan Hydrobromide + Doxylamine Succinate + Pseudoephedrine Hydrochloride), Night Relief Cold and Flu Liquid Capsules(Acetaminophen + Dextromethorphan Hydrobromide + Doxylamine Succinate + Pseudoephedrine Hydrochloride), Diclectin(Doxylamine Succinate + Pyridoxine Hydrochloride), Extra Strength Tylenol Sinus Nighttime Caplet(Acetaminophen + Doxylamine Succinate + Pseudoephedrine Hydrochloride), Mercodol with Decapryn(Doxylamine Succinate + Etafedrin Hydrochloride + Hydrocodone Bitartrate + Sodium Citrate), Nighttime Cold and Flu Relief(Acetaminophen + Dextromethorphan Hydrobromide + Doxylamine Succinate + Pseudoephedrine Hydrochloride), Nyquil Liquicaps(Acetaminophen + Dextromethorphan Hydrobromide + Doxylamine Succinate + Pseudoephedrine Hydrochloride), Nighttime Liquid Capsules Cold/Flu Medicine(Acetaminophen + Dextromethorphan Hydrobromide + Doxylamine Succinate + Pseudoephedrine Hydrochloride), Nighttime Cold and Flu Liquid Capsules(Acetaminophen + Dextromethorphan Hydrobromide + Doxylamine Succinate + Pseudoephedrine Hydrochloride), Sinus Medication Night Tablets(Acetaminophen + Doxylamine Succinate + Pseudoephedrine Hydrochloride), Sinus Medication(Acetaminophen + Doxylamine Succinate + Pseudoephedrine Hydrochloride) show less «
Category:	Hypnotics and Sedatives, Histamine H1 Antagonists, Antiemetics, Anti-Allergic Agents, Antitussive Agents
CAS number:	469-21-6

Pharmacology

Indication:	Used alone as a short-term sleep aid, in combination with other drugs as a night-time cold and allergy relief drug. Also used in combination with Vitamin B6 (pyridoxine) to prevent morning sickness in pregnant women.
Pharmacology:	Doxylamine is an antihistamine commonly used as a sleep aid. This drug is also used to relieve symptoms of hay fever (allergic rhinitis), hives (rash or itching), and other allergic reactions. Doxylamine is a member of the ethanolamine class of antihistamines and has anti-allergy power far superior to virtually every other antihistamine on the mark... show more » Doxylamine is an antihistamine commonly used as a sleep aid. This drug is also used to relieve symptoms of hay fever (allergic rhinitis), hives (rash or itching), and other allergic reactions. Doxylamine is a member of the ethanolamine class of antihistamines and has anti-allergy power far superior to virtually every other antihistamine on the market, with the exception of diphenhydramine (Benadryl). It is also the most powerful over-the-counter sedative available in the United States, and more sedating than many prescription hypnotics. In a study, it was found to be superior to even the barbiturate, phenobarbital for use as a sedative. Doxylamine is also a potent anticholinergic. show less «
Mechanism of Action:	Like other antihistamines, doxylamine acts by competitively inhibiting histamine at H1 receptors. It also has substantial sedative and anticholinergic effects.
Absorption:	Readily absorbed via the gastrointestinal tract.
Biotransformation:	Hepatic.
Half Life:	10 hours
Toxicity:	Signs of overdose include wheezing, tightness in the chest, fever, itching, bad cough, blue skin color, fits, swelling of face, lips, tongue, or throat.
Affected organisms:	Humans and other mammals

Interactions

Drug interaction:

Trimethobenzamide	Trimethobenzamide and Doxylamine, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Monitor for enhanced anticholinergic effects.
Tacrine	The therapeutic effects of the central acetylcholinesterase inhibitor, Tacrine, and/or the anticholinergic, Doxylamine, may be reduced due to antagonism. The interaction may be beneficial when the anticholinergic action is a side effect. Monitor for decreased efficacy of both agents.
Donepezil	Possible antagonism of action
Triprolidine	Triprolidine and Doxylamine, 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.
Trospium	Trospium and Doxylamine, two anticholinergics, may cause additive anticholinergic effects and enhanced adverse/toxic effects. Monitor for enhanced anticholinergic effects.

Targets

Histamine H1 receptor

Muscarinic acetylcholine receptor M1