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Doxylamine

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Doxylamine
Systematic (IUPAC) name
N,N-dimethyl-2- (1-phenyl-1-pyridin-2-yl-ethoxy)- ethanamine
Identifiers
CAS number 469-21-6
ATC code R06AA09
PubChem 3162
DrugBank APRD00937
Chemical data
Formula C17H22N2O 
Mol. weight 270.369 g/mol
Pharmacokinetic data
Bioavailability  ?
Metabolism Hepatic
Half life variable; 6-12 hours
Excretion  ?
Therapeutic considerations
Pregnancy cat.

A

Legal status

OTC

Routes Oral

Doxylamine succinate is one of the many sedating antihistamines used by itself as a short-term sleep aid, in combination with other drugs as a night-time cold and allergy relief drug, and a preparation is prescribed in combination with Vitamin B6 (pyridoxine) to prevent morning sickness in pregnant women. It is one of the active ingredients in NyQuil. In Commonwealth countries, such as Australia, Canada, the UK New Zealand and South Africa, doxylamine is available prepared with paracetamol/acetaminophen and codeine under the brand name Syndol or Mersyndol, as treatment for tension headache and other types of pain, or as a general OTC sleep-aid branded as Somnil, Donormyl, DSozile and Restavit containing Doxylamine Succinate only.

It is a member of the ethanolamine class of antihistamines and has anti-allergy power superior to almost every other antihistamine on the market, with the exception of diphenhydramine (Benadryl®).[citation needed] It is also the most effective over-the-counter sedative available in the United States, and more sedating than some prescription hypnotics. In a study, it was found that doxylamine succinate is possibly more effective than the barbiturate, phenobarbital for use as a sedative.[citation needed] For this reason, doxylamine has sometimes been used off label in a manner similar to diphenhydramine for the reduction of anxiety symptoms.

The dosage required to induce hypnosis (sleep) can be as low as 6.25 mg, but is usually effective in dosages of up to 25 mg. Higher doses are not recommended by the FDA. You should know how this drug affects you before operating heavy machinery or an automobile. Single dosage recommendations of up to 50 mg are common in countries like Australia, where it is marketed under the names Restavit® and Dozile®.

Doxylamine succinate is a potent anticholinergic and has a side-effect profile common to such drugs (including drymouth, ataxia, urinary retention, and drowsiness). Other drugs with well known anticholinergic effects include many antipsychotic and tricyclic antidepressant drugs.

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Antihistamines (primarily R06) edit
Aminoalkyl ethers:

Bromazine, Carbinoxamine, Clemastine, Chlorphenoxamine, Diphenylpyraline, Diphenhydramine, Doxylamine

Substituted alkylamines:

Brompheniramine, Chlorphenamine, Dexbrompheniramine , Dexchlorpheniramine, Dimetindene, Pheniramine, Talastine

Substituted ethylene diamines:

Chloropyramine, Histapyrrodine, Mepyramine, Methapyrilene

Phenothiazine derivatives:

Alimemazine, Hydroxyethylpromethazine, Isothipendyl, Mequitazine, Methdilazine, Oxomemazine, Promethazine

Piperazine derivatives:

Buclizine, Cetirizine, Chlorcyclizine, Cinnarizine, Cyclizine , Levocetirizine, Meclozine, Oxatomide

Others for systemic use:

Acrivastine, Antazoline, Astemizole, Azatadine , Azelastine, Bamipine, Cyproheptadine, Deptropine, Desloratadine, Ebastine, Epinastine, Ketotifen, Loratadine, Mebhydrolin, Mizolastine, Phenindamine, Pimethixene, Pyrrobutamine, Rupatadine, Terfenadine, Triprolidine

For topical use:

Bamipine, Chloropyramine, Chlorphenoxamine, Clemastine, Dimetindene, Diphenhydramine, Isothipendyl, Mepyramine , Promethazine, Thenalidine

Antiallergic agents
excluding corticosteroids
:

Antazoline, Azelastine , Fexofenadine

Other antiallergics:

Emedastine, Epinastine, Ketotifen, Olopatadine

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