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Encyclopedia > Doxylamine
Doxylamine chemical structure
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 Image File history File links Doxylamine. ... IUPAC nomenclature is a systematic way of naming organic chemical compounds. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences and alloys. ... The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs. ... A section of the Anatomical Therapeutic Chemical Classification System. ... PubChem is a database of chemical molecules . ... DrugBank is a database available at the University of Alberta that provides information about thousands of products. ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... General Name, Symbol, Number carbon, C, 6 Chemical series nonmetals Group, Period, Block 14, 2, p Appearance black (graphite) colorless (diamond) Atomic mass 12. ... General Name, Symbol, Number hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1, 1, s Appearance colorless Atomic mass 1. ... General Name, Symbol, Number nitrogen, N, 7 Chemical series nonmetals Group, Period, Block 15, 2, p Appearance colorless Atomic mass 14. ... General Name, Symbol, Number oxygen, O, 8 Chemical series Nonmetals, chalcogens Group, Period, Block 16, 2, p Appearance colorless (gas) very pale blue (liquid) Atomic mass 15. ... The molecular mass of a substance (less accurately called molecular weight and abbreviated as MW) is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... In pharmacology, bioavailability is used to describe the fraction of an administered dose of medication that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ... Metabolism (from Greek μεταβολισμός metabolismos) is the biochemical modification of chemical compounds in living organisms and cells. ... The elimination half-life of a drug (or any xenobiotic agent) refers to the timecourse necessary for the quantity of the xenobiotic agent in the body (or plasma concentration) to be reduced to half of its original level through various elimination processes. ... Excretion is the biological process by which an organism chemically separates waste products from its body. ... The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical, if it is used as directed by the mother during pregnancy. ...

Legal status

OTC The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ... Over-the-counter (OTC) drugs are medicines that may be sold without a prescription and without a visit to a medical professional, in contrast to prescription drugs. ...

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. In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body 1. ... Succinate is the anion of succinic acid. ... An antihistamine is a drug which serves to reduce or eliminate effects mediated by histamine, an endogenous chemical mediator released during allergic reactions, through action at the histamine receptor. ... Pyridoxine Vitamin B-6 is a water-soluble vitamin. ... Pyridoxine is one of the compounds that can be called vitamin B6, along with Pyridoxal and Pyridoxamine. ... Morning sickness, also called nausea and vomiting of pregnancy (NVP), or pregnancy sickness, affects between 50 and 95 percent of all pregnant women. ... To meet Wikipedias quality standards, this article or section may require cleanup. ... Tension headaches, which were recently renamed tension-type headaches by the International Headache Society, are the most common type of headaches. ... Look up Pain in Wiktionary, the free dictionary. ...


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. Ethanolamine, or 2-Amino ethanol, is a toxic flammable corrosive colorless viscous liquid with an odor similar to ammonia. ... Diphenhydramine hydrochloride (trade name Benadryl®, as produced by Pfizer or Dimedrol outside the US) is an over-the-counter (OTC) antihistamine and sedative. ... Hypnotic drugs are a class of drugs that induce sleep, used in the treatment of severe insomnia. ... Succinate is the anion of succinic acid. ... Barbiturates are drugs that act as central nervous system (CNS) depressants, and by virtue of this they produce a wide spectrum of effects, from mild sedation to anesthesia. ... Phenobarbital (also phenobarbitone) (Luminal®) is a weak acid with the chemical formula C12H12N2O3. ...


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®. Sleep is the state of natural rest observed in most mammals, birds, fish, as well as invertebrates such as the fruitfly Drosophila. ...


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. An anticholinergic agent is a member of a class of pharmaceutical compounds which serve to reduce the effects mediated by acetylcholine in the central nervous system and peripheral nervous system. ... Ataxia (from Greek ataxiā, meaning failure to put in order) is unsteady and clumsy motion of the limbs or trunk due to a failure of the gross coordination of muscle movements. ...


External links

  • Unisom (manufacturer's website)
  • Link page to external chemical sources.


Antihistamines (primarily R06) edit
Aminoalkyl ethers:

Bromazine, Carbinoxamine, Clemastine, Chlorphenoxamine, Diphenylpyraline, Diphenhydramine, Doxylamine An antihistamine is a drug which serves to reduce or eliminate effects mediated by histamine, an endogenous chemical mediator released during allergic reactions, through action at the histamine receptor. ... A section of the Anatomical Therapeutic Chemical Classification System. ... Ethers can refer to: In internet routing, the term associated with hosts In Organic chemistry, the plural of ether This is a disambiguation page — a navigational aid which lists other pages that might otherwise share the same title. ... Carbinoxamine is an antihistamine. ... Clemastine is an over-the-counter antihistamine sold in the United States under the name Tavist. ... Diphenylpyraline is an antihistamine. ... Diphenhydramine hydrochloride (trade name Benadryl®, as produced by Pfizer or Dimedrol outside the US) is an over-the-counter (OTC) antihistamine and sedative. ...

Substituted alkylamines:

Brompheniramine, Chlorphenamine, Dexbrompheniramine , Dexchlorpheniramine, Dimetindene, Pheniramine, Talastine Categories: Stub | Antihistamines ... Chlorphenamine (INN) or chlorpheniramine (USAN, former BAN), commonly marketed as its salt chlorphenamine maleate (CPM), is first-generation antihistamine used in the prevention of the symptoms of allergic conditions such as rhinitis and urticaria. ... Dexbrompheniramine maleate is an antihistamine used to treat allergic conditions such as hay fever or urticaria. ... Dexchlorpheniramine maleate (Polaramine®, Schering) is an antihistamine used to treat allergic conditions such as hay fever or urticaria. ... Pheniramine maleate is an antihistamine used to treat allergic conditions such as hay fever or urticaria. ...

Substituted ethylene diamines:

Chloropyramine, Histapyrrodine, Mepyramine, Methapyrilene Ethylene diamine (EDA or en), or 1,2-diaminoethane, is an organic compound from the amines group. ... Chloropyramine is a classical (old or first generation) antihistamine drug approved in some Eastern European countries for the treatment of allergic conjuctivitis, allergic rhinitis, bronchial asthma, and other atopic (allergic) conditions. ... Methapyrilene is a pyridine antihistamine. ...

Phenothiazine derivatives:

Alimemazine, Hydroxyethylpromethazine, Isothipendyl, Mequitazine, Methdilazine, Oxomemazine, Promethazine Phenothiazines are the largest of the 5 main classes of antipsychotic drugs. ... Mequitazine is an antihistamine. ... Methdilazine is an antihistamine. ... // General Remarks and Pharmacology Promethazine (sold as Phenergan and Promethegan) is a first-generation H1 receptor antagonist antihistamine and antiemetic|anti-nausea medication available by medical prescription|prescription in the United States, and over-the-counter in the United Kingdom, Switzerland, Australia, South Africa, New Zealand and many other countries. ...

Piperazine derivatives:

Buclizine, Cetirizine, Chlorcyclizine, Cinnarizine, Cyclizine , Levocetirizine, Meclozine, Oxatomide Basic piperazine structure Piperazine is a six-sided organic ring compound containing two opposing nitrogen atoms (see image). ... Buclizine is an antihistamine of the piperazine derivative family. ... Cetirizine hydrochloride is a medication used for the treatment of allergies, hay fever, angioedema, and hives. ... This article belongs in one or more categories. ... Cinnarizine is an anti histaminic drug which is mainly used for the contol of vomiting due to motion sickness. ... Cyclizine (brand names: Marezine; Marzine; Emoquil) is a drug used to treat nausea, vomiting and dizziness associated with motion sickness and vertigo. ... Levocetirizine (levocetirizine dihydrochloride, marketed as Xyzal in Europe) is a third generation antihistamine, developed from the second generation antihistamine cetirizine. ... Meclizine (proposed INN is meclozine) is an antihistamine, considered to be an antiemetic. ... Oxatomide is a piperazine antihistamine. ...

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 Systemic Relating to, or affecting a particular body system; especially the nervous system. ... Acrivastine is a medication used for the treatment of allergies and hay fever. ... Astemizole is a second generation antihistamine that has a long duration of action. ... Azatadine is an antihistamine. ... Azelastine hydrochloride is an antihistamine and mast cell stabilizer available as a nasal spray (Astelin®) for hay fever and as eye drops (Optilar®) for allergic conjunctivitis. ... Periactin® (cyproheptadine hydrochloride) is an antihistaminic and antiserotonergic agent. ... Desloratadine is a drug used to treat allergies. ... Ebastin is non sedating H1 antihistamine Does not penetratethe blood brain barrier and thus allow an effective blocked of H1 receptor in peripheral tissue without centeral side effect i. ... Epinastine hydrochloride (Elestat®) is an antihistamine that is used in eye drops to treat allergic conjunctivitis. ... Ketotifen fumarate (Zaditor®) is an H1-antihistamine available in two forms. ... Loratadine is a drug used to treat allergies. ... Rupatadine is a new selective histamine H1 receptor and platelet-activating factor (PAF) antagonist. ... Terfenadine is an antihistamine formerly used for the treatment of allergic conditions. ... Triprolidine hydrochloride is an over-the-counter antihistamine. ...

For topical use:

Bamipine, Chloropyramine, Chlorphenoxamine, Clemastine, Dimetindene, Diphenhydramine, Isothipendyl, Mepyramine , Promethazine, Thenalidine In medicine, a topical medication is applied to body surfaces such as the skin or mucous membranes such as the vagina, nasopharynx, or the eye. ... Chloropyramine is a classical (old or first generation) antihistamine drug approved in some Eastern European countries for the treatment of allergic conjuctivitis, allergic rhinitis, bronchial asthma, and other atopic (allergic) conditions. ... Clemastine is an over-the-counter antihistamine sold in the United States under the name Tavist. ... Diphenhydramine hydrochloride (trade name Benadryl®, as produced by Pfizer or Dimedrol outside the US) is an over-the-counter (OTC) antihistamine and sedative. ... // General Remarks and Pharmacology Promethazine (sold as Phenergan and Promethegan) is a first-generation H1 receptor antagonist antihistamine and antiemetic|anti-nausea medication available by medical prescription|prescription in the United States, and over-the-counter in the United Kingdom, Switzerland, Australia, South Africa, New Zealand and many other countries. ...

Antiallergic agents
excluding corticosteroids
:

Antazoline, Azelastine , Fexofenadine This article or section does not cite its references or sources. ... In physiology, corticosteroids are a class of steroid hormones that are produced in the adrenal cortex. ... Azelastine hydrochloride is an antihistamine and mast cell stabilizer available as a nasal spray (Astelin®) for hay fever and as eye drops (Optilar®) for allergic conjunctivitis. ... Fexofenadine hydrochloride (brand names include Allegra® and Telfast®) is an antihistamine drug used in the treatment of hayfever and similar allergy symptoms. ...

Other antiallergics:

Emedastine, Epinastine, Ketotifen, Olopatadine Emedastine difumarate (Emadine®) is an antihistamine used in eye drops to treat allergic conjunctivitis. ... Epinastine hydrochloride (Elestat®) is an antihistamine that is used in eye drops to treat allergic conjunctivitis. ... Ketotifen fumarate (Zaditor®) is an H1-antihistamine available in two forms. ... Olopatadine hydrochloride is an antihistamine and mast cell stabilizer, usually sold as a prescription eye drop (0. ...


  Results from FactBites:
 
Doxylamine facts and comparsions at Drugs.com (1070 words)
Doxylamine may be taken with or without food.
Doxylamine is not recommended for use in CHILDREN younger than 12 years of age.
Doxylamine is to be used only by the patient for whom it is prescribed.
Doxylamine succinate (IARC Summary & Evaluation, Volume 79, 2001) (0 words)
Doxylamine succinate is an ethanolamine-based antihistamine used in the management of insomnia and, in combination with antitussives and decongestants, in the relief of cough and cold symptoms.
Doxylamine induces thyroxine glucuronidation in mice, with concomitant decreases in serum thyroxine and increases in serum thyroid stimulating hormone concentrations.
Doxylamine succinate induced DNA damage in primary rat hepatocytes and inhibited intercellular communication, but it did not induce sister chromatid exchange in mammalian cells in culture or induce mutations in bacteria.
  More results at FactBites »


 

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