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Doxylamine
Systematic (IUPAC) name
(RS)-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
ChemSpider 3050
Chemical data
Formula C 17H22N2O 
Mol. mass 270.369 g/mol
SMILES eMolecules & PubChem
Pharmacokinetic data
Bioavailability Oral: 24.7%, Intranasal: 70.8% [1]
Metabolism Hepatic
Half life variable; 6–12 hours
Excretion Urine (primarily as metabolites)
Therapeutic considerations
Pregnancy cat. A(US)
Legal status OTC
Routes Oral
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Doxylamine succinate is one of the many sedating antihistamines used by itself as a short-term sedative, in combination with other drugs as a night-time cold and allergy relief drug, in combination with the analgesics paracetamol(acetaminophen) and codeine as an analgesic / calmative preparation, and is prescribed in combination with vitamin B6 (pyridoxine) to prevent morning sickness in pregnant women.

Contents

Indications

Doxylamine 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).[2] It is also the most effective over-the-counter sedative available in the United States,[2] and is more sedating than some prescription hypnotics. One study found that doxylamine succinate is possibly more effective than the barbiturate phenobarbital for use as a sedative.[2]

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 United States Food and Drug Administration, although single dosage recommendations of up to 50 mg are common in some countries, including Australia, where it is marketed under the names Restavit and Dozile.

Metabolites

The two main metabolites are desmethyldoxylamine and didesmethyldoxylamine.

Formulations

Side effects

Doxylamine succinate is a potent anticholinergic and has a side-effect profile common to such drugs, including dry mouth, ataxia, urinary retention, and drowsiness.

Toxicity

Doxylamine succinate is generally safe for administration to healthy adults. Typical preparations that contain doxylamine range from 6.25 mg to 25.0 mg. The LD50 is estimated to be 50–500 mg/kg in humans.[3] Symptoms of overdose may include dry mouth, dilated pupils, insomnia, euphoria, hallucinations, seizures, rhabdomyolysis, and death.[4] Fatalities, while rare, have been recorded.[5] Rarely, an overdose results in rhabdomyolysis and acute renal failure.[6]

References

  1. ^ http://www3.interscience.wiley.com/journal/98016819/abstract
  2. ^ a b c DrugBank: DB00366 (Doxylamine)
  3. ^ http://hazard.com/msds/mf/baker/baker/files/d8882.htm
  4. ^ Syed, Husnain; Sumit Som, Nazia Khan, Wael Faltas (17 March 2009). "Doxylamine toxicity: seizure, rhabdomyolysis and false positive urine drug screen for methadone". BMJ Case Reports (BMJ Group) 2003 (90): 845. doi:10.1136/bcr.09.2008.0879. http://casereports.bmj.com/cgi/content/abstract/2009/mar08_1/bcr0920080879. Retrieved 29 November 2009.  
  5. ^ http://www.medsafe.govt.nz/Profs/DataSheet/d/Dozilecap.htm
  6. ^ Leybishkis B, B; Fasseas P; Ryan KF. (July 2001). "Doxylamine overdose as a potential cause of rhabdomyolysis". American journal of the medical sciences (Lippincott Williams & Wilkins) 322 (1): 48–9. PMID 11465247.  
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