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Identification
NameDoxylamine
Accession NumberDB00366  (APRD00937)
Typesmall molecule
Groupsapproved
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. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
DossilaminaNot AvailableDCIT
DoxilminioSpanishINN
DoxylaminumLatinINN
SaltsNot Available
Brand namesNot Available
Brand mixtures
Brand NameIngredients
DiclectinDoxylamine Succinate + Pyridoxine Hydrochloride
Extra Strength Tylenol Sinus Nighttime CapletAcetaminophen + Doxylamine Succinate + Pseudoephedrine Hydrochloride
Mercodol with DecaprynDoxylamine Succinate + Etafedrin Hydrochloride + Hydrocodone Bitartrate + Sodium Citrate
Neocitran Cold & Flu SyrupAcetaminophen + Dextromethorphan Hydrobromide + Doxylamine Succinate + Pseudoephedrine Hydrochloride
Night Relief Cold and Flu Liquid CapsulesAcetaminophen + Dextromethorphan Hydrobromide + Doxylamine Succinate + Pseudoephedrine Hydrochloride
Nighttime Cold and Flu Liquid CapsulesAcetaminophen + Dextromethorphan Hydrobromide + Doxylamine Succinate + Pseudoephedrine Hydrochloride
Nighttime Cold and Flu ReliefAcetaminophen + Dextromethorphan Hydrobromide + Doxylamine Succinate + Pseudoephedrine Hydrochloride
Nighttime Liquid Capsules Cold/Flu MedicineAcetaminophen + Dextromethorphan Hydrobromide + Doxylamine Succinate + Pseudoephedrine Hydrochloride
Nitetime Cold MedicineAcetaminophen + Dextromethorphan Hydrobromide + Doxylamine Succinate + Pseudoephedrine Hydrochloride
Nyquil LiquicapsAcetaminophen + Dextromethorphan Hydrobromide + Doxylamine Succinate + Pseudoephedrine Hydrochloride
Regular Strength Sinus MedicationAcetaminophen + Doxylamine Succinate + Pseudoephedrine Hydrochloride
Sinus MedicationAcetaminophen + Doxylamine Succinate + Pseudoephedrine Hydrochloride
Sinus Medication Night TabletsAcetaminophen + Doxylamine Succinate + Pseudoephedrine Hydrochloride
Tylenol Cold & Flu NighttimeAcetaminophen + Dextromethorphan Hydrobromide + Doxylamine Succinate + Pseudoephedrine Hydrochloride
Categories
CAS number469-21-6
WeightAverage: 270.3694
Monoisotopic: 270.173213336
Chemical FormulaC17H22N2O
InChI KeyInChIKey=HCFDWZZGGLSKEP-UHFFFAOYSA-N
InChI
InChI=1S/C17H22N2O/c1-17(20-14-13-19(2)3,15-9-5-4-6-10-15)16-11-7-8-12-18-16/h4-12H,13-14H2,1-3H3
IUPAC Name
dimethyl({2-[1-phenyl-1-(pyridin-2-yl)ethoxy]ethyl})amine
SMILES
CN(C)CCOC(C)(C1=CC=CC=C1)C1=CC=CC=N1
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassBenzylethers
Direct parentBenzylethers
Alternative parentsPyridines and Derivatives; Tertiary Amines; Polyamines; Dialkyl Ethers
Substituentspyridine; tertiary amine; dialkyl ether; polyamine; ether; amine; organonitrogen compound
Classification descriptionThis compound belongs to the benzylethers. These are aromatic ethers with the general formula ROCR' (R = alkyl, aryl; R'=benzene).
Pharmacology
IndicationUsed 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.
PharmacodynamicsDoxylamine 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.
Mechanism of actionLike other antihistamines, doxylamine acts by competitively inhibiting histamine at H1 receptors. It also has substantial sedative and anticholinergic effects.
AbsorptionReadily absorbed via the gastrointestinal tract.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Hepatic.

Route of eliminationNot Available
Half life10 hours
ClearanceNot Available
ToxicitySigns 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
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9505
Blood Brain Barrier + 0.9491
Caco-2 permeable + 0.746
P-glycoprotein substrate Substrate 0.7449
P-glycoprotein inhibitor I Non-inhibitor 0.5123
P-glycoprotein inhibitor II Non-inhibitor 0.8383
Renal organic cation transporter Inhibitor 0.7507
CYP450 2C9 substrate Non-substrate 0.8153
CYP450 2D6 substrate Non-substrate 0.5432
CYP450 3A4 substrate Substrate 0.6801
CYP450 1A2 substrate Non-inhibitor 0.9092
CYP450 2C9 substrate Non-inhibitor 0.8957
CYP450 2D6 substrate Inhibitor 0.8361
CYP450 2C19 substrate Non-inhibitor 0.8764
CYP450 3A4 substrate Non-inhibitor 0.6894
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.736
Ames test Non AMES toxic 0.9133
Carcinogenicity Non-carcinogens 0.9183
Biodegradation Not ready biodegradable 1.0
Rat acute toxicity 2.9218 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.8765
hERG inhibition (predictor II) Inhibitor 0.5398
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
TabletOral
Prices
Unit descriptionCostUnit
Doxylamine succinate powder1.5USDg
Unisom sleep aid tablet0.34USDtablet
Sleep aid 25 mg tablet0.15USDtablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Stateliquid
Experimental Properties
PropertyValueSource
melting point< 25 °CPhysProp
boiling point139 °C at 5.00E-01 mm HgPhysProp
water solubility1 g/ml (succinate salt)Not Available
logP2.5Not Available
Predicted Properties
PropertyValueSource
water solubility5.41e-01 g/lALOGPS
logP2.9ALOGPS
logP2.96ChemAxon
logS-2.7ALOGPS
pKa (strongest basic)8.87ChemAxon
physiological charge1ChemAxon
hydrogen acceptor count3ChemAxon
hydrogen donor count0ChemAxon
polar surface area25.36ChemAxon
rotatable bond count6ChemAxon
refractivity82.24ChemAxon
polarizability31.09ChemAxon
number of rings2ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleYesChemAxon
MDDR-like ruleNoChemAxon
Spectra
Spectra
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ResourceLink
KEGG DrugD02327
PubChem Compound3162
PubChem Substance46506354
ChemSpider3050
ChEBI51380
ChEMBLCHEMBL1004
Therapeutic Targets DatabaseDAP000859
PharmGKBPA449419
Drug Product Database1946994
Drugs.comhttp://www.drugs.com/cdi/doxylamine.html
WikipediaDoxylamine
ATC CodesR06AA09
AHFS Codes
  • 04:04.04
PDB EntriesNot Available
FDA labelNot Available
MSDSshow(74 KB)
Interactions
Drug Interactions
Drug
DonepezilPossible antagonism of action
GalantaminePossible antagonism of action
PramlintideMay cause additive slowing of GI motility.
TacrineThe 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.
TrimethobenzamideTrimethobenzamide and Doxylamine, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Monitor for enhanced anticholinergic effects.
TriprolidineTriprolidine 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.
TrospiumTrospium and Doxylamine, two anticholinergics, may cause additive anticholinergic effects and enhanced adverse/toxic effects. Monitor for enhanced anticholinergic effects.
Food InteractionsNot Available

1. Histamine H1 receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Histamine H1 receptor P35367 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

2. Muscarinic acetylcholine receptor M1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: antagonist

Components

Name UniProt ID Details
Muscarinic acetylcholine receptor M1 P11229 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

1. CYP2B protein

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inducer

Components

Name UniProt ID Details
CYP2B protein Q14097 Details

References:

  1. Bookstaff RC, Murphy VA, Skare JA, Minnema D, Sanzgiri U, Parkinson A: Effects of doxylamine succinate on thyroid hormone balance and enzyme induction in mice. Toxicol Appl Pharmacol. 1996 Dec;141(2):584-94. Pubmed

Comments
Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:10