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Identification
Name Doxylamine
Accession Number DB00366 (APRD00937)
Type small molecule
Groups approved
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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
Dossilamina [DCIT]
Doxilminio [INN-Spanish]
Doxylaminum [INN-Latin]
Salts Not Available
Brand names Not Available
Brand mixtures
Brand Name Ingredients
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
Neocitran Cold & Flu Syrup Acetaminophen + Dextromethorphan Hydrobromide + Doxylamine Succinate + Pseudoephedrine Hydrochloride
Night Relief Cold and Flu Liquid Capsules Acetaminophen + Dextromethorphan Hydrobromide + Doxylamine Succinate + Pseudoephedrine Hydrochloride
Nighttime Cold and Flu Liquid Capsules Acetaminophen + Dextromethorphan Hydrobromide + Doxylamine Succinate + Pseudoephedrine Hydrochloride
Nighttime Cold and Flu Relief Acetaminophen + Dextromethorphan Hydrobromide + Doxylamine Succinate + Pseudoephedrine Hydrochloride
Nighttime Liquid Capsules Cold/Flu Medicine Acetaminophen + Dextromethorphan Hydrobromide + Doxylamine Succinate + Pseudoephedrine Hydrochloride
Nitetime Cold Medicine Acetaminophen + Dextromethorphan Hydrobromide + Doxylamine Succinate + Pseudoephedrine Hydrochloride
Nyquil Liquicaps Acetaminophen + Dextromethorphan Hydrobromide + Doxylamine Succinate + Pseudoephedrine Hydrochloride
Regular Strength Sinus Medication Acetaminophen + Doxylamine Succinate + Pseudoephedrine Hydrochloride
Sinus Medication Acetaminophen + Doxylamine Succinate + Pseudoephedrine Hydrochloride
Sinus Medication Night Tablets Acetaminophen + Doxylamine Succinate + Pseudoephedrine Hydrochloride
Tylenol Cold & Flu Nighttime Acetaminophen + Dextromethorphan Hydrobromide + Doxylamine Succinate + Pseudoephedrine Hydrochloride
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Categories
  • Hypnotics and Sedatives
  • Antiemetics
  • Anti-Allergic Agents
  • Histamine H1 Antagonists
  • Antitussive Agents
CAS number 469-21-6
Weight Average: 270.3694
Monoisotopic: 270.173213336
Chemical Formula C17H22N2O
InChI Key InChIKey=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
Plain Text
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
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Diphenhydramines
Substructures
  • Diphenhydramines
  • Benzyl Alcohols and Derivatives
  • Pyridines and Derivatives
  • Ethers
  • Benzene and Derivatives
  • Aliphatic and Aryl Amines
  • Heterocyclic compounds
  • Aromatic compounds
  • Imines
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.
Pharmacodynamics 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.
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.
Volume of distribution Not Available
Protein binding Not Available
Metabolism
Hepatic.
Route of elimination Not Available
Half life 10 hours
Clearance Not Available
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
Pathways Not Available
Pharmacoeconomics
Manufacturers Not Available
Packagers
Dosage forms
Form Route Strength
Tablet Oral
Prices
Unit description Cost Unit
Doxylamine succinate powder 1.5 USD g
Unisom sleep aid tablet 0.34 USD tablet
Sleep aid 25 mg tablet 0.15 USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents Not Available
Properties
State liquid
Experimental Properties
Property Value Source
melting point < 25 °C PhysProp
boiling point 139 °C at 5.00E-01 mm Hg PhysProp
water solubility 1 g/ml (succinate salt) Not Available
logP 2.5 Not Available
Predicted Properties
Property Value Source
water solubility 5.41e-01 g/l ALOGPS
logP 2.9 ALOGPS
logP 2.96 ChemAxon
logS -2.7 ALOGPS
pKa (strongest basic) 8.87 ChemAxon
physiological charge 1 ChemAxon
hydrogen acceptor count 3 ChemAxon
hydrogen donor count 0 ChemAxon
polar surface area 25.36 ChemAxon
rotatable bond count 6 ChemAxon
refractivity 82.24 ChemAxon
polarizability 31.09 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D02327 Link_out
PubChem Compound 3162 Link_out
PubChem Substance 46506354 Link_out
ChemSpider 3050 Link_out
ChEBI 51380 Link_out
ChEMBL 51380 Link_out
Therapeutic Targets Database DAP000859 Link_out
PharmGKB PA449419 Link_out
Drug Product Database 1946994 Link_out
Drugs.com http://www.drugs.com/cdi/doxylamine.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Doxylamine Link_out
ATC Codes
  • R06AA09
AHFS Codes
  • 04:04.04
PDB Entries Not Available
FDA label Not Available
MSDS show (74 KB)
Interactions
Drug Interactions
Drug Interaction
Donepezil Possible antagonism of action
Galantamine Possible antagonism of action
Pramlintide May cause additive slowing of GI motility.
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.
Trimethobenzamide Trimethobenzamide and Doxylamine, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Monitor for enhanced anticholinergic effects.
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.
Food Interactions Not Available
Targets

1. Histamine H1 receptor

Pharmacological action: yes
Actions: antagonist

In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system

Organism class: human
UniProt ID: P35367 Link_out
Gene: HRH1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Pharmacological action: unknown
Actions: antagonist

The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover

Organism class: human
UniProt ID: P11229 Link_out
Gene: CHRM1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
Enzymes

1. CYP2B protein

Actions: inducer
UniProt ID: Q14097 Link_out
Gene: CYP2B
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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 February 08, 2013 16:19