DrugBank: Doxylamine (DB00366)

targets (2)

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

Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure

Synonyms

Dossilamina [DCIT]
Doxilminio [INN-Spanish]
Doxylaminum [INN-Latin]

Brand names

Not Available

Brand name mixtures

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)

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=NC=CC=C1

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

Patents

Not Available

Properties

State

liquid

Melting point

< 25 oC

Experimental Properties

Property	Value	Source
water solubility	1 g/ml (succinate salt)	PhysProp
logP	2.5	PhysProp

Predicted Properties

Property	Value	Source
water solubility	5.41e-01 g/l	ALOGPS
logP	2.90	ALOGPS
logP	2.96	ChemAxon Molconvert
logS	-2.70	ALOGPS
pKa		ChemAxon Molconvert
hydrogen acceptor count	3	ChemAxon Molconvert
hydrogen donor count	0	ChemAxon Molconvert
polar surface area	25.36	ChemAxon Molconvert
rotatable bond count	6	ChemAxon Molconvert
refractivity	82.24	ChemAxon Molconvert
polarizability	31.09	ChemAxon Molconvert

References

Synthesis Reference

Not Available

General Reference

Not Available

External Links

Resource	Link
KEGG Drug	D02327
PubChem Compound	3162
PubChem Substance	46506354
ChemSpider	3050
ChEBI	51380
ChEMBL	51380
Therapeutic Targets Database	DAP000859
PharmGKB	PA449419
Drug Product Database	1946994
Drugs.com	http://www.drugs.com/cdi/doxylamine.html
Wikipedia	http://en.wikipedia.org/wiki/Doxylamine

ATC Codes

R06AA09

AHFS Codes

04:04.04

PDB Entries

Not Available

FDA label

Not Available

MSDS

show (74 KB)

Interactions

Drug Interactions

Not Available

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 Gene: HRH1 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed 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 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 Gene: CHRM1 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed 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

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:

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
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
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:

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
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

Comments

Drug created on June 13, 2005 07:24 / Updated on April 19, 2011 15:03

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.