U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C17H22N2O
Molecular Weight 270.3694
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DOXYLAMINE

SMILES

CN(C)CCOC(C)(C1=CC=CC=C1)C2=CC=CC=N2

InChI

InChIKey=HCFDWZZGGLSKEP-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Description

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. Like other antihistamines, doxylamine acts by competitively inhibiting histamine at H1 receptors. It also has substantial sedative and anticholinergic effects. 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.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
42.0 nM [Ki]
200.0 nM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unisom
Primary
Unisom

Cmax

ValueDoseCo-administeredAnalytePopulation
61.94 ng/mL
12.5 mg single, oral
DOXYLAMINE plasma
Homo sapiens
124.91 ng/mL
25 mg single, oral
DOXYLAMINE plasma
Homo sapiens
12.9 ng/mL
3.2 mg single, nasal
DOXYLAMINE plasma
Homo sapiens
18.9 ng/mL
6.3 mg single, nasal
DOXYLAMINE plasma
Homo sapiens
27.1 ng/mL
12.7 mg single, nasal
DOXYLAMINE plasma
Homo sapiens
142 ng/mL
25 mg single, oral
DOXYLAMINE plasma
Homo sapiens
99 ng/mL
25 mg single, oral
DOXYLAMINE plasma
Homo sapiens
83.3 ng/mL
20 mg single, oral
DOXYLAMINE plasma
Homo sapiens
168.6 ng/mL
40 mg 1 times / day multiple, oral
DOXYLAMINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
859.74 ng × h/mL
12.5 mg single, oral
DOXYLAMINE plasma
Homo sapiens
1697.58 ng × h/mL
25 mg single, oral
DOXYLAMINE plasma
Homo sapiens
81.1 ng × h/mL
3.2 mg single, nasal
DOXYLAMINE plasma
Homo sapiens
117.7 ng × h/mL
6.3 mg single, nasal
DOXYLAMINE plasma
Homo sapiens
161.8 ng × h/mL
12.7 mg single, nasal
DOXYLAMINE plasma
Homo sapiens
751.8 ng × h/mL
25 mg single, oral
DOXYLAMINE plasma
Homo sapiens
1280.9 ng × h/mL
20 mg single, oral
DOXYLAMINE plasma
Homo sapiens
3721.5 ng × h/mL
40 mg 1 times / day multiple, oral
DOXYLAMINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
12.23 h
12.5 mg single, oral
DOXYLAMINE plasma
Homo sapiens
12.45 h
25 mg single, oral
DOXYLAMINE plasma
Homo sapiens
10.2 h
3.2 mg single, nasal
DOXYLAMINE plasma
Homo sapiens
11.8 h
6.3 mg single, nasal
DOXYLAMINE plasma
Homo sapiens
10.1 h
12.7 mg single, nasal
DOXYLAMINE plasma
Homo sapiens
10.4 h
25 mg single, oral
DOXYLAMINE plasma
Homo sapiens
10.1 h
25 mg single, oral
DOXYLAMINE plasma
Homo sapiens
10.1 h
20 mg single, oral
DOXYLAMINE plasma
Homo sapiens
11.9 h
40 mg 1 times / day multiple, oral
DOXYLAMINE plasma
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer





Drug as perpetrator​

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
Usual Adult Dose for Allergic Rhinitis Doxylamine 5 mg oral tablet, chewable: 10 mg orally every 4 to 6 hours not to exceed 6 doses daily. Usual Adult Dose for Allergic Conjunctivitis Doxylamine 5 mg oral tablet, chewable: 10 mg orally every 4 to 6 hours not to exceed 6 doses daily. Usual Adult Dose for Insomnia 12 years of age and older: 25 mg orally 30 minutes before bed
Route of Administration: Oral
In Vitro Use Guide
Doxylamine at 50 ug/ml inhibited both differentiation and proliferation in rat embryo limb bud cell cultures