DOXYLAMINE

US Approved OTC

First approved in 1948

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 Search

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
Sources: http://www.drugbank.ca/drugs/DB00366
Curator's Comment: Description was created based on several sources, including https://www.drugs.com/cdi/doxylamine.html

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 Target	Pharmacology	Condition	Potency
Histamine H1 receptor 313 Target ID: CHEMBL231 Sources: https://pubmed.ncbi.nlm.nih.gov/23357028/	Antagonist 2760		42.0 nM [Ki]
Muscarinic acetylcholine receptor 160 Target ID: CHEMBL2094109 Sources: https://pubmed.ncbi.nlm.nih.gov/23357028/	Antagonist 2760		200.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Allergic rhinitis 100 Sources: https://www.drugs.com/cdi/doxylamine.html	Primary		Approved 8360	Unisom Approved Use Allergic rhinitis or other respiratory allergies (oral liquid only): Temporary relief of rhinorrhea, sneezing, itchy nose or throat, and itchy, watery eyes due to hay fever or other respiratory allergies Insomnia (tablets only): Reduce difficulty falling asleep Launch Date 2.56089604E11
Insomnia 108 Sources: https://www.drugs.com/cdi/doxylamine.html	Primary		Approved 8360	Unisom Approved Use Allergic rhinitis or other respiratory allergies (oral liquid only): Temporary relief of rhinorrhea, sneezing, itchy nose or throat, and itchy, watery eyes due to hay fever or other respiratory allergies Insomnia (tablets only): Reduce difficulty falling asleep Launch Date 2.56089604E11

C_max

Value	Dose	Co-administered	Analyte	Population
18.9 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29671128/	6.3 mg single, nasal dose: 6.3 mg route of administration: Nasal experiment type: SINGLE co-administered:		DOXYLAMINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
27.1 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29671128/	12.7 mg single, nasal dose: 12.7 mg route of administration: Nasal experiment type: SINGLE co-administered:		DOXYLAMINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
142 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29671128/	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered:		DOXYLAMINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
12.9 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29671128/	3.2 mg single, nasal dose: 3.2 mg route of administration: Nasal experiment type: SINGLE co-administered:		DOXYLAMINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
124.91 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23633146/	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered:		DOXYLAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
61.94 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23633146/	12.5 mg single, oral dose: 12.5 mg route of administration: Oral experiment type: SINGLE co-administered:		DOXYLAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
99 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4056080/	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered:		DOXYLAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
83.3 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021876s000lbl.pdf	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: PYRIDOXINE HYDROCHLORIDE	PYRIDOXINE HYDROCHLORIDE	DOXYLAMINE unknown	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
168.6 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021876s000lbl.pdf	40 mg 1 times / day multiple, oral dose: 40 mg route of administration: Oral experiment type: MULTIPLE co-administered: PYRIDOXINE HYDROCHLORIDE	PYRIDOXINE HYDROCHLORIDE	DOXYLAMINE unknown	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
117.7 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29671128/	6.3 mg single, nasal dose: 6.3 mg route of administration: Nasal experiment type: SINGLE co-administered:		DOXYLAMINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
161.8 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29671128/	12.7 mg single, nasal dose: 12.7 mg route of administration: Nasal experiment type: SINGLE co-administered:		DOXYLAMINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
751.8 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29671128/	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered:		DOXYLAMINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
81.1 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29671128/	3.2 mg single, nasal dose: 3.2 mg route of administration: Nasal experiment type: SINGLE co-administered:		DOXYLAMINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
1697.58 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23633146/	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered:		DOXYLAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
859.74 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23633146/	12.5 mg single, oral dose: 12.5 mg route of administration: Oral experiment type: SINGLE co-administered:		DOXYLAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
1280.9 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021876s000lbl.pdf	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: PYRIDOXINE HYDROCHLORIDE	PYRIDOXINE HYDROCHLORIDE	DOXYLAMINE unknown	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
3721.5 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021876s000lbl.pdf	40 mg 1 times / day multiple, oral dose: 40 mg route of administration: Oral experiment type: MULTIPLE co-administered: PYRIDOXINE HYDROCHLORIDE	PYRIDOXINE HYDROCHLORIDE	DOXYLAMINE unknown	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
11.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29671128/	6.3 mg single, nasal dose: 6.3 mg route of administration: Nasal experiment type: SINGLE co-administered:		DOXYLAMINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
10.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29671128/	12.7 mg single, nasal dose: 12.7 mg route of administration: Nasal experiment type: SINGLE co-administered:		DOXYLAMINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
10.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29671128/	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered:		DOXYLAMINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
10.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29671128/	3.2 mg single, nasal dose: 3.2 mg route of administration: Nasal experiment type: SINGLE co-administered:		DOXYLAMINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
12.45 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23633146/	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered:		DOXYLAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
12.23 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23633146/	12.5 mg single, oral dose: 12.5 mg route of administration: Oral experiment type: SINGLE co-administered:		DOXYLAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
10.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4056080/	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered:		DOXYLAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
10.1 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021876s000lbl.pdf	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: PYRIDOXINE HYDROCHLORIDE	PYRIDOXINE HYDROCHLORIDE	DOXYLAMINE unknown	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
11.9 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021876s000lbl.pdf	40 mg 1 times / day multiple, oral dose: 40 mg route of administration: Oral experiment type: MULTIPLE co-administered: PYRIDOXINE HYDROCHLORIDE	PYRIDOXINE HYDROCHLORIDE	DOXYLAMINE unknown	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
150 mg single, oral Overdose Dose: 150 mg Route: oral Route: single Dose: 150 mg Sources: https://pubmed.ncbi.nlm.nih.gov/25661472 Page: p.179	unknown, 2 n = 1 Health Status: unknown Age Group: 2 Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/25661472 Page: p.179	Other AEs: Agitation, Dilated pupils... Other AEs: Agitation Dilated pupils Sources: https://pubmed.ncbi.nlm.nih.gov/25661472 Page: p.179
25 mg single, oral Studied dose Dose: 25 mg Route: oral Route: single Dose: 25 mg Sources: https://pubmed.ncbi.nlm.nih.gov/23633146 Page: p.133	healthy, 28 - 58 n = 12 Health Status: healthy Age Group: 28 - 58 Sex: M+F Population Size: 12 Sources: https://pubmed.ncbi.nlm.nih.gov/23633146 Page: p.133	Other AEs: Somnolence... Other AEs: Somnolence (50%) Sources: https://pubmed.ncbi.nlm.nih.gov/23633146 Page: p.133
12.7 mg single, intranasal Highest studied dose Dose: 12.7 mg Route: intranasal Route: single Dose: 12.7 mg Sources: https://pubmed.ncbi.nlm.nih.gov/29671128 Page: p.133	unhealthy, 35.9 (8.00) n = 24 Health Status: unhealthy Condition: Chronic intermittent sleep impairment Age Group: 35.9 (8.00) Sex: M+F Population Size: 24 Sources: https://pubmed.ncbi.nlm.nih.gov/29671128 Page: p.133	Sources: https://pubmed.ncbi.nlm.nih.gov/29671128 Page: p.133
13 mg/kg single, oral Overdose Dose: 13 mg/kg Route: oral Route: single Dose: 13 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/29196111 Page: p.1	unknown Health Status: unknown Sources: https://pubmed.ncbi.nlm.nih.gov/29196111 Page: p.1	Other AEs: Rhabdomyolysis... Other AEs: Rhabdomyolysis Sources: https://pubmed.ncbi.nlm.nih.gov/29196111 Page: p.1
20 mg 2 times / day multiple, oral Recommended Dose: 20 mg, 2 times / day Route: oral Route: multiple Dose: 20 mg, 2 times / day Co-administed with:: pyridoxine hydrochloride(20 mg oral; 1-2/day) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/209661lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: Nausea and vomiting of pregnancy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/209661lbl.pdf Page: p.1	Other AEs: Somnolence... Other AEs: Somnolence Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/209661lbl.pdf Page: p.1
20 mg 2 times / day multiple, oral Recommended Dose: 20 mg, 2 times / day Route: oral Route: multiple Dose: 20 mg, 2 times / day Co-administed with:: pyridoxine hydrochloride(20 mg oral; 1-2/day) CNS depressants Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/209661lbl.pdf Page: p.3	unhealthy Health Status: unhealthy Condition: Nausea and vomiting of pregnancy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/209661lbl.pdf Page: p.3	Other AEs: Drowsiness... Other AEs: Drowsiness (grade 3) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/209661lbl.pdf Page: p.3
20 mg single, oral Recommended Dose: 20 mg Route: oral Route: single Dose: 20 mg Co-administed with:: pyridoxine hydrochloride(20 mg oral single dose) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/209661Orig1s000MedR.pdf Page: p.48	healthy n = 48 Health Status: healthy Sex: F Population Size: 48 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/209661Orig1s000MedR.pdf Page: p.48	Disc. AE: Vomiting... AEs leading to discontinuation/dose reduction: Vomiting Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/209661Orig1s000MedR.pdf Page: p.48
20 mg 2 times / day steady, oral Recommended Dose: 20 mg, 2 times / day Route: oral Route: steady Dose: 20 mg, 2 times / day Co-administed with:: pyridoxine hydrochloride(20 mg oral single dose) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/209661Orig1s000MedR.pdf Page: p.63	healthy n = 37 Health Status: healthy Sex: F Population Size: 37 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/209661Orig1s000MedR.pdf Page: p.63	Disc. AE: Vomiting, Decreased hemoglobin... AEs leading to discontinuation/dose reduction: Vomiting Decreased hemoglobin Visual impairment Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/209661Orig1s000MedR.pdf Page: p.63

AEs

AE	Significance	Dose	Population
Agitation		150 mg single, oral Overdose Dose: 150 mg Route: oral Route: single Dose: 150 mg Sources: https://pubmed.ncbi.nlm.nih.gov/25661472 Page: p.179	unknown, 2 n = 1 Health Status: unknown Age Group: 2 Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/25661472 Page: p.179
Dilated pupils		150 mg single, oral Overdose Dose: 150 mg Route: oral Route: single Dose: 150 mg Sources: https://pubmed.ncbi.nlm.nih.gov/25661472 Page: p.179	unknown, 2 n = 1 Health Status: unknown Age Group: 2 Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/25661472 Page: p.179
Somnolence	50%	25 mg single, oral Studied dose Dose: 25 mg Route: oral Route: single Dose: 25 mg Sources: https://pubmed.ncbi.nlm.nih.gov/23633146 Page: p.133	healthy, 28 - 58 n = 12 Health Status: healthy Age Group: 28 - 58 Sex: M+F Population Size: 12 Sources: https://pubmed.ncbi.nlm.nih.gov/23633146 Page: p.133
Rhabdomyolysis		13 mg/kg single, oral Overdose Dose: 13 mg/kg Route: oral Route: single Dose: 13 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/29196111 Page: p.1	unknown Health Status: unknown Sources: https://pubmed.ncbi.nlm.nih.gov/29196111 Page: p.1
Somnolence		20 mg 2 times / day multiple, oral Recommended Dose: 20 mg, 2 times / day Route: oral Route: multiple Dose: 20 mg, 2 times / day Co-administed with:: pyridoxine hydrochloride(20 mg oral; 1-2/day) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/209661lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: Nausea and vomiting of pregnancy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/209661lbl.pdf Page: p.1
Drowsiness	grade 3	20 mg 2 times / day multiple, oral Recommended Dose: 20 mg, 2 times / day Route: oral Route: multiple Dose: 20 mg, 2 times / day Co-administed with:: pyridoxine hydrochloride(20 mg oral; 1-2/day) CNS depressants Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/209661lbl.pdf Page: p.3	unhealthy Health Status: unhealthy Condition: Nausea and vomiting of pregnancy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/209661lbl.pdf Page: p.3
Vomiting	Disc. AE	20 mg single, oral Recommended Dose: 20 mg Route: oral Route: single Dose: 20 mg Co-administed with:: pyridoxine hydrochloride(20 mg oral single dose) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/209661Orig1s000MedR.pdf Page: p.48	healthy n = 48 Health Status: healthy Sex: F Population Size: 48 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/209661Orig1s000MedR.pdf Page: p.48
Decreased hemoglobin	Disc. AE	20 mg 2 times / day steady, oral Recommended Dose: 20 mg, 2 times / day Route: oral Route: steady Dose: 20 mg, 2 times / day Co-administed with:: pyridoxine hydrochloride(20 mg oral single dose) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/209661Orig1s000MedR.pdf Page: p.63	healthy n = 37 Health Status: healthy Sex: F Population Size: 37 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/209661Orig1s000MedR.pdf Page: p.63
Visual impairment	Disc. AE	20 mg 2 times / day steady, oral Recommended Dose: 20 mg, 2 times / day Route: oral Route: steady Dose: 20 mg, 2 times / day Co-administed with:: pyridoxine hydrochloride(20 mg oral single dose) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/209661Orig1s000MedR.pdf Page: p.63	healthy n = 37 Health Status: healthy Sex: F Population Size: 37 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/209661Orig1s000MedR.pdf Page: p.63
Vomiting	Disc. AE	20 mg 2 times / day steady, oral Recommended Dose: 20 mg, 2 times / day Route: oral Route: steady Dose: 20 mg, 2 times / day Co-administed with:: pyridoxine hydrochloride(20 mg oral single dose) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/209661Orig1s000MedR.pdf Page: p.63	healthy n = 37 Health Status: healthy Sex: F Population Size: 37 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/209661Orig1s000MedR.pdf Page: p.63

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
		CYP2B 32 CYP3A 126 CYP1A 56 CYP2E 9 CYP4A 14

Drug as perpetrator

Target	Modality	Activity
CYP1A 121	inducer 1542 Sources: https://pubmed.ncbi.nlm.nih.gov/8975784/	no
CYP2E 13	inducer 1542 Sources: https://pubmed.ncbi.nlm.nih.gov/8975784/	no
CYP4A 33	inducer 1542 Sources: https://pubmed.ncbi.nlm.nih.gov/8975784/	no
CYP2B 40	inducer 1542 Sources: https://pubmed.ncbi.nlm.nih.gov/8975784/	yes
CYP3A 295	inducer 1542 Sources: https://pubmed.ncbi.nlm.nih.gov/8975784/	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:51380	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:51380
ChemicalBook	CB6316736	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB6316736
MolPort	MolPort-005-935-542	https://www.molport.com/shop/molecule-link/MolPort-005-935-542
eMolecules	901808	https://www.emolecules.com/cgi-bin/more?vid=901808

PubMed

Title	Date	PubMed
Preventing recurrence of severe morning sickness.	2006 Dec	17279232
Therapy insight: drugs for gastrointestinal disorders in pregnant women.	2006 May	16673005
OTC product: Zicam Cold and Flu Medicated Spoons.	2006 Nov-Dec	17517566
[Transitory acute psychosis with serotoninergic syndrome at the time of an intoxication by dosulepin associated with doxylamine and ethanol].	2006 Nov-Dec	17348613
[Juvenile pityriasis rubra pilaris].	2006 Oct	16960730
[Unilateral laterothoracic exanthema].	2006 Oct	16957959
Vanished behind the counter. Starting this week, you'll need help buying your claritin and nyquil.	2006 Oct 2	17039645
The risk of risk reduction: can postmarket surveillance pose more risk than benefit?	2007	17915389
Efficacy of a single evening dose of syrup containing paracetamol, dextromethorphan hydrobromide, doxylamine succinate and ephedrine sulfate in subjects with multiple common cold symptoms.	2007 Apr	17474541
Comparison of lactated Ringer's solution and 0.9% saline in the treatment of rhabdomyolysis induced by doxylamine intoxication.	2007 Apr	17384382
Characterization of antihistamine-human serum protein interactions by capillary electrophoresis.	2007 Apr 20	17339039
Risk factors for rhabdomyolysis following doxylamine overdose.	2007 Aug	17884948
American Gastroenterological Association institute medical position statement on the use of gastrointestinal medication in pregnancy.	2007 Feb	17261292
Inactivation of anthracyclines by serum heme proteins.	2007 Jun	17497896
Separation of cold medicine ingredients using a precise MEKC method at elevated pH.	2007 Jun	17450538
Possible role of pseudoephedrine and other over-the-counter cold medications in the deaths of very young children.	2007 Mar	17316256
First-generation H1 antihistamines found in pilot fatalities of civil aviation accidents, 1990-2005.	2007 May	17539447
[Chemicotoxicological evaluation of doxylamine].	2007 May-Jun	17598444
An estimate of the proportion of drug-facilitation of sexual assault in four U.S. localities.	2007 Nov	18093069
Differentially expressed genes in embryonic cardiac tissues of mice lacking Folr1 gene activity.	2007 Nov 20	18028541
Managing nausea and vomiting of pregnancy: a survey of obstetrician-gynecologists.	2007 Oct	17977167
[Is good care (only) guaranteed by a specialist?].	2008 Apr 15	18505234
A thyrotoxicosis outbreak due to dietary pills in Paris.	2008 Dec	19337445
"DXemon juice:" analytical evaluation of an extraction process for the purification and freebasing of dextromethorphan from cold preparations.	2008 Dec	19031385
Representation and re-presentation in litigation science.	2008 Jan	18197311
Sleep complaints: Whenever possible, avoid the use of sleeping pills.	2008 Oct	19536941
Simultaneous determination of a ternary mixture of doxylamine succinate, pyridoxine hydrochloride, and folic acid by the ratio spectra-zero-crossing, double divisor-ratio spectra derivative, and column high-performance liquid chromatographic methods.	2008 Sep-Oct	18980119
Doxylamine toxicity: seizure, rhabdomyolysis and false positive urine drug screen for methadone.	2009	21686586
Extended suicide using an atypical stud gun.	2009 Aug 10	19428201
Pharmacokinetic comparison of a delayed-release combination of doxylamine succinate and pyridoxine hydrocholoride (Diclectin) and oral solutions of these drugs in healthy women of childbearing age.	2009 Fall	19923636
Long-term neurodevelopment of children exposed to maternal nausea and vomiting of pregnancy and diclectin.	2009 Jul	19394042
Comparison of chiral separation of basic drugs in capillary electrophoresis and liquid chromatography using neutral and negatively charged cyclodextrins.	2009 Jul 10	19481637
The identification of ingested dandelion juice in gastric contents of a deceased person by direct sequencing and GC-MS methods.	2009 May	19432748
Does advice from pharmacy staff vary according to the nonprescription medicine requested?	2009 Nov	19843841
Acute renal failure caused by pheniramine maleate induced rhabdomyolysis: an unusual case.	2009 Oct	20436692
Drugs associated with more suicidal ideations are also associated with more suicide attempts.	2009 Oct 2	19798416
Multiple-drug toxicity caused by the coadministration of 4-methylmethcathinone (mephedrone) and heroin.	2010 Apr	20406541
Learning curves for pediatric laparoscopy: how many operations are enough? The Amsterdam experience with laparoscopic pyloromyotomy.	2010 Aug	20174951
Commonly prescribed medications and potential false-positive urine drug screens.	2010 Aug 15	20689123
Optimal management of nausea and vomiting of pregnancy.	2010 Aug 4	21151729
Effectiveness of delayed-release doxylamine and pyridoxine for nausea and vomiting of pregnancy: a randomized placebo controlled trial.	2010 Dec	20843504
Rational quantitative structure-activity relationship (RQSAR) screen for PXR and CAR isoform-specific nuclear receptor ligands.	2010 Dec 5	20869355
Authenticity of claims made in drug promotional literature.	2010 Feb	20606845
Managing hyperemesis gravidarum: a multimodal challenge.	2010 Jul 15	20633258
[Hyperemesis gravidarum: a rare but potentially severe complication of the first trimester of pregnancy].	2010 Jun 20	20623888
A tendency for re-offending in drug-facilitated crime.	2010 Mar 20	20116946
Biotransformation of ginsenosides Rb1, Rg3 and Rh2 in rat gastrointestinal tracts.	2010 May 26	20504301
An unusual death involving a sensory deprivation tank.	2010 Nov	20533982
An overdose death involving the insufflation of extended-release oxymorphone tablets.	2010 Oct	21819798
Clinical practice. Nausea and vomiting in pregnancy.	2010 Oct 14	20942670

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

Name

Type

Language

DOXYLAMINE

Official Name

English

DOXYLAMINE [VANDF]

Common Name

English

PYRIDINE, 2-(.ALPHA.-(2-(DIMETHYLAMINO)ETHOXY)-.ALPHA.-METHYLBENZYL)-

Systematic Name

English

2-(.ALPHA.(2-(DIMETHYLAMINO)ETHOXY)-.ALPHA.-METHYLBENZYL)PYRIDINE

Systematic Name

English

(±)-DOXYLAMINE

Common Name

English

doxylamine [INN]

Common Name

English

ETHANAMINE, N,N-DIMETHYL-2-(1-PHENYL-1-(2-PYRIDINYL)ETHOXY)-

Systematic Name

English

DOXYLAMINE [MI]

Common Name

English

DOXYLAMINE [HSDB]

Common Name

English

Doxylamine [WHO-DD]

Common Name

English

N,N-DIMETHYL-2-(1-PHENYL-1-(2-PYRIDINYL)ETHOXY)ETHANAMINE

Systematic Name

English

Classification Tree Code System Code

WHO-ATC

R06AA59