DOXYLAMINE

US Approved OTC

First approved in 1948

Details

Stereochemistry	RACEMIC
Molecular Formula	C17H22N2O
Molecular Weight	270.37
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(c1ccccc1)(c2ccccn2)OCCN(C)C

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

Molecular Formula	C17H22N2O
Molecular Weight	270.37
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

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 304 Target ID: CHEMBL231 Sources: https://pubmed.ncbi.nlm.nih.gov/23357028/	Antagonist 2575		42.0 nM [Ki]
Muscarinic acetylcholine receptor 158 Target ID: CHEMBL2094109 Sources: https://pubmed.ncbi.nlm.nih.gov/23357028/	Antagonist 2575		200.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Allergic rhinitis 96 Sources: https://www.drugs.com/cdi/doxylamine.html	Primary		Approved 8043	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 100 Sources: https://www.drugs.com/cdi/doxylamine.html	Primary		Approved 8043	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 28 CYP3A 118 CYP1A 48 CYP2E 6 CYP4A 11

Drug as perpetrator

Target	Modality	Activity
CYP1A 110	inducer 1440 Sources: https://pubmed.ncbi.nlm.nih.gov/8975784/	no
CYP2E 10	inducer 1440 Sources: https://pubmed.ncbi.nlm.nih.gov/8975784/	no
CYP4A 29	inducer 1440 Sources: https://pubmed.ncbi.nlm.nih.gov/8975784/	no
CYP2B 36	inducer 1440 Sources: https://pubmed.ncbi.nlm.nih.gov/8975784/	yes
CYP3A 271	inducer 1440 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
[Hyperemesis gravidarum--etiology and treatment].	2003 Sep-Oct	14994923
Neuropharmacological profile of hydroalcohol extract of Valeriana edulis ssp. procera roots in mice.	2004 Apr	15162363
Pre-emptive therapy for severe nausea and vomiting of pregnancy and hyperemesis gravidarum.	2004 Aug	15369934
Is lack of morning sickness teratogenic? A prospective controlled study.	2004 Aug	15329830
Differential protonation and dynamic structure of doxylamine succinate in solution using 1H and 13C NMR.	2004 Jul	15181634
Determinants of women's decision making on whether to treat nausea and vomiting of pregnancy pharmacologically.	2004 Jul-Aug	15236716
Treatment of primary insomnia.	2004 May-Jun	15226287
Steady-state brain concentrations of antihistamines in rats: interplay of membrane permeability, P-glycoprotein efflux and plasma protein binding.	2004 Oct	15331914
Effect of (+) or (-) camphorsulfonic acid additives to the mobile phase on enantioseparations of some basic drugs on a Chiralcel OD column.	2005 Aug 12	16078699
Separation of enantiomers in capillary electrophoresis with contactless conductivity detection.	2005 Aug 5	16035366
Prophylactic Diclectin reduces the incidence of postoperative vomiting.	2005 Jan	15625257
[Efficacy of donormil in the treatment of insomnia in patients with vascular encephalopathy].	2006	16608114
Optimization by factorial design of a capillary zone electrophoresis method for the simultaneous separation of antihistamines.	2006 May 1	16549055
[Juvenile pityriasis rubra pilaris].	2006 Oct	16960730
[Unilateral laterothoracic exanthema].	2006 Oct	16957959
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
Risk factors for rhabdomyolysis following doxylamine overdose.	2007 Aug	17884948
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
[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
A thyrotoxicosis outbreak due to dietary pills in Paris.	2008 Dec	19337445
Representation and re-presentation in litigation science.	2008 Jan	18197311
Sleep complaints: Whenever possible, avoid the use of sleeping pills.	2008 Oct	19536941
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
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
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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

Substance Class	Chemical Created by `admin` on `Sat Jun 26 12:10:40 UTC 2021` Edited by `admin` on `Sat Jun 26 12:10:40 UTC 2021`
Record UNII	95QB77JKPL
Record Status	`Validated (UNII)`
Record Version

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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