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D3775

Sigma-Aldrich

Doxylamine succinate salt

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About This Item

Fórmula empírica (notación de Hill):
C17H22N2O · C4H6O4
Número de CAS:
562-10-7
Peso molecular:
388.46
EC Number:
209-228-7
MDL number:
MFCD00056168
UNSPSC Code:
12352116
PubChem Substance ID:
24278368
NACRES:
NA.77

form

powder

Quality Level

200

originator

Sanofi Aventis

SMILES string

OC(=O)CCC(O)=O.CN(C)CCOC(C)(c1ccccc1)c2ccccn2

InChI

1S/C17H22N2O.C4H6O4/c1-17(20-14-13-19(2)3,15-9-5-4-6-10-15)16-11-7-8-12-18-16;5-3(6)1-2-4(7)8/h4-12H,13-14H2,1-3H3;1-2H2,(H,5,6)(H,7,8)

InChI key

KBAUFVUYFNWQFM-UHFFFAOYSA-N

Gene Information

human ... HRH1(3269)

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General description

Doxylamine belongs to the ethanolaime class of antihistamines and is metabolized by the liver into N-demethyl doxylamine and N,N-didemethyl doxylamine. It is generally available as an over the counter (OTC) drug for allergy and cold symptoms.

Application

Doxylamine succinate salt has been used as a therapeutic drug to check developmental toxicity.
Doxylamine succinate salt has been used to study the effects of non-teratogenic exposures on morphology and gene expression in human embryonic stem cell aggregates (HESCA)-CSR, under low concentration of retinoic acid in CS medium.

Biochem/physiol Actions

H1 histamine receptor antagonist; hypnotic.
Doxylamine suppresses histamine at the H1 receptor. It is associated with the short term management of insomnia and temporary relief of common cold symptoms. On the other hand, doxylamine intoxication is linked with rhabdomyolysis and secondary acute renal failure.
Studies in mice show that doxylamine induces liver microsomal cytochrome P450 and other enzymes involved in thyroxine (T4) metabolism. In combination with pyridoxine hydrochloride, this drug is used to treat morning sickness.

Features and Benefits

This compound was developed by Sanofi Aventis. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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Husnain Syed et al.
BMJ case reports, 2009, doi:10-doi:10 (2009-01-01)
The present report highlights the possible adverse effects of doxylamine, a common over the counter sleep aid. Doxylamine is an antihistamine that at toxic doses can cause anticholinergic effects, including seizures, rhabdomyolysis and death. The following case describes a patient
D V Gauvin et al.
European journal of pharmacology, 294(1), 281-288 (1995-12-27)
Rats were trained to discriminate between 10 mg/kg cocaine and saline injections under a fixed ratio 10 schedule of food-motivated lever press responding. Once stimulus control was achieved, reinforced test sessions were conducted to assess the degree of generalization of
L F Soto et al.
Postgraduate medicine, 93(8), 227-229 (1993-06-01)
Clinicians should be aware of the complications of rhabdomyolysis in patients who ingest doxylamine succinate and other over-the-counter antihistamines. The easy availability of these substances increases the potential not only for intentional overdose by adults but also for inadvertent ingestion
Sebastián Videla et al.
Drugs in R&D, 12(4), 217-225 (2012-12-13)
Doxylamine succinate, an ethanolamine-based antihistamine, is used in the short-term management of insomnia because of its sedative effects. The data available on the pharmacokinetic profile of doxylamine in humans are limited, notwithstanding that this drug has been marketed in European
J Y Renault et al.
Toxicology and applied pharmacology, 130(2), 177-187 (1995-02-01)
Inhibition of chondrogenesis in limb bud cell micromass cultures has been proposed as a short-term teratogen detection test. Validation studies were performed by testing large series of reference compounds and comparing their teratogenic potential with their ability to inhibit chondrogenesis;
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