AZATADINE MALEATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C20H22N2.2C4H4O4
Molecular Weight	522.5464
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	2
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)\C=C/C(O)=O.OC(=O)\C=C/C(O)=O.CN1CCC(CC1)=C2C3=C(CCC4=C2N=CC=C4)C=CC=C3

InChI

InChIKey=SGHXFFAHXTZRQM-SPIKMXEPSA-N

InChI=1S/C20H22N2.2C4H4O4/c1-22-13-10-16(11-14-22)19-18-7-3-2-5-15(18)8-9-17-6-4-12-21-20(17)19;2*5-3(6)1-2-4(7)8/h2-7,12H,8-11,13-14H2,1H3;2*1-2H,(H,5,6)(H,7,8)/b;2*2-1-

HIDE SMILES / InChI

Molecular Formula	C20H22N2
Molecular Weight	290.4021
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C4H4O4
Molecular Weight	116.0722
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Description
Sources: https://www.drugs.com/mtm/optimine.html

Azatadine is an antihistamine, which blocks the effects of the naturally occurring chemical histamine in the body. Azatadine is used to treat sneezing; runny nose; itching, watery eyes; hives; rashes; and other symptoms of allergies and the common cold. The antihistamines antagonize those pharmacological effects of histamine, which are mediated through activation of H1- receptor sites and thereby reduce the intensity of allergic reactions and tissue injury response involving histamine release.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Histamine H1 receptor 315 Target ID: CHEMBL231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2568212	Antagonist 2778

Conditions

Condition	Modality	Highest Phase	Product
Sneezing 7 Sources: https://www.drugs.com/mtm/optimine.html	Palliative	Approved 8429	OPTIMINE Approved Use Azatadine is used to treat sneezing; runny nose; itching, watery eyes; hives; rashes; itching; and other symptoms of allergies and the common cold. Launch Date 1977
Itching 54 Sources: https://www.drugs.com/mtm/optimine.html	Palliative	Approved 8429	OPTIMINE Approved Use Azatadine is used to treat sneezing; runny nose; itching, watery eyes; hives; rashes; itching; and other symptoms of allergies and the common cold. Launch Date 1977
Hives 5 Sources: https://www.drugs.com/mtm/optimine.html	Palliative	Approved 8429	OPTIMINE Approved Use Azatadine is used to treat sneezing; runny nose; itching, watery eyes; hives; rashes; itching; and other symptoms of allergies and the common cold. Launch Date 1977
Rashes 5 Sources: https://www.drugs.com/mtm/optimine.html	Palliative	Approved 8429	OPTIMINE Approved Use Azatadine is used to treat sneezing; runny nose; itching, watery eyes; hives; rashes; itching; and other symptoms of allergies and the common cold. Launch Date 1977

C_max

Value	Dose	Co-administered	Analyte	Population
1.4 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21737359/	2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered:		AZATADINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
20.5 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21737359/	2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered:		AZATADINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
10.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21737359/	2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered:		AZATADINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
8 mg 1 times / day multiple, oral Highest studied dose Dose: 8 mg, 1 times / day Route: oral Route: multiple Dose: 8 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/37045	healthy, 18-25 years n = 32 Health Status: healthy Age Group: 18-25 years Sex: M Population Size: 32 Sources: https://pubmed.ncbi.nlm.nih.gov/37045	Sources: https://pubmed.ncbi.nlm.nih.gov/37045

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inducer 781

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	UGT2B10 127

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP3A4 1925	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/11996015/	yes

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
UGT2B10 127	substrate 3367 Sources: https://dmd.aspetjournals.org/content/dmd/early/2019/12/15/dmd.119.089482.full.pdf?with-ds=yes	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:2946	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:2946
ChemicalBook	CB21032244	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB21032244
ZINC	ZINC000000968337	http://zinc15.docking.org/substances/ZINC000000968337

PubMed

Title	Date	PubMed
Peripheral antihistamine and central sedative effects of three H1-receptor antagonists.	1985	2864258
Demonstration of inhibition of mediator release from human mast cells by azatadine base. In vivo and in vitro evaluation.	1986 Jan 10	2416958
"In vivo" and "in vitro" evaluation of four antihistamines (astemizole, azatadine, mequitazine, terfenadine).	1989 Mar-Apr	2476015
Effects of azatadine, terfenadine, and astemizole on allergen-induced nasal provocation.	1990 Feb	1968324
The effect of antihistamines on the immediate allergic response: a comparative review.	1993 Jun	8100058
Fungal biotransformation of the antihistamine azatadine by Cunninghamella elegans.	1996 Sep	8795241
Antiallergic effects of H1-receptor antagonists.	2000	11291777
Chromatographic analysis of phenethylamine-antihistamine combinations using C8, C18 or cyano columns and micellar sodium dodecyl sulfate-pentanol mixtures.	2001 Apr	11340978
Quantitation of antihistamines in pharmaceutical preparations by liquid chromatography with a micellar mobile phase of sodium dodecyl sulfate and pentanol.	2001 Nov-Dec	11767132
Antiallergic anti-inflammatory effects of H1-antihistamines in humans.	2002	12113215
Antihistamines in the treatment of dermatitis.	2003 Nov-Dec	15926215
Application of dummy molecularly imprinted solid-phase extraction in the analysis of cyproheptadine in bovine urine.	2009 May	19472275
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.	2010 Dec	21818443

Patents

Sample Use Guides

In Vivo Use Guide

The maximum amount of azatadine that you should take in 1 day is 2 mg. Azatadine can be taken with or without food.

Route of Administration: Oral

In Vitro Use Guide

Azatadine 0.1-10 uM significantly and dose dependently inhibited the release of leukotrienes from lung by 22-71%. Histamine release was also inhibited by azatadine 10 uM.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:08:36 GMT 2023` Edited by `admin` on `Fri Dec 15 15:08:36 GMT 2023`
Record UNII	F3Q391WTX7
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

AZATADINE MALEATE

Official Name

English

Azatadine maleate [WHO-DD]

Common Name

English

AZATADINE DIMALEATE [MI]

Common Name

English

AZATADINE MALEATE [USAN]

Common Name

English

AZATADINE MALEATE [VANDF]

Common Name

English

AZATADINE MALEATE [JAN]

Common Name

English

SCH 10649

Code

English

AZATADINE MALEATE [USP IMPURITY]

Common Name

English

OPTIMINE

Brand Name

English

AZATADINE MALEATE [ORANGE BOOK]

Common Name

English

NSC-759874

Code

English

AZATADINE MALEATE [MART.]

Common Name

English

5H-BENZO(5,6)CYCLOHEPTA(1,2-B)PYRIDINE, 6,11-DIHYDRO-11-(1-METHYL-4-PIPERIDINYLIDENE)-, (Z)-2-BUTENEDIOATE (1:2)

Systematic Name

English

6,11-Dihydro-11-(1-methyl-4-piperidylidene)-5H-benzo[5,6]cyclohepta[1,2-b]pyridine maleate (1:2)

Systematic Name

English

TRINALIN COMPONENT AZATADINE MALEATE

Common Name

English

AZATADINE MALEATE COMPONENT OF TRINALIN

Common Name

English

SCH-10649

Code

English

AZATADINE DIMALEATE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29578