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Details

Stereochemistry RACEMIC
Molecular Formula C20H22N2S
Molecular Weight 322.4689
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MEQUITAZINE

SMILES

c1ccc2c(c1)N(CC3CN4CCC3CC4)c5ccccc5S2

InChI

InChIKey=HOKDBMAJZXIPGC-UHFFFAOYSA-N
InChI=1S/C20H22N2S/c1-3-7-19-17(5-1)22(18-6-2-4-8-20(18)23-19)14-16-13-21-11-9-15(16)10-12-21/h1-8,15-16H,9-14H2

HIDE SMILES / InChI

Molecular Formula C20H22N2S
Molecular Weight 322.4689
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description
Curator's Comment:: description was created based on several sources, including https://www.drugbank.ca/drugs/DB01071

Mequitazine (PRIMALAN®) is a phenothiazine derivative and a histamine H1-receptor antagonist. It competes with histamine for the normal H1-receptor sites on effector cells of the gastrointestinal tract, blood vessels and respiratory tract. It provides effective, temporary relief of sneezing, watery and itchy eyes, and runny nose due to hay fever and other upper respiratory allergies.

CNS Activity

Curator's Comment:: It was concluded that mequitazine is mildly sedating. The effects of mequitazine are comparable to those of other second-generation antihistamines, in that it causes mild driving impairment, particularly at higher doses.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
280.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PRIMALAN

Approved Use

Antihistamine for the treatment of allergic conditions such as hay fever, perennial rhinitis, urticaria, pruritis of allergic origin and allergic reactions associated with insect bites and stings.

Launch Date

4.71743988E11
Primary
PRIMALAN

Approved Use

Antihistamine for the treatment of allergic conditions such as hay fever, perennial rhinitis, urticaria, pruritis of allergic origin and allergic reactions associated with insect bites and stings.

Launch Date

4.71743988E11
Primary
PRIMALAN

Approved Use

Antihistamine for the treatment of allergic conditions such as hay fever, perennial rhinitis, urticaria, pruritis of allergic origin and allergic reactions associated with insect bites and stings.

Launch Date

4.71743988E11
Primary
PRIMALAN

Approved Use

Antihistamine for the treatment of allergic conditions such as hay fever, perennial rhinitis, urticaria, pruritis of allergic origin and allergic reactions associated with insect bites and stings.

Launch Date

4.71743988E11
PubMed

PubMed

TitleDatePubMed
[Comparative study of a new antihistamine, mequitazine, and placebos].
1975 Nov
"In vivo" and "in vitro" evaluation of four antihistamines (astemizole, azatadine, mequitazine, terfenadine).
1989 Mar-Apr
The histamine H1-receptor antagonist binding site. A stereoselective pharmacophoric model based upon (semi-)rigid H1-antagonists and including a known interaction site on the receptor.
1995 Aug 18
In vivo and in vitro interaction of the novel selective histamine H1 receptor antagonist mizolastine with H1 receptors in the rodent.
1995 May
Efficacy of mequitazine in comparison with placebo assessed by ocular challenge with allergen in allergic conjunctivitis.
1997 Apr
Oxidation of histamine H1 antagonist mequitazine is catalyzed by cytochrome P450 2D6 in human liver microsomes.
1998 Feb
Ketoconazole potentiates terfenadine-induced apoptosis in human Hep G2 cells through inhibition of cytochrome p450 3A4 activity.
2002
A dose-ranging study of the effects of mequitazine on actual driving, memory and psychomotor performance as compared to dexchlorpheniramine, cetirizine and placebo.
2004 Feb
Inhibitory effects of nicardipine to cytochrome P450 (CYP) in human liver microsomes.
2005 May
[Efficacy of mequitazine (Primalan) on the relief of symptoms of allergic rhinoconjunctivitis in children. Documented clinical experience].
2005 Nov-Dec
Patents

Sample Use Guides

The usual dose for adults is one 5 mg tablet to be taken orally twice a day, although in elderly patients (over 65 years) caution should be used.
Route of Administration: Oral
In Vitro Use Guide
The affinity of mequitazine for H1 receptors in guinea pigs was compared with that of classical sedative antihistamines ((+)-chlorpheniramine and promethazine). In vitro determinations of Ki values of [3H]mepyramine binding in the brain reveal that mequitazine is 15 to 20 times less potent than (+)-chlorpheniramine and promethazine (Ki value was 280 nM, 12 nM and 17 nM, respectively).
Substance Class Chemical
Created
by admin
on Sat Jun 26 11:45:42 UTC 2021
Edited
by admin
on Sat Jun 26 11:45:42 UTC 2021
Record UNII
Y463242LY2
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MEQUITAZINE
INN   MART.   MI   WHO-DD  
INN  
Official Name English
MEQUITAZINE [MI]
Common Name English
MEQUITAZINE [JAN]
Common Name English
NSC-303612
Code English
MEQUITAZINE [MART.]
Common Name English
MEQUITAZINE [WHO-DD]
Common Name English
KITAZEMIN
Brand Name English
MEQUITAZINE [INN]
Common Name English
10-(3-QUINUCLIDINYLMETHYL)PHENOTHIAZINE
Systematic Name English
Classification Tree Code System Code
WHO-VATC QR06AD07
Created by admin on Sat Jun 26 11:45:42 UTC 2021 , Edited by admin on Sat Jun 26 11:45:42 UTC 2021
WHO-ATC R06AD07
Created by admin on Sat Jun 26 11:45:42 UTC 2021 , Edited by admin on Sat Jun 26 11:45:42 UTC 2021
Code System Code Type Description
MESH
C006069
Created by admin on Sat Jun 26 11:45:42 UTC 2021 , Edited by admin on Sat Jun 26 11:45:42 UTC 2021
PRIMARY
MERCK INDEX
M7201
Created by admin on Sat Jun 26 11:45:42 UTC 2021 , Edited by admin on Sat Jun 26 11:45:42 UTC 2021
PRIMARY Merck Index
EPA CompTox
29216-28-2
Created by admin on Sat Jun 26 11:45:42 UTC 2021 , Edited by admin on Sat Jun 26 11:45:42 UTC 2021
PRIMARY
RXCUI
29528
Created by admin on Sat Jun 26 11:45:42 UTC 2021 , Edited by admin on Sat Jun 26 11:45:42 UTC 2021
PRIMARY RxNorm
CAS
29216-28-2
Created by admin on Sat Jun 26 11:45:42 UTC 2021 , Edited by admin on Sat Jun 26 11:45:42 UTC 2021
PRIMARY
FDA UNII
Y463242LY2
Created by admin on Sat Jun 26 11:45:42 UTC 2021 , Edited by admin on Sat Jun 26 11:45:42 UTC 2021
PRIMARY
NCI_THESAURUS
C170162
Created by admin on Sat Jun 26 11:45:42 UTC 2021 , Edited by admin on Sat Jun 26 11:45:42 UTC 2021
PRIMARY
WIKIPEDIA
MEQUITAZINE
Created by admin on Sat Jun 26 11:45:42 UTC 2021 , Edited by admin on Sat Jun 26 11:45:42 UTC 2021
PRIMARY
DRUG BANK
DB01071
Created by admin on Sat Jun 26 11:45:42 UTC 2021 , Edited by admin on Sat Jun 26 11:45:42 UTC 2021
PRIMARY
PUBCHEM
4066
Created by admin on Sat Jun 26 11:45:42 UTC 2021 , Edited by admin on Sat Jun 26 11:45:42 UTC 2021
PRIMARY
INN
3672
Created by admin on Sat Jun 26 11:45:42 UTC 2021 , Edited by admin on Sat Jun 26 11:45:42 UTC 2021
PRIMARY
ChEMBL
CHEMBL1908311
Created by admin on Sat Jun 26 11:45:42 UTC 2021 , Edited by admin on Sat Jun 26 11:45:42 UTC 2021
PRIMARY
ECHA (EC/EINECS)
249-521-7
Created by admin on Sat Jun 26 11:45:42 UTC 2021 , Edited by admin on Sat Jun 26 11:45:42 UTC 2021
PRIMARY
DRUG CENTRAL
1707
Created by admin on Sat Jun 26 11:45:42 UTC 2021 , Edited by admin on Sat Jun 26 11:45:42 UTC 2021
PRIMARY
EVMPD
SUB08766MIG
Created by admin on Sat Jun 26 11:45:42 UTC 2021 , Edited by admin on Sat Jun 26 11:45:42 UTC 2021
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
ENANTIOMER -> RACEMATE
METABOLIC ENZYME -> SUBSTRATE
ENANTIOMER -> RACEMATE
Related Record Type Details
ACTIVE MOIETY