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
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
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 | ( + / - ) |
DescriptionCurator's Comment:: description was created based on several sources, including
https://www.drugbank.ca/drugs/DB01071
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/14987305
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.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL3943 Sources: https://www.drugbank.ca/drugs/DB01071 |
280.0 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | PRIMALAN Approved UseAntihistamine 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 Date4.71743988E11 |
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Primary | PRIMALAN Approved UseAntihistamine 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 Date4.71743988E11 |
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Primary | PRIMALAN Approved UseAntihistamine 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 Date4.71743988E11 |
|||
Primary | PRIMALAN Approved UseAntihistamine 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 Date4.71743988E11 |
PubMed
Title | Date | PubMed |
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"In vivo" and "in vitro" evaluation of four antihistamines (astemizole, azatadine, mequitazine, terfenadine). | 1989 Mar-Apr |
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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 |
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In vivo and in vitro interaction of the novel selective histamine H1 receptor antagonist mizolastine with H1 receptors in the rodent. | 1995 May |
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Efficacy of mequitazine in comparison with placebo assessed by ocular challenge with allergen in allergic conjunctivitis. | 1997 Apr |
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Oxidation of histamine H1 antagonist mequitazine is catalyzed by cytochrome P450 2D6 in human liver microsomes. | 1998 Feb |
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Ketoconazole potentiates terfenadine-induced apoptosis in human Hep G2 cells through inhibition of cytochrome p450 3A4 activity. | 2002 |
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/41044
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
Edited
Sat Jun 26 11:45:42 UTC 2021
by
admin
on
Sat Jun 26 11:45:42 UTC 2021
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Record UNII |
Y463242LY2
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Record Status |
Validated (UNII)
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Record Version |
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WHO-VATC |
QR06AD07
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WHO-ATC |
R06AD07
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Code System | Code | Type | Description | ||
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C006069
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M7201
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29216-28-2
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29528
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29216-28-2
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Y463242LY2
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C170162
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MEQUITAZINE
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DB01071
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4066
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3672
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CHEMBL1908311
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249-521-7
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1707
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SUB08766MIG
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Related Record | Type | Details | ||
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TARGET -> INHIBITOR | |||
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ENANTIOMER -> RACEMATE | |||
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METABOLIC ENZYME -> SUBSTRATE | |||
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ENANTIOMER -> RACEMATE |
Related Record | Type | Details | ||
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ACTIVE MOIETY |