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.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL3943 |
280.0 nM [Ki] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| 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 |
|||
| 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 |
|---|---|---|
| [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 |
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
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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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 |
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ACTIVE MOIETY |
