Details
Stereochemistry | ACHIRAL |
Molecular Formula | C22H27N3OS |
Molecular Weight | 381.534 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
C(CNC1=NC2=C(S1)C=CC=C2)COC3=CC=CC(CN4CCCCC4)=C3
InChI
InChIKey=KUBONGDXTUOOLM-UHFFFAOYSA-N
InChI=1S/C22H27N3OS/c1-4-13-25(14-5-1)17-18-8-6-9-19(16-18)26-15-7-12-23-22-24-20-10-2-3-11-21(20)27-22/h2-3,6,8-11,16H,1,4-5,7,12-15,17H2,(H,23,24)
Molecular Formula | C22H27N3OS |
Molecular Weight | 381.534 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Zolantidine is the novel benzthiazole derivative. It is a centrally acting potent antagonist of histamine at H2-receptors. It was found to be a competitive inhibitor of the histamine catabolising enzyme in brain, histamine N-methyltransferase. High aggression in histamine N-methyltransferase knockout mice was suppressed by treatment with zolantidine, indicating that abnormal histamine H2 receptor activation promoted aggression in knockout mice. Histamine H(3) receptor antagonist JNJ-10181457-induced anxiety-like behaviours were dominantly reduced by zolantidine. Zolantidine significantly attenuated the discriminative stimulus effects of morphine.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL4654 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2894879 |
6.3 null [pKi] | ||
Target ID: Q9EST2 Gene ID: 1.00135536E8 Gene Symbol: HNMT Target Organism: Cavia porcellus (Guinea pig) Sources: https://www.ncbi.nlm.nih.gov/pubmed/2894879 |
6.6 null [pKi] | ||
Target ID: P31389 Gene ID: NA Gene Symbol: HRH1 Target Organism: Cavia porcellus (Guinea pig) Sources: https://www.ncbi.nlm.nih.gov/pubmed/2894879 |
5.1 null [pKi] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
|||
Palliative | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
Zolantidine (SK&F 95282) is a potent selective brain-penetrating histamine H2-receptor antagonist. | 1988 Jan |
|
Histamine H(3)-receptor antagonism improves memory retention and reverses the cognitive deficit induced by scopolamine in a two-trial place recognition task. | 2001 Oct 15 |
|
Histamine H(2) -like receptors in chick cerebral cortex: effects on cyclic AMP synthesis and characterization by [(3) H]tiotidine binding. | 2002 Jun |
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Involvement of histaminergic system in the discriminative stimulus effects of morphine. | 2004 May 3 |
|
Enhanced antinociceptive effects of morphine in histamine H2 receptor gene knockout mice. | 2006 Sep |
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Mechanism of the histamine H(3) receptor-mediated increase in exploratory locomotor activity and anxiety-like behaviours in mice. | 2014 Jun |
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The Histamine H3 Receptor Antagonist E159 Reverses Memory Deficits Induced by Dizocilpine in Passive Avoidance and Novel Object Recognition Paradigm in Rats. | 2017 |
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[Mechanisms of histamine ameliorating memory impairment induced by pentylenetetrazole-kindling epilepsy in rats]. | 2017 Jan 25 |
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Histamine N-methyltransferase regulates aggression and the sleep-wake cycle. | 2017 Nov 21 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/29162912
10 mg/kg
Route of Administration:
Intraperitoneal
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2894879
Zolantidine also inhibited histamine stimulated adenylate cyclase in a guinea-pig cardiac ventricle homogenate. An IC50 value of 840 ± 60 nM was obtained, corresponding to a Ki value of 52 ± 4 nM, (pKi 7.3).
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 18:12:12 GMT 2023
by
admin
on
Fri Dec 15 18:12:12 GMT 2023
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Record UNII |
M1108XAY01
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Record Status |
Validated (UNII)
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Record Version |
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M1108XAY01
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DTXSID6048460
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91769
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C055302
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Zolantidine
Created by
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Related Record | Type | Details | ||
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ACTIVE MOIETY |