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Details

Stereochemistry ACHIRAL
Molecular Formula C15H24N4S
Molecular Weight 292.443
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of THIOPERAMIDE

SMILES

S=C(NC1CCCCC1)N2CCC(CC2)C3=CNC=N3

InChI

InChIKey=QKDDJDBFONZGBW-UHFFFAOYSA-N
InChI=1S/C15H24N4S/c20-15(18-13-4-2-1-3-5-13)19-8-6-12(7-9-19)14-10-16-11-17-14/h10-13H,1-9H2,(H,16,17)(H,18,20)

HIDE SMILES / InChI

Molecular Formula C15H24N4S
Molecular Weight 292.443
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/22918191 | https://www.ncbi.nlm.nih.gov/pubmed/16432504

Thioperamide is an antihistamine at H3 and H4 receptors. Thioperamide behaves as both antagonist and inverse agonist.Thioperamide is under preclinical development with Glaxo Wellcome (UK) for the treatment of short-term memory impairment. It has also demonstrated antiarrhythmic effects in preclinical trials. Active development of thioperamide appears to have been discontinued.

CNS Activity

Curator's Comment: Thioperamide is CNS active in animals. No human data available.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Role of central histaminergic system in lorazepam withdrawal syndrome in rats.
2001 Apr
Histamine and selective H3-receptor ligands: a possible role in the mechanism and management of epilepsy.
2001 Apr
Histaminergic modulation of GABAergic transmission in rat ventromedial hypothalamic neurones.
2001 Aug 1
Histamine H3 receptor activation inhibits glutamate release from rat striatal synaptosomes.
2001 Dec
Enhancement by histamine of vascular endothelial growth factor production in granulation tissue via H(2) receptors.
2001 Dec
Constitutive activity of histamine h(3) receptors stably expressed in SK-N-MC cells: display of agonism and inverse agonism by H(3) antagonists.
2001 Dec
[Identification and characterization of histamine H4 receptor].
2001 Jul
Novel histaprodifen analogues as potent histamine H1-receptor agonists in the pithed and in the anaesthetized rat.
2001 Jul
Disturbance of the prejunctional modulation of cholinergic neurotransmission during chronic granulomatous inflammation of the mouse ileum.
2001 Jul
Effects of histamine H3-receptor ligands on brain monoamine oxidase in various mammalian species.
2001 Jul 6
The H3 receptor is involved in cholecystokinin inhibition of food intake in rats.
2001 Jun 15
Regulation of IL-13 production by histamine in cloned murine T helper type 2 cells.
2001 Oct
Comparison of human, mouse, rat, and guinea pig histamine H4 receptors reveals substantial pharmacological species variation.
2001 Oct
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 H1 receptor-mediated inhibition of potassium-evoked release of 5-hydroxytryptamine from mouse forebrains.
2001 Oct 15
Regional differences in functional receptor distribution and calcium mobilization in the intact human lens.
2001 Sep
Muscarinic, adenosine A(2) and histamine H(3) receptor modulation of haloperidol-induced c-fos expression in the striatum and nucleus accumbens.
2002
Effects of histidine, a precursor of histamine, on pentylenetetrazole-induced seizures in rats.
2002 Apr
Putative effect of Helicobacter pylori and gastritis on gastric acid secretion in cat.
2002 Apr
Targeted disruption of H3 receptors results in changes in brain histamine tone leading to an obese phenotype.
2002 Dec
Histamine H3-receptor blockade in the rat nucleus basalis magnocellularis improves place recognition memory.
2002 Jan
Presynaptic H3 autoreceptors modulate histamine synthesis through cAMP pathway.
2002 Jan
Histamine regulation of interleukin-18-initiating cytokine cascade is associated with down-regulation of intercellular adhesion molecule-1 expression in human peripheral blood mononuclear cells.
2002 Jan
Mouse light/dark box test reveals anxiogenic-like effects by activation of histamine H1 receptors.
2002 Jan-Feb
Different role of the histamine H3-receptor in vagal-, betanechol-, pentagastrin-induced gastric acid secretion in anaesthetized rats.
2002 Jul
Rodent antinociception following acute treatment with different histamine receptor agonists and antagonists.
2002 Jun
Differential in vivo effects of H3 receptor ligands in a new mouse dipsogenia model.
2002 Jun
Modulation of the discriminative stimulus effects of cocaine and methamphetamine by the histaminergic system.
2002 Jun
Histamine H(2) -like receptors in chick cerebral cortex: effects on cyclic AMP synthesis and characterization by [(3) H]tiotidine binding.
2002 Jun
Evidence for activation of histamine H3 autoreceptors during handling stress in the prefrontal cortex of the rat.
2002 Mar 15
Endogenous central histamine-induced reversal of critical haemorrhagic hypotension in rats--studies with histamine N-methyltransferase inhibitor SKF 91488.
2002 Nov
Activation of the extraneuronal monoamine transporter (EMT) from rat expressed in 293 cells.
2002 Nov
Coordination of histamine H3 receptor antagonists with human adrenal cytochrome P450 enzymes.
2002 Nov
Characteristics of recombinantly expressed rat and human histamine H3 receptors.
2002 Oct 18
Role of histamine receptors in the regulation of edema and circulation postburn.
2003 Dec
Critical role of histamine H4 receptor in leukotriene B4 production and mast cell-dependent neutrophil recruitment induced by zymosan in vivo.
2003 Dec
Histamine-induced chloride secretion is mediated via H2-receptors in the pig proximal colon.
2003 Feb
Histamine inhibits lipopolysaccharide-induced tumor necrosis factor-alpha production in an intercellular adhesion molecule-1- and B7.1-dependent manner.
2003 Feb
Replacement of imidazole by a piperidine moiety differentially affects the potency of histamine H3-receptor antagonists.
2003 Jan
Functional identification of epithelial and smooth muscle histamine-dependent relaxing mechanisms in the bovine trachea, but not in bronchi.
2003 Jan
Two novel and selective nonimidazole histamine H3 receptor antagonists A-304121 and A-317920: I. In vitro pharmacological effects.
2003 Jun
Two novel and selective nonimidazole H3 receptor antagonists A-304121 and A-317920: II. In vivo behavioral and neurophysiological characterization.
2003 Jun
Activation of spinal histamine H3 receptors inhibits mechanical nociception.
2003 Jun 6
Regulation by prostaglandin E2 and histamine of angiogenesis in inflammatory granulation tissue.
2003 May
Possible role of L-carnosine in the regulation of blood glucose through controlling autonomic nerves.
2003 Nov
Generation and characterization of highly constitutive active histamine H3 receptors.
2003 Oct
Histamine h3 receptor antagonists potentiate methamphetamine self-administration and methamphetamine-induced accumbal dopamine release.
2004 Apr
Thioperamide-elicited increase of histamine release from basolateral amygdala of freely moving rats and its therapeutic implications.
2004 Mar
Pruritus-associated response mediated by cutaneous histamine H3 receptors.
2004 Mar
Involvement of histamine H4 and H1 receptors in scratching induced by histamine receptor agonists in Balb C mice.
2004 May
Patents

Sample Use Guides

mouse: thioperamide (10 μg, i.c.v.). rat: thioperamide (20, 50 μg, i.c.v.). rat: thioperamide (310 µg/kg, i.v.). mouse: thioperamide (10 mg/kg, i.p.)
Route of Administration: Other
Thioperamide inhibits firing in rat primary vestibular neurons at nanomolar range and membrane depolarization above 100 µM
Substance Class Chemical
Created
by admin
on Fri Dec 15 19:37:46 GMT 2023
Edited
by admin
on Fri Dec 15 19:37:46 GMT 2023
Record UNII
II4319BWUI
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
THIOPERAMIDE
Common Name English
1-PIPERIDINECARBOTHIOAMIDE, N-CYCLOHEXYL-4-(1H-IMIDAZOL-4-YL)-
Systematic Name English
MR-12842
Code English
1-PIPERIDINECARBOTHIOAMIDE, N-CYCLOHEXYL-4-(1H-IMIDAZOL-5-YL)-
Systematic Name English
Code System Code Type Description
PUBCHEM
3035905
Created by admin on Fri Dec 15 19:37:46 GMT 2023 , Edited by admin on Fri Dec 15 19:37:46 GMT 2023
PRIMARY
FDA UNII
II4319BWUI
Created by admin on Fri Dec 15 19:37:46 GMT 2023 , Edited by admin on Fri Dec 15 19:37:46 GMT 2023
PRIMARY
EPA CompTox
DTXSID50147555
Created by admin on Fri Dec 15 19:37:46 GMT 2023 , Edited by admin on Fri Dec 15 19:37:46 GMT 2023
PRIMARY
WIKIPEDIA
Thioperamide
Created by admin on Fri Dec 15 19:37:46 GMT 2023 , Edited by admin on Fri Dec 15 19:37:46 GMT 2023
PRIMARY
CAS
106243-16-7
Created by admin on Fri Dec 15 19:37:46 GMT 2023 , Edited by admin on Fri Dec 15 19:37:46 GMT 2023
PRIMARY
Related Record Type Details
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TARGET -> INHIBITOR
TARGET -> INHIBITOR