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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
Cognitive enhancing properties of thioperamide infused into the nucleus basalis magnocellularis of the rat.
2001 Apr
Histaminergic modulation of GABAergic transmission in rat ventromedial hypothalamic neurones.
2001 Aug 1
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
Histamine H3 receptor-mediated impairment of contextual fear conditioning and in-vivo inhibition of cholinergic transmission in the rat basolateral amygdala.
2001 Nov
Histamine H1 receptors mediate the anorectic action of the pancreatic hormone amylin.
2001 Nov
Dynamics of histamine H(3) receptor antagonists on brain histamine metabolism: do all histamine H(3) receptor antagonists act at a single site?
2001 Nov 16
Effect of L-carnosine on the hyperglycemia caused by intracranial injection of 2-deoxy-D-glucose in rats.
2001 Nov 2
Regulation of IL-13 production by histamine in cloned murine T helper type 2 cells.
2001 Oct
Inhibitory effect of histamine on axonal transport in cultured mouse dorsal root ganglion neurons.
2001 Oct
Comparison of human, mouse, rat, and guinea pig histamine H4 receptors reveals substantial pharmacological species variation.
2001 Oct
Involvement of central histamine in amygdaloid kindled seizures in rats.
2001 Oct 15
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
Contractile response of horse deep dorsal penile vein to histamine.
2002 Apr
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
Role of histamine H3 receptors in control of mouse intestinal motility in vivo and in vitro: comparison with alpha2-adrenoceptors.
2002 May
Experimental anxiety induced by histaminergics in mast cell-deficient and congenitally normal mice.
2002 May
Influence of SKF 91488, histamine N-methyltransferase inhibitor, on the central cardiovascular regulation during controlled, stepwise hemorrhagic hypotension in rats.
2002 May-Jun
Endogenous central histamine-induced reversal of critical haemorrhagic hypotension in rats--studies with histamine N-methyltransferase inhibitor SKF 91488.
2002 Nov
Coordination of histamine H3 receptor antagonists with human adrenal cytochrome P450 enzymes.
2002 Nov
High-frequency oscillation in the hippocampus of the behaving rat and its modulation by the histaminergic system.
2003
Role of histamine receptors in the regulation of edema and circulation postburn.
2003 Dec
Histamine inhibits lipopolysaccharide-induced tumor necrosis factor-alpha production in an intercellular adhesion molecule-1- and B7.1-dependent manner.
2003 Feb
Neuroimmune interactions in guinea pig stomach and small intestine.
2003 Jan
Central endogenous histamine modulates sympathetic outflow through H3 receptors in the conscious rabbit.
2003 Jul
Histamine H4 receptor mediates chemotaxis and calcium mobilization of mast cells.
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
Histamine induces cytoskeletal changes in human eosinophils via the H(4) receptor.
2003 Nov
Aminergic control of high-frequency (approximately 200 Hz) network oscillations in the hippocampus of the behaving rat.
2003 Sep 11
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 Sat Dec 17 03:11:30 UTC 2022
Edited
by admin
on Sat Dec 17 03:11:30 UTC 2022
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 Sat Dec 17 03:11:30 UTC 2022 , Edited by admin on Sat Dec 17 03:11:30 UTC 2022
PRIMARY
FDA UNII
II4319BWUI
Created by admin on Sat Dec 17 03:11:30 UTC 2022 , Edited by admin on Sat Dec 17 03:11:30 UTC 2022
PRIMARY
EPA CompTox
DTXSID50147555
Created by admin on Sat Dec 17 03:11:30 UTC 2022 , Edited by admin on Sat Dec 17 03:11:30 UTC 2022
PRIMARY
WIKIPEDIA
Thioperamide
Created by admin on Sat Dec 17 03:11:30 UTC 2022 , Edited by admin on Sat Dec 17 03:11:30 UTC 2022
PRIMARY
CAS
106243-16-7
Created by admin on Sat Dec 17 03:11:30 UTC 2022 , Edited by admin on Sat Dec 17 03:11:30 UTC 2022
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
TARGET -> INHIBITOR
TRANSPORTER -> INHIBITOR