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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
Effects of histamine H3 receptor agonists and antagonists on cognitive performance and scopolamine-induced amnesia.
1999 Oct
Identification of a histamine H(3)-like receptor in the zebrafish (Danio rerio) brain.
2000 Aug
Distinct pharmacology of rat and human histamine H(3) receptors: role of two amino acids in the third transmembrane domain.
2000 Dec
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
Histamine H3 receptor activation inhibits glutamate release from rat striatal synaptosomes.
2001 Dec
Cortical acetylcholine release elicited by stimulation of histamine H1 receptors in the nucleus basalis magnocellularis: a dual-probe microdialysis study in the freely moving rat.
2001 Jan
The rat H3 receptor: gene organization and multiple isoforms.
2001 Jan 12
[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
Cloning and pharmacological characterization of a fourth histamine receptor (H(4)) expressed in bone marrow.
2001 Mar
[Role of central histamine in amygdaloid kindled seizures].
2001 May
Activation of histamine H3 receptors inhibits renal noradrenergic neurotransmission in anesthetized dogs.
2001 May
Inhibitory effect of histamine on axonal transport in cultured mouse dorsal root ganglion neurons.
2001 Oct
Involvement of central histamine in amygdaloid kindled seizures in rats.
2001 Oct 15
Effects of histidine, a precursor of histamine, on pentylenetetrazole-induced seizures in rats.
2002 Apr
Behavioral characterization of mice lacking histamine H(3) receptors.
2002 Aug
Identification of a histamine H4 receptor on human eosinophils--role in eosinophil chemotaxis.
2002 Feb-Nov
Histamine H3-receptor blockade in the rat nucleus basalis magnocellularis improves place recognition memory.
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
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
Histamine excites GABAergic cells in the rat substantia nigra and ventral tegmental area in vitro.
2002 Mar 8
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
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
Histamine-induced chloride secretion is mediated via H2-receptors in the pig proximal colon.
2003 Feb
Replacement of imidazole by a piperidine moiety differentially affects the potency of histamine H3-receptor antagonists.
2003 Jan
Neuroimmune interactions in guinea pig stomach and small intestine.
2003 Jan
Antinociceptive mechanisms of orally administered decursinol in the mouse.
2003 Jun 13
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
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 Thu Jul 06 02:41:20 UTC 2023
Edited
by admin
on Thu Jul 06 02:41:20 UTC 2023
Record UNII
II4319BWUI
Record Status Validated (UNII)
Record Version
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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 Thu Jul 06 02:41:20 UTC 2023 , Edited by admin on Thu Jul 06 02:41:20 UTC 2023
PRIMARY
FDA UNII
II4319BWUI
Created by admin on Thu Jul 06 02:41:20 UTC 2023 , Edited by admin on Thu Jul 06 02:41:20 UTC 2023
PRIMARY
EPA CompTox
DTXSID50147555
Created by admin on Thu Jul 06 02:41:20 UTC 2023 , Edited by admin on Thu Jul 06 02:41:20 UTC 2023
PRIMARY
WIKIPEDIA
Thioperamide
Created by admin on Thu Jul 06 02:41:20 UTC 2023 , Edited by admin on Thu Jul 06 02:41:20 UTC 2023
PRIMARY
CAS
106243-16-7
Created by admin on Thu Jul 06 02:41:20 UTC 2023 , Edited by admin on Thu Jul 06 02:41:20 UTC 2023
PRIMARY
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