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Details

Stereochemistry ACHIRAL
Molecular Formula C15H24N4S
Molecular Weight 292.4445
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of THIOPERAMIDE

SMILES

C1CCC(CC1)N=C(N2CCC(CC2)c3cnc[nH]3)S

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 292.4445
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
Muscarinic, adenosine A(2) and histamine H(3) receptor modulation of haloperidol-induced c-fos expression in the striatum and nucleus accumbens.
2002
Characterisation of the calcium responses to histamine in capsaicin-sensitive and capsaicin-insensitive sensory neurones.
2002
Contractile response of horse deep dorsal penile vein to histamine.
2002 Apr
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
Behavioral characterization of mice lacking histamine H(3) receptors.
2002 Aug
Targeted disruption of H3 receptors results in changes in brain histamine tone leading to an obese phenotype.
2002 Dec
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
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
Effects of N-alpha-methyl-histamine on human H(2) receptors expressed in CHO cells.
2002 Jun
Betahistine dihydrochloride interaction with the histaminergic system in the cat: neurochemical and molecular mechanisms.
2002 Jun 20
Endogenous histamine in the medial septum-diagonal band complex increases the release of acetylcholine from the hippocampus: a dual-probe microdialysis study in the freely moving rat.
2002 May
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
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
Histamine h(4) and h(2) receptors control histamine-induced interleukin-16 release from human CD8(+) T cells.
2002 Oct
Histamine H3 receptor activation inhibits neurogenic sympathetic vasoconstriction in porcine nasal mucosa.
2002 Oct 11
Characteristics of recombinantly expressed rat and human histamine H3 receptors.
2002 Oct 18
High-frequency oscillation in the hippocampus of the behaving rat and its modulation by the histaminergic system.
2003
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
Histaminergic modulation of the intact respiratory network of adult mice.
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
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
H3 receptor blockade by thioperamide enhances cognition in rats without inducing locomotor sensitization.
2003 Jun
Histamine H4 receptor mediates chemotaxis and calcium mobilization of mast cells.
2003 Jun
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
Antinociceptive mechanisms of orally administered decursinol in the mouse.
2003 Jun 13
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
Histamine induces cytoskeletal changes in human eosinophils via the H(4) receptor.
2003 Nov
Generation and characterization of highly constitutive active histamine H3 receptors.
2003 Oct
Aminergic control of high-frequency (approximately 200 Hz) network oscillations in the hippocampus of the behaving rat.
2003 Sep 11
Critical role of L-selectin and histamine H4 receptor in zymosan-induced neutrophil recruitment from the bone marrow: comparison with carrageenan.
2004 Jul
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 Sat Jun 26 04:58:15 UTC 2021
Edited
by admin
on Sat Jun 26 04:58:15 UTC 2021
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 Sat Jun 26 04:58:15 UTC 2021 , Edited by admin on Sat Jun 26 04:58:15 UTC 2021
PRIMARY
FDA UNII
II4319BWUI
Created by admin on Sat Jun 26 04:58:15 UTC 2021 , Edited by admin on Sat Jun 26 04:58:15 UTC 2021
PRIMARY
EPA CompTox
106243-16-7
Created by admin on Sat Jun 26 04:58:15 UTC 2021 , Edited by admin on Sat Jun 26 04:58:15 UTC 2021
PRIMARY
WIKIPEDIA
Thioperamide
Created by admin on Sat Jun 26 04:58:15 UTC 2021 , Edited by admin on Sat Jun 26 04:58:15 UTC 2021
PRIMARY
CAS
106243-16-7
Created by admin on Sat Jun 26 04:58:15 UTC 2021 , Edited by admin on Sat Jun 26 04:58:15 UTC 2021
PRIMARY
Related Record Type Details
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TARGET -> INHIBITOR
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