CLOBENPROPIT

Details

Stereochemistry	ACHIRAL
Molecular Formula	C14H17ClN4S
Molecular Weight	308.83
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

ClC1=CC=C(CNC(=N)SCCCC2=CN=CN2)C=C1

InChI

InChIKey=UCAIEVHKDLMIFL-UHFFFAOYSA-N

InChI=1S/C14H17ClN4S/c15-12-5-3-11(4-6-12)8-18-14(16)20-7-1-2-13-9-17-10-19-13/h3-6,9-10H,1-2,7-8H2,(H2,16,18)(H,17,19)

HIDE SMILES / InChI

Molecular Formula	C14H17ClN4S
Molecular Weight	308.83
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Histamine H3 receptor 46 Target ID: CHEMBL264 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20833043	Antagonist 2849		1.0 nM [IC50]

PubMed

Title	Date	PubMed
The histamine H4 receptor is functionally expressed on T(H)2 cells.	2009-03	19281909
Histamine H4 receptor antagonism reduces hapten-induced scratching behaviour but not inflammation.	2009-01	18647342
Histamine H4 receptors modulate dendritic cell migration through skin--immunomodulatory role of histamine.	2008-10	18782117
Electrophysiology-based analysis of human histamine H(4) receptor pharmacology using GIRK channel coupling in Xenopus oocytes.	2008-09-04	18582456
Apomorphine-induced turning behavior in 6-hydroxydopamine lesioned rats is increased by histidine and decreased by histidine decarboxylase, histamine H1 and H2 receptor antagonists, and an H3 receptor agonist.	2008-09	18452981
Substance P is involved in the effect of histamine H3 receptor agonist, Sch 50971 on nasal allergic symptoms in mice.	2008-08	18550011
Histamine-induced itch and its relationship with pain.	2008-07-31	18667087
Human inflammatory dendritic epidermal cells express a functional histamine H4 receptor.	2008-07	18239617
Antagonist affinity measurements at the Gi-coupled human histamine H3 receptor expressed in CHO cells.	2008-06-06	18538007
Zebrafish: An in vivo model for the study of neurological diseases.	2008-06	18830398
Comparison of the effect of an H(3)-inverse agonist on energy intake and hypothalamic histamine release in normal mice and leptin resistant mice with high fat diet-induced obesity.	2008-04-09	18082276
Efficient approaches to S-alkyl-N-alkylisothioureas: syntheses of histamine H3 antagonist clobenpropit and its analogues.	2008-03-21	18278935
Carnosine protects against Abeta42-induced neurotoxicity in differentiated rat PC12 cells.	2008-02	18027086
The role of histamine in human mammary carcinogenesis: H3 and H4 receptors as potential therapeutic targets for breast cancer treatment.	2008-01	17932461
Histamine excites neurones in the human submucous plexus through activation of H1, H2, H3 and H4 receptors.	2007-09-01	17627982
Histamine downregulates monocyte CCL2 production through the histamine H4 receptor.	2007-08	17507084
The human histamine H3 receptor couples to GIRK channels in Xenopus oocytes.	2007-07-19	17537431
The histamine H3 receptor antagonist clobenpropit enhances GABA release to protect against NMDA-induced excitotoxicity through the cAMP/protein kinase A pathway in cultured cortical neurons.	2007-06-01	17350613
Histamine H3-receptor agonists and imidazole-based H3-receptor antagonists can be thermodynamically discriminated.	2007-06	17401438
Histamine H4 receptor agonists have more activities than H4 agonism in antigen-specific human T-cell responses.	2007-06	17346280
Correlation of apparent affinity values from H3-receptor binding assays with apparent affinity (pKapp) and intrinsic activity (alpha) from functional bioassays.	2007-05	17351664
Role of histamine in ghrelin-induced gastroprotection against acute gastric lesions.	2007-04	17806165
Histamine augments beta2-adrenoceptor-induced cyclic AMP accumulation in human prostate cancer cells DU-145 independently of known histamine receptors.	2007-03-15	17196553
[Reversing effect of histamine on neurotoxicity induced by beta-amyloid1-42].	2007-03	17443902
Pre-synaptic histamine H3 receptors regulate glutamate, but not GABA release in rat thalamus.	2007-02	17027043
Role of apolipoprotein E in anxiety.	2007	17710250
STAT1 phosphorylation and cleavage is regulated by the histamine (H4) receptor in human atopic and non-atopic lymphocytes.	2006-10	16919830
Constitutive activity of H3 autoreceptors modulates histamine synthesis in rat brain through the cAMP/PKA pathway.	2006-09	16769092
Detection of multiple H3 receptor affinity states utilizing [3H]A-349821, a novel, selective, non-imidazole histamine H3 receptor inverse agonist radioligand.	2006-07	16715122
Effect of endogenous histamine in the ventral hippocampus on fear memory deficits induced by scopolamine as evaluated by step-through avoidance response in rats.	2006-04-15	16488453
Role of substance P on histamine H(3) antagonist-induced scratching behavior in mice.	2006-04	16603804
Probing the importance of N-glycosylation for [(3)H] clobenpropit binding to human H (3) receptors expressed in HEK 293 cells . 3. Molecular and chemical aspects of the histamine receptors.	2006-04	16547815
Histamine excites neonatal rat sympathetic preganglionic neurons in vitro via activation of H1 receptors.	2006-04	16354729
N-(4-Trifluoromethylphenyl)amide group of the synthetic histamine receptor agonist inhibits nicotinic acetylcholine receptor-mediated catecholamine secretion.	2006-02-28	16384551
Histamine increases sickle erythrocyte adherence to endothelium.	2006-02	16412024
Histaminergic neurons protect the developing hippocampus from kainic acid-induced neuronal damage in an organotypic coculture system.	2006-01-25	16436594
Effects of intracerebroventricular administration of ultra low doses of histaminergic drugs on morphine state-dependent memory of passive avoidance in mice.	2006-01-06	16168500
Histamine (H3) receptors modulate the excitatory amino acid receptor response of the vestibular afferents.	2005-12-07	16310756
Cross state-dependent retrieval between histamine and lithium.	2005-09-15	16107272
Evaluation of histamine H1-, H2-, and H3-receptor ligands at the human histamine H4 receptor: identification of 4-methylhistamine as the first potent and selective H4 receptor agonist.	2005-09	15947036
G protein-dependent pharmacology of histamine H3 receptor ligands: evidence for heterogeneous active state receptor conformations.	2005-07	15821027
Generation of cell lines for drug discovery through random activation of gene expression: application to the human histamine H3 receptor.	2005-06	15971992
Histamine-3 receptor antagonists reduce superoxide anion generation and lipid peroxidation in rat brain homogenates.	2005-06	15969934
Influence of intracerebroventricular administration of histaminergic drugs on morphine state-dependent memory in the step-down passive avoidance test.	2005-05	15867477
Effect of combined histamine H1 and H3 receptor blockade on cutaneous microvascular permeability elicited by compound 48/80.	2005-03-04	15698856
Inhibition of tryptase release from human colon mast cells by histamine receptor antagonists.	2005-03	15997873
Histamine H3 receptors modulate reactive hyperemia in rat gut.	2004-09	15381834
Histamine H3 receptor activation inhibits dopamine D1 receptor-induced cAMP accumulation in rat striatal slices.	2004-07-08	15196671
Ligand identification for G-protein-coupled receptors: a lead generation perspective.	2004-06	15183327
Intracerebroventricular administration of histamine H3 receptor antagonists decreases seizures in rat models of epilepsia.	2004-05	15319804

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:03:29 GMT 2025` Edited by `admin` on `Mon Mar 31 19:03:29 GMT 2025`
Record UNII	RKU631JF4H
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CLOBENPROPIT

Common Name

English

VUF-9153

Preferred Name

English

CARBAMIMIDOTHIOIC ACID, N-((4-CHLOROPHENYL)METHYL)-, 3-(1H-IMIDAZOL-5-YL)PROPYL ESTER

Systematic Name

English

Code System Code Type Description

CAS

145231-45-4