Details of the Drug

General Information of Drug (ID: DM537OH)

Drug Name
Clobenpropit
Synonyms
clobenpropit; 145231-45-4; Vuf-9153; Vuf 9153; UNII-RKU631JF4H; S-(3-(4(5)-Imidazolyl))propyl-N-(4-chlorobenzyl)isothiourea; CHEBI:64177; RKU631JF4H; 3-(1h-imidazol-5-yl)propyl n'-(4-chlorobenzyl)carbamimidothioate; 3-(1H-imidazol-4-yl)propyl ((4-chlorophenyl)methyl)carbamimidothioate; Carbamimidothioic acid, ((4-chlorophenyl)methyl)-, 3-(1H-imidazol-4-yl)propyl ester; 3-(1H-imidazol-4-yl)propyl N-(4-chlorobenzyl)carbamimidothioate; Carbamimidothioic acid,N-[(4-chlorophenyl)methyl]-, 3-(1H-imidazol-5-yl)propyl ester
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 308.8
Logarithm of the Partition Coefficient (xlogp) 3
Rotatable Bond Count (rotbonds) 7
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 3
Chemical Identifiers
Formula
C14H17ClN4S
IUPAC Name
3-(1H-imidazol-5-yl)propyl N'-[(4-chlorophenyl)methyl]carbamimidothioate
Canonical SMILES
C1=CC(=CC=C1CN=C(N)SCCCC2=CN=CN2)Cl
InChI
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)
InChIKey
UCAIEVHKDLMIFL-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
2790
ChEBI ID
CHEBI:64177
CAS Number
145231-45-4
TTD ID
D0T8OD

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Histamine H3 receptor (H3R) TT9JNIC HRH3_HUMAN Antagonist [2]
Histamine H4 receptor (H4R) TTXJ178 HRH4_HUMAN Agonist [3]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
C-C motif chemokine 2 (CCL2) OTAD2HEL CCL2_HUMAN Gene/Protein Processing [4]
Histamine H3 receptor (HRH3) OT7GF3AI HRH3_HUMAN Protein Interaction/Cellular Processes [5]
Histamine H4 receptor (HRH4) OTBJO49O HRH4_HUMAN Drug Response [6]
Interferon gamma (IFNG) OTXG9JM7 IFNG_HUMAN Gene/Protein Processing [7]
Interleukin-5 (IL5) OTAFPSCO IL5_HUMAN Gene/Protein Processing [7]
Pro-interleukin-16 (IL16) OTZ2MO6B IL16_HUMAN Gene/Protein Processing [8]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Discovery agent
ICD Disease Classification N.A.
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Histamine H3 receptor (H3R) DTT HRH3 3.62E-02 -0.09 -0.22
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 1223).
2 The histamine H3 receptor: from gene cloning to H3 receptor drugs. Nat Rev Drug Discov. 2005 Feb;4(2):107-20.
3 Clobenpropit analogs as dual activity ligands for the histamine H3 and H4 receptors: synthesis, pharmacological evaluation, and cross-target QSAR s... Bioorg Med Chem. 2009 Jun 1;17(11):3987-94.
4 Histamine downregulates monocyte CCL2 production through the histamine H4 receptor. J Allergy Clin Immunol. 2007 Aug;120(2):300-7. doi: 10.1016/j.jaci.2007.03.024. Epub 2007 May 15.
5 Molecular determinants of ligand binding modes in the histamine H(4) receptor: linking ligand-based three-dimensional quantitative structure-activity relationship (3D-QSAR) models to in silico guided receptor mutagenesis studies. J Med Chem. 2011 Dec 8;54(23):8136-47. doi: 10.1021/jm201042n. Epub 2011 Nov 7.
6 Deletion and down-regulation of HRH4 gene in gastric carcinomas: a potential correlation with tumor progression. PLoS One. 2012;7(2):e31207. doi: 10.1371/journal.pone.0031207. Epub 2012 Feb 20.
7 Histamine H4 receptor agonists have more activities than H4 agonism in antigen-specific human T-cell responses. Immunology. 2007 Jun;121(2):266-75. doi: 10.1111/j.1365-2567.2007.02574.x. Epub 2007 Mar 7.
8 Histamine h(4) and h(2) receptors control histamine-induced interleukin-16 release from human CD8(+) T cells. J Pharmacol Exp Ther. 2002 Oct;303(1):300-7. doi: 10.1124/jpet.102.036939.