ilaprazole   Click here for help

GtoPdb Ligand ID: 10512

Synonyms: IY-81149 | IY81149 | Noltec®
Approved drug
ilaprazole is an approved drug (South Korea, China)
Compound class: Synthetic organic
Comment: Ilaprazole (IY-81149) is an irreversible proton pump inhibitor (PPI) [2]. It is a prodrug that is converted to an active sulfenamide form that binds to cysteine sulfhydryl groups on the proton pump H+/K+ ATPase of gastric parietal cells, and thereby inhibits gastric acid secretion [5].
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 91.49
Molecular weight 366.12
XLogP 1.13
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES COc1ccnc(c1C)CS(=O)c1nc2c([nH]1)cc(cc2)n1cccc1
Isomeric SMILES COc1ccnc(c1C)CS(=O)c1nc2c([nH]1)cc(cc2)n1cccc1
InChI InChI=1S/C19H18N4O2S/c1-13-17(20-8-7-18(13)25-2)12-26(24)19-21-15-6-5-14(11-16(15)22-19)23-9-3-4-10-23/h3-11H,12H2,1-2H3,(H,21,22)
InChI Key HRRXCXABAPSOCP-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Ji XQ, Du JF, Chen G, Chen G, Yu B. (2014)
Efficacy of ilaprazole in the treatment of duodenal ulcers: a meta-analysis.
World J Gastroenterol, 20 (17): 5119-23. [PMID:24803828]
2. Kwon D, Chae JB, Park CW, Kim YS, Lee SM, Kim EJ, Huh IH, Kim DY, Cho KD. (2001)
Effects of IY-81149, a newly developed proton pump inhibitor, on gastric acid secretion in vitro and in vivo.
Arzneimittelforschung, 51 (3): 204-13. [PMID:11304936]
3. Pu J, Wang F, Tang W, Zhu M. (2018)
Biotransformation of Ilaprazole in Human Liver Microsomes and Human: Role of CYP3A4 in Ilaprazole Clearance and Drug-Drug Interaction.
Drug Metab Dispos, 46 (10): 1453-1461. [PMID:30002078]
4. Wang L, Zhou L, Hu H, Lin S, Xia J. (2012)
Ilaprazole for the treatment of duodenal ulcer: a randomized, double-blind and controlled phase III trial.
Curr Med Res Opin, 28 (1): 101-9. [PMID:22070512]
5. Zhou G, Shi S, Zhang W, Tan Z, Chen Y, Guo D, Zhou H, Hu H, Tan J. (2010)
Identification of ilaprazole metabolites in human urine by HPLC-ESI-MS/MS and HPLC-NMR experiments.
Biomed Chromatogr, 24 (10): 1130-5. [PMID:20352613]