ESOMEPRAZOLE

ID: ALA1201320

Max Phase: Approved

First Approval: 2001

Molecular Formula: C17H19N3O3S

Molecular Weight: 345.42

Molecule Type: Small molecule

Associated Items:

Representations

Synonyms (4): Esomeprazole | Inexium paranova | Omeprazole, (s)- | A02BC05
Synonyms from Alternative Forms(4):

    Canonical SMILES:  COc1ccc2[nH]c([S@@+]([O-])Cc3ncc(C)c(OC)c3C)nc2c1

    Standard InChI:  InChI=1S/C17H19N3O3S/c1-10-8-18-15(11(2)16(10)23-4)9-24(21)17-19-13-6-5-12(22-3)7-14(13)20-17/h5-8H,9H2,1-4H3,(H,19,20)/t24-/m0/s1

    Standard InChI Key:  SUBDBMMJDZJVOS-DEOSSOPVSA-N

    Associated Targets(Human)

    Homo sapiens (32628 Activities)
    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
    DDAH1 Tchem N(G),N(G)-dimethylarginine dimethylaminohydrolase 1 (231 Activities)
    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
    MV4-11 (7307 Activities)
    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
    MOLM-13 (2241 Activities)
    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
    K562 (73714 Activities)
    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
    L02 (4864 Activities)
    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
    HUVEC (11049 Activities)
    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
    WDR5 Tchem Histone-lysine N-methyltransferase 2A/WDR5 (99 Activities)
    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
    HDAC6 Tclin Histone deacetylase 6 (20808 Activities)
    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Associated Targets(non-human)

    SARS-CoV-2 (38078 Activities)
    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
    rep Replicase polyprotein 1ab (11336 Activities)
    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Molecule Features

    Natural Product: YesOral: YesChemical Probe: NoParenteral: Yes
    Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
    Chirality: YesAvailability: YesProdrug: Yes

    Drug Indications

    MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

    Mechanisms of Action

    Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

    Properties

    Molecular Weight: 345.42Molecular Weight (Monoisotopic): 345.1147AlogP: 2.90#Rotatable Bonds: 5
    Polar Surface Area: 83.09Molecular Species: NEUTRALHBA: 5HBD: 1
    #RO5 Violations: 0HBA (Lipinski): 6HBD (Lipinski): 1#RO5 Violations (Lipinski): 0
    CX Acidic pKa: 9.68CX Basic pKa: 4.77CX LogP: 2.43CX LogD: 2.43
    Aromatic Rings: 3Heavy Atoms: 24QED Weighted: 0.72Np Likeness Score: -0.69

    References

    1. Jain KS, Shah AK, Bariwal J, Shelke SM, Kale AP, Jagtap JR, Bhosale AV..  (2007)  Recent advances in proton pump inhibitors and management of acid-peptic disorders.,  15  (3): [PMID:17150362] [10.1016/j.bmc.2006.07.068]
    2. Moda TL, Montanari CA, Andricopulo AD..  (2007)  Hologram QSAR model for the prediction of human oral bioavailability.,  15  (24): [PMID:17870541] [10.1016/j.bmc.2007.08.060]
    3. Fourches D, Barnes JC, Day NC, Bradley P, Reed JZ, Tropsha A..  (2010)  Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.,  23  (1): [PMID:20014752] [10.1021/tx900326k]
    4. WHO Anatomical Therapeutic Chemical Classification, 
    5.  (2014)  Dimethylarginine Dimethylaminohydrolase inhibitors and methods of use thereof, 
    6. Unpublished dataset, 
    7. Bernhard Ellinger, Denisa Bojkova, Andrea Zaliani, Jindrich Cinatl, Carsten Claussen, Sandra Westhaus, Jeanette Reinshagen, Maria Kuzikov, Markus Wolf, Gerd Geisslinger, Philip Gribbon, Sandra Ciesek.  (2020)  Identification of inhibitors of SARS-CoV-2 in-vitro cellular toxicity in human (Caco-2) cells using a large scale drug repurposing collection,  [10.21203/rs.3.rs-23951/v1]
    8. Katie Heiser, Peter F. McLean, Chadwick T. Davis, Ben Fogelson, Hannah B. Gordon, Pamela Jacobson, Brett Hurst, Ben Miller, Ronald W. Alfa, Berton A. Earnshaw, Mason L. Victors, Yolanda T. Chong, Imran S. Haque, Adeline S. Low, Christopher C. Gibson.  (2020)  Identification of potential treatments for COVID-19 through artificial intelligence-enabled phenomic analysis of human cells infected with SARS-CoV-2,  [10.1101/2020.04.21.054387]
    9. Maria Kuzikov, Elisa Costanzi, Jeanette Reinshagen, Francesca Esposito, Laura Vangeel, Markus Wolf, Bernhard Ellinger, Carsten Claussen, Gerd Geisslinger, Angela Corona, Daniela Iaconis, Carmine Talarico, Candida Manelfi, Rolando Cannalire, Giulia Rossetti, Jonas Gossen, Simone Albani, Francesco Musiani, Katja Herzog, Yang Ye, Barbara Giabbai, Nicola Demitri, Dirk Jochmans, Steven De Jonghe, Jasper Rymenants, Vincenzo Summa, Enzo Tramontano, Andrea R. Beccari, Pieter Leyssen, Paola Storici, Johan Neyts, Philip Gribbon, and Andrea Zaliani.  (2020)  Identification of inhibitors of SARS-Cov2 M-Pro enzymatic activity using a small molecule repurposing screen,  [10.6019/CHEMBL4495564]
    10. Andrea Zaliani, Laura Vangeel, Jeanette Reinshagen, Daniela Iaconis, Maria Kuzikov, Oliver Keminer, Markus Wolf, Bernhard Ellinger, Francesca Esposito, Angela Corona, Enzo Tramontano, Candida Manelfi, Katja Herzog, Dirk Jochmans, Steven De Jonghe, Winston Chiu, Thibault Francken, Joost Schepers, Caroline Collard, Kayvan Abbasi, Carsten Claussen , Vincenzo Summa, Andrea R. Beccari, Johan Neyts, Philip Gribbon and Pieter Leyssen.  (2020)  Cytopathic SARS-Cov2 screening on VERO-E6 cells in a large repurposing effort,  [10.6019/CHEMBL4495565]
    11. Ellen Van Damme.  (2021)  Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity,  [10.6019/CHEMBL4651402]
    12. Chen WL,Li DD,Chen X,Wang YZ,Xu JJ,Jiang ZY,You QD,Guo XK.  (2020)  Proton pump inhibitors selectively suppress MLL rearranged leukemia cells via disrupting MLL1-WDR5 protein-protein interaction.,  188  [PMID:31923859] [10.1016/j.ejmech.2019.112027]
    13. Bernhard Ellinger, Justus Dick, Vanessa Lage-Rupprecht, Bruce Schultz, Andrea Zaliani, Marcin Namysl, Stephan Gebel, Ole Pless, Jeanette Reinshagen, Christian Ebeling, Alexander Esser, Marc Jacobs, Carsten Claussen, and Martin Hofmann-Apitius.  (2021)  HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators,  [10.6019/CHEMBL4808148]