roxadustat   Click here for help

GtoPdb Ligand ID: 8454

Synonyms: ASP-1517 | ASP1517 | Evrenzo® | FG-4592 | FG4592
Approved drug PDB Ligand
roxadustat is an approved drug (EMA (2021))
Compound class: Synthetic organic
Comment: Roxadustat is a compound which inhibits hypoxia inducible factor prolyl hydroxylase (HIF-PH) activity. HIF-PH inhibitors are being investigated as novel therapies for anemia, especially anemia caused by chronic kindney disease (CKD) [2]. It is hoped that HIF-PH inhibitors will provide a more effective alternative to the use of erythropoetin replacement therapy plus iron supplementation in CKD patients.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 3
Rotatable bonds 6
Topological polar surface area 108.75
Molecular weight 352.11
XLogP 0.99
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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Canonical SMILES OC(=O)CNC(=O)c1nc(C)c2c(c1O)ccc(c2)Oc1ccccc1
Isomeric SMILES OC(=O)CNC(=O)c1nc(C)c2c(c1O)ccc(c2)Oc1ccccc1
InChI InChI=1S/C19H16N2O5/c1-11-15-9-13(26-12-5-3-2-4-6-12)7-8-14(15)18(24)17(21-11)19(25)20-10-16(22)23/h2-9,24H,10H2,1H3,(H,20,25)(H,22,23)
InChI Key YOZBGTLTNGAVFU-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. Bouchie A. (2013)
First-in-class anemia drug takes aim at Amgen's dominion.
Nat Biotechnol, 31 (11): 948-9. [PMID:24213751]
2. Forristal CE, Levesque JP. (2014)
Targeting the hypoxia-sensing pathway in clinical hematology.
Stem Cells Transl Med, 3 (2): 135-40. [PMID:24371328]
3. Joharapurkar AA, Pandya VB, Patel VJ, Desai RC, Jain MR. (2018)
Prolyl Hydroxylase Inhibitors: A Breakthrough in the Therapy of Anemia Associated with Chronic Diseases.
J Med Chem, 61 (16): 6964-6982. [PMID:29712435]
4. Liu C, Jursa T, Aschner M, Smith DR, Mukhopadhyay S. (2021)
Up-regulation of the manganese transporter SLC30A10 by hypoxia-inducible factors defines a homeostatic response to manganese toxicity.
Proc Natl Acad Sci U S A, 118 (35). DOI: 10.1073/pnas.2107673118 [PMID:34446561]