vadadustat   Click here for help

GtoPdb Ligand ID: 11831

Synonyms: AKB-6548 | AKB6548 | Vafseo®
Approved drug PDB Ligand
vadadustat is an approved drug (Japan (2020), EMA (2023), FDA (2024))
Compound class: Synthetic organic
Comment: Vadadustat is an orally bioavailable HIF prolyl-hydroxylase inhibitor. It targets the enzymes PHD1, PHD2 and PHD3 to mediate an increase in endogenous erythropoietin production which delivers anti-anemia action. See also enarodustat.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 3
Rotatable bonds 5
Topological polar surface area 99.52
Molecular weight 306.04
XLogP 0.49
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES OC(=O)CNC(=O)c1ncc(cc1O)c1cccc(c1)Cl
Isomeric SMILES c1cc(cc(c1)Cl)c1cc(c(nc1)C(=O)NCC(=O)O)O
InChI InChI=1S/C14H11ClN2O4/c15-10-3-1-2-8(4-10)9-5-11(18)13(16-6-9)14(21)17-7-12(19)20/h1-6,18H,7H2,(H,17,21)(H,19,20)
InChI Key JGRXMPYUTJLTKT-UHFFFAOYSA-N
References
1. 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]
2. Langley GW, Abboud MI, Lohans CT, Schofield CJ. (2019)
Inhibition of a viral prolyl hydroxylase.
Bioorg Med Chem, 27 (12): 2405-2412. [PMID:30737136]
3. Markham A. (2020)
Vadadustat: First Approval.
Drugs, 80 (13): 1365-1371. [PMID:32852744]
4. Yeh TL, Leissing TM, Abboud MI, Thinnes CC, Atasoylu O, Holt-Martyn JP, Zhang D, Tumber A, Lippl K, Lohans CT et al.. (2017)
Molecular and cellular mechanisms of HIF prolyl hydroxylase inhibitors in clinical trials.
Chem Sci, 8 (11): 7651-7668. [PMID:29435217]