A1Z

Vadadustat

Created:	2017-08-09
Last modified:	2020-06-05

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3 entries where A1Z is found as a standalone ligand

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Chemical Details
Formal Charge	0
Atom Count	32
Chiral Atom Count	0
Bond Count	33
Aromatic Bond Count	12

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Chemical Component Summary
Name	Vadadustat
Synonyms	GSK128863
Systematic Name (OpenEye OEToolkits)	2-[[5-(3-chlorophenyl)-3-oxidanyl-pyridin-2-yl]carbonylamino]ethanoic acid
Formula	C₁₄ H₁₁ Cl N₂ O₄
Molecular Weight	306.701
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	CACTVS	3.385	OC(=O)CNC(=O)c1ncc(cc1O)c2cccc(Cl)c2
SMILES	OpenEye OEToolkits	2.0.6	c1cc(cc(c1)Cl)c2cc(c(nc2)C(=O)NCC(=O)O)O
Canonical SMILES	CACTVS	3.385	OC(=O)CNC(=O)c1ncc(cc1O)c2cccc(Cl)c2
Canonical SMILES	OpenEye OEToolkits	2.0.6	c1cc(cc(c1)Cl)c2cc(c(nc2)C(=O)NCC(=O)O)O
InChI	InChI	1.03	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)
InChIKey	InChI	1.03	JGRXMPYUTJLTKT-UHFFFAOYSA-N

Drug Info: DrugBank

DrugBank ID	DB12255
Name	Vadadustat
Groups	investigational approved
Description	One of the most common symptoms of advanced renal disease is anemia, caused primarily by the inability of the kidney to respond to anemic conditions with a corresponding increase in [erythropoietin] (EPO) production.[A244165] The treatment of anemia associated with chronic kidney disease (CKD) has traditionally involved the administration of exogenous erythropoiesis-stimulating agents (ESAs), such as [darbepoetin alfa], to counter the decrease in endogenous EPO production. While efficacious, the overuse of ESAs has been associated with cardiovascular complications, progression of CKD, and increases in overall mortality.[A244165] A relatively new and alternative treatment option for patients with anemia associated with CKD is the use of small molecule inhibitors of hypoxia-inducible factor prolyl-hydroxylase (HIF-PH). These agents inhibit prolyl-hydroxylase domain oxygen sensors, mimicking hypoxic conditions and activating hypoxia-inducible factors. These transcription factors serve a multitude of roles, including the stimulation of erythropoiesis.[A244165] Vadadustat is an orally administered inhibitor of HIF-PH with a safety and efficacy profile non-inferior to [darbepoetin alfa] for the treatment of anemia in patients with CKD undergoing dialysis.[A244145,A244155] It was first approved in Japan, and in April 2023, it was approved by the EMA for the treatment of symptomatic anemia associated with CKD in adults on chronic maintenance dialysis.[L39610,L46936,L46951] Vadadustat is currently awaiting a regulatory decision by the FDA.[L39605] Vadadustat did not meet the prespecified noninferiority criterion for cardiovascular safety in patients with non-dialysis-dependent CKD.[A244150]
Synonyms	N-(5-(3-Chlorophenyl)-3-hydroxypyridine-2-carbonyl)glycine Vadadustat Glycine, N-((5-(3-chlorophenyl)-3-hydroxy-2-pyridinyl)carbonyl)-
Brand Names	Vafseo
Indication	Vadadustat is indicated for the treatment of symptomatic anemia associated with chronic kidney disease (CKD) in adults on chronic maintenance dialysis.[L46936]
Categories	Amino Acids Amino Acids, Peptides, and Proteins Antianemic Preparations BCRP/ABCG2 Inhibitors Blood and Blood Forming Organs Cytochrome P-450 CYP2B6 Inducers Cytochrome P-450 CYP2B6 Inducers (weak) Cytochrome P-450 CYP2C8 Inhibitors Cytochrome P-450 CYP2C8 Inhibitors (strength unknown) Cytochrome P-450 CYP2C9 Inhibitors Cytochrome P-450 CYP2C9 Inhibitors (strength unknown) Cytochrome P-450 Enzyme Inducers Cytochrome P-450 Enzyme Inhibitors Erythropoiesis-Stimulating Agents Hypoxia-Inducible Factor-Proline Dioxygenases, antagonists & inhibitors OAT3/SLC22A8 Inhibitors OAT3/SLC22A8 Substrates Pyridines UGT1A1 Inducers UGT1A1 Substrates UGT1A9 Substrates UGT2B7 substrates
ATC-Code	B03XA08
CAS number	1000025-07-9

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Egl nine homolog 1	MANDSGGPGGPSPSERDRQYCELCGKMENLLRCSRCRSSFYCCKEHQRQD...	unknown	inhibitor
Egl nine homolog 2	MDSPCQPQPLSQALPQLPGSSSEPLEPEPGRARMGVESYLPCPLLPSYHC...	unknown	inhibitor
Egl nine homolog 3	MPLGHIMRLDLEKIALEYIVPCLHEVGFCYLDNFLGEVVGDCVLERVKQL...	unknown	inhibitor
Hypoxia-inducible factor 1-alpha	MEGAGGANDKKKISSERRKEKSRDAARSRRSKESEVFYELAHQLPLPHNV...	unknown	stabilization
Endothelial PAS domain-containing protein 1	MTADKEKKRSSSERRKEKSRDAARCRRSKETEVFYELAHELPLPHSVSSH...	unknown	stabilization
UDP-glucuronosyltransferase 1-1	MAVESQGGRPLVLGLLLCVLGPVVSHAGKILLIPVDGSHWLSMLGAIQQL...	unknown	substrate,inducer
UDP-glucuronosyltransferase 1-7	MARAGWTGLLPLYVCLLLTCGFAKAGKLLVVPMDGSHWFTMQSVVEKLIL...	unknown	substrate
UDP-glucuronosyltransferase 1-8	MARTGWTSPIPLCVSLLLTCGFAEAGKLLVVPMDGSHWFTMQSVVEKLIL...	unknown	substrate
UDP-glucuronosyltransferase 1-9	MACTGWTSPLPLCVCLLLTCGFAEAGKLLVVPMDGSHWFTMRSVVEKLIL...	unknown	substrate
UDP-glucuronosyltransferase 2B7	MSVKWTSVILLIQLSFCFSSGNCGKVLVWAAEYSHWMNIKTILDELIQRG...	unknown	substrate
Cytochrome P450 2B6	MELSVLLFLALLTGLLLLLVQRHPNTHDRLPPGPRPLPLLGNLLQMDRRG...	unknown	inducer
Cytochrome P450 2C8	MEPFVVLVLCLSFMLLFSLWRQSCRRRKLPPGPTPLPIIGNMLQIDVKDI...	unknown	inhibitor
Cytochrome P450 3A4	MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...	unknown	downregulator
Cytochrome P450 2C9	MDSLVVLVLCLSCLLLLSLWRQSSGRGKLPPGPTPLPVIGNILQIGIKDI...	unknown	inhibitor
Serum albumin	MKWVTFISLLFLFSSAYSRGVFRRDAHKSEVAHRFKDLGEENFKALVLIA...	unknown	binder
ATP-binding cassette sub-family G member 2	MSSSNVEVFIPVSQGNTNGFPATASNDLKAFTEGAVLSFHNICYRVKLKS...	unknown	inhibitor
Solute carrier family 22 member 8	MTFSEILDRVGSMGHFQFLHVAILGLPILNMANHNLLQIFTAATPVHHCR...	unknown	substrate,inhibitor
Solute carrier family 22 member 6	MAFNDLLQQVGGVGRFQQIQVTLVVLPLLLMASHNTLQNFTAAIPTHHCR...	unknown	substrate
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682