Roxadustat

Identification

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Name
Roxadustat
Accession Number
DB04847
Type
Small Molecule
Groups
Investigational
Description

FibroGen completed the phase I single-dose, dose escalation studies as of July 2007. Multiple dose, dose escalation and phase II US studies are listed as ongoing.

Structure
Thumb
Synonyms
  • roxadustat
External IDs
ASP-1517 / ASP1517 / FG-4592
Categories
UNII
X3O30D9YMX
CAS number
Not Available
Weight
Average: 352.346
Monoisotopic: 352.105921623
Chemical Formula
C19H16N2O5
InChI Key
YOZBGTLTNGAVFU-UHFFFAOYSA-N
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)
IUPAC Name
2-[(4-hydroxy-1-methyl-7-phenoxyisoquinolin-3-yl)formamido]acetic acid
SMILES
CC1=NC(C(=O)NCC(O)=O)=C(O)C2=CC=C(OC3=CC=CC=C3)C=C12

Pharmacology

Indication

In clinical development for the treatment of anemia of chronic inflammatory disease.

Pharmacodynamics

FG-4592 represents one of several next generation PHI that has been optimized for multiple pharmacokinetic and pharmacodynamic parameters related to erythropoiesis, including selective inhibition of HIF prolyl and asparaginyl hydroxylases, potency, iron utilization, and ADME. FG-4592 represents one of several next generation HIF-PH inhibitors designed to selectively induce the expression of genes that mediate erythropoiesis for the treatment of anemia.

Mechanism of action

FG-4592 is an orally active second generation HIF-PH inhibitor. Preclinical studies show that FG-4592 increases production of endogenous erythropoietin (EPO), increases iron mobilization and utilization, and overcomes the suppressive effects of inflammation on red blood cell production.

TargetActionsOrganism
UEgl nine homolog 1Not AvailableHumans
UEgl nine homolog 2Not AvailableHumans
UEgl nine homolog 3Not AvailableHumans
Absorption

Orally active

Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
11256664
PubChem Substance
347827699
ChemSpider
9431690
BindingDB
50431015
ChEBI
132774
ChEMBL
CHEMBL2338329
Wikipedia
Roxadustat
ATC Codes
B03XA05 — Roxadustat

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableHealthy Volunteers1
1CompletedBasic ScienceAnemias / Hemodialysis Treatment / Impaired Renal Function1
1CompletedBasic ScienceHealthy Volunteers2
1CompletedBasic ScienceHealthy Volunteers / Hepatic Insufficiency / PK of FG-45921
1CompletedBasic ScienceHealthy Volunteers / PK for FG-45921
1CompletedBasic ScienceHealthy Volunteers / Pharmacokinetics of FG-45921
1CompletedTreatmentHealthy Adult Subjects1
1CompletedTreatmentHealthy Volunteers1
1CompletedTreatmentImpaired Renal Function / Normal Renal Function1
1Not Yet RecruitingBasic ScienceHealthy Adult Subjects1
2CompletedTreatmentAnaemia in Chronic Kidney Disease1
2CompletedTreatmentAnemia in Chronic Kidney Disease Patients Not on Dialysis1
2CompletedTreatmentAnemia in End Stage Renal Disease1
2CompletedTreatmentAnemias / Chronic Kidney Disease (CKD)2
2CompletedTreatmentAnemias / Dialysis therapy1
2CompletedTreatmentAnemias / End Stage Renal Disease (ESRD)1
2CompletedTreatmentRenal Anemia Associated With Chronic Renal Failure (CRF)1
2, 3Enrolling by InvitationTreatmentAnemias / Chronic Kidney Disease (CKD) / End Stage Renal Disease (ESRD)1
2, 3RecruitingTreatmentPrimary MDS Classified as Very Low, Low or Intermediate Risk With <5% Blasts1
3Active Not RecruitingTreatmentAnemia in Chronic Kidney Disease in Non-dialysis Patients1
3Active Not RecruitingTreatmentAnemias2
3Active Not RecruitingTreatmentChronic Kidney Disease (CKD)1
3CompletedTreatmentAnemia in Chronic Kidney Disease in Non-dialysis Patients1
3CompletedTreatmentAnemia in Incident Dialysis Patients1
3CompletedTreatmentAnemias2
3CompletedTreatmentAnemias / End Stage Renal Disease (ESRD)1
3CompletedTreatmentCKD Anemia1
3CompletedTreatmentCKD Anemia in Stable Dialysis Patients1
3CompletedTreatmentChronic Kidney Disease (CKD)1
3CompletedTreatmentESA-naive Hemodialysis Chronic Kidney Disease Patients With Anemia1
3CompletedTreatmentHemodialysis Patients With Renal Anemia1
3CompletedTreatmentIron Deficiency Anemia caused by hemodialysis-dependent chronic kidney disease (HDD-CKD)1
3CompletedTreatmentPeritoneal Dialysis Chronic Kidney Disease Patients With Anemia1
3RecruitingTreatmentPrimary MDS (Very Low, Low or Intermediate IPSS-R With <5% Blasts)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0115 mg/mLALOGPS
logP3.13ALOGPS
logP2.34ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)3.35ChemAxon
pKa (Strongest Basic)2.24ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area108.75 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity92.85 m3·mol-1ChemAxon
Polarizability35.65 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as n-acyl-alpha amino acids. These are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
N-acyl-alpha amino acids
Alternative Parents
Diarylethers / Isoquinolines and derivatives / Pyridinecarboxylic acids and derivatives / 2-heteroaryl carboxamides / Phenol ethers / Phenoxy compounds / Methylpyridines / Hydroxypyridines / Heteroaromatic compounds / Vinylogous acids
show 8 more
Substituents
N-acyl-alpha-amino acid / Diaryl ether / Isoquinoline / Pyridine carboxylic acid or derivatives / 2-heteroaryl carboxamide / Phenoxy compound / Phenol ether / Methylpyridine / Hydroxypyridine / Monocyclic benzene moiety
show 19 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Peptidyl-proline dioxygenase activity
Specific Function
Cellular oxygen sensor that catalyzes, under normoxic conditions, the post-translational formation of 4-hydroxyproline in hypoxia-inducible factor (HIF) alpha proteins. Hydroxylates a specific prol...
Gene Name
EGLN1
Uniprot ID
Q9GZT9
Uniprot Name
Egl nine homolog 1
Molecular Weight
46020.585 Da
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Peptidyl-proline 4-dioxygenase activity
Specific Function
Cellular oxygen sensor that catalyzes, under normoxic conditions, the post-translational formation of 4-hydroxyproline in hypoxia-inducible factor (HIF) alpha proteins. Hydroxylates a specific prol...
Gene Name
EGLN2
Uniprot ID
Q96KS0
Uniprot Name
Egl nine homolog 2
Molecular Weight
43650.03 Da
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Peptidyl-proline 4-dioxygenase activity
Specific Function
Cellular oxygen sensor that catalyzes, under normoxic conditions, the post-translational formation of 4-hydroxyproline in hypoxia-inducible factor (HIF) alpha proteins. Hydroxylates a specific prol...
Gene Name
EGLN3
Uniprot ID
Q9H6Z9
Uniprot Name
Egl nine homolog 3
Molecular Weight
27261.06 Da

Drug created on October 18, 2007 13:34 / Updated on August 02, 2019 07:41