U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C27H36N6O3S
Molecular Weight 524.678
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FEDRATINIB

SMILES

CC1=CN=C(NC2=CC=C(OCCN3CCCC3)C=C2)N=C1NC4=CC=CC(=C4)S(=O)(=O)NC(C)(C)C

InChI

InChIKey=JOOXLOJCABQBSG-UHFFFAOYSA-N
InChI=1S/C27H36N6O3S/c1-20-19-28-26(30-21-10-12-23(13-11-21)36-17-16-33-14-5-6-15-33)31-25(20)29-22-8-7-9-24(18-22)37(34,35)32-27(2,3)4/h7-13,18-19,32H,5-6,14-17H2,1-4H3,(H2,28,29,30,31)

HIDE SMILES / InChI
Molecular Formula C27H36N6O3S
Molecular Weight 524.678
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Approval Year

Unknown
86413
Substance Class Chemical
Created
by admin
on Sat Dec 16 01:55:21 UTC 2023
Edited
by admin
on Sat Dec 16 01:55:21 UTC 2023
Record UNII
6L1XP550I6
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FEDRATINIB
INN   USAN   WHO-DD  
USAN   INN  
Official Name English
fedratinib [INN]
Common Name English
BENZENESULFONAMIDE, N-(1,1-DIMETHYLETHYL)-3-((5-METHYL-2-((4-(2-(1-PYRROLIDINYL)ETHOXY)PHENYL)AMINO)-4-PYRIMIDINYL)AMINO)-
Systematic Name English
FEDRATINIB [MI]
Common Name English
Fedratinib [WHO-DD]
Common Name English
N-TERT-BUTYL-3-((5-METHYL-2-(4-(2-(PYRROLIDIN-1-YL)ETHOXY)ANILINO(PYRIMIDIN-4-YL)AMINO)BENZENESULFONAMIDE
Common Name English
N-TERT-BUTYL-3-(5-METHYL-2-(4-(2-PYRROLIDIN-1-YL-ETHOXY)-PHENYLAMINO)-PYRIMIDIN-4-YLAMINO)-BENZENESULFONAMIDE
Systematic Name English
SAR-302503
Code English
SAR302503
Code English
TG101348
Code English
TG-101348
Code English
FEDRATINIB [USAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C129825
Created by admin on Sat Dec 16 01:55:21 UTC 2023 , Edited by admin on Sat Dec 16 01:55:21 UTC 2023
NCI_THESAURUS C125450
Created by admin on Sat Dec 16 01:55:21 UTC 2023 , Edited by admin on Sat Dec 16 01:55:21 UTC 2023
Code System Code Type Description
DAILYMED
6L1XP550I6
Created by admin on Sat Dec 16 01:55:21 UTC 2023 , Edited by admin on Sat Dec 16 01:55:21 UTC 2023
PRIMARY
WIKIPEDIA
TG101348
Created by admin on Sat Dec 16 01:55:21 UTC 2023 , Edited by admin on Sat Dec 16 01:55:21 UTC 2023
PRIMARY
FDA UNII
6L1XP550I6
Created by admin on Sat Dec 16 01:55:21 UTC 2023 , Edited by admin on Sat Dec 16 01:55:21 UTC 2023
PRIMARY
MERCK INDEX
m12160
Created by admin on Sat Dec 16 01:55:21 UTC 2023 , Edited by admin on Sat Dec 16 01:55:21 UTC 2023
PRIMARY
USAN
AB-104
Created by admin on Sat Dec 16 01:55:21 UTC 2023 , Edited by admin on Sat Dec 16 01:55:21 UTC 2023
PRIMARY
ChEMBL
CHEMBL1287853
Created by admin on Sat Dec 16 01:55:21 UTC 2023 , Edited by admin on Sat Dec 16 01:55:21 UTC 2023
PRIMARY
DRUG CENTRAL
5347
Created by admin on Sat Dec 16 01:55:21 UTC 2023 , Edited by admin on Sat Dec 16 01:55:21 UTC 2023
PRIMARY
DRUG BANK
DB12500
Created by admin on Sat Dec 16 01:55:21 UTC 2023 , Edited by admin on Sat Dec 16 01:55:21 UTC 2023
PRIMARY
INN
9707
Created by admin on Sat Dec 16 01:55:21 UTC 2023 , Edited by admin on Sat Dec 16 01:55:21 UTC 2023
PRIMARY
EPA CompTox
DTXSID90239483
Created by admin on Sat Dec 16 01:55:21 UTC 2023 , Edited by admin on Sat Dec 16 01:55:21 UTC 2023
PRIMARY
NCI_THESAURUS
C88293
Created by admin on Sat Dec 16 01:55:21 UTC 2023 , Edited by admin on Sat Dec 16 01:55:21 UTC 2023
PRIMARY
CAS
936091-26-8
Created by admin on Sat Dec 16 01:55:21 UTC 2023 , Edited by admin on Sat Dec 16 01:55:21 UTC 2023
PRIMARY
EVMPD
SUB126288
Created by admin on Sat Dec 16 01:55:21 UTC 2023 , Edited by admin on Sat Dec 16 01:55:21 UTC 2023
PRIMARY
LACTMED
Fedratinib
Created by admin on Sat Dec 16 01:55:21 UTC 2023 , Edited by admin on Sat Dec 16 01:55:21 UTC 2023
PRIMARY
PUBCHEM
16722836
Created by admin on Sat Dec 16 01:55:21 UTC 2023 , Edited by admin on Sat Dec 16 01:55:21 UTC 2023
PRIMARY
RXCUI
2197490
Created by admin on Sat Dec 16 01:55:21 UTC 2023 , Edited by admin on Sat Dec 16 01:55:21 UTC 2023
PRIMARY
SMS_ID
100000151872
Created by admin on Sat Dec 16 01:55:21 UTC 2023 , Edited by admin on Sat Dec 16 01:55:21 UTC 2023
PRIMARY
Related Record Type Details
Structure of FEDRATINIB
EXCRETED UNCHANGED
AMOUNT EXCRETED
FECAL
CYTOCHROME P450 2C19
METABOLIC ENZYME -> SUBSTRATE
Metabolized by CYP3A4 (0 to 70%), CYP2C19 (0‐20%), and FMO3 (0‐33%) in vitro.
RECEPTOR-TYPE TYROSINE-PROTEIN KINASE FLT3
TARGET -> INHIBITOR
INHIBITOR
IC50
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
BINDING
Structure of FEDRATINIB
EXCRETED UNCHANGED
AMOUNT EXCRETED
URINE
RECEPTOR-TYPE TYROSINE-PROTEIN KINASE FLT3 D835Y
TARGET -> INHIBITOR
Structure of FEDRATINIB HYDROCHLORIDE
SALT/SOLVATE -> PARENT
OCT-2
TRANSPORTER -> INHIBITOR
IC50
TYROSINE-PROTEIN KINASE JAK2
TARGET -> INHIBITOR
Structure of FEDRATINIB
CUMULATIVE EXCRETION
Only 82% of radioactivity recovered
URINE
PROTO-ONCOGENE TYROSINE-PROTEIN KINASE RECEPTOR RET
TARGET -> INHIBITOR
INHIBITOR
IC50
MULTIDRUG AND TOXIN EXTRUSION PROTEIN 1
TRANSPORTER -> INHIBITOR
IC50
CYTOCHROME P450 3A4
METABOLIC ENZYME -> SUBSTRATE
Metabolized by CYP3A4 (0 to 70%), CYP2C19 (0‐20%), and FMO3 (0‐33%) in vitro.
TYROSINE-PROTEIN KINASE JAK2 V617F MUTANT
TARGET -> INHIBITOR
IC50
Structure of FEDRATINIB
CUMULATIVE EXCRETION
Only 82% of radioactivity recovered
FECAL
Structure of FEDRATINIB DIHYDROCHLORIDE ANHYDROUS
SALT/SOLVATE -> PARENT
THIAMINE TRANSPORTER 2
TRANSPORTER -> INHIBITOR
Patients being treated with fedratinib developed Wernicke?s encephalopathy (WE) (Sanofi, 2013), a neurological disorder linked to thiamine deficiency (Cook et al., 1998).
IC50
MATE-2
TRANSPORTER -> INHIBITOR
IC50
MULTIDRUG RESISTANCE PROTEIN 1
TRANSPORTER -> SUBSTRATE
FETAL HEPATIC FLAVIN-CONTAINING MONOOXYGENASE 3 (HUMAN)
METABOLIC ENZYME -> SUBSTRATE
Metabolized by CYP3A4 (0 to 70%), CYP2C19 (0‐20%), and FMO3 (0‐33%) in vitro.
TYROSINE-PROTEIN KINASE JAK1
TARGET -> INHIBITOR
NON-RECEPTOR TYROSINE-PROTEIN KINASE TYK2
TARGET -> INHIBITOR
IC50
TYROSINE-PROTEIN KINASE JAK3
TARGET -> INHIBITOR
MULTIDRUG RESISTANCE PROTEIN 1
TRANSPORTER -> INHIBITOR
IC50
ATP-BINDING CASSETTE SUB-FAMILY G MEMBER 2
TRANSPORTER -> INHIBITOR
IC50
Related Record Type Details
Structure of FEDRATINIB metabolite SAR318031
METABOLITE -> PARENT
Structure of FEDRATINIB metabolite SAR-317981
METABOLITE LESS ACTIVE -> PARENT
2 fold less active than parent. accounting for ~ 9% of the radioactivity AUC.
MAJOR
PLASMA
Related Record Type Details
Structure of FEDRATINIB
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC
Blood to Plasma Ratio PHARMACOKINETIC
Tmax PHARMACOKINETIC STEADY-STATE

ONCE DAILY DOSE

ORAL ADMINISTRATION

NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966