fedratinib   

GtoPdb Ligand ID: 5716

Synonyms: Inrebic® | SAR302503 | TG-101348 | TG101348
fedratinib is an approved drug (FDA (2019))
Compound class: Synthetic organic
Comment: Fedratinib (TG‑101348) was initially reported as an orally active JAK2-FLT3 kinase inhibitor, with biological activity via JAK2 inhibition [5]. More recently, this compound has been discovered to function, in addition, as a BRD4 (bromodomain) inhibitor [2]. It is suggested that TG‑101348 be termed a dual kinase-bromodomain inhibitor. Fedratinib is been identified and officially approved as an alternative to the JAK1/2 inhibitor ruxolitinib for the treatment of primary and secondary myelofibrosis [1].
2D Structure
Click here for structure editor
Physico-chemical Properties
Hydrogen bond acceptors 8
Hydrogen bond donors 3
Rotatable bonds 11
Topological polar surface area 116.86
Molecular weight 524.26
XLogP 4.26
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES Cc1cnc(nc1Nc1cccc(c1)S(=O)(=O)NC(C)(C)C)Nc1ccc(cc1)OCCN1CCCC1
Isomeric SMILES Cc1cnc(nc1Nc1cccc(c1)S(=O)(=O)NC(C)(C)C)Nc1ccc(cc1)OCCN1CCCC1
InChI 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)
InChI Key JOOXLOJCABQBSG-UHFFFAOYSA-N
Classification
Compound class Synthetic organic
Approved drug? Yes (FDA (2019))
IUPAC Name
N-tert-butyl-3-{[5-methyl-2-({4-[2-(pyrrolidin-1-yl)ethoxy]phenyl}amino)pyrimidin-4-yl]amino}benzene-1-sulfonamide
International Nonproprietary Names
INN number INN
9707 fedratinib
Synonyms
Inrebic® | SAR302503 | TG-101348 | TG101348
Database Links
CAS Registry No. 936091-26-8
ChEMBL Ligand CHEMBL1287853
DrugCentral Ligand 5347
GtoPdb PubChem SID 178102342
PubChem CID 16722836
RCSB PDB Ligand 2TA
Search Google for chemical match using the InChIKey JOOXLOJCABQBSG-UHFFFAOYSA-N
Search Google for chemicals with the same backbone JOOXLOJCABQBSG
Search PubMed clinical trials fedratinib
Search PubMed titles fedratinib
Search PubMed titles/abstracts fedratinib
Search UniChem for chemical match using the InChIKey JOOXLOJCABQBSG-UHFFFAOYSA-N
Search UniChem for chemicals with the same backbone JOOXLOJCABQBSG
Wikipedia TG101348