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Details

Stereochemistry ACHIRAL
Molecular Formula C24H27F2N5O4
Molecular Weight 487.5
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PEMIGATINIB

SMILES

CCN1c2c(cnc3c2cc(CN4CCOCC4)[nH]3)CN(c5c(c(cc(c5F)OC)OC)F)C1=O

InChI

InChIKey=HCDMJFOHIXMBOV-UHFFFAOYSA-N
InChI=1S/C24H27F2N5O4/c1-4-30-21-14(11-27-23-16(21)9-15(28-23)13-29-5-7-35-8-6-29)12-31(24(30)32)22-19(25)17(33-2)10-18(34-3)20(22)26/h9-11H,4-8,12-13H2,1-3H3,(H,27,28)

HIDE SMILES / InChI

Molecular Formula C24H27F2N5O4
Molecular Weight 487.5
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Pemigatinib, an oral kinases inhibitor, was approved under the brand name PEMAZYRE for the treatment of adults with previously treated, unresectable locally advanced, or metastatic cholangiocarcinoma with a fibroblast growth factor receptor 2 (FGFR2) fusion. The FDA-approved indication for pemigatinib was granted under accelerated approval based on the overall response rate and duration of response in pre-marketing clinical trials. The drug inhibited FGFR1-3 phosphorylation and signaling and decreased cell viability in cancer cell lines with activating FGFR amplification and fusions that resulted in constitutive activation of FGFR signaling.

CNS Activity

Curator's Comment:: pemigatinib crossed the blood-brain barrier at low levels after IV administration.

Originator

Curator's Comment:: was synthesized at Incyte Corporation (Wilmington, DE).

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P11362|||Q14307|||Q9UDF2
Gene ID: 2260.0
Gene Symbol: FGFR1
Target Organism: Homo sapiens (Human)
0.4 nM [IC50]
Target ID: P21802|||Q14301|||Q1KHY5|||Q9NZU3|||Q9UIH8
Gene ID: 2263.0
Gene Symbol: FGFR2
Target Organism: Homo sapiens (Human)
0.5 nM [IC50]
1.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PEMAZYRE

Approved Use

PEMAZYRE is a kinase inhibitor indicated for the treatment of adults with previously treated, unresectable locally advanced or metastatic cholangiocarcinoma with a fibroblast growth factor receptor 2 (FGFR2) fusion

Sample Use Guides

The recommended dosage is 13.5 mg orally once daily for 14 consecutive days followed by 7 days off therapy, in 21-day cycles. Continue treatment until disease progression or unacceptable toxicity occurs
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Sat Jun 26 12:10:47 UTC 2021
Edited
by admin
on Sat Jun 26 12:10:47 UTC 2021
Record UNII
Y6BX7BL23K
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PEMIGATINIB
INN   USAN  
Official Name English
3-(2,6-DIFLUORO-3,5-DIMETHOXYPHENYL)-1-ETHYL-8-(MORPHOLIN-4-YLMETHYL)-1,3,4,7-TETRAHYDRO-2H-PYRROLO(3',2':5,6)PYRIDO(4,3-D)PYRIMIDIN-2-ONE
Systematic Name English
INCB-054828
Common Name English
PEMIGATINIB [USAN]
Common Name English
FGFR INHIBITOR INCB054828
Common Name English
PEMIGATINIB [INN]
Common Name English
PEMIGATINIB [WHO-DD]
Common Name English
INCB054828
Code English
2H-PYRROLO(3',2':5,6)PYRIDO(4,3-D)PYRIMIDIN-2-ONE, 3-(2,6-DIFLUORO-3,5-DIMETHOXYPHENYL)-1-ETHYL-1,3,4,7-TETRAHYDRO-8-(4-MORPHOLINYLMETHYL)-
Systematic Name English
PEMAZYRE
Brand Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 624117
Created by admin on Sat Jun 26 12:10:47 UTC 2021 , Edited by admin on Sat Jun 26 12:10:47 UTC 2021
FDA ORPHAN DRUG 696419
Created by admin on Sat Jun 26 12:10:47 UTC 2021 , Edited by admin on Sat Jun 26 12:10:47 UTC 2021
NCI_THESAURUS C129825
Created by admin on Sat Jun 26 12:10:47 UTC 2021 , Edited by admin on Sat Jun 26 12:10:47 UTC 2021
EU-Orphan Drug EU/3/18/2066
Created by admin on Sat Jun 26 12:10:47 UTC 2021 , Edited by admin on Sat Jun 26 12:10:47 UTC 2021
NCI_THESAURUS C1967
Created by admin on Sat Jun 26 12:10:47 UTC 2021 , Edited by admin on Sat Jun 26 12:10:47 UTC 2021
Code System Code Type Description
INN
10712
Created by admin on Sat Jun 26 12:10:47 UTC 2021 , Edited by admin on Sat Jun 26 12:10:47 UTC 2021
PRIMARY
CAS
1513857-77-6
Created by admin on Sat Jun 26 12:10:47 UTC 2021 , Edited by admin on Sat Jun 26 12:10:47 UTC 2021
PRIMARY
PUBCHEM
86705695
Created by admin on Sat Jun 26 12:10:47 UTC 2021 , Edited by admin on Sat Jun 26 12:10:47 UTC 2021
PRIMARY
RXCUI
2359268
Created by admin on Sat Jun 26 12:10:47 UTC 2021 , Edited by admin on Sat Jun 26 12:10:47 UTC 2021
PRIMARY
DRUG BANK
DB15102
Created by admin on Sat Jun 26 12:10:47 UTC 2021 , Edited by admin on Sat Jun 26 12:10:47 UTC 2021
PRIMARY
DRUG CENTRAL
5390
Created by admin on Sat Jun 26 12:10:47 UTC 2021 , Edited by admin on Sat Jun 26 12:10:47 UTC 2021
PRIMARY
FDA UNII
Y6BX7BL23K
Created by admin on Sat Jun 26 12:10:47 UTC 2021 , Edited by admin on Sat Jun 26 12:10:47 UTC 2021
PRIMARY
NCI_THESAURUS
C121553
Created by admin on Sat Jun 26 12:10:47 UTC 2021 , Edited by admin on Sat Jun 26 12:10:47 UTC 2021
PRIMARY
Related Record Type Details
EXCRETED UNCHANGED
FECAL
METABOLIC ENZYME -> SUBSTRATE
MAJOR
BINDER->LIGAND
In vitro, pemigatinib was 90.6% bound to human plasma proteins at concentrations ranging from 1 to 10 ?M.
BINDING
TARGET -> INHIBITOR
IC50
TARGET -> INHIBITOR
IC50
EXCRETED UNCHANGED
URINE
TARGET -> INHIBITOR
IC50
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Tmax PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC