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Details

Stereochemistry ABSOLUTE
Molecular Formula C17H19F3N6O
Molecular Weight 380.3676
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of UPADACITINIB

SMILES

CC[C@@H]1CN(C[C@@H]1C2=CN=C3C=NC4=C(C=CN4)N23)C(=O)NCC(F)(F)F

InChI

InChIKey=WYQFJHHDOKWSHR-MNOVXSKESA-N
InChI=1S/C17H19F3N6O/c1-2-10-7-25(16(27)24-9-17(18,19)20)8-11(10)13-5-22-14-6-23-15-12(26(13)14)3-4-21-15/h3-6,10-11,21H,2,7-9H2,1H3,(H,24,27)/t10-,11+/m1/s1

HIDE SMILES / InChI
Molecular Formula C17H19F3N6O
Molecular Weight 380.3676
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Approval Year

Unknown
86413
Substance Class Chemical
Created
by admin
on Sat Dec 16 08:54:18 UTC 2023
Edited
by admin
on Sat Dec 16 08:54:18 UTC 2023
Record UNII
4RA0KN46E0
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
UPADACITINIB
INN   USAN   WHO-DD  
INN   USAN  
Official Name English
ABBV-599 COMPONENT UPADACITINIB
Common Name English
UPADACITINIB [ORANGE BOOK]
Common Name English
(3S,4R)-3-ETHYL-4-(3H-IMIDAZO(1,2-A)PYRROLO(2,3-E)PYRAZIN- 8-YL)-N-(2,2,2-TRIFLUOROETHYL)PYRROLIDINE-1-CARBOXAMIDE TYROSINE KINASE INHIBITOR
Common Name English
UPADACITINIB [MI]
Common Name English
UPADACITINIB [USAN]
Common Name English
(3S,4R)-3-ETHYL-4-(3H-IMIDAZO(1,2-A)PYRROLO(2,3-E)PYRAZIN-8-YL)-N-(2,2,2-TRIFLUOROETHYL)-1-PYRROLIDINECARBOXAMIDE
Systematic Name English
ABT-494
Code English
UPADACITINIB COMPONENT OF ABBV-599
Common Name English
Upadacitinib [WHO-DD]
Common Name English
1-PYRROLIDINECARBOXAMIDE, 3-ETHYL-4-(3H-IMIDAZO(1,2-A)PYRROLO(2,3-E)PYRAZIN-8-YL)-N-(2,2,2-TRIFLUOROETHYL)-, (3S,4R)-
Systematic Name English
UPADACITINIB ANHYDROUS
Common Name English
upadacitinib [INN]
Common Name English
REL-(-)-(3S,4R)-3-ETHYL-4-(3H-IMIDAZO(1,2-A)PYRROLO(2,3-E)PYRAZIN-8-YL)-N-(2,2,2-TRIFLUOROETHYL)PYRROLIDINE-1-CARBOXAMIDE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C1967
Created by admin on Sat Dec 16 08:54:19 UTC 2023 , Edited by admin on Sat Dec 16 08:54:19 UTC 2023
FDA ORPHAN DRUG 522916
Created by admin on Sat Dec 16 08:54:19 UTC 2023 , Edited by admin on Sat Dec 16 08:54:19 UTC 2023
FDA ORPHAN DRUG 524116
Created by admin on Sat Dec 16 08:54:19 UTC 2023 , Edited by admin on Sat Dec 16 08:54:19 UTC 2023
FDA ORPHAN DRUG 575517
Created by admin on Sat Dec 16 08:54:19 UTC 2023 , Edited by admin on Sat Dec 16 08:54:19 UTC 2023
Code System Code Type Description
USAN
CD-19
Created by admin on Sat Dec 16 08:54:19 UTC 2023 , Edited by admin on Sat Dec 16 08:54:19 UTC 2023
PRIMARY
RXCUI
2196092
Created by admin on Sat Dec 16 08:54:19 UTC 2023 , Edited by admin on Sat Dec 16 08:54:19 UTC 2023
PRIMARY
INN
10209
Created by admin on Sat Dec 16 08:54:19 UTC 2023 , Edited by admin on Sat Dec 16 08:54:19 UTC 2023
PRIMARY
WIKIPEDIA
Upadacitinib
Created by admin on Sat Dec 16 08:54:19 UTC 2023 , Edited by admin on Sat Dec 16 08:54:19 UTC 2023
PRIMARY
SMS_ID
100000173002
Created by admin on Sat Dec 16 08:54:19 UTC 2023 , Edited by admin on Sat Dec 16 08:54:19 UTC 2023
PRIMARY
DRUG CENTRAL
5346
Created by admin on Sat Dec 16 08:54:19 UTC 2023 , Edited by admin on Sat Dec 16 08:54:19 UTC 2023
PRIMARY
FDA UNII
4RA0KN46E0
Created by admin on Sat Dec 16 08:54:19 UTC 2023 , Edited by admin on Sat Dec 16 08:54:19 UTC 2023
PRIMARY
PUBCHEM
58557659
Created by admin on Sat Dec 16 08:54:19 UTC 2023 , Edited by admin on Sat Dec 16 08:54:19 UTC 2023
PRIMARY
DRUG BANK
DB15091
Created by admin on Sat Dec 16 08:54:19 UTC 2023 , Edited by admin on Sat Dec 16 08:54:19 UTC 2023
PRIMARY
DAILYMED
4RA0KN46E0
Created by admin on Sat Dec 16 08:54:19 UTC 2023 , Edited by admin on Sat Dec 16 08:54:19 UTC 2023
PRIMARY
NCI_THESAURUS
C152802
Created by admin on Sat Dec 16 08:54:19 UTC 2023 , Edited by admin on Sat Dec 16 08:54:19 UTC 2023
PRIMARY
MERCK INDEX
m12178
Created by admin on Sat Dec 16 08:54:19 UTC 2023 , Edited by admin on Sat Dec 16 08:54:19 UTC 2023
PRIMARY
CAS
1310726-60-3
Created by admin on Sat Dec 16 08:54:19 UTC 2023 , Edited by admin on Sat Dec 16 08:54:19 UTC 2023
PRIMARY
LACTMED
Upadacitinib
Created by admin on Sat Dec 16 08:54:19 UTC 2023 , Edited by admin on Sat Dec 16 08:54:19 UTC 2023
PRIMARY
EPA CompTox
DTXSID901027919
Created by admin on Sat Dec 16 08:54:19 UTC 2023 , Edited by admin on Sat Dec 16 08:54:19 UTC 2023
PRIMARY
Related Record Type Details
ATP-BINDING CASSETTE SUB-FAMILY G MEMBER 2
TRANSPORTER -> SUBSTRATE
CYTOCHROME P450 3A4
METABOLIC ENZYME -> SUBSTRATE
MAJOR
MULTIDRUG RESISTANCE PROTEIN 1
TRANSPORTER -> SUBSTRATE
CYTOCHROME P450 2C9
METABOLIC ENZYME -> INHIBITOR
In the direct inhibition assays, upadacitinib inhibited CYP2C9 with an IC50 value of 40.3 μM
IC50
CYTOCHROME P450 2D6
METABOLIC ENZYME -> SUBSTRATE
MINOR
Structure of UPADACITINIB HEMIHYDRATE
SOLVATE->ANHYDROUS
Structure of UPADACITINIB
EXCRETED UNCHANGED
AMOUNT EXCRETED
URINE
Structure of UPADACITINIB TARTRATE ANHYDROUS
SALT/SOLVATE -> PARENT
Structure of UPADACITINIB TARTRATE
SALT/SOLVATE -> PARENT
TYROSINE-PROTEIN KINASE JAK1
TARGET -> INHIBITOR
Structure of UPADACITINIB HEMIHYDRATE
SALT/SOLVATE -> PARENT
Structure of UPADACITINIB
EXCRETED UNCHANGED
AMOUNT EXCRETED
FECAL
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
BINDING
Related Record Type Details
Structure of 5-((3R,4S)-4-ETHYL-1-(2,2,2-TRIFLUOROETHYLCARBAMOYL)PYRROLIDIN-3-YL)-1H-IMIDAZOLE-2-CARBOXAMIDE
METABOLITE INACTIVE -> PARENT
URINE
Structure of (3S,4R)-3-ETHYL-4-(3H-IMIDAZO(1,2-A)PYRROLO(2,3-E)PYRAZIN-8-YL)-N-(2,2,2-TRIFLUORO-1-HYDROXYETHYL)PYRROLIDINE-1-CARBOXAMIDE
METABOLITE -> PARENT
TRACE
FECAL; URINE
Structure of 5-((3R,4S)-4-ETHYL-1-(2,2,2-TRIFLUOROETHYLCARBAMOYL)PYRROLIDIN-3-YL)-1H-IMIDAZOLE-2-CARBOXAMIDE
METABOLITE INACTIVE -> PARENT
FECAL
Structure of 5-((3R,4S)-4-ETHYL-1-(2,2,2-TRIFLUOROETHYLCARBAMOYL)PYRROLIDIN-3-YL)-1H-IMIDAZOLE-2-CARBOXAMIDE
METABOLITE INACTIVE -> PARENT
PLASMA
Related Record Type Details
Structure of UPADACITINIB
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC STEADY-STATE

blood to plasma ratio PHARMACOKINETIC
Tmax PHARMACOKINETIC FASTED CONDITION

ORAL ADMINISTRATION

Biological Half-life PHARMACOKINETIC FOLLOWING THE ADMINISTRATION OF ER FORMULATION

Tmax PHARMACOKINETIC ORAL ADMINISTRATION

FED CONDITION

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