Details of the Drug

General Information of Drug (ID: DM8T2OI)

Drug Name
Upadacitinib
Synonyms
Upadacitinib, ABT-494; J3.590.729G; Rinvoq; SB19218; SCHEMBL9991056; Upadacitinib; Upadacitinib (USAN/INN); Upadacitinib [USAN:INN]; 1-Pyrrolidinecarboxamide, 3-ethyl-4-(3H-imidazo(1,2-a)pyrrolo(2,3-e)pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)-, (3S,4R)-; 1310726-59-0; 1310726-60-3; 4RA0KN46E0; ABT 494; ABT-494; ABT-494 enantiomer; AC-30326; BCP19011; CHEMBL3622821; CS-6150; D10994; EX-A1628; GTPL9246; HY-19569; MFCD30502663; UNII-4RA0KN46E0
Indication
Disease Entry ICD 11 Status REF
Rheumatoid arthritis FA20 Approved [1]
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 380.4
Topological Polar Surface Area (xlogp) 2.7
Rotatable Bond Count (rotbonds) 3
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 6
ADMET Property
Absorption Tmax
The time to maximum plasma concentration (Tmax) is 2-4 h [2]
Clearance
The apparent oral clearance of drug is 53.7 L/h [3]
Elimination
Following administration of a single radio-labelled dose from the immediate-release formulation, approximately 53% of the total dose was excreted in the feces where 38% of the excreted dose was an unchanged parent drug [4]
Half-life
The concentration or amount of drug in body reduced by one-half in 8 - 14 hours [2]
Metabolism
The drug is metabolized via the CYP2D6 [2]
Vd
The volume of distribution (Vd) of drug is 224 L [4]
Chemical Identifiers
Formula
C17H19F3N6O
IUPAC Name
(3S,4R)-3-ethyl-4-(1,5,7,10-tetrazatricyclo[7.3.0.02,6]dodeca-2(6),3,7,9,11-pentaen-12-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide
Canonical SMILES
CCC1CN(CC1C2=CN=C3N2C4=C(NC=C4)N=C3)C(=O)NCC(F)(F)F
InChI
WYQFJHHDOKWSHR-MNOVXSKESA-N
InChIKey
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
Cross-matching ID
PubChem CID
58557659
CAS Number
1310726-60-3
DrugBank ID
DB15091
INTEDE ID
DR1660

Molecular Interaction Atlas of This Drug


Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4)
Main DME 		DE4LYSA CP3A4_HUMAN Substrate [5]
Cytochrome P450 2D6 (CYP2D6) DECB0K3 CP2D6_HUMAN Substrate [5]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Upadacitinib was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 FDA Approved Drug Products: RINVOQ (upadacitinib) extended-release tablets, for oral use
3 Klunder B, Mittapalli RK, Mohamed MF, Friedel A, Noertersheuser P, Othman AA: Population Pharmacokinetics of Upadacitinib Using the Immediate-Release and Extended-Release Formulations in Healthy Subjects and Subjects with Rheumatoid Arthritis: Analyses of Phase I-III Clinical Trials. Clin Pharmacokinet. 2019 Aug;58(8):1045-1058. doi: 10.1007/s40262-019-00739-3.
4 Upadacitinib Summary Review - FDA
5 Population pharmacokinetics of upadacitinib using the immediate-release and extended-release formulations in healthy subjects and subjects with rheumatoid arthritis: analyses of phase I-III clinical trials. Clin Pharmacokinet. 2019 Aug;58(8):1045-1058.
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17 CYP2D6 polymorphisms and tamoxifen metabolism: clinical relevance. Curr Oncol Rep. 2010 Jan;12(1):7-15.
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