Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D01513)
Name
Upadacitinib
Synonyms    Click to Show/Hide the Synonyms of This API
Upadacitinib; 1310726-60-3; ABT-494; Rinvoq; UNII-4RA0KN46E0; 4RA0KN46E0; 1310726-60-3 (free base); (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; MFCD30502663; Upadacitinib, ABT-494; Upadacitinib (USAN/INN); Upadacitinib [USAN:INN]; Upadacitinib (ABT-494); GTPL9246; SCHEMBL9991056; CHEMBL3622821; ABT 494; AMY16528; BCP19011; EX-A1628; BDBM50503287; s8162; CS-6150; DB15091; SB19218; ABT494;ABT-494;ABT 494; AC-30326; AS-56379; HY-19569; J3.590.729G; D10994; Q27074125; (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; (3S,4R)-3-ethyl-4-(3H-imidazo(1,2-a)pyrrolo(2,3-e)pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)-1-pyrrolidinecarboxamide; 1-Pyrrolidinecarboxamide, 3-ethyl-4-(3H-imidazo(1,2-a)pyrrolo(2,3-e)pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)-, (3S,4R)-
Clinical Status
Approved
PubChem CID
58557659
Formula
C17H19F3N6O
Canonical SMILES
CC[C@@H]1CN(C[C@@H]1C2=CN=C3N2C4=C(NC=C4)N=C3)C(=O)NCC(F)(F)F
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
InChIKey
WYQFJHHDOKWSHR-MNOVXSKESA-N
   Click to Show/Hide the Molecular Data (Structure/Property) of This API
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=58557659"></iframe>
3D MOL is unavailable 2D MOL
Physicochemical Properties Molecular Weight 380.4 Topological Polar Surface Area 78.3
XlogP 2.7 Complexity 561
Heavy Atom Count 27 Rotatable Bond Count 3
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 6
Full List of Drug Formulations (DFMs) Containing This API
          Upadacitinib 15 mg Extended-Release tablet Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Microcrystalline Cellulose; Hypromellose; Mannitol; Tartaric Acid; Colloidal Silicon Dioxide; Magnesium Stearate; Polyvinyl Alcohol; Polyethylene Glycol; Talc; Titanium Dioxide; Ferrosoferric Oxide; Iron Oxide Red
                   Dosage Form Extended-Release Tablet
                   Company Abbvie
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [1]
Hypromellose DIG Info Cytochrome P450 3A5 (IC50 = 19.4 uM) [2]
Polyvinyl alcohol DIG Info Debrisoquine 4-hydroxylase (EC50 = 354.8 uM) [2]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
Polyethylene glycol 4000 DIG Info Albendazole monooxygenase (Inhibition ratio < 40 %) [4]
References
1 Pharmacological property optimization for allosteric ligands: A medicinal chemistry perspective. Bioorg Med Chem Lett. 2017 Jun 1; 27(11):2239-2258.
2 Mediation of in vitro cytochrome p450 activity by common pharmaceutical excipients. Mol Pharm. 2013 Jul 1;10(7):2739-48.
3 Effects of commonly used excipients on the expression of CYP3A4 in colon and liver cells. Pharm Res. 2010 Aug;27(8):1703-12.
4 Pharmaceutical excipients inhibit cytochrome P450 activity in cell free systems and after systemic administration. Eur J Pharm Biopharm. 2008 Sep;70(1):279-88.

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