Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR1610)
Drug Name
Tofacitinib citrate
Synonyms
Tasocitinib citrate; Tofacitinib (CP-690550) Citrate; Tofacitinib (citrate); Tofacitinib citrate; Tofacitinib citrate [USAN]; UNII-O1FF4DIV0D; Xeljanz; Xeljanz Xr; citro; 3-((3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidin-1-yl)-3-oxopropanenitrile 2-hydroxypropane-1,2,3-tricarboxylate; 540737-29-9; CHEBI:71197; CP 690550 citrate; CP-690,550-10; CP-690550 citrate; CP-690550-10; O1FF4DIV0D
Indication Rheumatoid arthritis [ICD11: FA20] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 504.5 Topological Polar Surface Area 221
Heavy Atom Count 36 Rotatable Bond Count 8
Hydrogen Bond Donor Count 5 Hydrogen Bond Acceptor Count 12
Cross-matching ID
PubChem CID
10174505
ChEBI ID
CHEBI:71197
CAS Number
540737-29-9
TTD Drug ID
D0EG1I
Formula
C22H28N6O8
Canonical SMILES
CC1CCN(CC1N(C)C2=NC=NC3=C2C=CN3)C(=O)CC#N.C(C(=O)O)C(CC(=O)O)(C(=O)O)O
InChI
1S/C16H20N6O.C6H8O7/c1-11-5-8-22(14(23)3-6-17)9-13(11)21(2)16-12-4-7-18-15(12)19-10-20-16;7-3(8)1-6(13,5(11)12)2-4(9)10/h4,7,10-11,13H,3,5,8-9H2,1-2H3,(H,18,19,20);13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/t11-,13+;/m1./s1
InChIKey
SYIKUFDOYJFGBQ-YLAFAASESA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Tofacitinib citrate metabolite M1 DM006301 N. A. Oxidation - Oxidationn 1 [3]
Tofacitinib citrate metabolite M2 DM006302 N. A. Oxidation - Oxidationn 1 [3]
Tofacitinib citrate metabolite M3 DM006303 N. A. Oxidation - Oxidationn 1 [3]
Tofacitinib citrate metabolite M6 DM006298 N. A. Unclear 1 [4]
Tofacitinib citrate metabolite M4 DM006299 N. A. Unclear 2 [4]
Tofacitinib citrate metabolite M5 DM006300 N. A. Unclear 2 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR006763 Tofacitinib citrate Tofacitinib citrate metabolite M6 Unclear Unclear [4]
MR006766 Tofacitinib citrate Tofacitinib citrate metabolite M1 Oxidation - Oxidationn Unclear [3]
MR006767 Tofacitinib citrate Tofacitinib citrate metabolite M2 Oxidation - Oxidationn Unclear [3]
MR006768 Tofacitinib citrate Tofacitinib citrate metabolite M3 Oxidation - Oxidationn Unclear [3]
MR006764 Tofacitinib citrate metabolite M6 Tofacitinib citrate metabolite M4 Unclear Unclear [4]
MR006765 Tofacitinib citrate metabolite M6 Tofacitinib citrate metabolite M5 Unclear Unclear [4]
⏷ Show the Full List of 6 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[2]
References
1 Tofacitinib Citrate was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 The pharmacokinetics, metabolism, and clearance mechanisms of tofacitinib, a janus kinase inhibitor, in humans. Drug Metab Dispos. 2014 Apr;42(4):759-73.
3 Metabolic Activation of Tofacitinib Mediated by Myeloperoxidase in Vitro
4 Tofacitinib Is a Mechanism-Based Inactivator of Cytochrome P450 3A4

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