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

General Information of Drug (ID: DR1054)
Drug Name
Methylphenidate
Synonyms
Meridil; Metadate; Methyl phenidate; Methyl phenidyl acetate; Methyl phenidylacetate; Methylfenidan; Methylin; Methylphenidan; Methylphenidate HCl; Methylphenidatum; Methylphenidatum [INN-Latin]; Metilfenidato; Metilfenidato [INN-Spanish]; Metilfenidato [Italian]; Phenidylate; Plimasine; Ritalin; d-methylphenidate HCl; methylphenidate; Calocain; Concerta; Daytrana; 113-45-1; 4311/B Ciba; Methyl alpha-phenyl-alpha-(2-piperidyl)acetate; NCI-C56280; alpha-Phenyl-2-piperidineacetic acid methyl ester; methyl phenyl(piperidin-2-yl)acetate
Indication Attention deficit hyperactivity disorder [ICD11: 6A05] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 233.31 Topological Polar Surface Area 38.3
Heavy Atom Count 17 Rotatable Bond Count 4
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
4158
PubChem SID
9405 ; 5336253 ; 7979945 ; 8152600 ; 10504398 ; 14798219 ; 26746622 ; 29223265 ; 46505929 ; 47206727 ; 48416258 ; 49854760 ; 53789341 ; 57322165 ; 78286794 ; 85209963 ; 103209574 ; 103858000 ; 103958410 ; 104305599 ; 124954808 ; 127787857 ; 134337354 ; 134974024 ; 135709935 ; 136897384 ; 137007933 ; 142361369 ; 160963768 ; 163411030 ; 178103810 ; 179148478 ; 216106193 ; 223897828 ; 226423048 ; 249807024 ; 249948308 ; 252404612
ChEBI ID
ChEBI:6887
CAS Number
113-45-1
TTD Drug ID
D02PPN
Formula
C14H19NO2
Canonical SMILES
COC(=O)C(C1CCCCN1)C2=CC=CC=C2
InChI
1S/C14H19NO2/c1-17-14(16)13(11-7-3-2-4-8-11)12-9-5-6-10-15-12/h2-4,7-8,12-13,15H,5-6,9-10H2,1H3
InChIKey
DUGOZIWVEXMGBE-UHFFFAOYSA-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
6-Oxo-MPH DM004326 N. A. Unclear 1 [3]
Alpha-phenyl-2-piperidine acetic acid (ritalinic acid) DM000816
86863
Hydrolysis - Esterase hydrolyzation 1 [5] , [2]
Carbamide MPH DM004347 N. A. Unclear 1 [3]
Ethylphenidate DM004342
3080846
Unclear 1 [3]
p-Hydroxy-MPH DM004338 N. A. Unclear 1 [3]
Ritalic acid DM004327
11053160
Unclear 1 [3]
4-Hydroxy-EPH DM004344 N. A. Unclear 2 [3]
5-Hydroxy-EPH DM004343 N. A. Unclear 2 [3]
6-Oxo-5(or 4)-Hydroxy-MPH DM004333 N. A. Unclear 2 [3]
6-Oxo-ritalic acid DM004328
95162842
Unclear 2 [3]
Carbamide ritalic acid DM004348 N. A. Unclear 2 [3]
Ethyl 3-amino-6-oxo-2-phenylhexanoate DM004345
129858264
Unclear 2 [3]
p-Hydroxy-6-oxo-MPH DM004330 N. A. Unclear 2 [3]
p-Hydroxy-MPH-glucuronide DM004346 N. A. Unclear 2 [3]
p-Hydroxy-ritalic acid DM004339 N. A. Unclear 2 [3]
Ritalic acid DM004327
11053160
Unclear 2 [3]
2-(p-Hydroxy)-phenyl-N-(2-sulfoethyl)-2-(6-oxo)-piperidyl-acetamide DM004337 N. A. Unclear 3 [3]
6-Oxo-5(or 4)-hydroxy-ritalic acid DM004334 N. A. Unclear 3 [3]
6-Oxo-MPH p-O-glucuronide DM004336 N. A. Unclear 3 [3]
6-Oxo-MPH-5(or 4)glucuronide DM004341 N. A. Unclear 3 [3]
6-Oxo-ritalic acid DM004328
95162842
Unclear 3 [3]
6-Oxo-ritalic acid acyl glucuronide DM004329 N. A. Unclear 3 [3]
p-Hydroxy-6-oxo-ritalic acid DM004331 N. A. Unclear 3 [3]
Ritalic acidp-O-glucuronide DM004340 N. A. Unclear 3 [3]
6-Oxo-ritalic acid acyl glucuronide DM004329 N. A. Unclear 4 [3]
6-Oxo-ritalic acid p-O-glucuronide DM004332 N. A. Unclear 4 [3]
Ritalic acid5-O-glucuronide DM004335 N. A. Unclear 4 [3]
⏷ Show the Full List of 27  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR013369 Methylphenidate 6-Oxo-MPH Unclear Unclear [3]
MR013382 Methylphenidate Ritalic acid Unclear CES1 [3]
MR013383 Methylphenidate p-Hydroxy-MPH Unclear Unclear [3]
MR013387 Methylphenidate Ethylphenidate Unclear CES1 [3]
MR013392 Methylphenidate Carbamide MPH Unclear Unclear [3]
MR013394 Methylphenidate Alpha-phenyl-2-piperidine acetic acid (ritalinic acid) Hydrolysis - Esterase hydrolyzation CES1 [5], [2]
MR013370 6-Oxo-MPH Ritalic acid Unclear Unclear [3]
MR013373 6-Oxo-MPH p-Hydroxy-6-oxo-MPH Unclear Unclear [3]
MR013376 6-Oxo-MPH 6-Oxo-5(or 4)-Hydroxy-MPH Unclear Unclear [3]
MR013380 6-Oxo-MPH 6-Oxo-ritalic acid Unclear Unclear [3]
MR013393 Carbamide MPH Carbamide ritalic acid Unclear Unclear [3]
MR013388 Ethylphenidate 5-Hydroxy-EPH Unclear CYP2C19 [3]
MR013389 Ethylphenidate 4-Hydroxy-EPH Unclear CYP2C19 [3]
MR013390 Ethylphenidate Ethyl 3-amino-6-oxo-2-phenylhexanoate Unclear CYP2D6 [3]
MR013384 p-Hydroxy-MPH p-Hydroxy-ritalic acid Unclear Unclear [3]
MR013391 p-Hydroxy-MPH p-Hydroxy-MPH-glucuronide Unclear UGT [3]
MR013926 Ritalic acid 6-Oxo-ritalic acid Unclear Unclear [3]
MR013377 6-Oxo-5(or 4)-Hydroxy-MPH 6-Oxo-5(or 4)-hydroxy-ritalic acid Unclear Unclear [3]
MR013386 6-Oxo-5(or 4)-Hydroxy-MPH 6-Oxo-MPH-5(or 4)glucuronide Unclear Unclear [3]
MR013925 6-Oxo-ritalic acid 6-Oxo-ritalic acid acyl glucuronide Unclear Unclear [3]
MR013374 p-Hydroxy-6-oxo-MPH p-Hydroxy-6-oxo-ritalic acid Unclear Unclear [3]
MR013379 p-Hydroxy-6-oxo-MPH 6-Oxo-MPH p-O-glucuronide Unclear Unclear [3]
MR013381 p-Hydroxy-6-oxo-MPH 2-(p-Hydroxy)-phenyl-N-(2-sulfoethyl)-2-(6-oxo)-piperidyl-acetamide Unclear Unclear [3]
MR013385 P-Hydroxy-ritalic acid Ritalic acidp-O-glucuronide Unclear Unclear [3]
MR013371 Ritalic acid 6-Oxo-ritalic acid Unclear Unclear [3]
MR013378 6-Oxo-5(or 4)-hydroxy-ritalic acid Ritalic acid5-O-glucuronide Unclear Unclear [3]
MR013372 6-Oxo-ritalic acid 6-Oxo-ritalic acid acyl glucuronide Unclear Unclear [3]
MR013375 p-Hydroxy-6-oxo-ritalic acid 6-Oxo-ritalic acid p-O-glucuronide Unclear Unclear [3]
⏷ Show the Full List of 28 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Carboxylesterase 1 (CES1) DME0054 Homo sapiens
EST1_HUMAN
3.1.1.1
[2]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[3]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[3]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[3]
Unclear metabolic mechanism (DME-unclear) DME1391 Bifidobacterium ruminatum Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1393 Blautia hansenii Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1402 Clostridium botulinum Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1415 Eggerthella lenta Not Available Not Available [4]
⏷ Show the Full List of 8  DME(s)
References
1 Methylphenidate was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Methylphenidate is stereoselectively hydrolyzed by human carboxylesterase CES1A1. J Pharmacol Exp Ther. 2004 Aug;310(2):469-76.
3 Metabolomics of Methylphenidate and Ethylphenidate: Implications in Pharmacological and Toxicological Effects
4 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
5 Metabolism of methylphenidate in dog and rat

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