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

General Information of Drug (ID: DR1760)
Drug Name
Dexmethylphenidate
Synonyms
Dexmethylphenidate; Dexmethylphenidate (INN); Dexmethylphenidate [INN]; Focalin; Focalin XR; M32RH9MFGP; Methyl D-phenidate; d-Methylphenidate; Attenade; Dex methylphenidate; d-threo-Methylphenidate; dex-methylphenidate; dexmethylphenidatum; dexmetilfenidato; threo-(+)-Methylphenidate; (+)-threo-Methylphenidate; 40431-64-9; CHEBI:51860; CHEMBL827; D-MPH; D-TMP; UNII-M32RH9MFGP; methyl (2R)-2-phenyl-2-[(2R)-piperidin-2-yl]acetate; methyl (2R)-phenyl[(2R)-piperidin-2-yl]acetate; methyl (R)-phenyl[(R)-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
154101
ChEBI ID
CHEBI:51860
CAS Number
40431-64-9
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/t12-,13-/m1/s1
InChIKey
DUGOZIWVEXMGBE-CHWSQXEVSA-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-methylphenidate DM000818 N. A. Oxidation - Oxidation 1 [4]
Alpha-phenyl-2-piperidine acetic acid (ritalinic acid) DM000816
86863
Other reaction - Deesterification 1 [5]
p-hydroxy-methylphenidate DM000817
3045249
Oxidation - Hydroxylation 1 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000805 Dexmethylphenidate Ritalinic acid Other reaction - Deesterification CES1A1a [5]
MR000806 Dexmethylphenidate p-hydroxy-methylphenidate Oxidation - Hydroxylation Unclear [4]
MR000807 Dexmethylphenidate 6-oxo-methylphenidate Oxidation - Oxidation Unclear [4]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Carboxylesterase (CES1A1a) DMEN019 Homo sapiens
Q6LAP9_HUMAN
2.7.4.6
[2]
Carboxylesterase 1 (CES1) DME0054 Homo sapiens
EST1_HUMAN
3.1.1.1
[3]
References
1 Dexmethylphenidate 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. doi: 10.1124/jpet.104.067116.
3 Dexmethylphenidate hydrochloride in the treatment of attention deficit hyperactivity disorder. Neuropsychiatr Dis Treat. 2006 Dec;2(4):467-73.
4 Pharmacokinetics and clinical effectiveness of methylphenidate Clin Pharmacokinet. 1999 Dec;37(6):457-70. doi: 10.2165/00003088-199937060-00002.
5 Methylphenidate is stereoselectively hydrolyzed by human carboxylesterase CES1A1. J Pharmacol Exp Ther. 2004 Aug;310(2):469-76.

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