General
Preferred name
dexmethylphenidate
Synonyms
METHYLPHENIDATE HYDROCHLORIDE ()
DEXMETHYLPHENIDATE HYDROCHLORIDE ()
Dexmethylphenidate hcl ()
Focalin ()
Focalin Xr ()
Dex-methylphenidate hydrochloride ()
Methylphenidate d-threo-form hydrochloride ()
Methylphenidate d-threo-form ()
?(±)-threo-Methylphenidate (hydrochloride) ()
(±)-threo-Methylphenidate (hydrochloride) (CRM) ()
P&D ID
PD009284
CAS
19262-68-1
23655-65-4
52760-39-1
20748-11-2
40431-64-9
113-45-1
Tags
natural product
drug
available
Approved by
FDA
First approval
2001
Drug Status
investigational
approved
Drug indication
Attention deficit hyperactivity disorder
Max Phase
Phase 4
Probe control
Probe control not defined
Orthogonal probes
0
No orthogonal probes found
Similar probes
0
No structurally similar probes found
Structure
P&D probe-likeness score
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
TOXICITY
There is no difference in effect across genders[A177184,Label]. The difference in effect across racial groups, patients under 6 years, renal impairment, hepatic impairment, pregnancy, lactation, and geriatric patients has not been well studied. Patients with renal impairment are not expected to need dose adjustment as the drug is not mainly cleared renally[Label]. Animal studies in pregnant and lactating rats showed delayed fetal skeletal ossification, and reduced weight gain in male offspring[Label]. Due to these studies, caution must be exercised and the benefits and risks of taking this drug must be weighed[Label]. It is unlikely that dexmethylphenidate is carcinogenic but B6C3F1 mice, which are sensitive to the development of hepatic tumours, developed hepatoblastomas at 2 times the maximum recommended human dose[Label]. Methylpheidate was not found to be mutagenic but is weakly clastogenic in Chinese Hamster Ovary cells[Label]. Methylphenidate does not impair fertility in animal studies[Label].
DESCRIPTION
Dexmethylphenidate is a phenethylamine and piperidine class central nervous system stimulant. Chemically, it is the active dextrorotatory (R,R) enantiomer of racemic .
(GtoPdb)
METABOLISM
Dexmethylphenidate is metabolised to the inactive metabolite ritalinic acid by carboxylesterase 1A1 in the liver[Label,A176038]. Other minor pathways metabolise dexmethylphenidate to the inactive metabolites 6-oxo-methylphenidate and p-hydroxy-methylphenidate which are de-esterified and conjugated into other unknown metabolites[A177187].
ROE
Dexmethylphenidate is mainly eliminated renally[A177187]. After 48 hours, 90% of the dose is collected in the urine and 3.3% is collected from feces[A177187].
INDICATION
Dexmethylphenidate is used as a treatment for ADHD, ideally in conjunction with psychological, educational, behavioral or other forms of treatment[A177187,Label].
HALF-LIFE
The mean terminal half life is approximately 2.2 hours[Label]. However other studies have shown 3.8-3.9 hours[A177184], or 5.96 hours after intravenous administration and 5.69 hours following an oral dose[A177187].
MOA
Methylphenidate inhibits dopamine and norepinephrine reuptake transporters in synapses, especially in the thalamus and striatum[A177193]. One study shows no detectable difference in the caudal prefrontal cortex of treated or untreated monkeys, though multiple rat studies show activity on the prefrontal cortex[A177193]. Imaging of human brains after administration of methylphenidate shows changes to blood flow of various regions of the brain including the striatum, supplementary motor area, and posterior parietal cortex[A177193].
PHARMACODYNAMICS
Dexmethylphenidate is the d-enantiomer of methylphenidate[Label]. This enantiomer is more pharmacologically active than the racemic mixture and may block norepinephrine and dopamine reuptake in synapses[Label].
ABSORPTION
Taking dexmethylphenidate with or without food does not affect patients in a clinically relevant way[A177187]. 90% of an oral dose is absorbed[Label] but as a result of hepatic first pass metabolism, oral bioavailability of dexmethylphenidate is 23% compared to l-methylphenidate with an oral bioavailability of 5% [A177187]. Maximum concentration is generally reached in 1-1.5 hours[Label].
[[ p.pathway_name ]]
[[ compound.targets[tid].gene_name ]]
Cell lines
0
Organisms
1
Compound Sets
18
Concise Guide to Pharmacology 2017/18
Concise Guide to Pharmacology 2019/20
Concise Guide to Pharmacology 2021/22
Concise Guide to Pharmacology 2023/24
DrugBank
DrugBank Approved Drugs
DrugCentral
DrugCentral Approved Drugs
DrugMAP
DrugMAP Approved Drugs
Guide to Pharmacology
LSP-MoA library (Laboratory of Systems Pharmacology)
NCATS Inxight Approved Drugs
Novartis Chemogenetic Library (NIBR MoA Box)
NPC Screening Collection
[[ a.name ]]
[[ ligand_id ]]
free of charge
External IDs
58
Molecular Weight
233.14
Hydrogen Bond Acceptors
3
Hydrogen Bond Donors
1
Rotatable Bonds
3
Ring Count
2
Aromatic Ring Count
1
cLogP
2.09
TPSA
38.33
Fraction CSP3
0.5
Chiral centers
2.0
Largest ring
6.0
QED
0.81
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Member status
virtual
MOA
Dopamine Transporter (DAT) Inhibitors
Dopamine Reuptake Inhibitors
Source data
