SERDEXMETHYLPHENIDATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C25H29N3O8
Molecular Weight	499.5131
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC(=O)[C@@H]([C@H]1CCCCN1C(=O)OC[N+]2=CC(=CC=C2)C(=O)N[C@@H](CO)C([O-])=O)C3=CC=CC=C3

InChI

InChIKey=UBZPNQRBUOBBLN-PWRODBHTSA-N

InChI=1S/C25H29N3O8/c1-35-24(33)21(17-8-3-2-4-9-17)20-11-5-6-13-28(20)25(34)36-16-27-12-7-10-18(14-27)22(30)26-19(15-29)23(31)32/h2-4,7-10,12,14,19-21,29H,5-6,11,13,15-16H2,1H3,(H-,26,30,31,32)/t19-,20+,21+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C25H29N3O8
Molecular Weight	499.5131
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/021278s008,021802s009lbl.pdf | https://www.drugbank.ca/drugs/DB06701

Dexmethylphenidate is the dextrorotary form of methylphenidate. Dexmethylphenidate is marketed under the trade name Focalin. Focalin (dexmethylphenidate hydrochloride) is the d-threo-enantiomer of racemic methylphenidate hydrochloride, which is a 50/50 mixture of the d-threo and l-threoenantiomers. Focalin is a central nervous system (CNS) stimulant, available in three tablet strengths. Each tablet contains dexmethylphenidate hydrochloride 2.5, 5, or 10 mg for oral administration. Dexmethylphenidate is used as a treatment for ADHD, ideally in conjunction with psychological, educational, behavioral or other forms of treatment. Methylphenidate blocks dopamine uptake in central adrenergic neurons by blocking dopamine transport or carrier proteins. Methylphenidate acts at the brain stem arousal system and the cerebral cortex and causes increased sympathomimetic activity in the central nervous system. Methylphenidate is a catecholamine reuptake inhibitor that indirectly increases catecholaminergic neurotransmission by inhibiting the dopamine transporter (DAT) and norepinephrine transporter (NET), which are responsible for clearing catecholamines from the synapse, particularly in the striatum and meso-limbic system.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Dopamine transporter 183 Target ID: CHEMBL238 Sources: https://www.drugbank.ca/drugs/DB06701 \| https://www.ncbi.nlm.nih.gov/pubmed/17218796 \| https://www.ncbi.nlm.nih.gov/pubmed/21129986	Inhibitor 8504		161.0 nM [Ki]
Norepinephrine transporter 197 Target ID: CHEMBL222 Sources: https://www.drugbank.ca/drugs/DB06701 \| https://www.ncbi.nlm.nih.gov/pubmed/17218796 \| https://www.ncbi.nlm.nih.gov/pubmed/17489581	Inhibitor 8504		206.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Attention deficit hyperactivity disorder 70 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/021278s008,021802s009lbl.pdf	Primary		Approved 8583	FOCALIN Approved Use Focalin XR is indicated for the treatment of Attention Deficit Hyperactivity Disorder (ADHD) in patients aged 6 years and older. The effectiveness of Focalin XR in the treatment of ADHD in patients aged 6 years and older was established in two placebo-controlled studies in patients meeting DSM-IV criteria for ADHD. Launch Date 2001

C_max

Value	Dose	Analyte	Population
22.13 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/14747426	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:	DEXMETHYLPHENIDATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
23.72 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/14747426	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:	DEXMETHYLPHENIDATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
10.7 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28590363	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:	DEXMETHYLPHENIDATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED

AUC

Value	Dose	Analyte	Population
131.9 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/14747426	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:	DEXMETHYLPHENIDATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
120.9 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/14747426	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:	DEXMETHYLPHENIDATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
79.8 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28590363	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:	DEXMETHYLPHENIDATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED

T_1/2

Value	Dose	Analyte	Population
2.81 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/14747426	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:	DEXMETHYLPHENIDATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
2.68 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/14747426	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:	DEXMETHYLPHENIDATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
3.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28590363	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:	DEXMETHYLPHENIDATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED

Doses

Dose	Population	Adverse events
40 mg single, oral Overdose Dose: 40 mg Route: oral Route: single Dose: 40 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/021802s033lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/021802s033lbl.pdf	Other AEs: Vomiting, Agitation... Other AEs: Vomiting Agitation Tremor Hyperreflexia Muscle twitching Convulsions Euphoria Confusion Hallucinations Delirium Sweating Flushing Headache Hyperpyrexia Tachycardia Palpitations Cardiac arrhythmias Hypertension Mydriasis Mucosal dryness Rhabdomyolysis Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/021802s033lbl.pdf
30 mg 1 times / day multiple, oral Recommended Dose: 30 mg, 1 times / day Route: oral Route: multiple Dose: 30 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/021802s033lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/021802s033lbl.pdf	Disc. AE: Twitching, Anorexia... AEs leading to discontinuation/dose reduction: Twitching (1%) Anorexia (1%) Insomnia (1%) Tachycardia (1%) Insomnia (1.8%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/021802s033lbl.pdf
40 mg 1 times / day multiple, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/021802s033lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/021802s033lbl.pdf	Disc. AE: Cardiac disorders, Stroke... Other AEs: Increased blood pressure, Heart rate increased... AEs leading to discontinuation/dose reduction: Cardiac disorders (grade 3-5) Stroke (grade 3-5) Myocardial infarction (grade 3-5) Seizures Raynaud's phenomenon Other AEs: Increased blood pressure Heart rate increased Psychotic symptom (grade 3-5) Psychotic symptom Manic symptom Aggression Growth suppression Priapism Erection prolonged Vascular disorders Visual disturbance Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/021802s033lbl.pdf
40 mg 1 times / day multiple, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/021802s033lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/021802s033lbl.pdf	Disc. AE: Feeling jittery, Anorexia... AEs leading to discontinuation/dose reduction: Feeling jittery (1.8%) Anorexia (1.2%) Anxiety (1.2%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/021802s033lbl.pdf

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
	inhibitor 2438	inhibitor 2507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP2C8 1057 CYP2C19 2057 CYP2E1 1060 CYP3A 227	esterase 74 CES2 33 P-gp 2052

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
CYP1A2 2333	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021278s026lbl.pdf#page=11 Page: 11.0	no
CYP2C19 2141	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021278s026lbl.pdf#page=11 Page: 11.0	no
CYP2C8 1117	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021278s026lbl.pdf#page=11 Page: 11.0	no
CYP2C9 2497	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021278s026lbl.pdf#page=11 Page: 11.0	no
CYP2E1 1146	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021278s026lbl.pdf#page=11 Page: 11.0	no
CYP3A 317	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021278s026lbl.pdf#page=11 Page: 11.0	no
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021278s026lbl.pdf#page=11 Page: 11.0	no	no (co-administration study) Comment: Clinically, methylphenidate coadministration did not increase plasma concentrations of the CYP2D6 substrate desipramine. Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021278s026lbl.pdf#page=11 Page: 11.0

Drug as victim

Target	Modality	Activity
CES2 33	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15082749/ Page: -	no
P-gp 2052	substrate 4014 Sources: https://www.pharmgkb.org/pmid/16621932 Page: -	weak
esterase 74	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/12215063/ Page: -	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:51860	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:51860
ZINC	ZINC000000896711	http://zinc15.docking.org/substances/ZINC000000896711

PubMed

Title	Date	PubMed
Azido-iodo-N-benzyl derivatives of threo-methylphenidate (Ritalin, Concerta): Rational design, synthesis, pharmacological evaluation, and dopamine transporter photoaffinity labeling.	2011-01-01	21129986
Use of psychostimulants in patients with dementia.	2010-10	20736422
European consensus statement on diagnosis and treatment of adult ADHD: The European Network Adult ADHD.	2010-09-03	20815868
Testing tic suppression: comparing the effects of dexmethylphenidate to no medication in children and adolescents with attention-deficit/hyperactivity disorder and Tourette's disorder.	2010-08	20807066
Real-World Data on: Attention Deficit Hyperactivity Disorder Medication Side Effects.	2010-04	20508803
Attention-deficit hyperactivity disorder: recent advances in paediatric pharmacotherapy.	2010	20030423
Dexmethylphenidate extended release: a review of its use in the treatment of attention-deficit hyperactivity disorder.	2009-12	19958043
Efficacy of dexmethylphenidate for the treatment of fatigue after cancer chemotherapy: a randomized clinical trial.	2009-11	19896571
Dexmethylphenidate for attention deficit hyperactivity disorder.	2009-11	19874250
Efficacy and safety of dexmethylphenidate extended-release capsules administered once daily to children with attention-deficit/hyperactivity disorder.	2009-08	19702487
Ixabepilone: a new treatment option for the management of taxane-resistant metastatic breast cancer.	2009-06-29	21188125
A retrospective claims analysis of combination therapy in the treatment of adult attention-deficit/hyperactivity disorder (ADHD).	2009-06-08	19505334
Pharmacotherapy for adult ADHD.	2009-05	19552859
Once-daily medications for the pharmacological management of ADHD in adults.	2009-04	19536322
Focalin XR for ADHD.	2009-03-23	19305368
Long-term effectiveness and safety of dexmethylphenidate extended-release capsules in adult ADHD.	2009-03	19218542
Management of attention-deficit hyperactivity disorder in adults: focus on methylphenidate hydrochloride.	2009	19721722
Psychopharmacology of ADHD in pediatrics: current advances and issues.	2009	19557112
Attention-deficit/hyperactivity disorder in adults: evidence-based recommendations for management.	2008-09	18824823
Does chirality matter? pharmacodynamics of enantiomers of methylphenidate in patients with attention-deficit/hyperactivity disorder.	2008-06	18480679
Evolution of the treatment of attention-deficit/hyperactivity disorder in children: a review.	2008-05	18555941
Treatment of adult ADHD: is current knowledge useful to clinicians?	2008-02	18728815
A randomized, double-blind, crossover study of once-daily dexmethylphenidate in children with attention-deficit hyperactivity disorder: rapid onset of effect.	2008	18601306
Similar bioavailability of dexmethylphenidate extended (bimodal) release, dexmethyl-phenidate immediate release and racemic methylphenidate extended (bimodal) release formulations in man.	2007-12	18184535
Impact of attention-deficit/hyperactivity disorder (ADHD) on prescription dug spending for children and adolescents: increasing relevance of health economic evidence.	2007-11-15	18005403
The nonmedical use of prescription ADHD medications: results from a national Internet panel.	2007-10-31	17974020
The complexity of ADHD: diagnosis and treatment of the adult patient with comorbidities.	2007-08	17667893
Efficacy and safety of dexmethylphenidate extended-release capsules in adults with attention-deficit/hyperactivity disorder.	2007-06-15	17137560
Synthesis and pharmacology of site-specific cocaine abuse treatment agents: restricted rotation analogues of methylphenidate.	2007-05-31	17489581
[Pharmacotherapy of adult Attention Deficit/Hyperactivity Disorder (ADHD): a systematic review].	2007	18167421
A comparative study on the cost of new antibiotics and drugs of other therapeutic categories.	2006-12-20	17183637
Dexmethylphenidate hydrochloride in the treatment of attention deficit hyperactivity disorder.	2006-12	19412495
Illicit use of specific prescription stimulants among college students: prevalence, motives, and routes of administration.	2006-10	16999660
Efficacy and safety of dexmethylphenidate extended-release capsules in children with attention-deficit/hyperactivity disorder.	2006-07	16832318
Misuse of "study drugs:" prevalence, consequences, and implications for policy.	2006-06-09	16764722
[Medical treatments of hyperactive child: about the new pharmaceutical forms of methylphenidate marketed in France].	2006-01	16239100
ADHD in adolescence and adulthood, with a special focus on the dopamine transporter and nicotine.	2006	16640111
Dexmethylphenidate extended release: in attention-deficit hyperactivity disorder.	2006	16620143
Dexmethylphenidate extended-release capsules for attention deficit hyperactivity disorder.	2005-07	16026226
Differential effects of amphetamine isomers on dopamine release in the rat striatum and nucleus accumbens core.	2005-03	15719230
Attention deficit/hyperactivity disorder: pharmacotherapy.	2005-01	21179640
A double-blind, placebo-controlled trial of dexmethylphenidate hydrochloride and d,l-threo-methylphenidate hydrochloride in children with attention-deficit/hyperactivity disorder.	2004-11	15502600
Efficacy of two once-daily methylphenidate formulations compared across dose levels at different times of the day: preliminary indications from a secondary analysis of the COMACS study data.	2004-09-30	15458569
A single-dose, two-way crossover, bioequivalence study of dexmethylphenidate HCl with and without food in healthy subjects.	2004-02	14747426
Open-label study of dexmethylphenidate hydrochloride in children and adolescents with attention deficit hyperactivity disorder.	2004	15662147
A double-blind, placebo-controlled withdrawal trial of dexmethylphenidate hydrochloride in children with attention deficit hyperactivity disorder.	2004	15662146
D-Methylphenidate is non-genotoxic in in vitro and in vivo assays.	2003-05-09	12742508
Neurobehavioral effects of racemic threo-methylphenidate and its D and L enantiomers in rats.	2003-02	12543241
The use of a laboratory school protocol to evaluate concepts about efficacy and side effects of new formulations of stimulant medications.	2002	12685522
Dexmethylphenidate--Novartis/Celgene. Focalin, D-MPH, D-methylphenidate hydrochloride, D-methylphenidate, dexmethylphenidate, dexmethylphenidate hydrochloride.	2002	12455205

Patents

Sample Use Guides

In Vivo Use Guide

Focalin (Dexmethylphenidate) is administered twice daily, at least 4 hours apart. Focalin may be administered with or without food. The recommended starting dose of Focalin for patients who are not currently taking racemic methylphenidate, or for patients who are on stimulants other than methylphenidate, is 5 mg/day (2.5 mg twice daily). Dosage may be adjusted in 2.5 to 5 mg increments to a maximum of 20 mg/day (10 mg twice daily). In general, dosage adjustments may proceed at approximately weekly intervals.

Route of Administration: Oral

In Vitro Use Guide

Dexmethylphenidate inhibition [3H]dopamine uptake at human DAT expressed in mouse N2A cells with IC50 156 nM.

Substance Class	Chemical Created by `admin` on `Tue Apr 01 21:08:42 GMT 2025` Edited by `admin` on `Tue Apr 01 21:08:42 GMT 2025`
Record UNII	0H8KZ470DW
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SERDEXMETHYLPHENIDATE

Official Name

English

PYRIDINIUM, 3-((((1S)-1-CARBOXY-2-HYDROXYETHYL)AMINO)CARBONYL)-1-(((((2R)-2-((1R)-2-METHOXY-2-OXO-1-PHENYLETHYL)-1-PIPERIDINYL)CARBONYL)OXY)METHYL)-

Preferred Name

English

KP-415 INNER SALT

Code

English

serdexmethylphenidate [INN]

Common Name

English

SERDEXMETHYLPHENIDATE [USAN]

Common Name

English

N-(1-((((2R)-2-((1R)-2-METHOXY-2-OXO-1-PHENYLETHYL)PIPERIDINE-1-CARBONYL)OXY)METHYL)PYRIDIN-1-IUM-3-CARBONYL)-L-SERINATE

Systematic Name

English

Serdexmethylphenidate [WHO-DD]

Common Name

English

Classification Tree Code System Code

DEA NO.

1729