Dexmethylphenidate
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Also known as DexmetilfenidatoMethylphenidate d-threo-form(RR)-Methylphenidate(+/-)-threo-methylphenidate(+/-)-Mmethylphenidate
Summary
Dexmethylphenidate (CHEMBL827) is an approved small-molecule adrenergic agent (ATC N06BA11) targeting SLC6A2 and SLC6A3; indicated across 1 condition including attention deficit-hyperactivity disorder.
At a glance
- Status: Approved (max clinical phase 4)
- Modality: Small molecule
- ATC class: N06BA11
- Targets: 2 (SLC6A2, SLC6A3)
- Indications: 1 condition
- Clinical trials: 6
- Chemistry: 233.31 Da · C14H19NO2
Identifiers
Drug identity and classification
| Field | Value |
|---|---|
| ChEMBL ID | CHEMBL827 |
| Name | Dexmethylphenidate |
| Type | Small molecule |
| Max phase | 4 |
| FDA approved | yes |
| PubChem CID | 154101 |
| ChEBI | CHEBI:51860 |
| ATC | N06BA11 |
| Molecular formula | C14H19NO2 |
| Molecular weight | 233.31 |
| InChIKey | DUGOZIWVEXMGBE-CHWSQXEVSA-N |
SMILES: COC(=O)[C@@H]([C@H]1CCCCN1)C2=CC=CC=C2
IUPAC name: methyl (2R)-2-phenyl-2-[(2R)-piperidin-2-yl]acetate
ChEBI definition: A methyl phenyl(piperidin-2-yl)acetate in which both stereocentres have R configuration. It is the active enantiomer in the racemic drug methylphenidate.
Pharmacological roles (ChEBI): adrenergic agent.
Also known as: Dexmethylphenidate, Dexmetilfenidato, Methylphenidate d-threo-form, (RR)-Methylphenidate, (+/-)-threo-methylphenidate, DEXMETHYLPHENIDATE, (+/-)-Mmethylphenidate
Parent form; salt/anhydrous children: CHEMBL904
Patent coverage: 1,291 distinct patent families (4,631 SureChEMBL compound mentions), from 1 matched compound structure(s). Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.
Targets
Targets
Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).
| Gene | Target | Action | pAffinity | Cancer dependency | UniProt |
|---|---|---|---|---|---|
| SLC6A2 | NET | Inhibition | 6.57 | 0.4% | P23975 |
| SLC6A3 | DAT | Inhibition | 7.6 | 0.2% | Q01959 |
Broader ChEMBL bioactivity targets: 2 (assay-derived). Sample: Sodium-dependent dopamine transporter, Sodium-dependent dopamine transporter.
Bioactivity
ChEMBL activities: 9 potent at pChembl ≥ 5 of 9 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):
| Target | pChembl | Type | Value | Unit | Activity ID |
|---|---|---|---|---|---|
| SLC6A3 | 7.8 | Ki | 16 | nM | CHEMBL_ACT_10978278 |
| P23977 | 7.62 | IC50 | 24 | nM | CHEMBL_ACT_275629 |
| SLC6A3 | 7.6 | Ki | 25 | nM | CHEMBL_ACT_5130964 |
| P23977 | 7.08 | IC50 | 83 | nM | CHEMBL_ACT_194099 |
| P23977 | 7.08 | IC50 | 83 | nM | CHEMBL_ACT_275626 |
| P23977 | 7.08 | IC50 | 83 | nM | CHEMBL_ACT_3465583 |
| P23977 | 7.08 | IC50 | 83.18 | nM | CHEMBL_ACT_3467102 |
| SLC6A3 | 7.06 | IC50 | 88 | nM | CHEMBL_ACT_1151641 |
| SLC6A3 | 6.81 | IC50 | 156 | nM | CHEMBL_ACT_5130963 |
Target pathways
Aggregated over 2 target gene(s): SLC6A2, SLC6A3.
Top Reactome pathways
14 total, by targets touching each:
| Pathway | Targets | Genes |
|---|---|---|
| Disease | 2 | SLC6A2, SLC6A3 |
| Transport of small molecules | 2 | SLC6A2, SLC6A3 |
| R-HSA-425366 | 2 | SLC6A2, SLC6A3 |
| SLC-mediated transmembrane transport | 2 | SLC6A2, SLC6A3 |
| SLC-mediated transport of neurotransmitters | 2 | SLC6A2, SLC6A3 |
| SLC transporter disorders | 2 | SLC6A2, SLC6A3 |
| Disorders of transmembrane transporters | 2 | SLC6A2, SLC6A3 |
| Neurotransmitter clearance | 1 | SLC6A3 |
| Transmission across Chemical Synapses | 1 | SLC6A3 |
| Neuronal System | 1 | SLC6A3 |
| Dopamine clearance from the synaptic cleft | 1 | SLC6A3 |
| Defective neurotransmitter clearance by SLC6A3 causes Parkinsonism-dystonia infantile (PKDYS) | 1 | SLC6A3 |
| Defective SLC6A2 causes orthostatic intolerance (OI) | 1 | SLC6A2 |
| Defective transport of neurotransmitters by SLC6A3 causes Parkinsonism-dystonia infantile (PKDYS) | 1 | SLC6A3 |
Dominant GO biological processes
| GO term | Targets |
|---|---|
| neurotransmitter transport | 2 |
| amino acid transport | 2 |
| response to xenobiotic stimulus | 2 |
| obsolete monoamine transport | 2 |
| sodium ion transmembrane transport | 2 |
| dopamine uptake involved in synaptic transmission | 2 |
| norepinephrine uptake | 2 |
| transmembrane transport | 2 |
| chemical synaptic transmission | 1 |
| obsolete norepinephrine transport | 1 |
| response to pain | 1 |
| neuron cellular homeostasis | 1 |
| catecholamine uptake | 1 |
| neurotransmitter reuptake | 1 |
| chloride transmembrane transport | 1 |
Indications & clinical
Indications
1 indication (1 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).
| Indication | Trial phase | MONDO | EFO |
|---|---|---|---|
| attention deficit-hyperactivity disorder | 4 | MONDO:0007743 | EFO:0003888 |
Clinical trials
Total trials: 6.
Phase distribution
| Phase | Trials |
|---|---|
| PHASE3 | 2 |
| PHASE1 | 2 |
| PHASE4 | 1 |
| Not specified | 1 |
Top trials by phase / activity
| NCT | Phase | Status | Title |
|---|---|---|---|
| NCT06000501 | PHASE4 | COMPLETED | Duration and Efficacy of Azstarys on Adult ADHD Symptoms and Executive Function in Early Evening |
| NCT00301236 | PHASE3 | COMPLETED | Efficacy, Tolerability and Safety of Dexmethylphenidate HCl Extended-Release Capsules in Children With Attention-Deficit/Hyperactivity Disorder |
| NCT00393042 | PHASE3 | COMPLETED | Sleep and Tolerability Study: Comparing the Effects of Adderall XR and Focalin XR |
| NCT04449250 | PHASE1 | COMPLETED | Fed-Fast Crossover Study to Assess the Effect of Food With CTx-1301 in Healthy Subjects |
| NCT07119073 | PHASE1 | COMPLETED | In-clinic Crossover Study in Subjects With Two Treatments (Fed vs Fasted) |
| NCT04577417 | Not specified | COMPLETED | Stimulant Medication Effects on Auditory Sensitivity in Teens With ADHD |
Clinical evidence (CIViC)
No CIViC predictive evidence (expected for non-precision-medicine drugs).
Pharmacology
Pharmacogenomics
No CPIC/DPWG dosing guideline or drug-level clinical/variant annotations in PharmGKB for this molecule.
Related molecules
Related molecules
Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.
585 molecules share ≥1 primary target. Top 60 by shared-target count:
| Molecule | Source | Status | Shared targets |
|---|---|---|---|
| Afatinib | ChEMBL + PubChem | Phase 4 (approved) | SLC6A2, SLC6A3 |
| AMITRIPTYLINE | ChEMBL + PubChem | Phase 4 (approved) | SLC6A2, SLC6A3 |
| CRIZOTINIB | ChEMBL + PubChem | Phase 4 (approved) | SLC6A2, SLC6A3 |
| DACOMITINIB | ChEMBL + PubChem | Phase 4 (approved) | SLC6A2, SLC6A3 |
| GENTIAN VIOLET | ChEMBL + PubChem | Phase 4 (approved) | SLC6A2, SLC6A3 |
| Idelalisib | ChEMBL + PubChem | Phase 4 (approved) | SLC6A2, SLC6A3 |
| Olodaterol | ChEMBL + PubChem | Phase 4 (approved) | SLC6A2, SLC6A3 |
| PIMAVANSERIN | ChEMBL + PubChem | Phase 4 (approved) | SLC6A2, SLC6A3 |
| REGORAFENIB | ChEMBL + PubChem | Phase 4 (approved) | SLC6A2, SLC6A3 |
| TAFENOQUINE | ChEMBL + PubChem | Phase 4 (approved) | SLC6A2, SLC6A3 |
| UMECLIDINIUM | ChEMBL + PubChem | Phase 4 (approved) | SLC6A2, SLC6A3 |
| VORAPAXAR | ChEMBL + PubChem | Phase 4 (approved) | SLC6A2, SLC6A3 |
| ACETOPHENAZINE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3 |
| AMINOCAPROIC ACID | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3 |
| AMIODARONE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3 |
| AMLODIPINE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3 |
| AMODIAQUINE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3 |
| AMOXAPINE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3 |
| ARIPIPRAZOLE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3 |
| ASENAPINE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3 |
| ASTEMIZOLE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3 |
| ATOMOXETINE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3 |
| AZELASTINE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3 |
| BAZEDOXIFENE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3 |
| BENFLUOREX | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3 |
| BENOXINATE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3 |
| BENPERIDOL | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3 |
| BENZIODARONE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3 |
| BENZPHETAMINE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3 |
| BENZTROPINE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3 |
| BENZYDAMINE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3 |
| BENZYL BENZOATE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3 |
| BEPRIDIL | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3 |
| BEXAROTENE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3 |
| BITHIONOL | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3 |
| BOSUTINIB | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3 |
| BREXPIPRAZOLE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3 |
| BROMHEXINE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3 |
| BROMODIPHENHYDRAMINE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3 |
| BROMPERIDOL | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3 |
| BROMPHENIRAMINE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3 |
| BUPROPION | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3 |
| CABERGOLINE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3 |
| CALCITRIOL | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3 |
| CANDESARTAN CILEXETIL | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3 |
| CANNABIDIOL | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3 |
| CARBINOXAMINE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3 |
| CARVEDILOL | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3 |
| CASPOFUNGIN | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3 |
| CELECOXIB | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3 |
| CETIRIZINE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3 |
| CHLORHEXIDINE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3 |
| CHLORPHENIRAMINE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3 |
| CHLORPHENTERMINE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3 |
| CHLORPROMAZINE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3 |
| CHLORPROTHIXENE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3 |
| CINACALCET | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3 |
| CINNARIZINE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3 |
| CITALOPRAM | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3 |
| CLEMASTINE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3 |
Related Atlas pages
- Genes: SLC6A2, SLC6A3
- Diseases: attention deficit-hyperactivity disorder
- Drugs: Afatinib, Amitriptyline, Crizotinib, Dacomitinib, Idelalisib, Olodaterol, Pimavanserin, Regorafenib, Tafenoquine, Umeclidinium, Vorapaxar, Acetophenazine, Aminocaproic Acid, Amiodarone, Amlodipine, Amodiaquine, Amoxapine, Aripiprazole, Asenapine, Astemizole, Atomoxetine, Azelastine, Bazedoxifene, Benfluorex, Benoxinate, Benperidol, Benziodarone, Benzphetamine, Benztropine, Benzydamine, Benzyl Benzoate, Bepridil, Bexarotene, Bithionol, Bosutinib, Brexpiprazole, Bromhexine, Bromodiphenhydramine, Bromperidol, Brompheniramine, Bupropion, Cabergoline, Calcitriol, Candesartan Cilexetil, Cannabidiol, Carbinoxamine, Carvedilol, Caspofungin, Celecoxib, Cetirizine, Chlorhexidine, Chlorpheniramine, Chlorphentermine, Chlorpromazine, Chlorprothixene, Cinacalcet, Cinnarizine, Citalopram, Clemastine