Tasimelteon
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Also known as BMS-214,778BMS-214778HetliozHetlioz lqVEC-162
Summary
Tasimelteon (CHEMBL2103822) is an approved small-molecule melatonin receptor agonist (ATC N05CH03) targeting MTNR1A and MTNR1B; indicated across 9 conditions including sleep-wake disorder and circadian rhythm sleep disorder.
At a glance
- Status: Approved (max clinical phase 4)
- Modality: Small molecule
- ATC class: N05CH03
- Targets: 2 (MTNR1A, MTNR1B)
- Indications: 9 conditions
- Clinical trials: 25
- Chemistry: 245.32 Da · C15H19NO2
Identifiers
Drug identity and classification
| Field | Value |
|---|---|
| ChEMBL ID | CHEMBL2103822 |
| Name | Tasimelteon |
| Type | Small molecule |
| Max phase | 4 |
| FDA approved | yes |
| PubChem CID | 10220503 |
| ChEBI | CHEBI:79042 |
| ATC | N05CH03 |
| Molecular formula | C15H19NO2 |
| Molecular weight | 245.32 |
| InChIKey | PTOIAAWZLUQTIO-GXFFZTMASA-N |
SMILES: CCC(=O)NC[C@@H]1C[C@H]1C2=C3CCOC3=CC=C2
IUPAC name: N-[[(1R,2R)-2-(2,3-dihydro-1-benzofuran-4-yl)cyclopropyl]methyl]propanamide
ChEBI definition: A member of the class of 1-benzofurans that is propionamide in which one of the amide hydrogens is replaced by a [(1R,2R)-2-(2,3-dihydro-1-benzofuran-4-yl)cyclopropyl]methyl group. A melatonin receptor agonist used for the treatment of non-24-hour sleep-wake disorder.
Pharmacological roles (ChEBI): melatonin receptor agonist.
Also known as: BMS-214,778, BMS-214778, Hetlioz, Hetlioz lq, Tasimelteon, VEC-162, TASIMELTEON
Patent coverage: 185 distinct patent families (516 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 375 (73%) of the total. 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 |
|---|---|---|---|---|---|
| MTNR1A | MT1 receptor | Full agonist | 9.5 | 0% | P48039 |
| MTNR1B | MT2 receptor | Full agonist | 10.2 | 0.2% | P49286 |
Broader ChEMBL bioactivity targets: 1 (assay-derived). Sample: Melatonin receptor type 1B.
Bioactivity
ChEMBL activities: 1 potent at pChembl ≥ 5 of 1 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):
| Target | pChembl | Type | Value | Unit | Activity ID |
|---|---|---|---|---|---|
| MTNR1B | 10.15 | Ki | 0.07 | nM | CHEMBL_ACT_25521263 |
Target pathways
Aggregated over 2 target gene(s): MTNR1A, MTNR1B.
Top Reactome pathways
6 total, by targets touching each:
| Pathway | Targets | Genes |
|---|---|---|
| Signal Transduction | 2 | MTNR1A, MTNR1B |
| Signaling by GPCR | 2 | MTNR1A, MTNR1B |
| Class A/1 (Rhodopsin-like receptors) | 2 | MTNR1A, MTNR1B |
| GPCR downstream signalling | 2 | MTNR1A, MTNR1B |
| G alpha (i) signalling events | 2 | MTNR1A, MTNR1B |
| GPCR ligand binding | 2 | MTNR1A, MTNR1B |
Dominant GO biological processes
| GO term | Targets |
|---|---|
| G protein-coupled receptor signaling pathway | 2 |
| G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messenger | 2 |
| signal transduction | 2 |
| adenylate cyclase-inhibiting G protein-coupled receptor signaling pathway | 1 |
| mating behavior | 1 |
| circadian rhythm | 1 |
| chemical synaptic transmission | 1 |
| negative regulation of receptor guanylyl cyclase signaling pathway | 1 |
| glucose homeostasis | 1 |
| camera-type eye development | 1 |
| negative regulation of neuron apoptotic process | 1 |
| negative regulation of vasoconstriction | 1 |
| positive regulation of circadian sleep/wake cycle, non-REM sleep | 1 |
| negative regulation of insulin secretion | 1 |
| regulation of insulin secretion | 1 |
Indications & clinical
Indications
9 indications (4 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 |
|---|---|---|---|
| sleep-wake disorder | 4 | MONDO:0003406 | MONDO:0003406 |
| circadian rhythm sleep disorder | 4 | MONDO:0024361 | MONDO:0024361 |
| Smith-Magenis syndrome | 4 | MONDO:0008434 | Orphanet:68335 |
| insomnia | 3 | MONDO:0013600 | EFO:0004698 |
| major depressive disorder | 2 | MONDO:0002009 | MONDO:0002009 |
| liver disorder | 1 | MONDO:0005154 | EFO:0001421 |
| kidney disorder | 1 | MONDO:0005240 | EFO:0003086 |
| REM sleep behavior disorder | 0 | MONDO:0005937 | EFO:0007462 |
1 further indication record had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.
Clinical trials
Total trials: 25.
Phase distribution
| Phase | Trials |
|---|---|
| PHASE3 | 10 |
| PHASE1 | 10 |
| PHASE2/PHASE3 | 2 |
| PHASE2 | 2 |
| EARLY_PHASE1 | 1 |
Top trials by phase / activity
| NCT | Phase | Status | Title |
|---|---|---|---|
| NCT04652882 | PHASE3 | RECRUITING | Evaluating the Effects of Tasimelteon vs. Placebo in Delayed Sleep-Wake Phase Disorder (DSWPD) |
| NCT06701396 | PHASE3 | RECRUITING | Evaluating the Effects of Tasimelteon Vs. Placebo in Delayed Sleep-Wake Phase Disorder (DSWPD) and the CRY1Δ11 Variant |
| NCT06953869 | PHASE3 | RECRUITING | Evaluating the Effects of Tasimelteon vs. Placebo in Treating Pediatric Insomnia |
| NCT00291187 | PHASE3 | COMPLETED | VEC-162 Study in Healthy Adult Volunteers in a Model of Insomnia |
| NCT00548340 | PHASE3 | COMPLETED | VEC-162 Study in Adult Patients With Primary Insomnia |
| NCT01163032 | PHASE3 | COMPLETED | Efficacy and Safety of Tasimelteon Compared With Placebo in Totally Blind Subjects With Non-24-Hour Sleep-Wake Disorder |
| NCT01218789 | PHASE3 | UNKNOWN | Safety Study of Tasimelteon for Treatment of Non-24-Hour-Sleep-Wake Disorder in Blind Individuals With No Light Perception |
| NCT01428661 | PHASE2/PHASE3 | COMPLETED | Melatonin Agonist Effects of Tasimelteon Versus Placebo in Patients With Major Depressive Disorder |
| NCT01429116 | PHASE3 | COMPLETED | Tasimelteon for the Treatment of Non-24-hour Sleep-Wake Disorder (N24HSWD) in Blind Individuals With no Light Perception |
| NCT01430754 | PHASE3 | COMPLETED | Withdrawal Study to Demonstrate the Maintenance Effect in the Treatment of Non-24-Hour Sleep-Wake Disorder |
| NCT02231008 | PHASE2/PHASE3 | COMPLETED | Evaluating the Effects of Tasimelteon vs Placebo on Sleep Disturbances in SMS |
| NCT03373201 | PHASE3 | COMPLETED | Evaluating the Effects of Tasimelteon vs. Placebo on Jet Lag Type Insomnia |
| NCT00490945 | PHASE2 | COMPLETED | Safety and Efficacy of VEC-162 on Circadian Rhythm in Healthy Adult Volunteers |
| NCT03291041 | PHASE2 | COMPLETED | A Proof of Concept Study to Evaluate the Effects of Tasimelteon and Placebo in Travelers With Jet Lag Disorder |
| NCT01271387 | PHASE1 | COMPLETED | Pharmacokinetics of Tasimelteon in Subjects With Mild or Moderate Hepatic Impairment |
| NCT01402076 | PHASE1 | COMPLETED | A Study to Assess the Effect Tasimelteon on the Cytochrome P450 3A4 and 2C8 Enzymes in Healthy Subjects |
| NCT01477619 | PHASE1 | COMPLETED | Effects of Smoking, Age and Body Size on Pharmacokinetics, Safety and Tolerability on Tasimelteon in Healthy Subjects |
| NCT01526746 | PHASE1 | COMPLETED | Pharmacokinetics of Tasimelteon in Subjects With Renal Impairment and Matched Control Subjects With Relatively Normal Renal Function |
| NCT01540500 | PHASE1 | COMPLETED | Pharmacokinetics of Tasimelteon Alone and in Combination With CYP1A2 Inhibitor, Fluvoxamine |
| NCT01578057 | PHASE1 | COMPLETED | Evaluation of the Pharmacodynamic and Pharmacokinetic Interactions of Tasimelteon and Ethanol |
| NCT01637636 | PHASE1 | COMPLETED | Pharmacokinetics of Tasimelteon Alone and in Combination With a CYP3A4 Inhibitor, Ketoconazole, or a CYP3A4 Inducer, Rifampin. |
| NCT02776215 | PHASE1 | COMPLETED | Study of the Pharmacokinetics and Safety of Tasimelteon in Children and Adolescents |
| NCT05572281 | PHASE1 | COMPLETED | Bioequivalence Study Between Tasimelteon Capsule Formulation and Liquid Suspension Formulation in Healthy Volunteers |
| NCT06323655 | PHASE1 | COMPLETED | Evaluation of Next-Day Residual Effects of Tasimelteon Compared With Placebo and Active Control in Healthy Subjects |
| NCT05922995 | EARLY_PHASE1 | TERMINATED | The Effects of Tasimelteon in Participants With REM Behavior Disorder (RBD) |
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.
6 molecules share ≥1 primary target. Top 6 by shared-target count:
| Molecule | Source | Status | Shared targets |
|---|---|---|---|
| AGOMELATINE | ChEMBL | Phase 4 (approved) | MTNR1A, MTNR1B |
| CIANIDANOL | ChEMBL | Phase 4 (approved) | MTNR1A, MTNR1B |
| DOPAMINE | ChEMBL | Phase 4 (approved) | MTNR1A, MTNR1B |
| MELATONIN | ChEMBL | Phase 4 (approved) | MTNR1A, MTNR1B |
| RAMELTEON | ChEMBL | Phase 4 (approved) | MTNR1A, MTNR1B |
| MEBUFOTENIN | ChEMBL | Phase 2 | MTNR1A, MTNR1B |
Related Atlas pages
- Genes: MTNR1A, MTNR1B
- Diseases: sleep-wake disorder, circadian rhythm sleep disorder, Smith-Magenis syndrome, insomnia
- Drugs: Agomelatine, Cianidanol, Dopamine, Melatonin, Ramelteon