Tasimelteon

Overview

Tasimelteon, sold under the brand name Hetlioz, is a medication approved by the U.S. Food and Drug Administration (FDA) in January 2014, for the treatment of non-24-hour sleep–wake disorder (also called non-24, N24 and N24HSWD). In June 2014, the European Medicines Agency (EMA) accepted an EU filing application for tasimelteon and in July 2015, the drug was approved in the European Union for the treatment of non-24-hour sleep-wake rhythm disorder in totally blind adults, but not in the case of non-24 in sighted people.[1–4] WP

The most common side effects include headache, somnolence, nausea (feeling sick) and dizziness.[5] WP

Uses, dosage and effects

Medical uses

In the United States, tasimelteon capsules are indicated for the treatment of non-24-hour sleep–wake disorder (Non-24) in adults and for the treatment of nighttime sleep disturbances in Smith-Magenis Syndrome (SMS) in people sixteen years of age and older. Tasimelteon oral suspension is indicated for the treatment of nighttime sleep disturbances in SMS in children from 3 to 15 years of age.[6] WP

In the European Union, tasimelteon capsules are indicated for the treatment of non-24-hour sleep–wake disorder (Non-24) in totally blind adults.[5] WP

The capsule and liquid suspension forms of tasimelteon are not interchangeable.[6] WP

Tasimelteon is a selective agonist for the melatonin receptors MT₁ and MT₂, similar to other members of the melatonin receptor agonist class of which ramelteon (2005), melatonin (2007), and agomelatine (2009) were the first approved. As a treatment for N24HSWD, as with melatonin or other melatonin derivatives, the patient may experience improved sleep timing while taking the drug. Reversion to baseline sleep performance occurs within a month of discontinuation.[7][8] WP

Risks and side effects

Toxicity

Experiments with rodents revealed fertility impairments, an increase in certain cancers, and serious adverse events during pregnancy at dosages in excess of what is considered the "human dose".[9][10] WP

Chemistry

Formula

C15H19NO2 PC

CAS number

609799-22-6 PC

Molar mass (g/mol)

245.32 PC

IUPAC name (computed by PubChem)

N-[[(1R,2R)-2-(2,3-dihydro-1-benzofuran-4-yl)cyclopropyl]methyl]propanamide PC

SMILES

CCC(=O)NC[C@@H]1C[C@H]1C2=C3CCOC3=CC=C2 PC

InChIKey

PTOIAAWZLUQTIO-GXFFZTMASA-N PC

PubChem CID

10220503

Harm reduction information

No harm reduction data is on file for this compound yet. That means no dose, timing or combination data from PsychonautWiki or TripSit. Please don't guess a dose from similar compounds. If you have taken it and feel unwell, contact emergency services or a poison control center.

User reports

Pop culture

No references added yet.

Sources

1. Journal / agency FDA transcript approval minutes. November 14, 2013
2. Journal / agency Food and Drug Administration. FDA approves Hetlioz: first treatment for non-24 hour sleep-wake disorder. January 31, 2014
3. Other tasimelteon (Hetlioz) UKMi New Drugs Online Database
4. Other Hetlioz Receives European Commission Approval for the Treatment of Non-24-Hour Sleep-Wake Disorder in the Totally Blind. 7 July 2015
5. Journal / agency Hetlioz EPAR. 6 July 2017
6. Journal / agency Hetlioz- tasimelteon capsule
7. Journal / agency Vachharajani NN, Yeleswaram K, Boulton DW. Preclinical pharmacokinetics and metabolism of BMS-214778, a novel melatonin receptor agonist. Journal of Pharmaceutical Sciences. April 2003. doi:10.1002/jps.10348 · PMID 12661062
8. Journal / agency Sack RL, Brandes RW, Kendall AR, Lewy AJ. Entrainment of free-running circadian rhythms by melatonin in blind people. The New England Journal of Medicine. October 2000. doi:10.1056/NEJM200010123431503 · PMID 11027741
9. Other Side Effects Drug Center: Hetlioz Clinical Pharmacology. February 10, 2014
10. Other Side Effects Drug Center: Hetlioz Warnings and Precautions. February 10, 2014

Text and values on this page are quoted from Wikipedia (CC BY-SA 4.0), PubChem (public domain). Each value links to the exact revision it came from.