Tasimelteon

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Tasimelteon
Systematic (IUPAC) name
(1R, 2R)-N-[2-(2,3-dihydrobenzofuran-4-yl)cyclopropylmethyl]propanamide
Clinical data
Trade names Hetlioz
Pregnancy cat. C (US)
Legal status ℞-only (US)
Routes Oral
Pharmacokinetic data
Bioavailability not determined in humans[1]
Protein binding 89–90%
Metabolism extensive hepatic, primarily CYP1A2 and CYP3A4-mediated
Half-life 0.9–1.7 h / 0.8–5.9 h (terminal)
Excretion 80% in urine, 4% in feces
Identifiers
CAS number 609799-22-6 YesY
ATC code None
PubChem CID 10220503
UNII SHS4PU80D9 YesY
Chemical data
Formula C15H19NO2 
Mol. mass 245.32 g/mol
 YesY (what is this?)  (verify)

Tasimelteon (trade name Hetlioz, previously known as BMS-214,778) is a drug approved solely for the treatment of non-24-hour sleep–wake disorder in totally blind people.[2] It was under development for the treatment of insomnia and other sleep disorders.[3] It is a selective agonist for the melatonin receptors MT1 and MT2 in the suprachiasmatic nucleus of the brain, similar to older drugs such as ramelteon.[4] It has been through Phase III trials successfully and was shown to improve both onset and maintenance of sleep, with few side effects.[5]

A year-long (2011–2012) study at Harvard is testing the use of tasimelteon in blind subjects with non-24-hour sleep–wake disorder.[6] In May 2013 Vanda Pharmaceuticals submitted a New Drug Application to the Food and Drug Administration for tasimelteon for the treatment of non-24-hour sleep–wake disorder in totally blind people.[7] It was approved by the FDA on January 31, 2014 under the brand name Hetlioz.[2]

See also

  • Discovery and development of melatonin receptor agonists

References

  1. ↑ “Tasimelteon Advisory Committee Meeting Briefing Materials”, Vanda Pharmaceuticals Inc., November 2013.
  2. ↑ 2.0 2.1 Food and Drug Administration (January 31, 2014). "FDA NEWS RELEASE: FDA approves Hetlioz: first treatment for non-24 hour sleep-wake disorder in blind individuals". 
  3. ↑ 'Time-bending drug' for jet lag. BBC News. 2 December 2008
  4. ↑ Vachharajani, Nimish N., Yeleswaram, Krishnaswamy, Boulton, David W. (April 2003). "Preclinical pharmacokinetics and metabolism of BMS-214778, a novel melatonin receptor agonist". Journal of Pharmaceutical Sciences 92 (4): 760–72. doi:10.1002/jps.10348. PMID 12661062. 
  5. ↑ Shantha MW Rajaratnam, Mihael H Polymeropoulos, Dennis M Fisher, Thomas Roth, Christin Scott, Gunther Birznieks, Elizabeth B Klerman (2009-02-07). "Melatonin agonist tasimelteon (VEC-162) for transient insomnia after sleep-time shift: two randomised controlled multicentre trials". The Lancet 373 (9662): 482–491. doi:10.1016/S0140-6736(08)61812-7. PMID 19054552. Retrieved 2010-02-23. 
  6. ↑ Audio interview with Joseph Hull of Harvard, spring 2011
  7. ↑ Vanda Pharmaceuticals seeks FDA approval

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