Repinotan

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Repinotan
Repinotan.png
Systematic (IUPAC) name
(R)-(-)-2-[4-[(chroman-2-ylmethyl)-amino]-butyl]-1,1-dioxo-benzo[d]isothiazolone
Clinical data
Legal status Uncontrolled
Routes Oral
Identifiers
CAS number 144980-29-0 YesY
ATC code ?
PubChem CID 198757
UNII 05PB82Z52L N
ChEMBL CHEMBL1614652 N
Chemical data
Formula C21H24N2O4S 
Mol. mass 400.491 g/mol
 N (what is this?)  (verify)

Repinotan (BAYx3702) is a selective 5-HT1A receptor full agonist with high potency and efficacy.[1][2] It has neuroprotective effects in animal studies,[3][4][5] and was trialled in humans for reducing brain injury following head trauma.[6] It was subsequently trialled up to phase II for treatment of stroke, but while side effects were mild and consisted mainly of nausea, repinotan failed to demonstrate sufficient efficacy to justify further clinical trials.[7][8][9] However repinotan continues to be investigated for other applications, and was found to be effective at counteracting the respiratory depression produced by morphine, though with slight reduction in analgesic effects.[10]

See also[edit]

References[edit]

  1. ^ De Vry, J.; Schohe-Loop, R.; Heine, H. G.; Greuel, J. M.; Mauler, F.; Schmidt, B.; Sommermeyer, H.; Glaser, T. (1998). "Characterization of the aminomethylchroman derivative BAY x 3702 as a highly potent 5-hydroxytryptamine1A receptor agonist". The Journal of Pharmacology and Experimental Therapeutics 284 (3): 1082–1094. PMID 9495870.  edit
  2. ^ Dong, J.; De Montigny, C.; Blier, P. (1998). "Full agonistic properties of BAY x 3702 on presynaptic and postsynaptic 5-HT1A receptors electrophysiological studies in the rat hippocampus and dorsal raphe". The Journal of Pharmacology and Experimental Therapeutics 286 (3): 1239–1247. PMID 9732384.  edit
  3. ^ Alessandri, B.; Tsuchida, E.; Bullock, R. M. (1999). "The neuroprotective effect of a new serotonin receptor agonist, BAY X3702, upon focal ischemic brain damage caused by acute subdural hematoma in the rat". Brain Research 845 (2): 232–235. doi:10.1016/S0006-8993(99)01948-4. PMID 10536203.  edit
  4. ^ Kline, A. E.; Yu, J.; Horváth, E.; Marion, D. W.; Dixon, C. E. (2001). "The selective 5-HT(1A) receptor agonist repinotan HCl attenuates histopathology and spatial learning deficits following traumatic brain injury in rats". Neuroscience 106 (3): 547–555. doi:10.1016/S0306-4522(01)00300-1. PMID 11591455.  edit
  5. ^ Mauler, F.; Horváth, E. (2005). "Neuroprotective efficacy of repinotan HCl, a 5-HT1A receptor agonist, in animal models of stroke and traumatic brain injury". Journal of cerebral blood flow and metabolism : official journal of the International Society of Cerebral Blood Flow and Metabolism 25 (4): 451–459. doi:10.1038/sj.jcbfm.9600038. PMID 15674237.  edit
  6. ^ Ohman, J.; Braakman, R.; Legout, V.; Traumatic Brain Injury Study Group (2001). "Repinotan (BAY x 3702): a 5HT1A agonist in traumatically brain injured patients". Journal of neurotrauma 18 (12): 1313–1321. doi:10.1089/08977150152725614. PMID 11780862.  edit
  7. ^ Lutsep, H. L. (2005). "Repinotan, A 5-HT1A agonist, in the treatment of acute ischemic stroke". Current drug targets. CNS and neurological disorders 4 (2): 119–120. doi:10.2174/1568007053544165. PMID 15857296.  edit
  8. ^ Berends, A. C.; Luiten, P. G.; Nyakas, C. (2005). "A review of the neuroprotective properties of the 5-HT1A receptor agonist repinotan HCl (BAYx3702) in ischemic stroke". CNS Drug Reviews 11 (4): 379–402. doi:10.1111/j.1527-3458.2005.tb00055.x. PMID 16614737.  edit
  9. ^ Teal, P.; Davis, S.; Hacke, W.; Kaste, M.; Lyden, P.; Modified Randomized Exposure Controlled Trial Study Investigators; Fierus, M.; Bayer Healthcare, A. (2009). "A randomized, double-blind, placebo-controlled trial to evaluate the efficacy, safety, tolerability, and pharmacokinetic/pharmacodynamic effects of a targeted exposure of intravenous repinotan in patients with acute ischemic stroke: modified Randomized Exposure Controlled Trial (mRECT)". Stroke; a journal of cerebral circulation 40 (11): 3518–3525. doi:10.1161/STROKEAHA.109.551382. PMID 19745176.  edit
  10. ^ Guenther U, Wrigge H, Theuerkauf N, Boettcher MF, Wensing G, Zinserling J, Putensen C, Hoeft A (October 2010). "Repinotan, a selective 5-HT1A-R-agonist, antagonizes morphine-induced ventilatory depression in anesthetized rats". Anesthesia and Analgesia 111 (4): 901–7. doi:10.1213/ANE.0b013e3181eac011. PMID 20802053.