Ecopipam

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Ecopipam
Ecopipam structure.png
Systematic (IUPAC) name
(–)-trans-6,7,7a,8,9,13b-hexahydro-3-chloro-2-hydroxy-N-methyl-5H-benzo[d]naptho-(2,1-b)azepine
Clinical data
Legal status ?
Identifiers
CAS number 112108-01-7 YesY
ATC code None
PubChem CID 107930
UNII 0X748O646K YesY
Chemical data
Formula C19H20ClNO 
Mol. mass 313.821 g/mol
 YesY (what is this?)  (verify)

Ecopipam (SCH-39166) is a synthetic benzazepine derivative drug that acts as a selective dopamine D1/D5 receptor antagonist, with little affinity for either dopamine D2-like or 5-HT2 receptors.[1] It has sedative, antipsychotic and anorectic effects, and was researched for human use although never approved for medical prescription, mainly because of side effects such as depression and anxiety.[2][3]

Chemical synthesis[edit]

Ecopipam can be synthesized from a simple tetralin derivative:[4]

Ecopipam scheme.png

Clinical trials[edit]

Ecopipam is currently being used in a clinical trial conducted by the biotechnology company Psyadon for the treatment of Lesch-Nyhan Syndrome,[5] as well as for Tourette syndrome.[6]

References[edit]

  1. ^ Chipkin RE, Iorio LC, Coffin VL, McQuade RD, Berger JG, Barnett A (December 1988). "Pharmacological profile of SCH39166: a dopamine D1 selective benzonaphthazepine with potential antipsychotic activity". The Journal of Pharmacology and Experimental Therapeutics 247 (3): 1093–102. PMID 2905002. 
  2. ^ Hou D, Schumacher D (November 2001). "The selection of a commercial route for the D1 antagonist Sch-39166". Current Opinion in Drug Discovery & Development 4 (6): 792–9. PMID 11899619. 
  3. ^ Astrup A, Greenway FL, Ling W, Pedicone L, Lachowicz J, Strader CD, Kwan R (July 2007). "Randomized controlled trials of the D1/D5 antagonist ecopipam for weight loss in obese subjects". Obesity (Silver Spring, Md.) 15 (7): 1717–31. doi:10.1038/oby.2007.205. PMID 17636090. 
  4. ^ Hou, D; Schumacher, D (2001). "The selection of a commercial route for the D1 antagonist Sch-39166.". Current opinion in drug discovery & development 4 (6): 792–9. PMID 11899619. 
  5. ^ http://www.psyadonrx.com/ongoingclinicaltrials.html
  6. ^ http://clinicaltrials.gov/ct2/show/study/NCT01244633