Aptiganel

Chemical compound From Wikipedia, the free encyclopedia

Aptiganel (Cerestat; CNS-1102) is an unsuccessful drug candidate which acts as a noncompetitive NMDA antagonist, and that was under development by Cambridge Neuroscience, Inc as a treatment for stroke.[1] It has neuroprotective effects and was researched for potential use in the treatment of stroke,[2] but despite positive results in animal studies,[3] human trials showed limited efficacy,[4] as well as undesirable side effects such as sedation and hallucinations,[5][6] and clinical development was ultimately not continued.[7]

ATC code
  • none
Legal status
  • In general: uncontrolled
Quick facts Clinical data, ATC code ...
Aptiganel
Clinical data
ATC code
  • none
Legal status
Legal status
  • In general: uncontrolled
Identifiers
  • 1-(3-ethylphenyl)-1-methyl-2-naphthalen-1-yl-guanidine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC20H21N3
Molar mass303.409 g·mol−1
3D model (JSmol)
  • CCC1=CC(=CC=C1)N(C)C(=NC2=CC=CC3=CC=CC=C32)N
  • InChI=1S/C20H21N3/c1-3-15-8-6-11-17(14-15)23(2)20(21)22-19-13-7-10-16-9-4-5-12-18(16)19/h4-14H,3H2,1-2H3,(H2,21,22) checkY
  • Key:BFNCJMURTMZBTE-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)
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The drug's failure led to the collapse of Cambridge Neuroscience in 1998[8] and its eventual sale to CeNeS Pharmaceuticals in 2000.[9]

Other guanidine substances that the company had been bowling on was Cns-1145 & CNS1237.

Synthesis

Aptiganel synthesis:[10][11]

1-Naphthylamine is reacted with cyanogen bromide to give 2. Treatment of this intermediate with 3-ethyl-N-methylaniline leads to addition to the cyano group and formation of the corresponding diaryl guanidine, aptiganel, 3.

See also

References

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