Aptiganel

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]

Aptiganel

Clinical data
ATC code	none
Legal status
Legal status	In general: uncontrolled
Identifiers
IUPAC name 1-(3-ethylphenyl)-1-methyl-2-naphthalen-1-yl-guanidine
CAS Number	137159-92-3 N
PubChem CID	60840
ChemSpider	54827 Y
UNII	46475LV84I
ChEMBL	ChEMBL92484 Y
CompTox Dashboard (EPA)	DTXSID4048432
Chemical and physical data
Formula	C20H21N3
Molar mass	303.409 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCC1=CC(=CC=C1)N(C)C(=NC2=CC=CC3=CC=CC=C32)N
InChI 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) Y Key:BFNCJMURTMZBTE-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

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

• Ditolylguanidine
• CNS1237 shares predominantly most of the same structural entities.