IS-159

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Column 1
IS159; Serotonin-O-carboxymethylglycyltyrosinamide; Serotonin-carboxylmethyleneoxy-L-tyrosylglycinamide; 2-(3-(2-aminoethyl)-1H-indol-5-yloxy)acetyl-L-tyrosyl-glycinamide
Intranasal, subcutaneous
Serotonin 5-HT1B and 5-HT1D receptor agonist; Triptan-like drug; Antimigraine agent
.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}None
15–20 minutes (TmaxTooltip time to peak levels)
2–2.5 hours
IUPAC name
(2S)-2-[[2-[[3-(2-aminoethyl)-1H-indol-5-yl]oxy]acetyl]amino]-N-(2-amino-2-oxoethyl)-3-(4-hydroxyphenyl)propanamide
133790-13-3
196859
170507
7N2D7W2TCJ
DTXSID80928273
C23H27N5O5
453.499 g·mol−1
Interactive image
SMILES
C1=CC(=CC=C1CC@@HNC(=O)COC2=CC3=C(C=C2)NC=C3CCN)O
InChI
InChI=1S/C23H27N5O5/c24-8-7-15-11-26-19-6-5-17(10-18(15)19)33-13-22(31)28-20(23(32)27-12-21(25)30)9-14-1-3-16(29)4-2-14/h1-6,10-11,20,26,29H,7-9,12-13,24H2,(H2,25,30)(H,27,32)(H,28,31)/t20-/m0/s1Key:PBRWGFLPYQYNGI-FQEVSTJZSA-N

IS-159, also known as serotonin-O-carboxymethylglycyltyrosinamide, is a triptan-like serotonin 5-HT1B and 5-HT1D receptor agonist which was under development for the treatment of migraine but was never marketed. It is taken intranasally or subcutaneously.

The drug is a small serotonin-containing peptide and is described as being peripherally selective. It acts as a selective and potent serotonin 5-HT1B and 5-HT1D receptor agonist (Ki = 3.2 nM and 1.6 nM, respectively). IS-159 has more than 300-fold lower affinity for the serotonin 5-HT1A receptor (Ki = 1,000) and is inactive at the serotonin 5-HT1E and 5-HT1F receptors (Ki = >10,000 nM). The drug's pharmacokinetics in humans have been studied.

IS-159 was originated by Immunotech in France and was under development by Immunotech and The Medicines Company in the 1990s and early 2000s, but development was discontinued in 2003. The drug reached phase 2 clinical trials prior to the discontinuation of its development.

• List of investigational headache and migraine drugs

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