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IS-159

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Pharmaceutical compound
IS-159
Clinical data
Other namesIS159; Serotonin-O-carboxymethylglycyltyrosinamide; Serotonin-carboxylmethyleneoxy-L-tyrosylglycinamide; 2-(3-(2-aminoethyl)-1H-indol-5-yloxy)acetyl-L-tyrosyl-glycinamide
Routes of
administration		Intranasal,subcutaneous[1][2][3]
Drug classSerotonin5-HT1B and5-HT1D receptoragonist;Triptan-like drug;Antimigraine agent
ATC code
  • None
Pharmacokinetic data
Onset of action15–20 minutes (TmaxTooltip time to peak levels)[2][4]
Eliminationhalf-life2–2.5 hours[2][4][5]
Identifiers
  • (2S)-2-[[2-[[3-(2-aminoethyl)-1H-indol-5-yl]oxy]acetyl]amino]-N-(2-amino-2-oxoethyl)-3-(4-hydroxyphenyl)propanamide
CAS Number
PubChemCID
ChemSpider
UNII
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC23H27N5O5
Molar mass453.499 g·mol−1
3D model (JSmol)
  • C1=CC(=CC=C1C[C@@H](C(=O)NCC(=O)N)NC(=O)COC2=CC3=C(C=C2)NC=C3CCN)O
  • 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/s1
  • Key:PBRWGFLPYQYNGI-FQEVSTJZSA-N

IS-159, also known asserotonin-O-carboxymethylglycyltyrosinamide, is atriptan-likeserotonin5-HT1B and5-HT1D receptoragonist which was under development for the treatment ofmigraine but was never marketed.[1][2][3][6][5][7] It is takenintranasally orsubcutaneously.[1][2][3]

The drug is a smallserotonin-containingpeptide and is described as beingperipherally selective.[3] It acts as aselective andpotent serotonin 5-HT1B and 5-HT1D receptor agonist (Ki = 3.2 nM and 1.6 nM, respectively).[8][4] IS-159 has more than 300-fold loweraffinity for the serotonin5-HT1A receptor (Ki = 1,000) and is inactive at the serotonin5-HT1E and5-HT1F receptors (Ki = >10,000 nM).[8][9][10] The drug'spharmacokinetics in humans have been studied.[2][4][5]

IS-159 was originated by Immunotech inFrance and was under development by Immunotech and The Medicines Company in the 1990s and early 2000s, but development was discontinued in 2003.[1][2] The drug reachedphase 2clinical trials prior to the discontinuation of its development.[1][2][5]

See also

[edit]

References

[edit]
  1. ^abcde"IS 159".AdisInsight. 17 January 2020. Retrieved25 January 2026.
  2. ^abcdefgh"IS 159".Drugs in R&D.2 (6):390–391. December 1999.doi:10.2165/00126839-199902060-00006.PMID 10763448.
  3. ^abcdMucke H (December 2002). "Therapies in development for the treatment of migraine".Expert Opinion on Investigational Drugs.11 (12):1813–1820.doi:10.1517/13543784.11.12.1813.PMID 12457440.
  4. ^abcdRamadan NM (2001). "Acute treatments: future developments".Current Medical Research and Opinion. 17 Suppl 1:s81–s86.doi:10.1185/0300799039117018.PMID 12463284.
  5. ^abcdDingemanse J, Soubrouillard C, Paris J, Pisano P, Blin O (August 2000). "Pronounced effect of caprylocaproyl macrogolglycerides on nasal absorption of IS-159, a peptide serotonin 1B/1D-receptor agonist".Clinical Pharmacology and Therapeutics.68 (2):114–121.doi:10.1067/mcp.2000.108196.PMID 10976542.
  6. ^Ramadan NM, Buchanan TM, Pearlman SH (2004)."Clinical Science: Peripheral and Central Trigeminal Targets for Acute Migraine Therapy: Early Clinical Trial Results".Headache Currents.1 (1):7–12.doi:10.1111/j.1743-5013.2004.10104.x.ISSN 1743-5005. Retrieved25 January 2026.
  7. ^Chauveau J, Delaage MA (1997)."IS-159: A High-Affinity Specific 5-HT1D Full Receptor Agonist, Effective in the Acute Treatment of Migraine".Frontiers in Headache Research. 6th International Headache Research Seminar; 1995 Nov 17-19.6. Copenhagen:287–292.
  8. ^abMartin GR (1997)."Serotonin Receptor Involvement in the Pathogenesis and Treatment of Migraine". In Goadsby VG, Silberstein SD (eds.).Blue Books of Practical Neurology. Vol. 17. pp. 25–38.ISBN 978-0-7506-9871-9.
  9. ^Waeber C (November 2003). "Emerging drugs in migraine treatment".Expert Opinion on Emerging Drugs.8 (2):437–456.doi:10.1517/14728214.8.2.437.PMID 14661998.
  10. ^van den Broek RW (13 March 2002).Vascular Effects of Antimigraine Drugs: pharmacology of human in vitro models in migraine.RePub, Erasmus University Repository (Doctoral thesis). Erasmus University Rotterdam. Retrieved25 January 2026.
5-HT1
5-HT1A
5-HT1B
5-HT1D
5-HT1E
5-HT1F
5-HT2
5-HT2A
5-HT2B
5-HT2C
5-HT3–7
5-HT3
5-HT4
5-HT5A
5-HT6
5-HT7
Tryptamines
4-Hydroxytryptamines
andesters/ethers
5-Hydroxy- and
5-methoxytryptamines
N-Acetyltryptamines
α-Alkyltryptamines
α-Ketotryptamines
Cyclized tryptamines
Isotryptamines
Related compounds
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