GT-2203

Last updated

GT-2203
GT-2203.svg
Clinical data
Other namesVUF-5296; (1R,2R)-Cyclopropylhistamine; (1R,2R)-trans-2-(1H-imidazol-4-yl)cyclopropylamine
Routes of
administration 		Unspecified [1]
Drug class Histamine H3 receptor agonist
ATC code
  • None
Identifiers
  • trans-(1R,2R)-2-(1H-imidazol-5-yl)cyclopropan-1-amine
ChEMBL
Chemical and physical data
Formula C6H9N3
Molar mass 123.159 g·mol−1
3D model (JSmol)
  • C1[C@H]([C@@H]1N)C2=CN=CN2
  • InChI=1S/C6H9N3/c7-5-1-4(5)6-2-8-3-9-6/h2-5H,1,7H2,(H,8,9)/t4-,5-/m1/s1
  • Key:OWWNABDDYQLERE-RFZPGFLSSA-N

GT-2203, also known as VUF-5296, (1R,2R)-cyclopropylhistamine, or (1R,2R)-trans-2-(1H-imidazol-4-yl)cyclopropylamine, is a histamine H3 receptor agonist which was under development for the treatment of insomnia and anxiety disorders but was never marketed. [1] [2] [3] Its route of administration was unspecified. [1]

Contents

Pharmacology

The drug is a synthetic derivative of the neurotransmitter histamine. [3] The other enantiomer, (1S,2S)-cyclopropylhistamine (VUF-5297), is about 10-fold more potent than GT-2203 as a histamine H3 receptor agonist. [3] Both enantiomers are partial agonists of the receptor and both enantiomers show additional weak activity at the histamine H1 and H2 receptors. [3]

History

GT-2203 was under development by Gliatech. [1] [2] It reached the preclinical research stage of development for insomnia and anxiety disorders prior to the discontinuation of its development in 2004. [1] [2] The drug was first described in the scientific literature by 1997. [4] Aside from immethridine (BP-1-5375), GT-2203 is the only other selective histamine H3 receptor agonist to have been developed for potential pharmaceutical use. [1] [5] [6]

See also

References

  1. 1 2 3 4 5 6 "GT 2203". AdisInsight. 16 September 2004. Retrieved 27 September 2025.
  2. 1 2 3 "Delving into the Latest Updates on GT-2203 with Synapse". Synapse. 13 September 2025. Retrieved 27 September 2025.
  3. 1 2 3 4 De Esch IJ, Vollinga RC, Goubitz K, Schenk H, Appelberg U, Hacksell U, et al. (April 1999). "Characterization of the binding site of the histamine H3 receptor. 1. Various approaches to the synthesis of 2-(1H-imidazol-4-yl)cyclopropylamine and histaminergic activity of (1R,2R)- and (1S,2S)-2-(1H-imidazol-4-yl)-cyclopropylamine". Journal of Medicinal Chemistry. 42 (7): 1115–1122. doi:10.1021/jm9810912. PMID   10197956.
  4. ↑ Khan M, Yates SL, Tedford CE, Kirschbaum K, Phillips JG (1997). "Diastereoselective synthesis of trans-2-(1-triphenylmethyl-1H-imidazol-4-yl)cyclopropanecarboxylic acids: key intermediates for the preparation of potent and chiral histamine H3 receptor agents". Bioorganic & Medicinal Chemistry Letters. 7 (23): 3017–3022. doi:10.1016/S0960-894X(97)10137-8 . Retrieved 27 September 2025.
  5. ↑ "Immethridine". AdisInsight. 16 July 2016. Retrieved 27 September 2025.
  6. ↑ Kitbunnadaj R, Zuiderveld OP, Christophe B, Hulscher S, Menge WM, Gelens E, et al. (May 2004). "Identification of 4-(1H-imidazol-4(5)-ylmethyl)pyridine (immethridine) as a novel, potent, and highly selective histamine H(3) receptor agonist". Journal of Medicinal Chemistry. 47 (10): 2414–2417. doi:10.1021/jm049932u. PMID   15115383.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.