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GT-2203

From Wikipedia, the free encyclopedia

Pharmaceutical compound
GT-2203
Clinical data
Other namesVUF-5296; (1R,2R)-Cyclopropylhistamine; (1R,2R)-trans-2-(1H-imidazol-4-yl)cyclopropylamine
Routes of
administration		Unspecified[1]
Drug classHistamineH3 receptoragonist
ATC code
  • None
Identifiers
  • trans-(1R,2R)-2-(1H-imidazol-5-yl)cyclopropan-1-amine
CAS Number
PubChemCID
ChemSpider
ChEMBL
Chemical and physical data
FormulaC6H9N3
Molar mass123.159 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 asVUF-5296,(1R,2R)-cyclopropylhistamine, or(1R,2R)-trans-2-(1H-imidazol-4-yl)cyclopropylamine, is ahistamineH3 receptoragonist which was under development for the treatment ofinsomnia andanxiety disorders but was never marketed.[1][2][3] Itsroute of administration was unspecified.[1]

Pharmacology

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The drug is asyntheticderivative of theneurotransmitterhistamine.[3] The otherenantiomer, (1S,2S)-cyclopropylhistamine (VUF-5297), is about 10-fold morepotent than GT-2203 as a histamine H3 receptor agonist.[3] Both enantiomers arepartial agonists of the receptor and both enantiomers show additional weak activity at the histamineH1 andH2 receptors.[3]

History

[edit]

GT-2203 was under development by Gliatech.[1][2] It reached thepreclinical 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 thescientific literature by 1997.[4] Aside fromimmethridine (BP-1-5375), GT-2203 is the only otherselective histamine H3 receptor agonist to have been developed for potentialpharmaceutical use.[1][5][6]

See also

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References

[edit]
  1. ^abcdef"GT 2203".AdisInsight. 16 September 2004. Retrieved27 September 2025.
  2. ^abc"Delving into the Latest Updates on GT-2203 with Synapse".Synapse. 13 September 2025. Retrieved27 September 2025.
  3. ^abcdDe 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. Retrieved27 September 2025.
  5. ^"Immethridine".AdisInsight. 16 July 2016. Retrieved27 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.
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