LY-341495

Quality 0.50 · 0 views · Updated 2 months ago

Chemical compound

title: "LY-341495" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["drugs-developed-by-eli-lilly-and-company", "mglu2-receptor-antagonists", "mglu3-receptor-antagonists", "psychoplastogens", "xanthenes"] description: "Chemical compound" topic_path: "general/drugs-developed-by-eli-lilly-and-company" source: "https://en.wikipedia.org/wiki/LY-341495" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Chemical compound ::

::data[format=table title="Infobox drug"]

FieldValue
Verifiedfieldschanged
Watchedfieldschanged
verifiedrevid424772766
IUPAC_name2-[(1S,2S)-2-carboxycyclopropyl]-3-(9H-xanthen-9-yl)-D-alanine
imageLY-341,495.svg
image_classskin-invert-image
width200
pregnancy_AU
pregnancy_US
legal_AU
legal_CA
legal_UK
legal_US
routes_of_administration
excretion
CAS_number_Ref
CAS_number201943-63-7
UNII_Ref
UNIIAQ73SP6QSF
DrugBank_Ref
ChemSpiderID_Ref
ChemSpiderID7995676
C
H19
N1
O5
synonyms(2S)-2-Amino-2-[(1S,2S)-2-carboxycycloprop-1-yl]-3-(xanth-9-yl)propanoic acid
smilesC1C@@HC(=O)O
StdInChI_Ref
StdInChI1S/C20H19NO5/c21-20(19(24)25,15-9-13(15)18(22)23)10-14-11-5-1-3-7-16(11)26-17-8-4-2-6-12(14)17/h1-8,13-15H,9-10,21H2,(H,22,23)(H,24,25)/t13-,15-,20-/m0/s1
StdInChIKey_Ref
StdInChIKeyVLZBRVJVCCNPRJ-KPHUOKFYSA-N
::

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 424772766 | IUPAC_name = 2-[(1S,2S)-2-carboxycyclopropyl]-3-(9H-xanthen-9-yl)-D-alanine | image = LY-341,495.svg | image_class = skin-invert-image | width = 200

| tradename = | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = | legal_CA = | legal_UK = | legal_US = | legal_status = | routes_of_administration = | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion = | CAS_number_Ref = | CAS_number = 201943-63-7 | UNII_Ref = | UNII = AQ73SP6QSF | ATC_prefix = | ATC_suffix = | PubChem = | DrugBank_Ref = | DrugBank = | ChemSpiderID_Ref = | ChemSpiderID = 7995676

| C = 20 | H = 19 | N = 1 | O = 5 | synonyms = (2S)-2-Amino-2-[(1S,2S)-2-carboxycycloprop-1-yl]-3-(xanth-9-yl)propanoic acid | smiles = C1C@@HC(=O)O | StdInChI_Ref = | StdInChI = 1S/C20H19NO5/c21-20(19(24)25,15-9-13(15)18(22)23)10-14-11-5-1-3-7-16(11)26-17-8-4-2-6-12(14)17/h1-8,13-15H,9-10,21H2,(H,22,23)(H,24,25)/t13-,15-,20-/m0/s1 | StdInChIKey_Ref = | StdInChIKey = VLZBRVJVCCNPRJ-KPHUOKFYSA-N

LY-341495 is a research drug developed by the pharmaceutical company Eli Lilly, which acts as a potent and selective orthosteric antagonist for the group II metabotropic glutamate receptors (mGluR2/3).

It is used in scientific research in several different areas, showing antidepressant effects in animal models, increasing the behavioural effects of hallucinogenic drugs in animal tests, and increasing the analgesic effects of μ-opioid agonists, as well as modulating dopamine receptor function.

The 1-fluorocyclopropane analog has a superior pharmacokinetic profile and similar mGluR2/3 affinity, and making a prodrug from this with the heptyl ester increases bioavailability still further.

::figure[src="https://upload.wikimedia.org/wikipedia/commons/7/7f/LY-341,495_prodrug.svg" caption="1-fluoro-LY-341,495 heptyl ester"] ::

References

References

  1. (January 1998). "2-substituted (2SR)-2-amino-2-((1SR,2SR)-2-carboxycycloprop-1-yl)glycines as potent and selective antagonists of group II metabotropic glutamate receptors. 2. Effects of aromatic substitution, pharmacological characterization, and bioavailability". Journal of Medicinal Chemistry.
  2. (1998). "LY341495 is a nanomolar potent and selective antagonist of group II metabotropic glutamate receptors". Neuropharmacology.
  3. (December 1998). "The potent mGlu receptor antagonist LY341495 identifies roles for both cloned and novel mGlu receptors in hippocampal synaptic plasticity". Neuropharmacology.
  4. (October 1999). "[3H]-LY341495 as a novel antagonist radioligand for group II metabotropic glutamate (mGlu) receptors: characterization of binding to membranes of mGlu receptor subtype expressing cells". Neuropharmacology.
  5. (March 2008). "Mood disorders: regulation by metabotropic glutamate receptors". Biochemical Pharmacology.
  6. (August 2007). "Group-II metabotropic glutamate receptor ligands as adjunctive drugs in the treatment of depression: a new strategy to shorten the latency of antidepressant medication?". Molecular Psychiatry.
  7. (September 2014). "Requirement of AMPA receptor stimulation for the sustained antidepressant activity of ketamine and LY341495 during the forced swim test in rats". Behavioural Brain Research.
  8. (December 2016). "Fast-acting antidepressants rapidly stimulate ERK signaling and BDNF release in primary neuronal cultures". Neuropharmacology.
  9. (November 2000). "Behavioral evidence for interactions between a hallucinogenic drug and group II metabotropic glutamate receptors". Neuropsychopharmacology.
  10. (August 2007). "A selective positive allosteric modulator of metabotropic glutamate receptor subtype 2 blocks a hallucinogenic drug model of psychosis". Molecular Pharmacology.
  11. (January 2015). "The role of 5-HT2A, 5-HT 2C and mGlu2 receptors in the behavioral effects of tryptamine hallucinogens N,N-dimethyltryptamine and N,N-diisopropyltryptamine in rats and mice". Psychopharmacology.
  12. (2018). "5-HT2A Receptors in the Central Nervous System".
  13. (June 2008). "Increased efficacy of micro-opioid agonist-induced antinociception by metabotropic glutamate receptor antagonists in C57BL/6 mice: comparison with (-)-6-phosphonomethyl-deca-hydroisoquinoline-3-carboxylic acid (LY235959)". Psychopharmacology.
  14. (February 2008). "Morphine in combination with metabotropic glutamate receptor antagonists on schedule-controlled responding and thermal nociception". The Journal of Pharmacology and Experimental Therapeutics.
  15. (October 2003). "Group II metabotropic glutamate receptor antagonists LY341495 and LY366457 increase locomotor activity in mice". Neuropharmacology.
  16. (October 2006). "Blockade of group II metabotropic glutamate receptors in the nucleus accumbens produces hyperlocomotion in rats previously exposed to amphetamine". Neuropharmacology.
  17. (September 2008). "Blockade of group II metabotropic glutamate receptors produces hyper-locomotion in cocaine pre-exposed rats by interactions with dopamine receptors". Neuropharmacology.
  18. (April 2008). "Synthesis, in vitro pharmacology, and pharmacokinetic profiles of 2-[1-amino-1-carboxy-2-(9H-xanthen-9-yl)-ethyl]-1-fluorocyclopropanecarboxylic acid and its 6-heptyl ester, a potent mGluR2 antagonist". Bioorganic & Medicinal Chemistry.

::callout[type=info title="Wikipedia Source"] This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page. ::

drugs-developed-by-eli-lilly-and-companymglu2-receptor-antagonistsmglu3-receptor-antagonistspsychoplastogensxanthenes