CCK-4

Quality 0.50 · 1 view · Updated 2 months ago

Anxiogenic agent

title: "CCK-4" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["cholecystokinin-agonists", "tetrapeptides", "anxiogenics", "methylthio-compounds"] description: "Anxiogenic agent" topic_path: "general/cholecystokinin-agonists" source: "https://en.wikipedia.org/wiki/CCK-4" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Anxiogenic agent ::

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 431772029 | IUPAC_name = (3S)-3-[(2S)-2-amino-3-phenylpropanamido]-3-{[(1S)-1-{[(1S)-1-carboxy -2-(indol-3-yl)ethyl]carbamoyl}-3-(methylsulfanyl)propyl]carbamoyl}propanoic acid | image = Cck-4.svg | image_class = skin-invert-image | width = 240

| tradename = | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = | legal_CA = | legal_UK = | legal_US = | legal_status = | routes_of_administration = Intravenous

| bioavailability = 100% | protein_bound = | metabolism = Plasma protease enzymes | elimination_half-life = 13 minutes | excretion = N/A

| synonyms = Tetragastrin; Cholecystokinin tetrapeptide | CAS_number_Ref = | CAS_number = 1947-37-1 | ATC_prefix = None | ATC_suffix = | UNII_Ref = | UNII = 0OL293AV80 | PubChem = 446569 | DrugBank_Ref = | DrugBank = | ChemSpiderID_Ref = | ChemSpiderID = 393888 | ChEBI = 137728 | StdInChI_Ref = | StdInChIKey_Ref = | StdInChI = 1S/C29H36N6O6S/c1-42-12-11-22(33-27(39)20(30)14-18-16-32-21-10-6-5-9-19(18)21)28(40)35-24(15-25(36)37)29(41)34-23(26(31)38)13-17-7-3-2-4-8-17/h2-10,16,20,22-24,32H,11-15,30H2,1H3,(H2,31,38)(H,33,39)(H,34,41)(H,35,40)(H,36,37)/t20-,22-,23-,24-/m0/s1 | StdInChIKey = RGYLYUZOGHTBRF-BIHRQFPBSA-N

| C = 29 | H = 35 | N = 5 | O = 7 | S = 1 | smiles = CSCCC@@HNC(=O)C@HN

Cholecystokinin tetrapeptide (CCK-4, tetragastrin, Trp-Met-Asp-Phe-NH2) is a peptide fragment derived from the larger peptide hormone cholecystokinin. Unlike cholecystokin which has a variety of roles in the gastrointestinal system as well as central nervous system effects, CCK-4 acts primarily in the brain as an anxiogenic, although it does retain some GI effects, but not as much as CCK-8 or the full length polypeptide CCK-58.

CCK-4 reliably causes severe anxiety symptoms when administered to humans in a dose of as little as 50 μg, and is commonly used in scientific research to induce panic attacks for the purpose of testing new anxiolytic drugs. Since it is a peptide, CCK-4 must be administered by injection, and is rapidly broken down once inside the body so has only a short duration of action, although numerous synthetic analogues with modified properties are known.

References

References

  1. (January 2005). "Panic induction with cholecystokinin-tetrapeptide (CCK-4) Increases plasma concentrations of the neuroactive steroid 3alpha, 5alpha tetrahydrodeoxycorticosterone (3alpha, 5alpha-THDOC) in healthy volunteers". Neuropsychopharmacology.
  2. (July 1993). "Neurobiological investigations into the role of cholecystokinin in panic disorder". Journal of Psychiatry & Neuroscience.
  3. (July 2006). "Functional magnetic resonance imaging characterization of CCK-4-induced panic attack and subsequent anticipatory anxiety". NeuroImage.
  4. (July 2007). "Evaluation of the CCK-4 model as a challenge paradigm in a population of healthy volunteers within a proof-of-concept study". Psychopharmacology.
  5. (February 2009). "Functional neuroanatomy of CCK-4-induced panic attacks in healthy volunteers". Human Brain Mapping.
  6. (August 1982). "Degradation of cholecystokinin octapeptide, related fragments and analogs by human and rat plasma in vitro". Regulatory Peptides.
  7. (February 1997). "Structure-based design of new constrained cyclic agonists of the cholecystokinin CCK-B receptor". Journal of Medicinal Chemistry.
  8. (October 2000). "Replacement of glycine with dicarbonyl and related moieties in analogues of the C-terminal pentapeptide of cholecystokinin: CCK(2) agonists displaying a novel binding mode". Journal of Medicinal Chemistry.
  9. (January 2001). "Involvement of D2 dopamine receptors in the opposing effects of two CCK-B agonists in a spatial recognition memory task: role of the anterior nucleus accumbens". Psychopharmacology.
  10. (2003). "How a single inversion of configuration leads to a reversal of the binding mode: proposal of a novel arrangement of CCK2 ligands in their receptor, and contribution to the development of peptidomimetic or non-peptide CCK2 ligands". European Journal of Medicinal Chemistry.
  11. (November 2004). "New CCK2 agonists confirming the heterogeneity of CCK2 receptors: characterisation of BBL454". Naunyn-Schmiedeberg's Archives of Pharmacology.
  12. (2005). "[Biological activity of cholecystokinin-(30-33) tetrapeptide analogs]". Bioorganicheskaia Khimiia.
  13. (2006). "[Effect of a cholecystokinin tetrapeptide analogue on opioid reception under acute and chronic morphine administration]". Bioorganicheskaia Khimiia.
  14. (May 2006). "Structure-activity relationships of bifunctional peptides based on overlapping pharmacophores at opioid and cholecystokinin receptors". Journal of Medicinal Chemistry.
  15. (2007). "Pharmacology of CCKRs and SAR studies of peptidic analog ligands". Current Topics in Medicinal Chemistry.
  16. (2007). "Strategies for design of non peptide CCK1R agonist/antagonist ligands". Current Topics in Medicinal Chemistry.
  17. (2007). "Strategies for the design of non-peptide CCK2 receptor agonist and antagonist ligand". Current Topics in 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. ::

cholecystokinin-agoniststetrapeptidesanxiogenicsmethylthio-compounds