Page last updated: 2024-09-27

tetragastrin

Description

Tetragastrin: L-Tryptophyl-L-methionyl-L-aspartyl-L-phenylalaninamide. The C-terminal tetrapeptide of gastrin. It is the smallest peptide fragment of gastrin which has the same physiological and pharmacological activity as gastrin. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

tetragastrin : A tetrapeptide composed of L-tryptophan, L-methione, L-aspartic acid and L-phenylalaninamide residues joined in sequence. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID446569
CHEMBL ID120632
CHEBI ID137728
CHEBI ID32210
SCHEMBL ID9710792
MeSH IDM0021228

Synonyms (46)

Synonym
unii-0ol293av80
0ol293av80 ,
l-phenylalaninamide, n-((phenylmethoxy)carbonyl)-l-tryptophyl-l-methionyl-l-aspartyl-
l-phenylalaninamide, l-tryptophyl-l-methionyl-l-alpha-aspartyl-
tetragastrin [jan]
tetragastrin
l-triptophyl-l-methyionyl-l-alpha-aspartyl-l-phenylalaninamide
gastrin tetrapeptide
gastrin tetrapeptide amide
n-((phenylmethoxy)carbonyl)-l-tryptophyl-l-methionyl-l-aspartyl-l-phenylalaninamide
cholecystokinin tetrapeptide
ccris 3246
tetragastrin (jan)
D01456
1947-37-1
trp-met-asp-phe-nh(2)
cck-4
CHEBI:137728
l-tryptophyl-l-methionyl-l-alpha-aspartyl-l-phenylalaninamide
wmdf-nh(2)
cholecystokinin-4
l-trp-l-met-l-asp-l-phe-nh(2)
l-tryptophyl-l-methionyl-l-aspartyl-l-phenylalaninamide
(3s)-3-[[(2s)-2-[[(2s)-2-amino-3-(1h-indol-3-yl)propanoyl]amino]-4-methylsulfanylbutanoyl]amino]-4-[[(2s)-1-amino-1-oxo-3-phenylpropan-2-yl]amino]-4-oxobutanoic acid
4-7-cholecystokinin-7 (swine)
CHEMBL120632 ,
bdbm50024317
3-{2-[2-amino-3-(1h-indol-3-yl)-propionylamino]-4-methylsulfanyl-butyrylamino}-n-(1-carbamoyl-2-phenyl-ethyl)-succinamic acid
tetragastrin [who-dd]
l-phenylalaninamide, l-tryptophyl-l-methionyl-l-.alpha.-aspartyl-
SCHEMBL9710792
mfcd00076492
gastrin(14-17)(human)
(3s)-3-[(2s)-2-[(2s)-2-amino-3-(1h-indol-3-yl)propanamido]-4-(methylsulfanyl)butanamido]-3-{[(1s)-1-carbamoyl-2-phenylethyl]carbamoyl}propanoic acid
SR-01000883973-1
sr-01000883973
l-tryptophyl-l-methionyl-l-aspartylphenyl-alaninamide
CHEBI:32210
(s)-4-(((s)-1-amino-1-oxo-3-phenylpropan-2-yl)amino)-3-((s)-2-((s)-2-amino-3-(1h-indol-3-yl)propanamido)-4-(methylthio)butanamido)-4-oxobutanoic acid
(s)-4-((s)-1-amino-1-oxo-3-phenylpropan-2-ylamino)-3-((s)-2-((s)-2-amino-3-(1h-indol-3-yl)propanamido)-4-(methylthio)butanamido)-4-oxobutanoic acid
BRD-K70369756-001-01-3
MS-30582
DTXSID601027522
CS-0092217
HY-125556
AKOS040744602

Actions

ExcerptReference
"Tetragastrin did not increase the amino acid output in the gastric juice."( Goto, H; Kobayashi, E; Nakazawa, S; Segawa, K; Tsukamoto, Y; Yamaguchi, H, 1985)

Treatment

ExcerptReference
"Rats treated with tetragastrin or 6-OHDA had a significantly lower labelling index of the antral mucosa, and this index was significantly decreased by combined administration of tetragastrin and 6-OHDA, as compared with labeling indices observed after treatment with tetragastrin or 6-OHDA alone."( Baba, M; Iishi, H; Taniguchi, H; Tatsuta, M, 1989)

Roles (2)

RoleDescription
anxiogenicAny psychotropic drug that induces anxiety or panic.
human metaboliteAny mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (2)

ClassDescription
tetrapeptideAny molecule that contains four amino-acid residues connected by peptide linkages.
peptidyl amideA peptide that has a carbamoyl group at the C-terminus.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Gastrin/cholecystokinin type B receptorRattus norvegicus (Norway rat)Ki0.09300.00060.11960.6800AID51458; AID51461
Gastrin/cholecystokinin type B receptorHomo sapiens (human)Ki0.01720.00010.03660.3450AID1409549; AID50951; AID50955
Cholecystokinin receptor type ACavia porcellus (domestic guinea pig)Ki36.13300.00030.13770.6310AID52580; AID52582
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Gastrin/cholecystokinin type B receptorRattus norvegicus (Norway rat)EC50 (µMol)0.00140.00040.00080.0014AID51295
Gastrin/cholecystokinin type B receptorHomo sapiens (human)Kd0.02170.00050.00530.0217AID1409548
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (9)

Processvia Protein(s)Taxonomy
gastric acid secretionGastrin/cholecystokinin type B receptorHomo sapiens (human)
cell surface receptor signaling pathwayGastrin/cholecystokinin type B receptorHomo sapiens (human)
phospholipase C-activating G protein-coupled receptor signaling pathwayGastrin/cholecystokinin type B receptorHomo sapiens (human)
positive regulation of cytosolic calcium ion concentrationGastrin/cholecystokinin type B receptorHomo sapiens (human)
positive regulation of cell population proliferationGastrin/cholecystokinin type B receptorHomo sapiens (human)
cholecystokinin signaling pathwayGastrin/cholecystokinin type B receptorHomo sapiens (human)
pH reductionGastrin/cholecystokinin type B receptorHomo sapiens (human)
digestive tract developmentGastrin/cholecystokinin type B receptorHomo sapiens (human)
gland developmentGastrin/cholecystokinin type B receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (6)

Processvia Protein(s)Taxonomy
cholecystokinin receptor activityGastrin/cholecystokinin type B receptorHomo sapiens (human)
protein bindingGastrin/cholecystokinin type B receptorHomo sapiens (human)
gastrin receptor activityGastrin/cholecystokinin type B receptorHomo sapiens (human)
peptide hormone bindingGastrin/cholecystokinin type B receptorHomo sapiens (human)
type B gastrin/cholecystokinin receptor bindingGastrin/cholecystokinin type B receptorHomo sapiens (human)
1-phosphatidylinositol-3-kinase regulator activityGastrin/cholecystokinin type B receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (2)

Processvia Protein(s)Taxonomy
plasma membraneGastrin/cholecystokinin type B receptorHomo sapiens (human)
intracellular membrane-bounded organelleGastrin/cholecystokinin type B receptorHomo sapiens (human)
plasma membraneGastrin/cholecystokinin type B receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (12)

Assay IDTitleYearJournalArticle
AID1409549Displacement of non-sulfated CCK-8 from CCKB receptor (unknown origin) expressed in HEK cells after 4 hrs by RP-LC-ICPMS analysis2018Journal of medicinal chemistry, 11-21, Volume: 61, Issue:22
Receptor-Ligand Interaction Measured by Inductively Coupled Plasma Mass Spectrometry and Selenium Labeling.
AID51295Affinity against Cholecystokinin type B receptor expressed in CHO cells on rat brain.2000Journal of medicinal chemistry, Oct-05, Volume: 43, Issue:20
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.
AID52580Inhibition of [3H]pCCK-8 binding to Cholecystokinin type A receptor of Guinea pig pancreatic membranes1997Journal of medicinal chemistry, Feb-28, Volume: 40, Issue:5
Structure-based design of new constrained cyclic agonists of the cholecystokinin CCK-B receptor.
AID1409548Binding affinity to CCKB receptor (unknown origin) expressed in HEK cells after 4 hrs by RP-LC-ICPMS analysis2018Journal of medicinal chemistry, 11-21, Volume: 61, Issue:22
Receptor-Ligand Interaction Measured by Inductively Coupled Plasma Mass Spectrometry and Selenium Labeling.
AID50951Inhibition of [3H]pCCK-8 binding to Guinea pig cortex membrane Cholecystokinin type B receptor1997Journal of medicinal chemistry, Feb-28, Volume: 40, Issue:5
Structure-based design of new constrained cyclic agonists of the cholecystokinin CCK-B receptor.
AID52407Displacement of [3H]pentagastrin from Cholecystokinin receptor of mouse cerebral cortex1987Journal of medicinal chemistry, Apr, Volume: 30, Issue:4
Synthesis and binding affinities of analogues of cholecystokinin-(30-33) as probes for central nervous system cholecystokinin receptors.
AID50955Binding affinity against cholecystokinin type B receptor on guinea pig cortex.2000Journal of medicinal chemistry, Oct-05, Volume: 43, Issue:20
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.
AID52582Affinity against Cholecystokinin type A receptor on guinea pig pancreatic membranes.2000Journal of medicinal chemistry, Oct-05, Volume: 43, Issue:20
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.
AID51461Compound was tested for binding affinity against Cholecystokinin type B receptor expressed in CHO cells on the rat brain.2000Journal of medicinal chemistry, Oct-05, Volume: 43, Issue:20
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.
AID51458Affinity to inhibit [3H]pCCK-8 specific binding on rat brain Cholecystokinin type B receptor expressed in CHO cells1997Journal of medicinal chemistry, Feb-28, Volume: 40, Issue:5
Structure-based design of new constrained cyclic agonists of the cholecystokinin CCK-B receptor.
AID231773Ratio of compound affinity on CCK-A receptor with respect to CCK-B receptor1997Journal of medicinal chemistry, Feb-28, Volume: 40, Issue:5
Structure-based design of new constrained cyclic agonists of the cholecystokinin CCK-B receptor.
AID1409554Binding affinity to CCKB receptor (unknown origin) expressed in HEK cells Binding affinity to CCKB receptor (unknown origin) expressed in HEK cells assessed per million cells after 4 hrs by RP-LC-ICPMS analysis after 4 hrs by RP-LC-ICPMS analysis2018Journal of medicinal chemistry, 11-21, Volume: 61, Issue:22
Receptor-Ligand Interaction Measured by Inductively Coupled Plasma Mass Spectrometry and Selenium Labeling.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (506)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990179 (35.38)18.7374
1990's193 (38.14)18.2507
2000's98 (19.37)29.6817
2010's34 (6.72)24.3611
2020's2 (0.40)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials72 (13.24%)5.53%
Reviews14 (2.57%)6.00%
Case Studies3 (0.55%)4.05%
Observational0 (0.00%)0.25%
Other455 (83.64%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research Highlights

Safety/Toxicity (1)

ArticleYear
Translocator protein (18 kD) as target for anxiolytics without benzodiazepine-like side effects.
Science (New York, N.Y.), Jul-24, Volume: 325, Issue: 5939
2009
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Long-term Use (5)

ArticleYear
[Effect of GB-115 dipeptide on anxiety in rats with model benzodiazepine withdrawal syndrome].
Eksperimental'naia i klinicheskaia farmakologiia, Volume: 74, Issue: 10
2011
[The absence of tolerance and withdrawal syndrome after the treatment with the new L-tryptophane-containing dipeptide anxiolytic GB-115].
Vestnik Rossiiskoi akademii meditsinskikh nauk, Issue: 7
2011
Translocator protein (18 kD) as target for anxiolytics without benzodiazepine-like side effects.
Science (New York, N.Y.), Jul-24, Volume: 325, Issue: 5939
2009
Acute and chronic role of 5-HT3 neuronal system on behavioral and neuroendocrine changes induced by intravenous cholecystokinin tetrapeptide administration in humans.
Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology, Volume: 20, Issue: 2
1999
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Pharmacokinetics (1)

ArticleYear
Second generation "peptoid" CCK-B receptor antagonists: identification and development of N-(adamantyloxycarbonyl)-alpha-methyl-(R)-tryptophan derivative (CI-1015) with an improved pharmacokinetic profile.
Journal of medicinal chemistry, Jan-01, Volume: 41, Issue: 1
1998
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioavailability (6)

ArticleYear
Intestinal metabolism and absorption of cholecystokinin analogs in rats.
Biochemical and biophysical research communications, Apr-05, Volume: 292, Issue: 3
2002
[Improvement of intestinal absorption of peptide and protein drugs by chemical modification with fatty acids].
Nihon rinsho. Japanese journal of clinical medicine, Volume: 56, Issue: 3
1998
Second generation "peptoid" CCK-B receptor antagonists: identification and development of N-(adamantyloxycarbonyl)-alpha-methyl-(R)-tryptophan derivative (CI-1015) with an improved pharmacokinetic profile.
Journal of medicinal chemistry, Jan-01, Volume: 41, Issue: 1
1998
Alternate drug delivery routes for A-71623, a potent cholecystokinin-A receptor agonist tetrapeptide.
Journal of drug targeting, Volume: 4, Issue: 2
1996
CCK-B agonist or antagonist activities of structurally hindered and peptidase-resistant Boc-CCK4 derivatives.
Journal of medicinal chemistry, Jan-08, Volume: 36, Issue: 1
1993
Actions of nizatidine, a selective histamine H2-receptor antagonist, on gastric acid secretion in dogs, rats and frogs.
The Journal of pharmacology and experimental therapeutics, Volume: 239, Issue: 2
1986
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Dosage (21)

ArticleYear
Experimental panic provocation in healthy man-a translational role in anti-panic drug development?
Dialogues in clinical neuroscience, Volume: 13, Issue: 4
2011
Blockade of the mineralocorticoid receptor in healthy men: effects on experimentally induced panic symptoms, stress hormones, and cognition.
Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology, Volume: 32, Issue: 1
2007
Vigabatrin decreases cholecystokinin-tetrapeptide (CCK-4) induced panic in healthy volunteers.
Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology, Volume: 25, Issue: 5
2001
Stimulation of either cholecystokinin receptor subtype reduces while antagonists potentiate or sensitize a morphine-induced excitatory response.
Peptides, Volume: 22, Issue: 8
2001
Second generation "peptoid" CCK-B receptor antagonists: identification and development of N-(adamantyloxycarbonyl)-alpha-methyl-(R)-tryptophan derivative (CI-1015) with an improved pharmacokinetic profile.
Journal of medicinal chemistry, Jan-01, Volume: 41, Issue: 1
1998
The cholecystokinin-B receptor antagonist CI-988 failed to affect CCK-4 induced symptoms in panic disorder patients.
Psychopharmacology, Volume: 129, Issue: 3
1997
The panic-inducing properties of the cholecystokinin tetrapeptide CCK4 in patients with panic disorder.
European neuropsychopharmacology : the journal of the European College of Neuropsychopharmacology, Volume: 6, Issue: 3
1996
Novel CCK analogues and bombesin: a detailed analysis between phosphoinositide breakdown and high-dose inhibition of pancreatic enzyme secretion in three rodent species.
The Journal of pharmacology and experimental therapeutics, Volume: 268, Issue: 2
1994
Dose-response studies of acid secretion after administration of tetragastrin. Studies in duodenal ulcer patients before and after highly selective vagotomy, hemigastrectomy and truncal vagotomy plus antrectomy.
American journal of surgery, Volume: 139, Issue: 6
1980
[Effect of tetragastrin on electrical and contractile activities of the canine stomach and duodenum (author's transl)].
Nihon Heikatsukin Gakkai zasshi, Volume: 16, Issue: 2
1980
The effect of gastric inhibitory polypeptide (GIP) on gastric acid secretion in dogs.
Gastroenterologia Japonica, Volume: 16, Issue: 1
1981
In vitro and in vivo effect of proglumide on cholecystokinin-stimulated amylase release in mouse pancreatic acini.
Gastroenterologia Japonica, Volume: 19, Issue: 1
1984
Effects of C-terminal fragments of cholecystokinin on exocrine and endocrine secretion from isolated perfused rat pancreas.
Endocrinology, Volume: 113, Issue: 6
1983
Effects of portacaval shunt on the rat stomach.
Acta physiologica Scandinavica, Volume: 124, Issue: 3
1985
Stimulation of gastric acid secretion in the rhesus monkey.
Digestive diseases and sciences, Volume: 30, Issue: 1
1985
A behavioral pharmacological study on CCK-8 related peptides in mice.
Neuropeptides, Volume: 8, Issue: 3
1986
Clinical pharmacology of famotidine.
Digestion, Volume: 32 Suppl 1
1985
Stimulation of oxyntic and histaminergic cells in gastric mucosa by gastrin C-terminal tetrapeptide.
The American journal of physiology, Volume: 251, Issue: 4 Pt 1
1986
[Clinico-pharmacological evaluation of omeprazole, as a proton pump inhibitor, compared with H2-blockers].
Nihon rinsho. Japanese journal of clinical medicine, Volume: 50, Issue: 1
1992
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]