Page last updated: 2024-11-08

tetragastrin

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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

Research Excerpts

Actions

ExcerptReferenceRelevance
"Tetragastrin did not increase the amino acid output in the gastric juice."( Amino acid in gastric juice of peptic ulcer patients.
Goto, H; Kobayashi, E; Nakazawa, S; Segawa, K; Tsukamoto, Y; Yamaguchi, H, 1985
)
0.99

Treatment

ExcerptReferenceRelevance
"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."( Effect of 6-hydroxydopamine on gastric carcinogenesis and tetragastrin inhibition of gastric carcinogenesis induced by N-methyl-N'-nitro-N-nitrosoguanidine in Wistar rats.
Baba, M; Iishi, H; Taniguchi, H; Tatsuta, M, 1989
)
0.84

Pharmacokinetics

ExcerptReferenceRelevance
" Thus, there was a need to identify an analogue with an improved pharmacokinetic (PK) profile."( 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.
Boden, P; Eden, JM; Field, MJ; Hill, D; Hinton, JP; Holmes, A; Kneen, C; Padia, JK; Pritchard, MC; Rose, S; Singh, L; Suman-Chauhan, N; Trivedi, BK; Webdale, L; Wright, DS, 1998
)
0.3

Bioavailability

ExcerptReferenceRelevance
"37 microM, indicating high bioavailability and favorable partitioning and distribution effects from the sublingual cavity for this formulation."( Alternate drug delivery routes for A-71623, a potent cholecystokinin-A receptor agonist tetrapeptide.
Adjei, LA; Cannon, JB; Garren, K; Lu, MY, 1996
)
0.29
" However, during its development, it was determined that CI-988 had low bioavailability in both rodent and nonrodent species."( 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.
Boden, P; Eden, JM; Field, MJ; Hill, D; Hinton, JP; Holmes, A; Kneen, C; Padia, JK; Pritchard, MC; Rose, S; Singh, L; Suman-Chauhan, N; Trivedi, BK; Webdale, L; Wright, DS, 1998
)
0.3
"It is well known that the oral bioavailability of peptide and protein drugs is generally poor because they are extensively degraded by proteases in the gastrointestinal tract and impermeable through the intestinal mucosa."( [Improvement of intestinal absorption of peptide and protein drugs by chemical modification with fatty acids].
Yamamoto, A, 1998
)
0.3

Dosage Studied

Dose-response studies were performed using intravenous histamine or tetragastrin. D50 (the dose required for half-maximal response) was found to be similar between the two treatments.

ExcerptRelevanceReference
" Dose-response curves to TG showed nonparallel increases in both parameters."( Stimulation of oxyntic and histaminergic cells in gastric mucosa by gastrin C-terminal tetrapeptide.
Michelangeli, F; Ruiz, MC, 1986
)
0.27
" Dose-response quantitative generalization was obtained by using 1 and 2 micrograms/kg caerulein."( Neuroleptic-like properties of cholecystokinin analogs: distinctive mechanisms underlying similar behavioral profiles depending on the route of administration.
De Witte, P; Gewiss, M; Roques, B; Vanderhaeghen, JJ,
)
0.13
" However, no obvious dose-response relationship was observed in either intensity or duration of inhibitory action of ceruletide."( A behavioral pharmacological study on CCK-8 related peptides in mice.
Hagino, Y; Moroji, T, 1986
)
0.27
" Dose-response studies were performed using intravenous histamine or tetragastrin."( Stimulation of gastric acid secretion in the rhesus monkey.
Harmon, JW; Trout, HH; Zinner, M, 1985
)
0.5
" Analysis of the dose-response curves for the enzyme-activating effect of pentagastrin and cholecystokinin-octapeptide indicated that the D50 values for these two stimulants were not altered by shunting but that the maximal enzyme activation was greatly elevated."( Effects of portacaval shunt on the rat stomach.
Ekelund, M; Håkanson, R; Holmin, T; Oscarson, J; Rehfeld, JF; Sundler, F; Westrin, P, 1985
)
0.27
" CCK octapeptide (CCK-8) induced biphasic dose-response curves for stimulation of pancreatic juice and amylase secretion."( Effects of C-terminal fragments of cholecystokinin on exocrine and endocrine secretion from isolated perfused rat pancreas.
Baba, S; Ohki, A; Okabayashi, Y; Otsuki, M; Sakamoto, C, 1983
)
0.27
" Dose-response curves to CCK for amylase release shifted to the right with increase in proglumide concentration."( In vitro and in vivo effect of proglumide on cholecystokinin-stimulated amylase release in mouse pancreatic acini.
Akanuma, Y; Iwamoto, Y; Nakamura, R, 1984
)
0.27
" Lineweaver-Burk and Dowd-Riggs transformations of dose-response data obtained with tetragastrin alone and tetragastrin plus GIP showed similar D50 (the dose required for half-maximal response)."( The effect of gastric inhibitory polypeptide (GIP) on gastric acid secretion in dogs.
Iinuma, Y, 1981
)
0.49
" The strength of regular contraction of the stomach was dependent on the dosage of gastrin."( [Effect of tetragastrin on electrical and contractile activities of the canine stomach and duodenum (author's transl)].
Kawauchi, M, 1980
)
0.65
" The downward portion of the dose-response curve has been referred to as "high-dose" inhibition."( Novel CCK analogues and bombesin: a detailed analysis between phosphoinositide breakdown and high-dose inhibition of pancreatic enzyme secretion in three rodent species.
Bianchi, BR; Lin, CW; Miller, TR; Witte, DG, 1994
)
0.29
" To further explore the utility of pentagastrin as a challenge agent and to determine whether its effects are dose-related, a dose-response study was conducted in ten healthy volunteers."( Peptides and anxiety: a dose-response evaluation of pentagastrin in healthy volunteers.
Geraci, M; McCann, UD; Slate, SO; Uhde, TW,
)
0.13
" Although the compound is less water soluble than CI-988, oral bioavailability in rat was improved nearly 10 times relative to CI-988 when dosed in HP beta CD."( 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.
Boden, P; Eden, JM; Field, MJ; Hill, D; Hinton, JP; Holmes, A; Kneen, C; Padia, JK; Pritchard, MC; Rose, S; Singh, L; Suman-Chauhan, N; Trivedi, BK; Webdale, L; Wright, DS, 1998
)
0.3
" Both lorglumide and PD-135,158 induced a significant shift to the left in the morphine dose-response curves as well as a significant decrease in ED50 of the STR."( Stimulation of either cholecystokinin receptor subtype reduces while antagonists potentiate or sensitize a morphine-induced excitatory response.
Cacheiro, RG; Cruz, TN; Felicio, LF; Flório, JC; Mazzini, BK; Nasello, AG, 2001
)
0.31
" Blockade of MR with spironolactone increases baseline cortisol secretion and impairs cognitive function but has no effect on experimentally induced panic symptoms in humans, for the study design and dosage of spironolactone used."( Blockade of the mineralocorticoid receptor in healthy men: effects on experimentally induced panic symptoms, stress hormones, and cognition.
Kellner, M; Koop, M; Madrischewski, AM; Moritz, S; Otte, C; Wiedemann, K; Yassouridis, A, 2007
)
0.34
" Small sample sizes in many panic provocation studies, lack of dose-response aspects, and still-insufficient knowledge about the biological underpinning of experimental and spontaneous panic limit the interpretation of existing findings and should inspire further research."( Experimental panic provocation in healthy man-a translational role in anti-panic drug development?
Kellner, M, 2011
)
0.37
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

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]

Market Indicators

Research Demand Index: 15.46

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index15.46 (24.57)
Research Supply Index6.42 (2.92)
Research Growth Index4.25 (4.65)
Search Engine Demand Index15.26 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (15.46)

All Compounds (24.57)

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]