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Identification
NamePentagastrin
Accession NumberDB00183  (APRD01172)
TypeSmall Molecule
GroupsApproved
Description

A synthetic pentapeptide that has effects like gastrin when given parenterally. It stimulates the secretion of gastric acid, pepsin, and intrinsic factor, and has been used as a diagnostic aid. [PubChem]

Structure
Thumb
SynonymsNot Available
External Identifiers
  • AY-6608
  • ICI 50,123
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Peptavlon Liq Inj 0.25mg/mlliquid.25 mgintramuscular; intravenous; subcutaneousWyeth Ayerst Canada Inc.1994-12-311998-09-18Canada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Pentagastrinsolution250 ug/1.6mLintravenousAnazao Health Corporation2012-06-19Not applicableUs
International Brands
NameCompany
PeptavlonNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIEF0NX91490
CAS number5534-95-2
WeightAverage: 767.9
Monoisotopic: 767.33124736
Chemical FormulaC37H49N7O9S
InChI KeyNEYNJQRKHLUJRU-DZUOILHNSA-N
InChI
InChI=1S/C37H49N7O9S/c1-37(2,3)53-36(52)39-16-14-30(45)41-28(19-23-21-40-25-13-9-8-12-24(23)25)34(50)42-26(15-17-54-4)33(49)44-29(20-31(46)47)35(51)43-27(32(38)48)18-22-10-6-5-7-11-22/h5-13,21,26-29,40H,14-20H2,1-4H3,(H2,38,48)(H,39,52)(H,41,45)(H,42,50)(H,43,51)(H,44,49)(H,46,47)/t26-,27-,28-,29-/m0/s1
IUPAC Name
(3S)-3-[(2S)-2-[(2S)-2-(3-{[(tert-butoxy)carbonyl]amino}propanamido)-3-(1H-indol-3-yl)propanamido]-4-(methylsulfanyl)butanamido]-3-{[(1S)-1-carbamoyl-2-phenylethyl]carbamoyl}propanoic acid
SMILES
CSCC[[email protected]](NC(=O)[[email protected]](CC1=CNC2=C1C=CC=C2)NC(=O)CCNC(=O)OC(C)(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC1=CC=CC=C1)C(N)=O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as hybrid peptides. These are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentHybrid peptides
Alternative Parents
Substituents
  • Hybrid peptide
  • Phenylalanine or derivatives
  • Aspartic acid or derivatives
  • Methionine or derivatives
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Triptan
  • Beta amino acid or derivatives
  • N-substituted-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Amphetamine or derivatives
  • 3-alkylindole
  • Indole or derivatives
  • Indole
  • Substituted pyrrole
  • Monocyclic benzene moiety
  • Fatty acyl
  • N-acyl-amine
  • Fatty amide
  • Benzenoid
  • Heteroaromatic compound
  • Carbamic acid ester
  • Pyrrole
  • Primary carboxylic acid amide
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Azacycle
  • Thioether
  • Monocarboxylic acid or derivatives
  • Sulfenyl compound
  • Dialkylthioether
  • Organoheterocyclic compound
  • Carboxylic acid
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Organonitrogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationUsed as a diagnostic aid for evaluation of gastric acid secretory function
PharmacodynamicsPentagastrin is indicated as a diagnostic aid for evaluation of gastric acid secretory function. It is effective in testing for anacidity (achlorhydria) in patients with suspected pernicious anemia, atrophic gastritis, or gastric carcinoma. It is also effective in determining the reduction in acid output after operations for peptic ulcer, such as vagotomy or gastric resection.
Mechanism of actionThe exact mechanism by which pentagastrin stimulates gastric acid, pepsin, and intrinsic factor secretion is unknown; however, since pentagastrin is an analogue of natural gastrin, it is believed that it excites the oxyntic cells of the stomach to secrete to their maximum capacity. Pentagastrin stimulates pancreatic secretion, especially when administered in large intramuscular doses. Pentagastrin also increases gastrointestinal motility by a direct effect on the intestinal smooth muscle. However, it delays gastric emptying time probably by stimulation of terminal antral contractions, which enhance retropulsion.
Related Articles
AbsorptionRapidly absorbed after parenteral administration.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Primarily hepatic

Route of eliminationNot Available
Half life10 minutes or less
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9781
Blood Brain Barrier-0.8889
Caco-2 permeable-0.7803
P-glycoprotein substrateSubstrate0.8173
P-glycoprotein inhibitor IInhibitor0.5349
P-glycoprotein inhibitor IINon-inhibitor0.8697
Renal organic cation transporterNon-inhibitor0.8741
CYP450 2C9 substrateNon-substrate0.7942
CYP450 2D6 substrateNon-substrate0.7192
CYP450 3A4 substrateSubstrate0.5854
CYP450 1A2 substrateNon-inhibitor0.7808
CYP450 2C9 inhibitorNon-inhibitor0.6841
CYP450 2D6 inhibitorNon-inhibitor0.8705
CYP450 2C19 inhibitorNon-inhibitor0.6693
CYP450 3A4 inhibitorNon-inhibitor0.7511
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7453
Ames testNon AMES toxic0.7568
CarcinogenicityNon-carcinogens0.9366
BiodegradationNot ready biodegradable0.9946
Rat acute toxicity3.2696 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9773
hERG inhibition (predictor II)Inhibitor0.5659
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Wyeth ayerst laboratories
PackagersNot Available
Dosage forms
FormRouteStrength
Solutionintravenous250 ug/1.6mL
Liquidintramuscular; intravenous; subcutaneous.25 mg
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point229 dec °CPhysProp
logP1.6Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00261 mg/mLALOGPS
logP1.66ALOGPS
logP1.05ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area250.91 Å2ChemAxon
Rotatable Bond Count22ChemAxon
Refractivity200.04 m3·mol-1ChemAxon
Polarizability78.01 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis ReferenceNot Available
General References
  1. Weintraub HS, Rudolph A: Combination therapy for managing difficult-to-treat patients with stage 2 hypertension: focus on valsartan-based combinations. Am J Ther. 2011 Nov;18(6):e227-43. doi: 10.1097/MJT.0b013e3181da0437. [PubMed:20535014 ]
External Links
ATC CodesV04CG04
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Type b gastrin/cholecystokinin receptor binding
Specific Function:
Receptor for gastrin and cholecystokinin. The CKK-B receptors occur throughout the central nervous system where they modulate anxiety, analgesia, arousal, and neuroleptic activity. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system.Isoform 2 is constitutively activated and may regulate cancer cell proliferation v...
Gene Name:
CCKBR
Uniprot ID:
P32239
Molecular Weight:
48418.51 Da
References
  1. Radu D, Ahlin A, Svanborg P, Lindefors N: Anxiogenic effects of the CCK(B) agonist pentagastrin in humans and dose-dependent increase in plasma C-peptide levels. Psychopharmacology (Berl). 2002 Jun;161(4):396-403. Epub 2002 Apr 17. [PubMed:12073167 ]
  2. Khan S, Liberzon I, Abelson JL: Effect of repeat exposure on neuroendocrine and symptom responses to pentagastrin. Psychiatry Res. 2004 May 30;126(3):189-95. [PubMed:15157745 ]
  3. Makovec F, Peris W, Revel L, Giovanetti R, Mennuni L, Rovati LC: Structure-antigastrin activity relationships of new (R)-4-benzamido-5-oxopentanoic acid derivatives. J Med Chem. 1992 Jan;35(1):28-38. [PubMed:1732532 ]
  4. Singh P, Walker JP, Townsend CM Jr, Thompson JC: Role of gastrin and gastrin receptors on the growth of a transplantable mouse colon carcinoma (MC-26) in BALB/c mice. Cancer Res. 1986 Apr;46(4 Pt 1):1612-6. [PubMed:3004700 ]
  5. Nishida A, Kobayashi-Uchida A, Akuzawa S, Takinami Y, Shishido T, Kamato T, Ito H, Yamano M, Yuki H, Nagakura Y, et al.: Gastrin receptor antagonist YM022 prevents hypersecretion after long-term acid suppression. Am J Physiol. 1995 Nov;269(5 Pt 1):G699-705. [PubMed:7491961 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inducer
General Function:
Identical protein binding
Specific Function:
Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name:
BCHE
Uniprot ID:
P06276
Molecular Weight:
68417.575 Da
References
  1. Chernysheva SV, Iaremko EE: [Cholinergic and hormonal correlations in the regulation of the secretory function of the small intestine]. Fiziol Zh SSSR Im I M Sechenova. 1983 Jun;69(6):827-31. [PubMed:6873393 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23