Identification

Name
Pentagastrin
Accession Number
DB00183  (APRD01172)
Type
Small Molecule
Groups
Approved
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
Synonyms
Not Available
External IDs
AY-6608 / ICI 50,123
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Peptavlon Liq Inj 0.25mg/mlLiquid.25 mgIntramuscular; Intravenous; SubcutaneousWyeth Ayerst Canada Inc.1994-12-311998-09-18Canada
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
PentagastrinPentagastrin (250 ug/1.6mL)SolutionIntravenousAnazao Health Corporation2012-06-19Not applicableUs
International/Other Brands
Peptavlon
Categories
UNII
EF0NX91490
CAS number
5534-95-2
Weight
Average: 767.9
Monoisotopic: 767.33124736
Chemical Formula
C37H49N7O9S
InChI Key
NEYNJQRKHLUJRU-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[C@H](NC(=O)[C@H](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

Pharmacology

Indication

Used as a diagnostic aid for evaluation of gastric acid secretory function

Associated Conditions
Pharmacodynamics

Pentagastrin 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 action

The 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.

TargetActionsOrganism
AGastrin/cholecystokinin type B receptor
agonist
Human
Absorption

Rapidly absorbed after parenteral administration.

Volume of distribution
Not Available
Protein binding
Not Available
Metabolism

Primarily hepatic

Route of elimination
Not Available
Half life

10 minutes or less

Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

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
KEGG Drug
D01631
PubChem Compound
9853654
PubChem Substance
46507747
ChemSpider
8029364
BindingDB
50024321
ChEBI
31974
ChEMBL
CHEMBL1328
Therapeutic Targets Database
DNC001170
PharmGKB
PA450849
IUPHAR
870
Guide to Pharmacology
GtP Drug Page
Wikipedia
Pentagastrin
ATC Codes
V04CG04 — Pentagastrin

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
  • Wyeth ayerst laboratories
Packagers
Not Available
Dosage forms
FormRouteStrength
SolutionIntravenous250 ug/1.6mL
LiquidIntramuscular; Intravenous; Subcutaneous.25 mg
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)229 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 FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Peptidomimetics
Sub Class
Hybrid peptides
Direct Parent
Hybrid peptides
Alternative Parents
Phenylalanine and derivatives / Aspartic acid and derivatives / Methionine and derivatives / N-acyl-alpha amino acids and derivatives / Tryptamines and derivatives / Alpha amino acid amides / Beta amino acids and derivatives / 3-alkylindoles / Amphetamines and derivatives / Substituted pyrroles
show 16 more
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
show 35 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not 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 me...
Gene Name
CCKBR
Uniprot ID
P32239
Uniprot Name
Gastrin/cholecystokinin type B receptor
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
Uniprot Name
Cholinesterase
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]

Drug created on June 13, 2005 07:24 / Updated on November 02, 2018 04:38