Identification
- Summary
Pentagastrin is a gastrin-like molecule used as a diagnostic aid for the evaluation of gastric acid secretory function, gastric hypersecretion, and Zollinger-Ellison tumors.
- Generic Name
- Pentagastrin
- DrugBank Accession Number
- DB00183
- Background
A synthetic pentapeptide that mimics the actions of endogenous gastrin when given parenterally. It works by stimulating the secretion of gastric acid, pepsin, and intrinsic factor. It has also been used as a diagnostic aid.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Pentagastrin (DB00183)
- Weight
- Average: 767.9
Monoisotopic: 767.33124736 - Chemical Formula
- C37H49N7O9S
- Synonyms
- Pentagastrin
- External IDs
- AY-6608
- ICI 50,123
Pharmacology
- Indication
Used as a diagnostic aid for evaluation of gastric acid secretory function
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- Contraindications & Blackbox Warnings
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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.
Target Actions Organism AGastrin/cholecystokinin type B receptor agonistHumans - 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
- Adverse Effects
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Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareHistamine The serum concentration of Histamine can be increased when it is combined with Pentagastrin. 
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- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- Peptavlon
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Pentagastrin Solution 250 ug/1.6mL Intravenous Anazao Health Corporation 2012-06-19 Not applicable US 
Peptavlon Liq Inj 0.25mg/ml Liquid .25 mg / mL Intramuscular; Intravenous; Subcutaneous Wyeth Ayerst Canada Inc. 1994-12-31 1998-09-18 Canada 
- Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Pentagastrin Pentagastrin (250 ug/1.6mL) Solution Intravenous Anazao Health Corporation 2012-06-19 Not applicable US
Categories
- ATC Codes
- V04CG04 — Pentagastrin
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- 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
- 3-alkylindole / Alpha-amino acid amide / Alpha-amino acid or derivatives / Amphetamine or derivatives / Aromatic heteropolycyclic compound / Aspartic acid or derivatives / Azacycle / Benzenoid / Beta amino acid or derivatives / Carbamic acid ester show 35 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- EF0NX91490
- CAS number
- 5534-95-2
- 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
References
- General References
- 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. [Article]
- External Links
- KEGG Drug
- D01631
- PubChem Compound
- 9853654
- PubChem Substance
- 46507747
- ChemSpider
- 8029364
- BindingDB
- 50024321
- 7993
- ChEBI
- 31974
- ChEMBL
- CHEMBL1328
- ZINC
- ZINC000008214644
- Therapeutic Targets Database
- DNC001170
- PharmGKB
- PA450849
- Guide to Pharmacology
- GtP Drug Page
- Wikipedia
- Pentagastrin
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count Not Available Completed Not Available Gastric Acid Secretory Disorders 1
Pharmacoeconomics
- Manufacturers
- Wyeth ayerst laboratories
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Solution Intravenous 250 ug/1.6mL Liquid Intramuscular; Intravenous; Subcutaneous .25 mg / mL - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 229 dec °C PhysProp logP 1.6 Not Available - Predicted Properties
Property Value Source Water Solubility 0.00261 mg/mL ALOGPS logP 1.66 ALOGPS logP 1.05 Chemaxon logS -5.5 ALOGPS pKa (Strongest Acidic) 4 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 8 Chemaxon Hydrogen Donor Count 8 Chemaxon Polar Surface Area 250.91 Å2 Chemaxon Rotatable Bond Count 22 Chemaxon Refractivity 200.04 m3·mol-1 Chemaxon Polarizability 78.01 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9781 Blood Brain Barrier - 0.8889 Caco-2 permeable - 0.7803 P-glycoprotein substrate Substrate 0.8173 P-glycoprotein inhibitor I Inhibitor 0.5349 P-glycoprotein inhibitor II Non-inhibitor 0.8697 Renal organic cation transporter Non-inhibitor 0.8741 CYP450 2C9 substrate Non-substrate 0.7942 CYP450 2D6 substrate Non-substrate 0.7192 CYP450 3A4 substrate Substrate 0.5854 CYP450 1A2 substrate Non-inhibitor 0.7808 CYP450 2C9 inhibitor Non-inhibitor 0.6841 CYP450 2D6 inhibitor Non-inhibitor 0.8705 CYP450 2C19 inhibitor Non-inhibitor 0.6693 CYP450 3A4 inhibitor Non-inhibitor 0.7511 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7453 Ames test Non AMES toxic 0.7568 Carcinogenicity Non-carcinogens 0.9366 Biodegradation Not ready biodegradable 0.9946 Rat acute toxicity 3.2696 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9773 hERG inhibition (predictor II) Inhibitor 0.5659
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- Kind
- Protein
- Organism
- Humans
- 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
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- 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
- 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. [Article]
Drug created at June 13, 2005 13:24 / Updated at October 02, 2023 22:05