Identification

Name
Betazole
Accession Number
DB00272  (APRD00714)
Type
Small Molecule
Groups
Approved
Description

A histamine H2 agonist used clinically to test gastric secretory function. [PubChem]

Structure
Thumb
Synonyms
  • 1H-pyrazole-3-ethanamine
  • 2-(1H-Pyrazol-5-yl)ethanamine
  • 2-(3-Pyrazolyl)ethylamine
  • 3-(2-Aminoethyl)pyrazole
  • 3-(beta-aminoethyl)pyrazole
  • 3-(β-aminoethyl)pyrazole
  • Ametazole
  • Betazol
  • Betazolum
Product Ingredients
IngredientUNIICASInChI Key
Betazole hydrochloride66ABP6C83F138-92-1BUXCUOWXTOKEMQ-UHFFFAOYSA-N
International/Other Brands
Gastramine / Histalog (Lilly)
Categories
UNII
1C065P542O
CAS number
105-20-4
Weight
Average: 111.1451
Monoisotopic: 111.079647303
Chemical Formula
C5H9N3
InChI Key
JXDFEQONERDKSS-UHFFFAOYSA-N
InChI
InChI=1S/C5H9N3/c6-3-1-5-2-4-7-8-5/h2,4H,1,3,6H2,(H,7,8)
IUPAC Name
2-(1H-pyrazol-5-yl)ethan-1-amine
SMILES
NCCC1=CC=NN1

Pharmacology

Indication

For use clinically to test gastric secretory function.

Structured Indications
Not Available
Pharmacodynamics

Betazole is a histamine H2 agonist used in a test for measuring maximal production of gastric acidity or anacidity. This measurement can be used to diagnose diseases such as Zollinger-Ellison syndrome, whereby the volume of gastric and basal secretions is measured following betazole administration (greater than 60% of the maximal acid secretion following betazole stimulation). In another test, gastritis can be diagnosed given late absence of gastric acid which is unresponsive to betazole stimulation. Betazole can be used as a gastric secretory stimulant instead of histamine with the advantage of not provoking side effects and thus not requiring the use of antihistaminic compounds.

Mechanism of action

Betazole is a histamine analogue. It produces the same effects as histamine, binding the H2 receptor which is a mediator of gastric acid secretion. This agonist action thereby results in an increase in the volume of gastric acid produced.

TargetActionsOrganism
AHistamine H2 receptor
agonist
Human
Absorption

Rapid and complete.

Volume of distribution
Not Available
Protein binding

> 99%

Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Betazole Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference

Jones, R.G.; US. Patent 2,785,177; March 12,1957; assigned to Eli Lilly and Company.

General References
Not Available
External Links
Human Metabolome Database
HMDB14417
PubChem Compound
7741
PubChem Substance
46506808
ChemSpider
7455
ChEBI
59170
ChEMBL
CHEMBL1201323
Therapeutic Targets Database
DAP001081
PharmGKB
PA164784036
Wikipedia
Betazole
ATC Codes
V04CG02 — Betazole

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
  • Eli lilly and co
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Liquid
Experimental Properties
PropertyValueSource
melting point (°C)< 25 °CPhysProp
boiling point (°C)118-123Jones, R.G.; US. Patent 2,785,177; March 12,1957; assigned to Eli Lilly and Company.
logP0.1Not Available
Predicted Properties
PropertyValueSource
Water Solubility156.0 mg/mLALOGPS
logP-0.64ALOGPS
logP-0.62ChemAxon
logS0.15ALOGPS
pKa (Strongest Acidic)14.52ChemAxon
pKa (Strongest Basic)9.79ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area54.7 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity32.96 m3·mol-1ChemAxon
Polarizability11.96 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9935
Blood Brain Barrier+0.9645
Caco-2 permeable-0.54
P-glycoprotein substrateNon-substrate0.7217
P-glycoprotein inhibitor INon-inhibitor0.9449
P-glycoprotein inhibitor IINon-inhibitor0.9285
Renal organic cation transporterNon-inhibitor0.5842
CYP450 2C9 substrateNon-substrate0.9186
CYP450 2D6 substrateNon-substrate0.7147
CYP450 3A4 substrateNon-substrate0.7619
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9232
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.9435
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9246
Ames testNon AMES toxic0.6534
CarcinogenicityNon-carcinogens0.7378
BiodegradationNot ready biodegradable0.9569
Rat acute toxicity2.3391 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9255
hERG inhibition (predictor II)Non-inhibitor0.8321
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (7.03 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
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 2-arylethylamines. These are primary amines that have the general formula RCCNH2, where R is an organic group.
Kingdom
Organic compounds
Super Class
Organic nitrogen compounds
Class
Organonitrogen compounds
Sub Class
Amines
Direct Parent
2-arylethylamines
Alternative Parents
Aralkylamines / Pyrazoles / Heteroaromatic compounds / Azacyclic compounds / Organopnictogen compounds / Monoalkylamines / Hydrocarbon derivatives
Substituents
2-arylethylamine / Aralkylamine / Heteroaromatic compound / Pyrazole / Azole / Azacycle / Organoheterocyclic compound / Organopnictogen compound / Hydrocarbon derivative / Primary aliphatic amine
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
pyrazoles, primary amino compound (CHEBI:59170)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Histamine receptor activity
Specific Function
The H2 subclass of histamine receptors mediates gastric acid secretion. Also appears to regulate gastrointestinal motility and intestinal secretion. Possible role in regulating cell growth and diff...
Gene Name
HRH2
Uniprot ID
P25021
Uniprot Name
Histamine H2 receptor
Molecular Weight
40097.65 Da
References
  1. Hammond JB, Offen WW: Effect of nizatidine and cimetidine on betazole-stimulated gastric secretion of normal subjects: comparison of effects on acid, water, and pepsin. Am J Gastroenterol. 1988 Jan;83(1):32-6. [PubMed:2892392]
  2. Leth R, Elander B, Haglund U, Olbe L, Fellenius E: Histamine H2-receptor of human and rabbit parietal cells. Am J Physiol. 1987 Oct;253(4 Pt 1):G497-501. [PubMed:3661710]
  3. Katz LB, Tobia AJ, Shriver DA: Effects of ORF 17583, other histamine H2-receptor antagonists and omeprazole on gastric acid secretory states in rats and dogs. J Pharmacol Exp Ther. 1987 Aug;242(2):437-42. [PubMed:2886642]
  4. Katz LB, Scott CK, Shriver DA: Pharmacological comparison of ORF 17910, a potent, long-acting histamine H2-receptor antagonist, to cimetidine and ranitidine. J Pharmacol Exp Ther. 1986 Aug;238(2):587-93. [PubMed:2874214]
  5. Ribeiro TC, Salgado JA, Castro Lde P: Effect of cimetidine on basal and betazole-stimulated gastric acid secretion in peptic ulcer. Arq Gastroenterol. 1980 Jan-Mar;17(1):4-6. [PubMed:7213132]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]

Drug created on June 13, 2005 07:24 / Updated on November 07, 2017 01:35