Betazole
Identification
- Generic Name
- Betazole
- DrugBank Accession Number
- DB00272
- Background
A histamine H2 agonist used clinically to test gastric secretory function.
- Type
- Small Molecule
- Groups
- Approved
- Structure
- Weight
- Average: 111.1451
Monoisotopic: 111.079647303 - Chemical Formula
- C5H9N3
- 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
- Betazole
- Betazolum
Pharmacology
- Indication
For use clinically to test gastric secretory function.
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- 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.
Target Actions Organism AHistamine H2 receptor agonistHumans - 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
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
Pathway Category Betazole Action Pathway Drug action - 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.Not Available
- Food Interactions
- Not Available
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.
- Product Ingredients
Ingredient UNII CAS InChI Key Betazole hydrochloride 66ABP6C83F 138-92-1 BUXCUOWXTOKEMQ-UHFFFAOYSA-N - International/Other Brands
- Gastramine / Histalog (Lilly)
Categories
- ATC Codes
- V04CG02 — Betazole
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- 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 / Aromatic heteromonocyclic compound / Azacycle / Azole / Heteroaromatic compound / Hydrocarbon derivative / Organoheterocyclic compound / Organopnictogen compound / Primary aliphatic amine
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- pyrazoles, primary amino compound (CHEBI:59170)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 1C065P542O
- CAS number
- 105-20-4
- 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
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
- HMDB0014417
- PubChem Compound
- 7741
- PubChem Substance
- 46506808
- ChemSpider
- 7455
- ChEBI
- 59170
- ChEMBL
- CHEMBL1201323
- ZINC
- ZINC000000001028
- Therapeutic Targets Database
- DAP001081
- PharmGKB
- PA164784036
- Wikipedia
- Betazole
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Eli lilly and co
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Liquid
- Experimental Properties
Property Value Source melting point (°C) < 25 °C PhysProp boiling point (°C) 118-123 Jones, R.G.; US. Patent 2,785,177; March 12,1957; assigned to Eli Lilly and Company. logP 0.1 Not Available - Predicted Properties
Property Value Source Water Solubility 156.0 mg/mL ALOGPS logP -0.64 ALOGPS logP -0.62 Chemaxon logS 0.15 ALOGPS pKa (Strongest Acidic) 14.52 Chemaxon pKa (Strongest Basic) 9.79 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 54.7 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 32.96 m3·mol-1 Chemaxon Polarizability 11.96 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9935 Blood Brain Barrier + 0.9645 Caco-2 permeable - 0.54 P-glycoprotein substrate Non-substrate 0.7217 P-glycoprotein inhibitor I Non-inhibitor 0.9449 P-glycoprotein inhibitor II Non-inhibitor 0.9285 Renal organic cation transporter Non-inhibitor 0.5842 CYP450 2C9 substrate Non-substrate 0.9186 CYP450 2D6 substrate Non-substrate 0.7147 CYP450 3A4 substrate Non-substrate 0.7619 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.9232 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.9435 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9246 Ames test Non AMES toxic 0.6534 Carcinogenicity Non-carcinogens 0.7378 Biodegradation Not ready biodegradable 0.9569 Rat acute toxicity 2.3391 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9255 hERG inhibition (predictor II) Non-inhibitor 0.8321
Spectra
- Mass Spec (NIST)
- Download (7.03 KB)
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available 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

- Kind
- Protein
- Organism
- Humans
- 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
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Drug created at June 13, 2005 13:24 / Updated at April 07, 2023 13:20