You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameBetazole
Accession NumberDB00272  (APRD00714)
Typesmall molecule
Groupsapproved
Description

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

Structure
Thumb
Synonyms
SynonymLanguageCode
1H-pyrazole-3-ethanamineNot AvailableNot Available
3-(beta-aminoethyl)pyrazoleNot AvailableNot Available
3-(β-aminoethyl)pyrazoleNot AvailableNot Available
AmetazoleNot AvailableNot Available
BetazolSpanishINN
BetazolumLatinINN
Salts
Name/CAS Structure Properties
Betazole hydrochloride
Thumb Not applicable DBSALT000898
Brand names
NameCompany
GastramineNot Available
HistalogLilly
Brand mixturesNot Available
Categories
CAS number105-20-4
WeightAverage: 111.1451
Monoisotopic: 111.079647303
Chemical FormulaC5H9N3
InChI KeyJXDFEQONERDKSS-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
Mass Specshow(7.03 KB)
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassAzoles
SubclassPyrazoles
Direct parentPyrazoles
Alternative parentsPolyamines; Monoalkylamines
Substituentspolyamine; primary amine; primary aliphatic amine; amine; organonitrogen compound
Classification descriptionThis compound belongs to the pyrazoles. These are compounds containing a pyrazole ring, which is a five-member aromatic ring with two nitrogen atoms (at positions 1 and 2) and three carbon atoms.
Pharmacology
IndicationFor use clinically to test gastric secretory function.
PharmacodynamicsBetazole 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 actionBetazole 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.
AbsorptionRapid and complete.
Volume of distributionNot Available
Protein binding> 99%
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Betazole Action PathwayDrug actionSMP00736
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 substrate Non-inhibitor 0.9071
CYP450 2D6 substrate Non-inhibitor 0.9232
CYP450 2C19 substrate Non-inhibitor 0.9025
CYP450 3A4 substrate 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
Pharmacoeconomics
Manufacturers
  • Eli lilly and co
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Stateliquid
Experimental Properties
PropertyValueSource
melting point< 25 °CPhysProp
boiling point118-123Jones, R.G.; US. Patent 2,785,177; March 12,1957; assigned to Eli Lilly and Company.
logP0.1Not Available
Predicted Properties
PropertyValueSource
water solubility1.56e+02 g/lALOGPS
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 area54.7ChemAxon
rotatable bond count2ChemAxon
refractivity32.96ChemAxon
polarizability11.96ChemAxon
number of rings1ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

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

General ReferenceNot Available
External Links
ResourceLink
PubChem Compound7741
PubChem Substance46506808
ChemSpider7455
ChEBI59170
ChEMBL
Therapeutic Targets DatabaseDAP001081
PharmGKBPA164784036
WikipediaBetazole
ATC CodesV04CG02
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Histamine H2 receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Histamine H2 receptor P25021 Details

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
  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
  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
  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
  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
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on April 01, 2014 12:53