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
2-(1H-Pyrazol-5-yl)ethanamineNot AvailableNot Available
2-(3-Pyrazolyl)ethylamineNot AvailableNot Available
3-(2-Aminoethyl)pyrazoleNot AvailableNot Available
3-(beta-aminoethyl)pyrazoleNot AvailableNot Available
3-(β-aminoethyl)pyrazoleNot AvailableNot Available
AmetazoleNot AvailableNot Available
BetazolSpanishINN
BetazolumLatinINN
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
GastramineNot Available
HistalogLilly
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Betazole hydrochloride
ThumbNot applicableDBSALT000898
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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.
KingdomOrganic compounds
Super ClassOrganonitrogen compounds
ClassAmines
Sub ClassAralkylamines
Direct ParentAralkylamines
Alternative Parents
Substituents
  • Aralkylamine
  • Heteroaromatic compound
  • Pyrazole
  • Azole
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Primary amine
  • Primary aliphatic amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
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%
MetabolismNot Available
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
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 substrateNon-inhibitor0.9071
CYP450 2D6 substrateNon-inhibitor0.9232
CYP450 2C19 substrateNon-inhibitor0.9025
CYP450 3A4 substrateNon-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
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 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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (7.03 KB)
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
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