Bitolterol (CHEM016592)

Record Information
Version1.0
Creation Date2016-05-22 03:37:58 UTC
Update Date2026-05-14 16:52:19 UTC
Accession NumberCHEM016592
Identification
Common NameBitolterol
ClassSmall Molecule
Description
Bitolterol mesylate was used to treat bronchospasms in asthma and COPD. It is a beta-2-adrenergic receptor agonist. Bitolterol was withdrawn from the market by Elan Pharmaceuticals in 2001.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
4-(2-(Tert-butylamino)-1-hydroxyethyl)-O-phenylene di-p-toluateChEBI
4-[2-(Tert-butylamino)-1-hydroxyethyl]-O-phenylene di-p-toluateChEBI
Bis(4-methylbenzoic acid) 4-[2-(tert-butylamino)-1-hydroxyethyl]-1,2-phenylene esterChEBI
BitolterolumChEBI
4-(2-(Tert-butylamino)-1-hydroxyethyl)-O-phenylene di-p-toluic acidGenerator
4-[2-(Tert-butylamino)-1-hydroxyethyl]-O-phenylene di-p-toluic acidGenerator
Bis(4-methylbenzoate) 4-[2-(tert-butylamino)-1-hydroxyethyl]-1,2-phenylene esterGenerator
Dura brand OF bitolterol methanesulfonateMeSH
Bitolterol mesylateMeSH
TornalateMeSH
Bitolterol methanesulfonateMeSH
Chemical FormulaC28H31NO5
Average Molecular Mass461.549 g/mol
Monoisotopic Mass461.220 g/mol
CAS Registry Number30392-40-6
IUPAC Name4-[2-(tert-butylamino)-1-hydroxyethyl]-2-(4-methylbenzoyloxy)phenyl 4-methylbenzoate
Traditional Namebitolterol
SMILESCC1=CC=C(C=C1)C(=O)OC1=C(OC(=O)C2=CC=C(C)C=C2)C=C(C=C1)C(O)CNC(C)(C)C
InChI IdentifierInChI=1S/C28H31NO5/c1-18-6-10-20(11-7-18)26(31)33-24-15-14-22(23(30)17-29-28(3,4)5)16-25(24)34-27(32)21-12-8-19(2)9-13-21/h6-16,23,29-30H,17H2,1-5H3
InChI KeyFZGVEKPRDOIXJY-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as depsides and depsidones. These are polycyclic compounds that is either a polyphenolic compound composed of two or more monocyclic aromatic units linked by an ester bond (depside), or a compound containing the depsidone structure (depsidone).
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassDepsides and depsidones
Sub ClassNot Available
Direct ParentDepsides and depsidones
Alternative Parents
Substituents
  • Depside backbone
  • Benzoate ester
  • Phenol ester
  • Benzoic acid or derivatives
  • Phenoxy compound
  • Benzoyl
  • Aralkylamine
  • Toluene
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Benzenoid
  • Secondary alcohol
  • Amino acid or derivatives
  • 1,2-aminoalcohol
  • Carboxylic acid ester
  • Secondary amine
  • Carboxylic acid derivative
  • Secondary aliphatic amine
  • Aromatic alcohol
  • Organic oxide
  • Alcohol
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00048 g/LALOGPS
logP4.69ALOGPS
logP6.3ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)14ChemAxon
pKa (Strongest Basic)9.59ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area84.86 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity132.76 m³·mol⁻¹ChemAxon
Polarizability50.91 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDDB00901
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkBitolterol
Chemspider IDNot Available
ChEBI ID3133
PubChem Compound ID35330
Kegg Compound IDC06853
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=3278878
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=473792