ContaminantDB: Bitolterol

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-22 03:37:58 UTC

Update Date

2016-11-09 01:15:26 UTC

Accession Number

CHEM016592

Identification

Common Name

Bitolterol

Class

Small 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 Bitolterol was withdrawn from the market by Elan Pharmaceuticals in 2001.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 Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
4-(2-(Tert-butylamino)-1-hydroxyethyl)-O-phenylene di-p-toluate	ChEBI
4-[2-(Tert-butylamino)-1-hydroxyethyl]-O-phenylene di-p-toluate	ChEBI
Bis(4-methylbenzoic acid) 4-[2-(tert-butylamino)-1-hydroxyethyl]-1,2-phenylene ester	ChEBI
Bitolterolum	ChEBI
4-(2-(Tert-butylamino)-1-hydroxyethyl)-O-phenylene di-p-toluic acid	Generator
4-[2-(Tert-butylamino)-1-hydroxyethyl]-O-phenylene di-p-toluic acid	Generator
Bis(4-methylbenzoate) 4-[2-(tert-butylamino)-1-hydroxyethyl]-1,2-phenylene ester	Generator
Dura brand OF bitolterol methanesulfonate	MeSH
Bitolterol mesylate	MeSH
Tornalate	MeSH
Bitolterol methanesulfonate	MeSH

Chemical Formula

C₂₈H₃₁NO₅

Average Molecular Mass

461.549 g/mol

Monoisotopic Mass

461.220 g/mol

CAS Registry Number

30392-40-6

IUPAC Name

4-[2-(tert-butylamino)-1-hydroxyethyl]-2-(4-methylbenzoyloxy)phenyl 4-methylbenzoate

Traditional Name

bitolterol

SMILES

CC1=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 Identifier

InChI=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 Key

FZGVEKPRDOIXJY-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).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Depsides and depsidones

Sub Class

Not Available

Direct Parent

Depsides 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 Framework

Aromatic homomonocyclic compounds

External Descriptors

diester (CHEBI:3133 )
carboxylic ester (CHEBI:3133 )
secondary alcohol (CHEBI:3133 )
secondary amino compound (CHEBI:3133 )
ethanolamines (CHEBI:3133 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.00048 g/L	ALOGPS
logP	4.69	ALOGPS
logP	6.3	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	14	ChemAxon
pKa (Strongest Basic)	9.59	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	84.86 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	132.76 m³·mol⁻¹	ChemAxon
Polarizability	50.91 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-06dr-9515300000-9183ab463ea023a403bf	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-07bf-0206900000-0d2add6387daa82a668a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-06du-0409400000-bb41c3be88071d157bd2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-5931000000-5bf735cde96a513326c6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03dl-2203900000-2ae4baeac004d904db77	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0076-8519700000-66927241cb18ed810572	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000l-7931000000-151a6828e2b9760ef552	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05n0-0406900000-3abf7d0e232423e8dc9f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kr-3409400000-5ffcffe98e28c353480b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9100000000-e6b66fd8168c15691318	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0002900000-898b8130cb2475df346a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01vo-0029500000-546df6039034f820cc04	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-8379500000-a31b75ebcff135547850	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB00901

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Bitolterol

Chemspider ID

Not Available

ChEBI ID

3133

PubChem Compound ID

35330

Kegg Compound ID

C06853

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. https://www.ncbi.nlm.nih.gov/pubmed/?term=3278878

2. https://www.ncbi.nlm.nih.gov/pubmed/?term=473792

Bitolterol (CHEM016592)

Structure for CHEM016592: Bitolterol