Basic information
- CAS
30392-40-6- Standard SMILES
Cc1ccc(C(=O)Oc2ccc(C(O)CNC(C)(C)C)cc2OC(=O)c2ccc(C)cc2)cc1- InChIKey
FZGVEKPRDOIXJY-UHFFFAOYSA-N- Molecular formula
- C28H31NO5
- Average molar mass
- 461.5 g/mol
- Monoisotopic mass
- 461.22022309
Overview
Bitolterol is the di-4-toluate ester of (+-)-N-tert-butylnoradrenaline (colterol). A pro-drug for colterol, a beta2-adrenergic receptor agonist, bitolterol is used as its methanesulfonate salt for relief of bronchospasm in conditions such as asthma, chronic bronchitis and emphysema. It has a role as a beta-adrenergic agonist, a bronchodilator agent, an anti-asthmatic drug and a prodrug. It is a member of ethanolamines, a carboxylic ester, a secondary alcohol, a secondary amino compound and a diester.
Names & identifiers
- Preferred name
- Bitolterol
- IUPAC
- [4-[2-(tert-butylamino)-1-hydroxyethyl]-2-(4-methylbenzoyl)oxyphenyl] 4-methylbenzoate
- English name
- Bitolterol
- Molecular formula
- C28H31NO5
- Molecular weight
- 461.55
Names & synonyms
Bitolterol30392-40-6BitolterolumDTXSID10226839KY0QXD6LICHEBI:3133DTXCID002683Benzoic acid, 4-methyl-, 4-(2-((1,1-dimethylethyl)amino)-1-hydroxyethyl)-1,2-phenylene ester4-(2-(tert-butylamino)-1-hydroxyethyl)-o-phenylene di-p-toluate4-[2-(tert-Butylamino)-1-hydroxyethyl]-o-phenylene di-p-toluatebis(4-methylbenzoic acid) 4-[2-(tert-butylamino)-1-hydroxyethyl]-1,2-phenylene esterbitolterolo
Show more names
C06853Bitolterol USP/EP/BPBis(p-toluic acid)4-[2-(tert-butylamino)-1-hydroxyethyl]-1,2-phenylene esterBis(4-methylbenzoic acid)4-[2-(tert-butylamino)-1-hydroxyethyl]-1,2-phenylene ester
bis(4-methylbenzoic acid) 4-(2-(tert-butylamino)-1-hydroxyethyl)-1,2-phenylene esterRefChem:120554R03AC175-(2-(tert-butylamino)-1-hydroxyethyl)-2-(4-methylbenzoyloxy)phenyl 4-methylbenzoate[4-[2-(tert-butylamino)-1-hydroxyethyl]-2-(4-methylbenzoyl)oxyphenyl] 4-methylbenzoateWIN 32784Bitolterol (INN)Benzoic acid, 4-methyl-, 1,1'-[4-[2-[(1,1-dimethylethyl)amino]-1-hydroxyethyl]-1,2-phenylene] ester
Properties
Computed structural properties
- XLogP
- 5.2
- Topological polar surface area
- 84.9 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 10
- Heavy atoms
- 34
- Formal charge
- 0
- Complexity
- 658
Experimental & physicochemical properties
Human DrugsBreast Feeding; Lactation; Milk, Human; Anti-Asthmatic Agents; Bronchodilator Agents; Beta Adrenergic Agonists
Physicochemical properties
- Boiling point
- 640.5 · 640.5±55.0 °C(Predicted)
- Density
- 1.169 · 1.169±0.06 g/cm3(Predicted)
- pka
- 13.61 · 13.61±0.20(Predicted)
- FDA UNII
- 9 KY0QXD6LI · 9KY0QXD6LI
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Toxicology
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
Bitolterol
DILI Negative
DOI:10.1016/j.drudis.2019.09.022
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Chemistry & industry
Pharmacology
ATC Code
R - Respiratory system
QR - Respiratory system
Pharmacodynamics
Bitolterol, an adrenergic bronchodilator, is a prodrug that widens constricted airways in the lungs by relaxing the smooth muscles that surround the bronchial passages. Bitolterol probably does not affect the inflammation in the lung, such as in bronchitis. Bitolterol is unique in that it is a prodrug because it must first be metabolized by the body before it becomes active.
Mechanism of Action
Bitolterol is an adrenergic beta-2 agonist. Asthma results from a narrowing of the bronchial tubes. This narrowing is caused by muscle spasm and inflammation within the bronchial tubes. Agonism of the beta-2 adrenergic receptors by bitolterol leads to a relaxation of the smooth muscles surrounding these airway tubes which then increases the diameter and ease of air flow through the tubes.
MeSH Pharmacological Classification
Agents that cause an increase in the expansion of a bronchus or bronchial tubes.
Compounds bind to and activate ADRENERGIC BETA-2 RECEPTORS.
Applications
UsesBitolterol is a is a β2-adrenergic receptor agonist used for the relief of bronchospasm in conditions such as asthma and COPD.
Suppliers7 total
湖北扬信医药科技有限公司0714-3999001 19171453112 · [email protected]
上海陶素生化科技有限公司021-33632979 · [email protected]
上海陶术生物科技股份有限公司13564774135 · [email protected]
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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