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Bambuterol

Bambuterol structure

CAS No:
81732-65-2
Formula:
C18H29N3O5
Chemical Name:
Bambuterol
Synonyms:
Carbamic acid,N,N-dimethyl-,C,C′-[5-[2-[(1,1-dimethylethyl)amino]-1-hydroxyethyl]-1,3-phenylene] ester;Carbamic acid,dimethyl-,5-[2-[(1,1-dimethylethyl)amino]-1-hydroxyethyl]-1,3-phenylene ester;Bambuterol;(±)-Bambuterol;Terbutaline bisdimethylcarbamate;Bambudil;MR 36621;105284-25-1
Categories:
Organic Chemistry > Amides

Description

Bambuterol is a long acting beta-adrenoceptor agonist (LABA) used in the treatment of asthma; it also is a prodrug of terbutaline.IC50 value:Target: beta-adrenoceptor agonistBambuterol is contraindicated in pregnancy and in people with seriously impaired liver function. It can be used by people with renal impairment, but dose adjustments are necessary. The adverse effect profile of bambuterol is similar to that of salbutamol, and may include fatigue, nausea, palpitations, headache, dizzi

Solid

Bambuterol is a carbamate ester that is terbutaline in which both of the phenolic hydroxy groups have been protected as the corresponding N,N-dimethylcarbamates. A long acting beta-adrenoceptor agonist used in the treatment of asthma, it is a prodrug for terbutaline. It has a role as a beta-adrenergic agonist, a prodrug, a bronchodilator agent, an anti-asthmatic drug, an EC 3.1.1.7 (acetylcholinesterase) inhibitor, a sympathomimetic agent and a tocolytic agent. It is a carbamate ester and a member of phenylethanolamines. It derives from a terbutaline.|Bambuterol is a long acting beta-adrenoceptor agonist used in the treatment of asthma. It is a prodrug of terbutaline.

Bambuterol Basic Attributes

Molecular Weight：

367.44

Exact Mass：

367.44

EC Number：

1533716-785-6

DSSTox ID：

DTXSID5048550

ATC Code：

R - Respiratory system

Characteristics

PSA：

91.34000

XLogP3：

2.61980

Appearance：

off-white powder

Density：

1.154 g/cm3

Boiling Point：

500.9ºC at 760 mmHg

Flash Point：

256.7ºC

Water Solubility：

H2O: ~33 mg/mL, soluble

Toxicity：

LDLo ipr-mus: 0.3 mg/kg JPETAB 293,896,2000

Collision Cross Section：

189.7 Å² [M+H]+ [CCS Type: TW, Method: Major Mix IMS/Tof Calibration Kit (Waters)]

Safety Information

wgk germany：

Drug Information

Drug Indication：

For the prevention and reversal of bronchospasm in patients 12 years of age and older with asthma and reversible bronchospasm associated with bronchitis and emphysema.

Pharmacology：

Bambuterol is a long acting beta2-adrenoceptor agonist used in the treatment of asthma. It is a prodrug of terbutaline. Bambuterol causes smooth muscle relaxation, resulting in dilation of bronchial passages.

MeSH：

Agents that cause an increase in the expansion of a bronchus or bronchial tubes. (See all compounds classified as Bronchodilator Agents.)

Absorption：

Bioavailability is 20% following oral administration.

Metabolism/Metabolites：

Hepatic, extensive. Further metabolized to terbutaline by plasma cholinesterase.

Biological Half-Life：

13 hours for bambuterol and 21 hours for the primary active metabolite terbutaline.

Mechanism of Action：

The pharmacologic effects of bambuterol are at least in part attributable to stimulation through beta-adrenergic receptors (beta 2 receptors) of intracellular adenyl cyclase, the enzyme that catalyzes the conversion of adenosine triphosphate (ATP) to cyclic AMP. Increased cyclic AMP levels are associated with relaxation of bronchial smooth muscle and inhibition of release of mediators of immediate hypersensitivity from cells, especially from mast cells.

MeSH Entry Terms：

5-(2-(tert-butylamino)-1-hydroxyethyl)-3-phenylene bis(dimethylcarbamate)

Bambuterol Use and Manufacturing

Use Classification：

Pharmaceuticals

Computed Properties

Molecular Weight:367.4
XLogP3:1.2
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:8
Exact Mass:367.21072103
Monoisotopic Mass:367.21072103
Topological Polar Surface Area:91.3
Heavy Atom Count:26
Complexity:446
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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CAS No.: 81732-65-2

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