U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C18H29N3O5
Molecular Weight 367.44
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BAMBUTEROL

SMILES

CN(C)C(=O)OC1=CC(=CC(OC(=O)N(C)C)=C1)C(O)CNC(C)(C)C

InChI

InChIKey=ANZXOIAKUNOVQU-UHFFFAOYSA-N
InChI=1S/C18H29N3O5/c1-18(2,3)19-11-15(22)12-8-13(25-16(23)20(4)5)10-14(9-12)26-17(24)21(6)7/h8-10,15,19,22H,11H2,1-7H3

HIDE SMILES / InChI

Molecular Formula C18H29N3O5
Molecular Weight 367.44
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description
Curator's Comment: Description was created based on several sources, including https://www.medicines.org.uk/emc/medicine/9574 | http://www.meppo.com/pdf/drugs/2596-BAMBEC-ORAL-SOLUTION-1427211370.pdf | https://www.ncbi.nlm.nih.gov/pubmed/2906603

Bambuterol is an active precursor of the selective beta2-adrenergic agonist terbutaline. Bambuterol is the bis-N,N-dimethyl-carbamate of terbutaline. Bambuterol is a remarkably selective and potent inhibitor of cholinesterase. BAMBEC (Bambuterol hydrochloride) oral solution or tablets are indicated for the management of asthma, bronchospasm and/or reversible airways obstruction.

CNS Activity

Curator's Comment: Bambuterol distribution to CNS is negligible, however chronic, but not acute, treatment with bambuterol relieves allodynia in a murine model of neuropathy.

Originator

Curator's Comment: # AB Draco (Subsidiary of AB Astra, now AstraZeneca)

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
BAMBEC

Approved Use

BAMBEC (Bambuterol hydrochloride) oral solution or tablets are indicated for the management of asthma, bronchospasm and/or reversible airways obstruction.
Primary
BAMBEC

Approved Use

BAMBEC (Bambuterol hydrochloride) oral solution or tablets are indicated for the management of asthma, bronchospasm and/or reversible airways obstruction.
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
3.69 nM
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BAMBUTEROL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
4.35 nM
10 mg 1 times / day steady-state, oral
dose: 10 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
BAMBUTEROL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
8.56 nM
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BAMBUTEROL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
10.3 nM
20 mg 1 times / day steady-state, oral
dose: 20 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
BAMBUTEROL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
14.23 nM
30 mg single, oral
dose: 30 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BAMBUTEROL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
16.75 nM
30 mg 1 times / day steady-state, oral
dose: 30 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
BAMBUTEROL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
7.1 nM
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TERBUTALINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
12.2 nM
10 mg 1 times / day steady-state, oral
dose: 10 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
TERBUTALINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
12.17 nM
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TERBUTALINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
20.4 nM
20 mg 1 times / day steady-state, oral
dose: 20 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
TERBUTALINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
16.32 nM
30 mg single, oral
dose: 30 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TERBUTALINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
31.36 nM
30 mg 1 times / day steady-state, oral
dose: 30 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
TERBUTALINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
37.3 nM × h
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BAMBUTEROL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
20.1 nM × h
10 mg 1 times / day steady-state, oral
dose: 10 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
BAMBUTEROL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
66.8 nM × h
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BAMBUTEROL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
55.3 nM × h
20 mg 1 times / day steady-state, oral
dose: 20 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
BAMBUTEROL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
108.6 nM × h
30 mg single, oral
dose: 30 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BAMBUTEROL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
123.7 nM × h
30 mg 1 times / day steady-state, oral
dose: 30 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
BAMBUTEROL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
208.1 nM × h
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TERBUTALINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
196 nM × h
10 mg 1 times / day steady-state, oral
dose: 10 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
TERBUTALINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
387.6 nM × h
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TERBUTALINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
350.9 nM × h
20 mg 1 times / day steady-state, oral
dose: 20 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
TERBUTALINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
556.9 nM × h
30 mg single, oral
dose: 30 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TERBUTALINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
550 nM × h
30 mg 1 times / day steady-state, oral
dose: 30 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
TERBUTALINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
20.14 h
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BAMBUTEROL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
20.9 h
10 mg 1 times / day steady-state, oral
dose: 10 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
BAMBUTEROL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
18.47 h
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BAMBUTEROL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
16.52 h
20 mg 1 times / day steady-state, oral
dose: 20 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
BAMBUTEROL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
16.85 h
30 mg single, oral
dose: 30 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BAMBUTEROL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
15.04 h
30 mg 1 times / day steady-state, oral
dose: 30 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
BAMBUTEROL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
26.5 h
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TERBUTALINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
22.25 h
10 mg 1 times / day steady-state, oral
dose: 10 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
TERBUTALINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
22.46 h
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TERBUTALINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
22.81 h
20 mg 1 times / day steady-state, oral
dose: 20 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
TERBUTALINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
22.1 h
30 mg single, oral
dose: 30 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TERBUTALINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
22.64 h
30 mg 1 times / day steady-state, oral
dose: 30 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
TERBUTALINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
50%
BAMBUTEROL plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
30 mg 1 times / day multiple, oral
Highest studied dose
Dose: 30 mg, 1 times / day
Route: oral
Route: multiple
Dose: 30 mg, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
0.4 mg/kg 1 times / day multiple, oral
Highest studied dose
Dose: 0.4 mg/kg, 1 times / day
Route: oral
Route: multiple
Dose: 0.4 mg/kg, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Overview

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer




Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
yes [IC50 2 uM]
Tox targets
PubMed

PubMed

TitleDatePubMed
Influence of differential expression of acetylcholinesterase in brain and muscle on respiration.
2009-01-01
Stereoselective inhibition of human, mouse, and horse cholinesterases by bambuterol enantiomers.
2008-09-25
Effects of acetylcholinesterase and butyrylcholinesterase inhibition on breathing in mice adapted or not to reduced acetylcholinesterase.
2005-01
Cholinesterases: new roles in brain function and in Alzheimer's disease.
2003-04
Oral bambuterol compared to inhaled salmeterol in patients with partially reversible chronic obstructive pulmonary disease.
1999-01
Can oral beta2 agonists cause heart failure?
1998-10-03
Risk of non-fatal cardiac failure and ischaemic heart disease with long acting beta 2 agonists.
1998-07
Therapeutic equivalence between bambuterol, 10 mg once daily, and terbutaline controlled release, 5 mg twice daily, in mild to moderate asthma.
1993-11
Tremor in healthy volunteers after bambuterol and terbutaline CR-tablets.
1993
Bambuterol and terbutaline in human cerebrospinal fluid and plasma.
1993
New lipophilic terbutaline ester prodrugs with long effect duration.
1984-01
Patents

Sample Use Guides

BAMBEC (Bambuterol hydrochloride) Tablets 10 mg. The recommended starting doses are 10 mg–20 mg. The 10 mg dose may be increased to 20 mg if necessary after 1–2 weeks, depending on the clinical effect. In patients who have previously tolerated beta2-agonists well, the recommended starting dose, as well as maintenance dose, is 20 mg. BAMBEC (Bambuterol hydrochloride) oral solution 1mg/ml. The recommended initial dose is 10mg (10ml). The dose may be increased to 20mg (20ml) after 1-2 weeks, depending on the clinical effect. In patients who previously have tolerated oral beta2-agonists well, the recommended initial dose is 20mg (20ml).
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:47:05 GMT 2025
Edited
by admin
on Mon Mar 31 18:47:05 GMT 2025
Record UNII
Y1850G1OVC
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BAMBUTEROL
INN   MI   WHO-DD  
INN  
Official Name English
BAMBUTEROL [MI]
Preferred Name English
bambuterol [INN]
Common Name English
(±)-5-(2-(TERT-BUTYLAMINO)-1-HYDROXYETHYL)-M-PHENYLENE BIS(DIMETHYLCARBAMATE)
Systematic Name English
Bambuterol [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-VATC QR03CC12
Created by admin on Mon Mar 31 18:47:05 GMT 2025 , Edited by admin on Mon Mar 31 18:47:05 GMT 2025
WHO-ATC R03CC12
Created by admin on Mon Mar 31 18:47:05 GMT 2025 , Edited by admin on Mon Mar 31 18:47:05 GMT 2025
NCI_THESAURUS C48149
Created by admin on Mon Mar 31 18:47:05 GMT 2025 , Edited by admin on Mon Mar 31 18:47:05 GMT 2025
Code System Code Type Description
CAS
81732-65-2
Created by admin on Mon Mar 31 18:47:05 GMT 2025 , Edited by admin on Mon Mar 31 18:47:05 GMT 2025
PRIMARY
WIKIPEDIA
BAMBUTEROL
Created by admin on Mon Mar 31 18:47:05 GMT 2025 , Edited by admin on Mon Mar 31 18:47:05 GMT 2025
PRIMARY
EPA CompTox
DTXSID5048550
Created by admin on Mon Mar 31 18:47:05 GMT 2025 , Edited by admin on Mon Mar 31 18:47:05 GMT 2025
PRIMARY
PUBCHEM
54766
Created by admin on Mon Mar 31 18:47:05 GMT 2025 , Edited by admin on Mon Mar 31 18:47:05 GMT 2025
PRIMARY
FDA UNII
Y1850G1OVC
Created by admin on Mon Mar 31 18:47:05 GMT 2025 , Edited by admin on Mon Mar 31 18:47:05 GMT 2025
PRIMARY
MERCK INDEX
m2216
Created by admin on Mon Mar 31 18:47:05 GMT 2025 , Edited by admin on Mon Mar 31 18:47:05 GMT 2025
PRIMARY Merck Index
CHEBI
553827
Created by admin on Mon Mar 31 18:47:05 GMT 2025 , Edited by admin on Mon Mar 31 18:47:05 GMT 2025
PRIMARY
ChEMBL
CHEMBL521589
Created by admin on Mon Mar 31 18:47:05 GMT 2025 , Edited by admin on Mon Mar 31 18:47:05 GMT 2025
PRIMARY
DRUG CENTRAL
285
Created by admin on Mon Mar 31 18:47:05 GMT 2025 , Edited by admin on Mon Mar 31 18:47:05 GMT 2025
PRIMARY
RXCUI
18751
Created by admin on Mon Mar 31 18:47:05 GMT 2025 , Edited by admin on Mon Mar 31 18:47:05 GMT 2025
PRIMARY RxNorm
IUPHAR
6601
Created by admin on Mon Mar 31 18:47:05 GMT 2025 , Edited by admin on Mon Mar 31 18:47:05 GMT 2025
PRIMARY
EVMPD
SUB06095MIG
Created by admin on Mon Mar 31 18:47:05 GMT 2025 , Edited by admin on Mon Mar 31 18:47:05 GMT 2025
PRIMARY
INN
5304
Created by admin on Mon Mar 31 18:47:05 GMT 2025 , Edited by admin on Mon Mar 31 18:47:05 GMT 2025
PRIMARY
SMS_ID
100000088425
Created by admin on Mon Mar 31 18:47:05 GMT 2025 , Edited by admin on Mon Mar 31 18:47:05 GMT 2025
PRIMARY
DRUG BANK
DB01408
Created by admin on Mon Mar 31 18:47:05 GMT 2025 , Edited by admin on Mon Mar 31 18:47:05 GMT 2025
PRIMARY
MESH
C047766
Created by admin on Mon Mar 31 18:47:05 GMT 2025 , Edited by admin on Mon Mar 31 18:47:05 GMT 2025
PRIMARY
NCI_THESAURUS
C81692
Created by admin on Mon Mar 31 18:47:05 GMT 2025 , Edited by admin on Mon Mar 31 18:47:05 GMT 2025
PRIMARY
Related Record Type Details
ENANTIOMER -> RACEMATE
TARGET -> AGONIST
ENANTIOMER -> RACEMATE
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY