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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

CNS Non-penetrant
1014
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

AstraZeneca
124
Curator's Comment: # AB Draco (Subsidiary of AB Astra, now AstraZeneca)

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2678
Inhibitor
8297
 17.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
BAMBEC

Approved Use

BAMBEC (Bambuterol hydrochloride) oral solution or tablets are indicated for the management of asthma, bronchospasm and/or reversible airways obstruction.
Primary
Approved
8429
BAMBEC

Approved Use

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

PubMed

TitleDatePubMed
New lipophilic terbutaline ester prodrugs with long effect duration.
1984 Jan
Tremor in healthy volunteers after bambuterol and terbutaline CR-tablets.
1993
Therapeutic equivalence between bambuterol, 10 mg once daily, and terbutaline controlled release, 5 mg twice daily, in mild to moderate asthma.
1993 Nov
Risk of non-fatal cardiac failure and ischaemic heart disease with long acting beta 2 agonists.
1998 Jul
Can oral beta2 agonists cause heart failure?
1998 Oct 3
Oral bambuterol compared to inhaled salmeterol in patients with partially reversible chronic obstructive pulmonary disease.
1999 Jan
Cholinesterases: new roles in brain function and in Alzheimer's disease.
2003 Apr
Effects of acetylcholinesterase and butyrylcholinesterase inhibition on breathing in mice adapted or not to reduced acetylcholinesterase.
2005 Jan
Stereoselective inhibition of human, mouse, and horse cholinesterases by bambuterol enantiomers.
2008 Sep 25
Patents

Patents

JP2006504666A
10
JP2007500151A
16

Sample Use Guides

In Vivo Use Guide
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 Fri Dec 15 17:28:24 GMT 2023
Edited
by admin
on Fri Dec 15 17:28:24 GMT 2023
Record UNII
Y1850G1OVC
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BAMBUTEROL
INN   MI   WHO-DD  
INN  
Official Name English
bambuterol [INN]
Common Name English
(±)-5-(2-(TERT-BUTYLAMINO)-1-HYDROXYETHYL)-M-PHENYLENE BIS(DIMETHYLCARBAMATE)
Systematic Name English
BAMBUTEROL [MI]
Common Name English
Bambuterol [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-VATC QR03CC12
Created by admin on Fri Dec 15 17:28:24 GMT 2023 , Edited by admin on Fri Dec 15 17:28:24 GMT 2023
WHO-ATC R03CC12
Created by admin on Fri Dec 15 17:28:24 GMT 2023 , Edited by admin on Fri Dec 15 17:28:24 GMT 2023
NCI_THESAURUS C48149
Created by admin on Fri Dec 15 17:28:24 GMT 2023 , Edited by admin on Fri Dec 15 17:28:24 GMT 2023
Code System Code Type Description
CAS
81732-65-2
Created by admin on Fri Dec 15 17:28:24 GMT 2023 , Edited by admin on Fri Dec 15 17:28:24 GMT 2023
PRIMARY
WIKIPEDIA
BAMBUTEROL
Created by admin on Fri Dec 15 17:28:24 GMT 2023 , Edited by admin on Fri Dec 15 17:28:24 GMT 2023
PRIMARY
EPA CompTox
DTXSID5048550
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PRIMARY
PUBCHEM
54766
Created by admin on Fri Dec 15 17:28:24 GMT 2023 , Edited by admin on Fri Dec 15 17:28:24 GMT 2023
PRIMARY
FDA UNII
Y1850G1OVC
Created by admin on Fri Dec 15 17:28:24 GMT 2023 , Edited by admin on Fri Dec 15 17:28:24 GMT 2023
PRIMARY
MERCK INDEX
m2216
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PRIMARY Merck Index
CHEBI
553827
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PRIMARY
ChEMBL
CHEMBL521589
Created by admin on Fri Dec 15 17:28:24 GMT 2023 , Edited by admin on Fri Dec 15 17:28:24 GMT 2023
PRIMARY
DRUG CENTRAL
285
Created by admin on Fri Dec 15 17:28:24 GMT 2023 , Edited by admin on Fri Dec 15 17:28:24 GMT 2023
PRIMARY
RXCUI
18751
Created by admin on Fri Dec 15 17:28:24 GMT 2023 , Edited by admin on Fri Dec 15 17:28:24 GMT 2023
PRIMARY RxNorm
IUPHAR
6601
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PRIMARY
EVMPD
SUB06095MIG
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PRIMARY
INN
5304
Created by admin on Fri Dec 15 17:28:24 GMT 2023 , Edited by admin on Fri Dec 15 17:28:24 GMT 2023
PRIMARY
SMS_ID
100000088425
Created by admin on Fri Dec 15 17:28:24 GMT 2023 , Edited by admin on Fri Dec 15 17:28:24 GMT 2023
PRIMARY
DRUG BANK
DB01408
Created by admin on Fri Dec 15 17:28:24 GMT 2023 , Edited by admin on Fri Dec 15 17:28:24 GMT 2023
PRIMARY
MESH
C047766
Created by admin on Fri Dec 15 17:28:24 GMT 2023 , Edited by admin on Fri Dec 15 17:28:24 GMT 2023
PRIMARY
NCI_THESAURUS
C81692
Created by admin on Fri Dec 15 17:28:24 GMT 2023 , Edited by admin on Fri Dec 15 17:28:24 GMT 2023
PRIMARY
Related Record Type Details
Structure of BAMBUTEROL, (S)-
ENANTIOMER -> RACEMATE
Structure of BAMBUTEROL, (R)-
ENANTIOMER -> RACEMATE
BETA-2 ADRENERGIC RECEPTOR
TARGET -> AGONIST
SHORT-ACTING
Structure of BAMBUTEROL HYDROCHLORIDE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of BAMBUTEROL
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