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Details

Stereochemistry RACEMIC
Molecular Formula C18H29N3O5.ClH
Molecular Weight 403.901
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BAMBUTEROL HYDROCHLORIDE

SMILES

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

InChI

InChIKey=LBARATORRVNNQM-UHFFFAOYSA-N
InChI=1S/C18H29N3O5.ClH/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;1H

HIDE SMILES / InChI
Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
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
Bambuterol and terbutaline in human cerebrospinal fluid and plasma.
1993
Therapeutic equivalence between bambuterol, 10 mg once daily, and terbutaline controlled release, 5 mg twice daily, in mild to moderate asthma.
1993 Nov
Can oral beta2 agonists cause heart failure?
1998 Oct 3
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
Influence of differential expression of acetylcholinesterase in brain and muscle on respiration.
2009 Jan 1
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 17:18:28 UTC 2023
Edited
by admin
on Fri Dec 15 17:18:28 UTC 2023
Record UNII
786Q84QZ3F
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BAMBUTEROL HYDROCHLORIDE
EP   MART.   MI   WHO-DD  
Common Name English
BAMBUTEROL HYDROCHLORIDE [EP IMPURITY]
Common Name English
(RS)-5-(2-TERT-BUTYLAMINO-1-HYDROXYETHYL)-M-PHENYLENE BIS(DIMETHYLCARBAMATE) HYDROCHLORIDE
Systematic Name English
Bambuterol hydrochloride [WHO-DD]
Common Name English
BAMBEC
Brand Name English
KWD-2183
Code English
BAMBUTEROL HYDROCHLORIDE [EP MONOGRAPH]
Common Name English
BAMBUTEROL HCL
Common Name English
BAMBUTEROL HYDROCHLORIDE [MI]
Common Name English
BAMBUTEROL HYDROCHLORIDE [MART.]
Common Name English
NSC-758916
Code English
Code System Code Type Description
PUBCHEM
54765
Created by admin on Fri Dec 15 17:18:28 UTC 2023 , Edited by admin on Fri Dec 15 17:18:28 UTC 2023
PRIMARY
DRUG BANK
DB01408
Created by admin on Fri Dec 15 17:18:28 UTC 2023 , Edited by admin on Fri Dec 15 17:18:28 UTC 2023
PRIMARY
EPA CompTox
DTXSID8045515
Created by admin on Fri Dec 15 17:18:28 UTC 2023 , Edited by admin on Fri Dec 15 17:18:28 UTC 2023
PRIMARY
CAS
81732-46-9
Created by admin on Fri Dec 15 17:18:28 UTC 2023 , Edited by admin on Fri Dec 15 17:18:28 UTC 2023
PRIMARY
FDA UNII
786Q84QZ3F
Created by admin on Fri Dec 15 17:18:28 UTC 2023 , Edited by admin on Fri Dec 15 17:18:28 UTC 2023
PRIMARY
SMS_ID
100000092785
Created by admin on Fri Dec 15 17:18:28 UTC 2023 , Edited by admin on Fri Dec 15 17:18:28 UTC 2023
PRIMARY
RXCUI
235862
Created by admin on Fri Dec 15 17:18:28 UTC 2023 , Edited by admin on Fri Dec 15 17:18:28 UTC 2023
PRIMARY RxNorm
CHEBI
59167
Created by admin on Fri Dec 15 17:18:28 UTC 2023 , Edited by admin on Fri Dec 15 17:18:28 UTC 2023
PRIMARY
NSC
758916
Created by admin on Fri Dec 15 17:18:28 UTC 2023 , Edited by admin on Fri Dec 15 17:18:28 UTC 2023
PRIMARY
MESH
C047766
Created by admin on Fri Dec 15 17:18:28 UTC 2023 , Edited by admin on Fri Dec 15 17:18:28 UTC 2023
PRIMARY
MERCK INDEX
m2216
Created by admin on Fri Dec 15 17:18:28 UTC 2023 , Edited by admin on Fri Dec 15 17:18:28 UTC 2023
PRIMARY Merck Index
EVMPD
SUB00659MIG
Created by admin on Fri Dec 15 17:18:28 UTC 2023 , Edited by admin on Fri Dec 15 17:18:28 UTC 2023
PRIMARY
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ENANTIOMER -> RACEMATE
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