3-[2-(tert-butylamino)-1-hydroxyethyl]-5-[(dimethylcarbamoyl)oxy]phenyl N,N-dimethylcarbamate

• ChemBase ID: 1217
• Molecular Formular: C18H29N3O5
• Molecular Mass: 367.43996
• Monoisotopic Mass: 367.21072104
• SMILES: OC(CNC(C)(C)C)c1cc(OC(=O)N(C)C)cc(OC(=O)N(C)C)c1
• Canonical SMILES: O=C(N(C)C)Oc1cc(cc(c1)OC(=O)N(C)C)C(CNC(C)(C)C)O
• InChI: 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
• InChIKey: ANZXOIAKUNOVQU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[2-(tert-butylamino)-1-hydroxyethyl]-5-[(dimethylcarbamoyl)oxy]phenyl N,N-dimethylcarbamate
• IUPAC Traditional name: @bambuterol
• Brand Name: Bambec; Oxeol
• Synonyms: Bambuterol hydrochloride; Bambuterol

Database IDs

• CAS Number: 81732-46-9
• PubChem SID: 46505785; 160964677
• PubChem CID: 54766

CALCULATED PROPERTIES

JChem

• Acid pKa: 13.909502
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -1.7781748
• LogD (pH = 7.4): -0.69715315
• Log P: 1.3973545
• Molar Refractivity: 98.2791 cm^3
• Polarizability: 38.362434 Å^3
• Polar Surface Area: 91.34 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.69
• LOG S: -2.89
• Solubility (Water): 4.69e-01 g/l

DETAILS

DrugBank - DB01408

• Drug Groups: approved
• Description: Bambuterol is a long acting beta-adrenoceptor agonist used in the treatment of asthma. It is a prodrug of terbutaline.
• 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.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic, extensive. Further metabolized to terbutaline by plasma cholinesterase.
• Absorption: Bioavailability is 20% following oral administration.
• Half Life: 13 hours for bambuterol and 21 hours for the primary active metabolite terbutaline.
• External Links: Wikipedia