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

• ChemBase ID: 154167
• Molecular Formular: C18H30ClN3O5
• Molecular Mass: 403.9009
• Monoisotopic Mass: 403.18739876
• SMILES: CC(C)(C)NCC(c1cc(cc(c1)OC(=O)N(C)C)OC(=O)N(C)C)O.Cl
• Canonical SMILES: O=C(N(C)C)Oc1cc(cc(c1)OC(=O)N(C)C)C(CNC(C)(C)C)O.Cl
• InChI: 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
• InChIKey: LBARATORRVNNQM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[2-(tert-butylamino)-1-hydroxyethyl]-5-[(dimethylcarbamoyl)oxy]phenyl N,N-dimethylcarbamate hydrochloride
• IUPAC Traditional name: bambuterol hydrochloride; 3-[2-(tert-butylamino)-1-hydroxyethyl]-5-[(dimethylcarbamoyl)oxy]phenyl N,N-dimethylcarbamate hydrochloride
• Synonyms: Dimethylcarbmic acid 5-[2-[(1,1-dimethylethyl)amino]-1-hydroxyethyl]-1,3-phenylene ester; Bambuterol hydrochloride; N,N-Dimethylcarbamic Acid 3-[[(Dimethylamino)carbonyl]oxy]-5-[2-[(1,1-dimethylethyl)amino]-1-hydroxyethyl]phenyl Ester Hydrochloride; Dimethylcarbamic Acid 5-[2-[(1,1-Dimethylethyl)amino]-1-hydroxyethyl]-1,3-phenylene Ester Monohydrochloride; Bambec; KWD 2183; Bambuterol Hydrochloride

Database IDs

• CAS Number: 81732-46-9; 81732-65-2
• MDL Number: MFCD03427293
• PubChem SID: 162248306
• PubChem CID: 54765

CALCULATED PROPERTIES

• 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

PROPERTIES

Physical Property

• Solubility: DMSO; H2O: soluble ~33 mg/mL; Methanol
• Apperance: off-white powder; White Solid
• Melting Point: 222-224°C

Safety Information

• Storage Condition: -20°C Freezer
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Mechanism of Action: Beta 2 -Adrenoceptor agonist; Bronchodilator

Product Information

• Purity: >98% (HPLC)
• Salt Data: HCl
• Application(s): Antiasthmatic; Bronchodilator
• Linear Formula: C18H29N3O5 · HCl

DETAILS

Sigma Aldrich - B8684

Biochem/physiol Actions
β-adrenoceptor agonist; bronchodilator; anti-asthmatic; terbutaline prodrug

Toronto Research Chemicals - B117500

Ester prodrug of the β2-adrenergic agonist Terbutaline (T109750). Bronchodilator.

REFERENCES

• Ollsson, O.A.T., et al.: Pharm. Res., 19, (1984)
• Persson, G., et al.: Eur. Respir. J., 1, 223 (1984)
• Persson, H. et al., Acta Med. Scand., Suppl., 1970, 11, (pharmacol)
• Svensson, L.A. et al., Kem. Tidskr., 1971, 83, 30, (synth, rev)
• Wetterlin, K., J. Med. Chem., 1972, 15, 1182, (resoln)
• Cattabeni, F. et al., Adv. Mass Spectrom. Biochem. Med., Proc. Int. Symp. Mass Spectrom. Biochem. Med. 2nd, 3rd, 1976, 1, 517, (ms)
• McPhillips, J.J., Pharmacol. Biochem. Prop. Drug Subst., 1977, 1, 311, (rev)
• LeFerink, J.G. et al., Arzneim.-Forsch., 1982, 32, 159, (pharmacol)
• Eur. Pat., 1982, 43 807; CA, 96, 199263, (Bambuterol)
• Svensson, L.A., Acta Pharm. Suec., 1987, 24, 333, (rev, Bambuterol)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 2532
• Ahujo, S. et al., Anal. Profiles Drug Subst., 1990, 19, 601, (Bambuterol, rev)
• Bauer, C.A. et al., Drugs of Today (Barcelona), 1992, 28, 547, (Bambuterol, rev)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 1241; 1257
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, TAN100; TAN250