Enantioselective resolution of  Rac ‐terbutaline and evaluation of optically pure  R ‐terbutaline hydrochloride as an efficient anti‐asthmatic drug | Zendy

Beng Huimin | Zendy; Zhang Hao | Zendy; Jayachandra R. | Zendy; Li Junxiao | Zendy; Wu Jie | Zendy; Tan Wen | Zendy

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Enantioselective resolution of Rac ‐terbutaline and evaluation of optically pure R ‐terbutaline hydrochloride as an efficient anti‐asthmatic drug

Author(s) -

Beng Huimin,

Zhang Hao,

Jayachandra R.,

Li Junxiao,

Wu Jie,

Tan Wen

Publication year - 2018

Publication title -

chirality

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.43

H-Index - 77

eISSN - 1520-636X

pISSN - 0899-0042

DOI - 10.1002/chir.22846

Subject(s) - terbutaline , chemistry , enantiomer , hydrochloride , enantioselective synthesis , pharmacology , bronchodilator , stereochemistry , asthma , organic chemistry , medicine , catalysis

Terbutaline is a β 2 ‐adrenoceptor agonist for the treatment of asthma and chronic obstructive pulmonary disease (COPD). Among the two isomers of terbutaline (TBT 2), R ‐isomer was found to be the potent enantiomer in generating therapeutic effect, while S ‐isomer has been reported to show side effects. In this study, R ‐terbutaline hydrochloride ( R ‐TBH 6) was synthesized through chiral resolution from the racemic terbutaline sulfate ( rac ‐TBS 1) with 99.9% enantiomeric excess (ee) in good overall yield (53.6%). Further, R ‐TBH 6 nebulized solution was prepared in half dosage of Bricanyl®, which is a marketed product of racemic terbutaline and evaluated in vitro aerosol performance and in vivo anti‐asthmatic effect on guinea pigs via . pulmonary delivery. From the investigation, it is evident that R ‐TBH 6 nebulized solution of half dosage performed similar fine aerosol characteristics and anti‐asthmatic effect with Bricanyl®.

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