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Tulobuterol

Tulobuterol
Clinical data
AHFS/Drugs.comInternational Drug Names
Routes of
administration		Inhaled, oral, transdermal patch
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • In general: ℞ (Prescription only)
Identifiers
  • (RS)-2-(tert-butylamino)-1-(2-chlorophenyl)ethanol
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.168.691 Edit this at Wikidata
Chemical and physical data
FormulaC12H18ClNO
Molar mass227.73 g·mol−1
3D model (JSmol)
  • Clc1ccccc1C(O)CNC(C)(C)C
  • InChI=1S/C12H18ClNO/c1-12(2,3)14-8-11(15)9-6-4-5-7-10(9)13/h4-7,11,14-15H,8H2,1-3H3 checkY
  • Key:YREYLAVBNPACJM-UHFFFAOYSA-N checkY
"Hokunarin Tape" used to treat asthma and bronchitis

Tulobuterol (INN) is a long-acting beta2-adrenergic receptor agonist, marketed in Japan as a transdermal patch under the name Hokunalin tape (ホクナリンテープ).[1]

Currently, it is only legal in 7 countries: Japan, Germany, China, South Korea, Bangladesh, Pakistan, and Venezuela. It is available in India also.

Synthesis

[edit]

The oxidation of 2'-chloroacetophenone (1) with selenium dioxide gives o-chlorophenylglyoxal (2). Condensation with tert-butylamine gives the imine (3). Reduction with sodium borohydride completes the synthesis of tulobuterol.[2]

References

[edit]
  1. ^ Horiguchi T, Kondo R, Miyazaki J, Fukumokto K, Torigoe H (2011). "Clinical evaluation of a transdermal therapeutic system of the beta2-agonist tulobuterol in patients with mild or moderate persistent bronchial asthma". Arzneimittel-Forschung. 54 (5): 280–5. doi:10.1055/s-0031-1296971. PMID 15212190. S2CID 9765046.
  2. ^ Wu CJ, Peng P, Xia LT, Liu X, Yu CX, Zheng ZB, et al. (2023). "Development of a New Process for Tulobuterol Hydrochloride". Pharmaceutical Fronts. 05: e31–e37. doi:10.1055/s-0043-1764464.
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