Tulobuterol

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]

Tulobuterol

Clinical data
AHFS/Drugs.com	International Drug Names
Routes of administration	Inhaled, oral, transdermal patch
ATC code	R03AC11 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) In general: ℞ (Prescription only)
Identifiers
IUPAC name (RS)-2-(tert-butylamino)-1-(2-chlorophenyl)ethanol
CAS Number	41570-61-0 Y
PubChem CID	5606
ChemSpider	5404 Y
UNII	591I9SU0F7
KEGG	D02151 Y
ChEMBL	ChEMBL1159717 Y
CompTox Dashboard (EPA)	DTXSID7048457
ECHA InfoCard	100.168.691
Chemical and physical data
Formula	C12H18ClNO
Molar mass	227.73 g·mol−1
3D model (JSmol)	Interactive image
SMILES Clc1ccccc1C(O)CNC(C)(C)C
InChI 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 Y Key:YREYLAVBNPACJM-UHFFFAOYSA-N Y

"Hokunarin Tape" used to treat asthma and bronchitis

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

Synthesis

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]