Tulobuterol

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 ;
PubChem CID	5606;
ChemSpider	5404 ;
UNII	591I9SU0F7;
KEGG	D02151 ;
ChEMBL	ChEMBL1159717 ;
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 ; Key:YREYLAVBNPACJM-UHFFFAOYSA-N ;

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

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

^ 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.
^ 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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[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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