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 ;
	(what is this?) (verify)

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 [2142-68-9] (1) with SeO2 gives o-chlorophenylglyoxal, PC12463886 [27993-71-1] (2). Condensation with tert-butylamine gives the imine (3). The reduction with sodium borohydride completes the synthesis of tulobuterol (3).

References[edit]

^ 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.
^ Castaer, J .; Thorpe, P .; C 78. Drugs Fut 1976, 1, 5, 217.
^ Hideo Kato, Sakae Kurata, DE2244737 (1979 to Hokuriku Pharmaceutical Co., Ltd., Katsuyama, Fukui (Japan)).
^ Wu, C.-J., Peng, P., Xia, L.-T., Liu, X., Yu, C.-X., Zheng, Z.-B., Zhao, C.-M., Zhang, F.-L. (March 2023). "Development of a New Process for Tulobuterol Hydrochloride". Pharmaceutical Fronts. 05 (01): e31–e37. doi:10.1055/s-0043-1764464.
^ Song H, Lin J, Tan H, Shen L, Zhang N, Zhang Y, Tan X, Yang Y, Pan X, Zheng W. Synthesis of High Purified Tulobuterol and Its Study of the Organic Impurities. J Chromatogr Sci. 2019 Apr 1;57(4):299-304. doi: 10.1093/chromsci/bmy083. PMID: 30722025.
^ Jing Yajun, He Shuwang, & Guo Wei, CN105439875 (2016 to SHANDONG DAYIN MARINE BIOTECHNOLOGICAL PHARM HOLDINGS CO Ltd).
^ 颜世强, et al. CN111205194 (2020 to Shandong Dyne Marine Biotechnological Pharm Holdings Co ltd).
^ Ranade, Vasant V. (1984). "Synthesis of benzylic carbon-14 labelled tulobuterol-HCl". Journal of Labelled Compounds and Radiopharmaceuticals. 21 (4): 381–389. doi:10.1002/jlcr.2580210413.

This drug article relating to the respiratory system is a stub. You can help Wikipedia by expanding it.

[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] Castaer, J .; Thorpe, P .; C 78. Drugs Fut 1976, 1, 5, 217.

[3] Hideo Kato, Sakae Kurata, DE2244737 (1979 to Hokuriku Pharmaceutical Co., Ltd., Katsuyama, Fukui (Japan)).

[4] Wu, C.-J., Peng, P., Xia, L.-T., Liu, X., Yu, C.-X., Zheng, Z.-B., Zhao, C.-M., Zhang, F.-L. (March 2023). "Development of a New Process for Tulobuterol Hydrochloride". Pharmaceutical Fronts. 05 (01): e31–e37. doi:10.1055/s-0043-1764464.

[5] Song H, Lin J, Tan H, Shen L, Zhang N, Zhang Y, Tan X, Yang Y, Pan X, Zheng W. Synthesis of High Purified Tulobuterol and Its Study of the Organic Impurities. J Chromatogr Sci. 2019 Apr 1;57(4):299-304. doi: 10.1093/chromsci/bmy083. PMID: 30722025.

[6] Jing Yajun, He Shuwang, & Guo Wei, CN105439875 (2016 to SHANDONG DAYIN MARINE BIOTECHNOLOGICAL PHARM HOLDINGS CO Ltd).

[7] 颜世强, et al. CN111205194 (2020 to Shandong Dyne Marine Biotechnological Pharm Holdings Co ltd).

[8] Ranade, Vasant V. (1984). "Synthesis of benzylic carbon-14 labelled tulobuterol-HCl". Journal of Labelled Compounds and Radiopharmaceuticals. 21 (4): 381–389. doi:10.1002/jlcr.2580210413.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

Synthesis[edit]

See also[edit]

References[edit]