Arotinolol

Arotinolol
Clinical data
Trade names	Almarl
Other names	S-596
AHFS/Drugs.com	International Drug Names
Routes of; administration	Oral (tablets)
ATC code	none;
Legal status
Legal status	In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	2 hours
Elimination half-life	10 hours
Identifiers
	IUPAC name (RS)-5-(2-{[3-(tert-butylamino)-2-hydroxypropyl]sulfanyl}- 1,3-thiazol-4-yl)thiophene-2-carboxamide;
CAS Number	68377-92-4 ;
PubChem CID	2239;
ChemSpider	2152 ;
UNII	394E3P3B99;
KEGG	D07465 ;
ChEMBL	ChEMBL93298 ;
CompTox Dashboard (EPA)	DTXSID3022619 ;
Chemical and physical data
Formula	C15H21N3O2S3
Molar mass	371.53 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(C)(C)NCC(CSC1=NC(=CS1)C2=CC=C(S2)C(=O)N)O;
	InChI InChI=1S/C15H21N3O2S3/c1-15(2,3)17-6-9(19)7-21-14-18-10(8-22-14)11-4-5-12(23-11)13(16)20/h4-5,8-9,17,19H,6-7H2,1-3H3,(H2,16,20) ; Key:BHIAIPWSVYSKJS-UHFFFAOYSA-N ;
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Arotinolol (INN, marketed under the tradename Almarl) is a medication in the class of mixed alpha/beta blockers.^[1] It also acts as a β₃ receptor agonist.^[2] A 1979 publication suggests arotinolol as having first been described in the scientific literature by Sumitomo Chemical as "β-adrenergic blocking, antiarrhythmic compound S-596".^[3]

Medical uses

It is used in the treatment of high blood pressure^[4] and essential tremor.^[5]^[6] Recommended dosage is 10 to 30 mg per day.^{[citation needed]}

References

^ Zhao J, Golozoubova V, Cannon B, Nedergaard J (July 2001). "Arotinolol is a weak partial agonist on beta 3-adrenergic receptors in brown adipocytes". Canadian Journal of Physiology and Pharmacology. 79 (7): 585–593. doi:10.1139/cjpp-79-7-585. PMID 11478592.
^ Takahashi H, Yoshida T, Nishimura M, Nakanishi T, Kondo M, Yoshimura M (September 1992). "Beta-3 adrenergic agonist, BRL-26830A, and alpha/beta blocker, arotinolol, markedly increase regional blood flow in the brown adipose tissue in anesthetized rats". Japanese Circulation Journal. 56 (9): 936–942. doi:10.1253/jcj.56.936. PMID 1383578.
^ Hara Y, Sato E, Miyagishi A, Aono S, Nakatani H (1979). "新しいβ-受容体遮断薬，dl-2-(3'-t-Butylamino-2'-hydroxypropylthio)-4-(5'-carbamoyl-2'-thienyl)-thiazole hydrochloride (S-596) の薬理作用" [Pharmacological properties of dl-2-(3'-t-butylamino-2'-hydroxypropylthio)-4-(5'-carbamoyl-2'-thienyl)thiazole hydrochloride (S-596), a new β-adrenergic blocking agent]. Folia Pharmacologica Japonica (English abstract) (in Japanese). 75 (7): 707–720. doi:10.1254/fpj.75.707. ISSN 1347-8397.
^ Wu H, Zhang Y, Huang J, Zhang Y, Liu G, Sun N, et al. (September 2001). "Clinical trial of arotinolol in the treatment of hypertension: dippers vs. non-dippers" (PDF). Hypertension Research. 24 (5): 605–610. doi:10.1291/hypres.24.605. PMID 11675958.
^ Lee KS, Kim JS, Kim JW, Lee WY, Jeon BS, Kim D (August 2003). "A multicenter randomized crossover multiple-dose comparison study of arotinolol and propranolol in essential tremor". Parkinsonism & Related Disorders. 9 (6): 341–347. doi:10.1016/S1353-8020(03)00029-4. PMID 12853233.
^ "Almarl (アルマール) Arotinolol HCl Tablets. Full Prescribing Information" (PDF). Sumitomo Dainippon Pharma Co., Ltd. Archived from the original (PDF) on 7 May 2012. Retrieved 6 March 2016.

External links

(in Japanese) Almarl Full Prescribing Information. Revised November 2009 Sumitomo Dainippon Pharma Co., Ltd.
(in Japanese) Official Sumitomo Dainippon Pharma Website Archived 2020-07-01 at the Wayback Machine
"Arotinolol Hydrochloride". Drug Monograph. Drug Information Research Institute. Archived from the original on 2011-07-22.

[pmid11478592-1] Zhao J, Golozoubova V, Cannon B, Nedergaard J (July 2001). "Arotinolol is a weak partial agonist on beta 3-adrenergic receptors in brown adipocytes". Canadian Journal of Physiology and Pharmacology. 79 (7): 585–593. doi:10.1139/cjpp-79-7-585. PMID 11478592.

[pmid1383578-2] Takahashi H, Yoshida T, Nishimura M, Nakanishi T, Kondo M, Yoshimura M (September 1992). "Beta-3 adrenergic agonist, BRL-26830A, and alpha/beta blocker, arotinolol, markedly increase regional blood flow in the brown adipose tissue in anesthetized rats". Japanese Circulation Journal. 56 (9): 936–942. doi:10.1253/jcj.56.936. PMID 1383578.

[3] Hara Y, Sato E, Miyagishi A, Aono S, Nakatani H (1979). "新しいβ-受容体遮断薬，dl-2-(3'-t-Butylamino-2'-hydroxypropylthio)-4-(5'-carbamoyl-2'-thienyl)-thiazole hydrochloride (S-596) の薬理作用" [Pharmacological properties of dl-2-(3'-t-butylamino-2'-hydroxypropylthio)-4-(5'-carbamoyl-2'-thienyl)thiazole hydrochloride (S-596), a new β-adrenergic blocking agent]. Folia Pharmacologica Japonica (English abstract) (in Japanese). 75 (7): 707–720. doi:10.1254/fpj.75.707. ISSN 1347-8397.

[pmid11675958-4] Wu H, Zhang Y, Huang J, Zhang Y, Liu G, Sun N, et al. (September 2001). "Clinical trial of arotinolol in the treatment of hypertension: dippers vs. non-dippers" (PDF). Hypertension Research. 24 (5): 605–610. doi:10.1291/hypres.24.605. PMID 11675958.

[pmid12853233-5] Lee KS, Kim JS, Kim JW, Lee WY, Jeon BS, Kim D (August 2003). "A multicenter randomized crossover multiple-dose comparison study of arotinolol and propranolol in essential tremor". Parkinsonism & Related Disorders. 9 (6): 341–347. doi:10.1016/S1353-8020(03)00029-4. PMID 12853233.

[6] "Almarl (アルマール) Arotinolol HCl Tablets. Full Prescribing Information" (PDF). Sumitomo Dainippon Pharma Co., Ltd. Archived from the original (PDF) on 7 May 2012. Retrieved 6 March 2016.

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v t e Beta blockers (C07)
β, non-selective	Alprenolol Bopindolol Bupranolol Carteolol Cloranolol Mepindolol Nadolol Oxprenolol Penbutolol Pindolol/Iodopindolol Propranolol^# Sotalol Tertatolol Timolol^#
β₁-selective	Acebutolol Atenolol Betaxolol Bevantolol Bisoprolol^# Celiprolol Epanolol Esmolol Landiolol Metoprolol Nebivolol Practolol Talinolol
β₂-selective	Butaxamine
α₁- + β-selective	Arotinolol Carvedilol Labetalol
^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III