arotinolol

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| verifiedrevid = 457153102

| IUPAC_name = (RS)-5-(2-{[3-(tert-butylamino)-2-hydroxypropyl]sulfanyl}- 1,3-thiazol-4-yl)thiophene-2-carboxamide

| image = Arotinolol.svg

| width = 275px

| tradename = Almarl

| Drugs.com = {{drugs.com|international|arotinolol}}

| pregnancy_AU =

| pregnancy_US =

| pregnancy_category =

| legal_AU =

| legal_CA =

| legal_UK =

| legal_US =

| legal_status = Rx-only

| routes_of_administration = Oral (tablets)

| bioavailability = 2 hours

| protein_bound =

| metabolism =

| elimination_half-life = 10 hours

| excretion =

| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 68377-92-4

| ATC_prefix = none

| ATC_suffix =

| ATC_supplemental =

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 93298

| PubChem = 2239

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank =

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 394E3P3B99

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D07465

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 2152

| synonyms = S-596

| C=15 | H=21 | N=3 | O=2 | S=3

| SMILES = CC(C)(C)NCC(CSC1=NC(=CS1)C2=CC=C(S2)C(=O)N)O

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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)

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = BHIAIPWSVYSKJS-UHFFFAOYSA-N

}}

Arotinolol (INN, marketed under the tradename Almarl) is a medication in the class of mixed alpha/beta blockers.{{cite journal | vauthors = Zhao J, Golozoubova V, Cannon B, Nedergaard J | title = Arotinolol is a weak partial agonist on beta 3-adrenergic receptors in brown adipocytes | journal = Canadian Journal of Physiology and Pharmacology | volume = 79 | issue = 7 | pages = 585–593 | date = July 2001 | pmid = 11478592 | doi = 10.1139/cjpp-79-7-585 }}{{Closed access}} It also acts as a β₃ receptor agonist.{{cite journal | vauthors = Takahashi H, Yoshida T, Nishimura M, Nakanishi T, Kondo M, Yoshimura M | title = Beta-3 adrenergic agonist, BRL-26830A, and alpha/beta blocker, arotinolol, markedly increase regional blood flow in the brown adipose tissue in anesthetized rats | journal = Japanese Circulation Journal | volume = 56 | issue = 9 | pages = 936–942 | date = September 1992 | pmid = 1383578 | doi = 10.1253/jcj.56.936 | doi-access = free }} 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".{{Cite journal|title = 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|year = 1979| vauthors = Hara Y, Sato E, Miyagishi A, Aono S, Nakatani H |journal = Folia Pharmacologica Japonica|volume = 75|issue = 7|doi = 10.1254/fpj.75.707|issn = 1347-8397|pages = 707–720|language = Japanese|type = English abstract|trans-title= 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|doi-access = free}}{{Open access}}