Xamoterol

{{Short description|Cardiac stimulant drug}}

{{Drugbox

| Verifiedfields = verified

| Watchedfields = verified

| verifiedrevid = 470632689

| IUPAC_name = (RS)-N-(2-{[2-hydroxy-3-(4-hydroxyphenoxy)propyl]amino}ethyl)morpholine-4-carboxamide

| image = Xamoterol.svg

| width = 250px

| tradename = Corwin, Carwin, Corwil, Xamtol

| pregnancy_AU =

| pregnancy_US =

| pregnancy_category =

| legal_AU =

| legal_CA =

| legal_UK =

| legal_US =

| legal_status =

| routes_of_administration = By mouth{{cite journal | vauthors = Furlong R, Brogden RN | title = Xamoterol. A preliminary review of its pharmacodynamic and pharmacokinetic properties, and therapeutic use | journal = Drugs | volume = 36 | issue = 4 | pages = 455–474 | date = October 1988 | pmid = 2906865 | doi = 10.2165/00003495-198836040-00004 | url = }}

| bioavailability = Oral: 5%

| protein_bound =

| metabolism =

| elimination_half-life = 16–27{{nbsp}}hours

| excretion =

| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 81801-12-9

| ATC_prefix = C01

| ATC_suffix = CX07

| PubChem = 155774

| IUPHAR_ligand = 538

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

| DrugBank = DB13781

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

| ChemSpiderID = 137213

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

| UNII = 7HE0JQL703

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

| KEGG = D06328

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

| ChEMBL = 75753

| synonyms =

| C=16 | H=25 | N=3 | O=5

| SMILES = O=C(NCCNCC(O)COc1ccc(O)cc1)N2CCOCC2

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

| StdInChI = 1S/C16H25N3O5/c20-13-1-3-15(4-2-13)24-12-14(21)11-17-5-6-18-16(22)19-7-9-23-10-8-19/h1-4,14,17,20-21H,5-12H2,(H,18,22)

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

| StdInChIKey = DXPOSRCHIDYWHW-UHFFFAOYSA-N

}}

Xamoterol, sold under the brand names Corwin, Carwin, Corwil, and Xamtol among others, is a cardiac stimulant which is used in the treatment of heart failure.{{cite journal | vauthors = Marlow HF | title = Xamoterol, a beta 1-adrenoceptor partial agonist: review of the clinical efficacy in heart failure | journal = British Journal of Clinical Pharmacology | volume = 28 | pages = 23S–30S | date = 1989 | issue = Suppl 1 | pmid = 2572251 | pmc = 1379873 | doi = 10.1111/j.1365-2125.1989.tb03570.x }} It acts as a selective partial agonist of the β₁-adrenergic receptor with around 50% intrinsic sympathomimetic activity (ISA) (i.e., intrinsic activity).{{cite journal | vauthors = Campbell RW | title = The management of heart failure and the scope for new therapies: what role for xamoterol? | journal = Br J Clin Pharmacol | volume = 28 Suppl 1 | issue = Suppl 1 | pages = 59S–64S | date = 1989 | pmid = 2572256 | pmc = 1379877 | doi = 10.1111/j.1365-2125.1989.tb03574.x | url = }}{{cite journal | vauthors = Cruickshank JM | title = The xamoterol experience in the treatment of heart failure | journal = Am J Cardiol | volume = 71 | issue = 9 | pages = 61C–64C | date = March 1993 | pmid = 8465800 | doi = 10.1016/0002-9149(93)90088-t | url = }} The drug has no significant β₂-adrenergic receptor agonistic activity.{{cite web | title=Xamoterol: Uses, Interactions, Mechanism of Action | website=DrugBank Online | date=23 June 2017 | url=https://go.drugbank.com/drugs/DB13781 | access-date=23 July 2024}} Xamoterol provides cardiac stimulation at rest but acts as a blocker during exercise.{{cite book| vauthors = Rang HP, Dale MM, Ritter JM, Moore PK |title=Pharmacology|date=1999|publisher=Churchill Livingstone|location=Edinburgh; New York|isbn=0443059748|page=163|edition=5th}} It is taken by mouth.

Xamoterol is not available in the United States.{{cite web | title=Drugs@FDA: FDA-Approved Drugs | website=accessdata.fda.gov | url=https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm | access-date=23 July 2024}}{{cite book | author=Schweizerischer Apotheker-Verein | title=Index Nominum 2000: International Drug Directory | publisher=Medpharm Scientific Publishers | series=Index nominum | year=2000 | isbn=978-3-88763-075-1 | url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA1099 | access-date=23 July 2024 | page=1099}} It is marketed in the United Kingdom, Austria, Belgium, and Luxembourg.

Xamoterol is a hydrophilic compound with a predicted log P of -0.31 to -1.11.{{cite web | title=Xamoterol | website=PubChem | url=https://pubchem.ncbi.nlm.nih.gov/compound/155774 | access-date=1 August 2024}}{{cite web | title=Xamoterol: Uses, Interactions, Mechanism of Action | website=DrugBank Online | date=23 June 2017 | url=https://go.drugbank.com/drugs/DB13781 | access-date=1 August 2024}}{{cite web | title=Xamoterol [USAN:BAN:INN] | website=ChemSpider | date=21 July 2022 | url=https://www.chemspider.com/Chemical-Structure.137213.html | access-date=1 August 2024}}{{cite journal | vauthors = Vigholt-Sørensen E, Faergeman O, Snow HM | title = Effects of xamoterol, a beta 1 adrenoceptor partial agonist, in patients with ischaemic dysfunction of the left ventricle | journal = Br Heart J | volume = 62 | issue = 5 | pages = 335–341 | date = November 1989 | pmid = 2574049 | pmc = 1224831 | doi = 10.1136/hrt.62.5.335 | url = }} Due to its hydrophilicity, xamoterol does not cross the blood–brain barrier and has no central nervous system effects. Hence, it is a peripherally selective drug.