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Xamoterol

Clinical data
Trade names	Corwin, Carwin, Corwil, Xamtol
Routes of administration	By mouth
ATC code	C01CX07 (WHO)
Pharmacokinetic data
Bioavailability	Oral: 5%
Elimination half-life	16–27 hours
Identifiers
IUPAC name (RS)-N-(2-{amino}ethyl)morpholine-4-carboxamide
CAS Number	81801-12-9
PubChem CID	155774
IUPHAR/BPS	538
DrugBank	DB13781
ChemSpider	137213
UNII	7HE0JQL703
KEGG	D06328
ChEMBL	ChEMBL75753
CompTox Dashboard (EPA)	DTXSID8045222
Chemical and physical data
Formula	C16H25N3O5
Molar mass	339.392 g·mol
3D model (JSmol)	Interactive image
SMILES O=C(NCCNCC(O)COc1ccc(O)cc1)N2CCOCC2
InChI InChI=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) Key:DXPOSRCHIDYWHW-UHFFFAOYSA-N
(verify)

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. It acts as a selective partial agonist of the β₁-adrenergic receptor with around 50% intrinsic sympathomimetic activity (ISA) (i.e., intrinsic activity). The drug has no significant β₂-adrenergic receptor agonistic activity. Xamoterol provides cardiac stimulation at rest but acts as a blocker during exercise. It is taken by mouth.

Xamoterol is not available in the United States. 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. 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.

See also

• Alifedrine
• Prenalterol

References

1. ^ Furlong R, Brogden RN (October 1988). "Xamoterol. A preliminary review of its pharmacodynamic and pharmacokinetic properties, and therapeutic use". Drugs. 36 (4): 455–474. doi:10.2165/00003495-198836040-00004. PMID 2906865.
2. ^ Marlow HF (1989). "Xamoterol, a beta 1-adrenoceptor partial agonist: review of the clinical efficacy in heart failure". British Journal of Clinical Pharmacology. 28 (Suppl 1): 23S–30S. doi:10.1111/j.1365-2125.1989.tb03570.x. PMC 1379873. PMID 2572251.
3. Campbell RW (1989). "The management of heart failure and the scope for new therapies: what role for xamoterol?". Br J Clin Pharmacol. 28 Suppl 1 (Suppl 1): 59S–64S. doi:10.1111/j.1365-2125.1989.tb03574.x. PMC 1379877. PMID 2572256.
4. Cruickshank JM (March 1993). "The xamoterol experience in the treatment of heart failure". Am J Cardiol. 71 (9): 61C–64C. doi:10.1016/0002-9149(93)90088-t. PMID 8465800.
5. "Xamoterol: Uses, Interactions, Mechanism of Action". DrugBank Online. 23 June 2017. Retrieved 23 July 2024.
6. Rang HP, Dale MM, Ritter JM, Moore PK (1999). Pharmacology (5th ed.). Edinburgh; New York: Churchill Livingstone. p. 163. ISBN 0443059748.
7. "Drugs@FDA: FDA-Approved Drugs". accessdata.fda.gov. Retrieved 23 July 2024.
8. ^ Schweizerischer Apotheker-Verein (2000). Index Nominum 2000: International Drug Directory. Index nominum. Medpharm Scientific Publishers. p. 1099. ISBN 978-3-88763-075-1. Retrieved 23 July 2024.
9. "Xamoterol". PubChem. Retrieved 1 August 2024.
10. "Xamoterol: Uses, Interactions, Mechanism of Action". DrugBank Online. 23 June 2017. Retrieved 1 August 2024.
11. "Xamoterol [USAN:BAN:INN]". ChemSpider. 21 July 2022. Retrieved 1 August 2024.
12. ^ Vigholt-Sørensen E, Faergeman O, Snow HM (November 1989). "Effects of xamoterol, a beta 1 adrenoceptor partial agonist, in patients with ischaemic dysfunction of the left ventricle". Br Heart J. 62 (5): 335–341. doi:10.1136/hrt.62.5.335. PMC 1224831. PMID 2574049.

• 4-Morpholinyl compounds
• Beta1-adrenergic agonists
• Cardiac stimulants
• Inotropic agents
• Peripherally selective drugs
• Phenol ethers
• 4-Hydroxyphenyl compounds