Compound: Xamoterol
SMILES: O=C(N1CCOCC1)NCCNCC(O)COc2ccc(O)cc2
InChIKey: DXPOSRCHIDYWHW-UHFFFAOYSA-N
Synonyms: Xamoterol, 81801-12-9, Xamoterolum, ICI-118587, N-(2-((2-hydroxy-3-(4-hydroxyphenoxy)propyl)amino)ethyl)morpholine-4-carboxamide, N-[2-[[2-hydroxy-3-(4-hydroxyphenoxy)propyl]amino]ethyl]morpholine-4-carboxamide, 7HE0JQL703, DTXSID8045222, ICI-118,587, N-(2-{[2-hydroxy-3-(4-hydroxyphenoxy)propyl]amino}ethyl)morpholine-4-carboxamide, 4-Morpholinecarboxamide, N-(2-((2-hydroxy-3-(4-hydroxyphenoxy)propyl)amino)ethyl)-, (+-)-, DTXCID6025222, (+-)-N-(2-((2-Hydroxy-3-(p-hydroxyphenoxy)propyl)amino)ethyl)-4-morpholinecarboxamide, Fumarate, Xamoterol, Hemifumarate, Xamoterol, RefChem:195096, Monohydrobromide, Xamoterol, Monohydrochloride, Xamoterol, C01CX07, ICI118587, ICI 118587, Xamoterolum [Latin], Corwin, Xamoterol (fumarate), NCGC00016099-04, CHEBI:10055, Xamoterol (USAN), XAMOTEROL [USAN], ICI 118587; ICI-118587; ICI118587; Xamoterol hemifumarate; Xamtol, SR-01000075155, UNII-7HE0JQL703, Xamoterol [USAN:INN:BAN], N-[2-[[(2R)-2-Hydroxy-3-(4-hydroxyphenoxy)propyl]amino]ethyl]-4-morpholinecarboxamide, XAMOTEROL [INN], XAMOTEROL [MI], Prestwick0_000923, Prestwick1_000923, Prestwick2_000923, Prestwick3_000923, GlyTouCan:G23793AP, XAMOTEROL [WHO-DD], Lopac0_001259, SCHEMBL64461, BSPBio_000826, GTPL538, CHEMBL75753, SPBio_003005, BPBio1_000910, orb1694838, DXPOSRCHIDYWHW-UHFFFAOYSA-N, HMS2089I13, G23793AP, Tox21_110304, BDBM50248358, EBC-26649, MFCD00661103, AKOS027420460, CCG-205333, DB13781, SB50140, NCGC00016099-03, NCGC00016099-05, NCGC00024897-02, NCGC00024897-03, DA-02619, CAS-81801-12-9, HY-101327, AB00514723, CS-0021161, D06328, AB00514723-05, EN300-18457256, L000630, Q4021708, SR-01000075155-1, SR-01000075155-3, BRD-A59337442-051-05-3, N-(2-((2-hydroxy-3-(4-hydroxyphenoxy)propyl)amino)ethyl)-4-morpholinecarboxamide, (+/-)-N-(2-((2-HYDROXY-3-(P-HYDROXYPHENOXY)PROPYL)AMINO)ETHYL)-4-MORPHOLINECARBOXAMIDE, (+/-)-N-[2-[[Hydroxy-3-(4-hydroxy)propyl]amino]ethyl-4-morpholinecarboxamide hemifumarate salt, 4-MORPHOLINECARBOXAMIDE, N-(2-((2-HYDROXY-3-(4-HYDROXYPHENOXY)PROPYL)AMINO)ETHYL)-, (+/-)-, 69630-08-6
Theoretical properties:
molecular_formula: C16H25N3O5
molecular_weight: 339.39 g/mol
exact_mass: 339.17942091 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 4
hydrogen_bond_acceptor_count: 6
rotatable_bond_count: 8
heavy_atom_count: 24
topological_polar_surface_area: 103 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Xamoterol is a member of morpholines.
chembl: XAMOTEROL is a small molecule listed in the ChEMBL database and has reached clinical trial phase 2.0.
wikipedia: 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.