Compound: metoprolol
SMILES: O(c1ccc(CCOC)cc1)CC(O)CNC(C)C
InChIKey: IUBSYMUCCVWXPE-UHFFFAOYSA-N
Synonyms: metoprolol, 51384-51-1, (RS)-Metoprolol, Beatrolol, dl-Metoprolol, Seroken, 37350-58-6, Metoprololum, Spesikor, 1-(Isopropylamino)-3-(4-(2-methoxyethyl)phenoxy)propan-2-ol, CGP 2175, CGP-2175, Metoprolol slow release, 1-[4-(2-methoxyethyl)phenoxy]-3-(propan-2-ylamino)propan-2-ol, GEB06NHM23, 1-(isopropylamino)-3-[4-(2-methoxyethyl)phenoxy]propan-2-ol, DTXSID2023309, 2-Propanol, 1-[4-(2-methoxyethyl)phenoxy]-3-[(1-methylethyl)amino]-, H-93/26, 2-Propanol, 1-(4-(2-methoxyethyl)phenoxy)-3-((1-methylethyl)amino)-, CHEBI:6904, DTXCID503309, Betaloc-Astra, 1-(4-(2-methoxyethyl)phenoxy)-3-(propan-2-ylamino)propan-2-ol, Beloc Duriles, Betaloc Astra, {2-hydroxy-3-[4-(2-methoxyethyl)phenoxy]propyl}(propan-2-yl)amine, 1-(4-(2-Methoxyethyl)-phenoxy)-3-((1-methylethyl)amino)-2-propanol, CGP2175, metoprololo, (2-hydroxy-3-(4-(2-methoxyethyl)phenoxy)propyl)(propan-2-yl)amine, metoprolol CR-XL, Metoprolol CR XL, RefChem:6036, H 9326, H 93 26, C07AB02, 2-Propanol, 1-(4-(2-methoxyethyl)phenoxy)-3-((1-methylethyl)amino)-, (+-)-, (+-)-1-(Isopropylamino)-3-(p-(beta-methoxyethyl)phenoxy)-2-propanol, 253-483-7, 257-166-4, Spesicor, Meijoprolol, Metohexal, Preblok, Presolol, MFCD00599534, 1-[4-(2-methoxyethyl)phenoxy]-3-propan-2-ylamino-propan-2-ol, (+/-)-Metoprolol, CHEMBL13, rac Metoprolol, 1-[4-(2-methoxyethyl)phenoxy]-3-[(propan-2-yl)amino]propan-2-ol, Selo-Zok, Lopresoretic, Betalok, Metoprololum [INN-Latin], Metoprolol [USAN:INN:BAN], Loresor, Neobloc, Metoprolol S-Isomer, 2-Propanol, 1-[4-(2-methoxyethyl)phenoxy]-3-[(1-methylethyl)amino]-, (.+/-.)-, LOPRESSIDONE, CCRIS 4198, HSDB 6531, Metoprolol (USAN/INN), UNII-GEB06NHM23, 51384-51-1 (free base), EINECS 257-166-4, Lopresol (Salt/Mix), METOPROLOL [MI], Lopresoretic (Salt/Mix), METOPROLOL [INN], (.+/-.)-Metoprolol, GlyTouCan:G46992WB, METOPROLOL [HSDB], METOPROLOL [USAN], METOPROLOL [VANDF], METOPROLOL [MART.], SCHEMBL4093, METOPROLOL [WHO-DD], GTPL553, H 93/26 (Salt/Mix), BDBM25756, METOPROLOL, (+/-)-, HMS2090B15, HMS3886O04, HMS5084K22, BCA38451, G46992WB, GP-2175E, Tox21_303972, EBC-03826, s5430, STL301858, 1-[(1-methylethyl)amino]-3-({4-[2-(methyloxy)ethyl]phenyl}oxy)propan-2-ol, AKOS005927923, BG-0006, CCG-204813, CS-3159, DB00264, SDCCGSBI-0050706.P005, NCGC00021148-03, NCGC00021148-04, NCGC00021148-05, NCGC00021148-21, NCGC00356981-01, 54163-88-1, AC-19022, HY-17503, SBI-0050706.P004, CAS-51384-51-1, DB-049097, AB00053499, NS00000197, C07202, D02358, EN300-317058, AB00053499-21, AB00053499_22, AB00053499_23, L000669, Q409468, SR-01000003148-2, BRD-A03623303-045-02-0, BRD-A03623303-045-05-3, BRD-A03623303-045-09-5, BRD-A03623303-046-14-3, Z398538014, 1-(Isopropylamino)-3-[4-(2-methoxyethyl)phenoxy]-2-propanol, 1-(Isopropylamino)-3-[p-(2-methoxyethyl)phenoxy]-2-propanol, 1-Isopropylamino-3-[4-(2-methoxy-ethyl)-phenoxy]-propan-2-ol, (+/-)-1-(Isopropylamino)-3-(p-(beta-methoxyethyl)phenoxy)-2-propanol, 1-(4-(2-METHOXYETHYL)PHENOXY)-3-((1-METHYLETHYL)AMINO)-2-PROPANOL, [(2S)-1-[4-(2-Methoxyethyl)phenoxy]-3-[(1-methylethyl)-amino]propan-2-ol, (2R,3R)-2,3-dihydroxysuccinic acid;1-(isopropylamino)-3-[4-(2-methoxyethyl)phenoxy]propan-2-ol
Theoretical properties:
molecular_formula: C15H25NO3
molecular_weight: 267.36 g/mol
exact_mass: 267.18344366 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 9
heavy_atom_count: 19
topological_polar_surface_area: 50.7 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
boiling_point: 398ºC (estimate)
solubility: Soluble (tartrate form)
Descriptions:
pubchem: Metoprolol is a propanolamine that is 1-(propan-2-ylamino)propan-2-ol substituted by a 4-(2-methoxyethyl)phenoxy group at position 1. It has a role as a geroprotector, a beta-adrenergic antagonist, an antihypertensive agent, a xenobiotic and an environmental contaminant. It is a propanolamine, an aromatic ether, a secondary alcohol and a secondary amino compound.
chebi: A propanolamine that is 1-(propan-2-ylamino)propan-2-ol substituted by a  4-(2-methoxyethyl)phenoxy group at position 1.
chembl: METOPROLOL is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Metoprolol, sold under the brand names Lopressor and Toprol-XL among others, is a medication used to treat angina, high blood pressure and a number of conditions involving an abnormally fast heart rate. It is also used to prevent further heart problems after myocardial infarction and to prevent headaches in those with migraines. It is a beta blocker, specifically a selective β1 receptor blocker, and is taken by mouth or is given intravenously.
Common side effects include trouble sleeping, feeling tired, feeling faint, and abdominal discomfort. Large doses may cause serious toxicity. Risk in pregnancy has not been ruled out. It appears to be safe in breastfeeding. The metabolism of metoprolol can vary widely among patients, often as a result of hepatic impairment or CYP2D6 polymorphism.
Metoprolol was first made in 1969, patented in 1970, and approved for medical use in 1978. It is on the World Health Organization's List of Essential Medicines. It is available as a generic medication. In 2023, it was the sixth most commonly prescribed medication in the United States, with more than 59 million prescriptions.