Atenolol

Title: Atenolol
CAS Registry Number: 29122-68-7
CAS Name: 4-[2-Hydroxy-3-[(1-methylethyl)amino]propoxy]benzeneacetamide
Additional Names: 2-[p-[2-hydroxy-3-(isopropylamino)propoxy]phenyl]acetamide; 1-p-carbamoylmethylphenoxy-3-isopropylamino-2-propanol
Manufacturers' Codes: ICI-66082
Trademarks: Atehexal (Hexal); Ateno basan (Schoenenberger); Atenol (AstraZeneca); Cuxanorm (TAD); Myocord (Ivax); Prenormine (AstraZeneca); Seles Beta (Schwarz); Tenoblock (Leiras); Tenormin (AstraZeneca); Uniloc (Nycomed)
Molecular Formula: C14H22N2O3
Molecular Weight: 266.34
Percent Composition: C 63.13%, H 8.33%, N 10.52%, O 18.02%
Literature References: Cardioselective b-adrenergic blocker. Prepn: Barrett et al., DE 2007751; eidem, US 3663607 and US 3836671 (1970, 1972, 1974 all to I.C.I.). Pharmacology and clinical studies: Giudicelli et al., C.R. Seances Soc. Biol. Ses Fil. 167, 232 (1973); Hansson et al., Acta Med. Scand. 194, 549 (1973); Amery et al., N. Engl. J. Med. 290, 284 (1974). Clinical trial in treatment of alcohol withdrawal syndrome: M. L. Kraus et al., ibid. 313, 905 (1985). HPLC determn of enantiomers in plasma and urine: S. K. Chin et al., J. Chromatogr. 489, 438 (1989). Comprehensive description: V. Caplar et al., Anal. Profiles Drug Subs. 13, 1-25 (1984). Review: J. D. Fitzgerald in Pharmacological and Biochemical Properties of Drug Substances vol. 2, M. E. Goldberg, Ed. (Am. Pharm. Assoc., Washington, DC, 1979) pp 98-147; E. Marmo, Drugs Exp. Clin. Res. 6, 639-663 (1980). Symposium on clinical studies: Drugs 25, Suppl. 2, 1-346 (1983).
Properties: Crystals from ethyl acetate, mp 146-148°. Also reported as mp 150-152° (Caplar). Freely sol in methanol; sol in acetic acid, DMSO; sparingly sol in 96% ethanol; slightly sol in water, isopropanol; very slightly sol in acetone, dioxane. Practically insol in acetonitrile, ethylacetate, chloroform. pKa 9.6. Partition coefficient (n-octanol/phosphate buffer): 0.008 (pH 7.0); 0.052 (pH 8.0). Dipole moment: 5.71 ±0.20 D at 20° in propionic acid. uv max (methanol): 225, 275, 283 nm. LD50 in mice, rats (mg/kg): 2000, 3000 orally; 98.7, 59.24 i.v. (Fitzgerald).
Melting point: mp 146-148°; mp 150-152° (Caplar)
pKa: pKa 9.6
Log P: Partition coefficient (n-octanol/phosphate buffer): 0.008 (pH 7.0); 0.052 (pH 8.0)
Absorption maximum: uv max (methanol): 225, 275, 283 nm
Toxicity data: LD50 in mice, rats (mg/kg): 2000, 3000 orally; 98.7, 59.24 i.v. (Fitzgerald)
Therap-Cat: Antihypertensive, antianginal, antiarrhythmic (class II).
Keywords: ?Adrenergic Blocker; Antianginal; Antiarrhythmic; Antihypertensive; Aryloxypropanolamine Derivatives.
Atevirdine Athamantin Atipamezole Atisine Atomoxetine

Atenolol
Atenolol.svg
Atenolol 3d structure.png
Systematic (IUPAC) name
(RS)-2-{4-[2-Hydroxy-3-(propan-2-ylamino)propoxy]phenyl}acetamide
Clinical data
Trade names Tenormin
AHFS/Drugs.com monograph
MedlinePlus a684031
Licence data US FDA:link
Pregnancy cat. C (AU) D (US)
Legal status Prescription only
Routes Oral or IV
Pharmacokinetic data
Bioavailability 40-50%
Protein binding 6-16%
Metabolism Hepatic <10%
Half-life 6-7 hours
Excretion Renal
Lactic (In lactiferous females)
Identifiers
CAS number 29122-68-7 YesY
ATC code C07AB03
PubChem CID 2249
IUPHAR ligand 548
DrugBank DB00335
ChemSpider 2162 YesY
UNII 50VV3VW0TI YesY
KEGG D00235 YesY
ChEBI CHEBI:2904 YesY
ChEMBL CHEMBL24 YesY
Chemical data
Formula C14H22N2O3 
Mol. mass 266.336 g/mol
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Atenolol is a selective β1 receptor antagonist, a drug belonging to the group of beta blockers (sometimes written β-blockers), a class of drugs used primarily in cardiovascular diseases. Introduced in 1976, atenolol was developed as a replacement for propranolol in the treatment of hypertension. The chemical works by slowing down the heart and reducing its workload. Unlike propranolol, atenolol does not pass through the blood–brain barrier thus avoiding various central nervous system side effects.[1]

Atenolol is one of the most widely used β-blockers in the United Kingdom and was once the first-line treatment for hypertension. The role for β-blockers in hypertension was downgraded in June 2006 in the United Kingdom to fourth-line, as they perform less appropriately or effectively than newer drugs, particularly in the elderly.