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Benzeneacetamide,4-[2-hydroxy-3-[(1-methylethyl)amino]propoxy]-(CAS No. 29122-68-7)

Benzeneacetamide,4-[2-hydroxy-3-[(1-methylethyl)amino]propoxy]- C14H22N2O3 (cas 29122-68-7) Molecular Structure

29122-68-7 Structure

Identification and Related Records

【Name】
Benzeneacetamide,4-[2-hydroxy-3-[(1-methylethyl)amino]propoxy]-
【CAS Registry number】
29122-68-7
【Synonyms】
Acetamide,2-[p-[2-hydroxy-3-(isopropylamino)propoxy]phenyl]- (8CI)
(RS)-Atenolol
Alinor
Altol
Anselol
Antipressan
Apo-Atenolol
AteHexal
Atecard
Atelol
Atenblock
Atendol
Atenet
Ateni
Ateno
Atenolol
Aterol
B-Vasc
Betacard
Tenormin
Tenormine
Tensimin
Tredol
Urosin
Vericordin
Xaten
1-p-Carbamoylmethylphenoxy-3-isopropylamino-2-propanol
Catenol
Catenolol
Corotenol
Farnormin
Hipres
ICI 66082
Internolol
Lo-ten
Lotenal
Normalol
Noten
Oraday
Prenormine
SelesBeta
Serten
Telol
Teno-basan
Tenolin
Tenoprin
【EINECS(EC#)】
249-451-7
【Molecular Formula】
C14H22N2O3 (Products with the same molecular formula)
【Molecular Weight】
266.34
【Inchi】
InChI=1/C14H22N2O3/c1-10(2)16-8-12(17)9-19-13-5-3-11(4-6-13)7-14(15)18/h3-6,10,12,16-17H,7-9H2,1-2H3,(H2,15,18)
【InChIKey】
METKIMKYRPQLGS-UHFFFAOYSA-N
【Canonical SMILES】
CC(C)NCC(COC1=CC=C(C=C1)CC(=O)N)O
【MOL File】
29122-68-7.mol

Chemical and Physical Properties

【Appearance】
White to off-white crystalline powder
【Density】
1.125 g/cm3
【Melting Point】
152 C
【Flash Point】
261.1°C
【Water】
Insoluble
【Solubilities】
Insoluble
【Color/Form】
white to off-white
【Stability】
No data.
【Storage temp】
Keep in a cool, dry, dark location in a tightly sealed container or cylinder. Keep away from incompatible materials, ignition sources and untrained individuals. Secure and label area. Protect containers/cylinders from physical damage.
【Spectral properties】
UV max (methanol): 225, 275, 283
【Computed Properties】
Molecular Weight:266.33608 [g/mol]
Molecular Formula:C14H22N2O3
XLogP3:0.2
H-Bond Donor:3
H-Bond Acceptor:4
Rotatable Bond Count:8
Tautomer Count:3
Exact Mass:266.163043
MonoIsotopic Mass:266.163043
Topological Polar Surface Area:84.6
Heavy Atom Count:19
Formal Charge:0
Complexity:263
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:1
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:3
Feature 3D Donor Count:3
Feature 3D Cation Count:1
Feature 3D Hydrophobe Count:1
Feature 3D Ring Count:1
Effective Rotor Count:8
Conformer Sampling RMSD:1
CID Conformer Count:93

Safety and Handling

【Hazard Codes】
UN NO.
【Risk Statements】
R22
【Safety Statements 】
22-24/25-36-26
【Safety】

Safety Information of?Atenolol (CAS NO.29122-68-7):
Hazard Codes: Xn
Risk Statements: 22-36/37/38-20/21/22
22: Harmful if swallowed
36/37/38: Irritating to eyes, respiratory system and skin
20/21/22: Harmful by inhalation, in contact with skin and if swallowed
Safety Statements: 22-24/25-36-26
22: Do not breathe dust
24/25: Avoid contact with skin and eyes
36: Wear suitable protective clothing
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
WGK Germany: 2
RTECS: AC3600000

【Formulations/Preparations】
Oral tablets, 25 mg, Tenormin (with povidone), AstraZeneca; 50 mg, atenolol tablets, Tenormin (with povidone; scored), AstraZeneca; 100 mg, atenolol tablets, Tenormin (with povidone), AstraZeneca; parenteral injection, for IV use, 0.5 mg/ml Tenormin, AstraZeneca.
Atehexal, Ateno basan, Atenol, Cuxanorm, Ibinolo, Myocord, Prenormine, Seles Beta, Tenoblock, Tenormin, Uniloc
【Exposure Standards and Regulations】
Atenolol, used as a beta adrenergic blocking agent, was approved by FDA for marketing in the United States 8/81.
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed drug products, incl atenolol, approved on the basis of safety and effectiveness by FDA under sections 505 and 507 of the Federal Food, Drug, and Cosmetic Act.
Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392). [
【Specification】

First Aid Measures of Atenolol (CAS NO.29122-68-7):
Ingestion:Seek medical attention. If individual is drowsy or unconscious, do not give anything by mouth; place individual on the left side with the head down. Contact a physician, medical facility, or poison control center for advice about whether to induce vomiting. If possible, do not leave individual unattended.
Inhalation:If symptoms develop, move individual away from exposure and into fresh air. If symptoms persist, seek medical attention. If breathing is difficult, administer oxygen. Keep person warm and quiet; seek immediate medical attention.
Skin:Flush skin with plenty of soap and water for at least 15 minutes while removing contaminated clothing and shoes.
Eyes:If symptoms develop, immediately move individual away from exposure and into fresh air. Flush eyes gently with water for at least 15 minutes while holding eyelids apart; seek immediate medical attention.
Storage:
Keep in a cool, dry, dark location in a tightly sealed container or cylinder. Keep away from incompatible materials, ignition sources and untrained individuals. Secure and label area. Protect containers/cylinders from physical damage.

【Octanol/Water Partition Coefficient】
log Kow= 0.16
【Disposal Methods】
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Use and Manufacturing

【Usage】

Cardioselective ?adrenergic blocker. Antihypertensive, antianginal, antiarrhythmic (class II)

Biomedical Effects and Toxicity

【Biological Activity】
Cardioselective β -adrenergic blocker. Antihypertensive, antianginal, antiarrhythmic.
【Pharmacological Action】
- Drugs that bind to and block the activation of ADRENERGIC BETA-1 RECEPTORS.
- Agents used for the treatment or prevention of cardiac arrhythmias. They may affect the polarization-repolarization phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibers. Anti-arrhythmia agents are often classed into four main groups according to their mechanism of action: sodium channel blockade, beta-adrenergic blockade, repolarization prolongation, or calcium channel blockade.
- Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS.
- Drugs that inhibit the actions of the sympathetic nervous system by any mechanism. The most common of these are the ADRENERGIC ANTAGONISTS and drugs that deplete norepinephrine or reduce the release of transmitters from adrenergic postganglionic terminals (see ADRENERGIC AGENTS). Drugs that act in the central nervous system to reduce sympathetic activity (e.g., centrally acting alpha-2 adrenergic agonists, see ADRENERGIC ALPHA-AGONISTS) are included here.
【Therapeutic Uses】
Adrenergic beta-Antagonists; Anti-Arrhythmia Agents; Antihypertensive Agents; Sympatholytics
Atenolol has been used with good results alone or in conjunction with a benzodiazepine in the management of acute alcohol withdrawal in a limited number of patients.
Atenolol ... /is/ indicated in the treatment of classic angina pectoris, also referred to as "effort-associated angina". /Included in US product labeling/
Atenolol /is/ used in the treatment of mitral value prolapse syndrome. /NOT included in US product labeling/
Atenolol ... /is/ used for thyrotoxicosis. /NOT included in US product labeling/
... Atenolol ... may be used to treat tremors. /NOT included in US product labeling/
... Atenolol /is/ useful for prophylaxis of migrane. /NOT included in US product labeling/
... /Atenolol may be used/ in the management of symptoms of tachycardia due to excessive beta-receptor stimulation in pheochromocytoma. However, it should be used only after primary treatment with an alpha-adrenergic blocking agent (since use without concomitant alpha-blockade could lead to serious blood pressure elevation). /NOT included in US product labeling/
Atenolol ... /is/ indicated in clinically stable patients recovering from an initial definite or suspected acute myocardial infarction in order to reduce cardiovascular mortality and to decrease the risk of reinfarction. /Included in US product labeling/
Atenolol /is/ ... indicated in the management of angina, palpitations, and syncope associated with hypertrophic subaortic stenosis. /NOT included in US product labeling/
... Atenolol /is/ indicated in the treatment of hypertension when used alone or in combination with other antihypertensive medication. ... /Included in US product labeling/
... Atenolol ... /is/ used for their antiarrhythmic effects, especially in supraventricular arrhythmias and ventricular tachycardias. /NOT included in US product labeling/
【Biomedical Effects and Toxicity】
In animals, atenolol is well distributed into most tissues and fluids except brain and /cerebrospinal fluid/. Unlike propranolol, only a small portion of atenolol is apparently distributed into the CNS.
Approximately 5-15% of atenolol is bound to plasma protein.
Atenolol readily crosses the placenta, and has been detected in cord blood. During continuous administration, fetal serum concentrations of the drug are probably equivalent to those in maternal serum. Atenolol is distributed into milk; peak milk concentrations of the drug are higher than peak serum concentrations after an individual dose, and the area under the milk concentration-time (AUC) is substantially greater than that of the serum AUC in lactating women receiving the drug continuously.
Atenolol is rapidly but incompletely absorbed from the GI tract. Only about 50-60% of an oral dose of atenolol is absorbed. In healthy adults, peak plasma concentrations of 1-2 ug/ml are achieved 2-4 hours after oral administration of a single 200 mg dose of atenolol. An approximately fourfold interindividual variation in plasma concentrations attained has been reported with a specific oral dose of atenolol. Peak plasma atenolol concentrations are achieved within 5 minutes following direct IV injection of the drug, and decline rapidly during an initial distribution phase; after the first 7 hours, plasma concentrations reportedly decline with an elimination half-life similar to that of orally administered drug.
In patients with normal renal function, atenolol has a plasma half-life (t1/2) of 6-7 hours. Children with normal renal function may exhibit a shorter elimination half-life. In one study in children 5-16 (mean: 8.9) years of age with arhythmias and normal renal and hepatic function, the terminal elimination half-life averaged 4.6 hours. Plasma t1/2 of the drug increases to 16-27 hours in patients with creatinine clearances of 15-35 ml/minute per 1.73 m2 and exceeds 27 hours with progressive renal impairment. Little or no metabolism of atenolol occurs in the liver. Approximately 40-50% of an oral dose of the drug is excreted in urine unchanged. The remainder is excreted unchanged in feces, principally as unabsorbed drug. About 1-12% of atenolol is reportedly removed by hemodialysis.
The pharmacokinetics of atenolol (Tenormin) enantiomers in 6 healthy male subjects (aged 23-65 yr) who received a single oral tablet of 50 mg racemic atenolol and in rats who received an intravenous injection of 10 mg/kg of the racemic drug were studied. In humans the areas under the plasma concentration time curves were 1640 + or - 602 and 1860 + or - 652 (ng/ml)hr for the S- and R-enantiomers, respectively. The small difference was due to a slight but statistically significant difference in the renal clearance of the enantiomers. The enantiomers did not differ from each other with respect to volume of distribution or terminal elimination rate constant. In rats, the area under the plasma concentration time curves of the R-enantiomer was 4020 + or - 1080, compared with 3630 + or - 1040 for the S-enantiomer. As for humans, this difference was due to a stereoselective renal clearance in favor of the S-enantiomer. The elimination rate constant in rats was the same for both enantiomers. [Mehvar R et al; J Pharm Sci 79 (Oct): 881-5 (1990)] PubMed Abstract

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