Atenolol
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Basic Info
Common Name | Atenolol(F04843) |
2D Structure | |
Description | Atenolol is a so-called beta1-selective (or 'cardioselective') drug. That means that it exerts greater blocking activity on myocardial beta1-receptors than on beta2 ones in the lung. The beta2 receptors are responsible to keep the bronchial system open. If these receptors are blocked, bronchospasm with serious lack of oxygen in the body can result. However, due to its cardioselective properties, the risk of bronchospastic reactions if using atenolol is reduced compared to nonselective drugs as propranolol. Nonetheless, this reaction may also be encountered with atenolol, particularly with high doses. Extreme caution should be exerted if atenolol is given to asthma patients, who are particularly at risk; the dose should be as low as possible. If an asthma attack occurs, the inhalation of a beta2-mimetic antiasthmatic, such as hexoprenalin or salbutamol, will usually suppress the symptoms. Atenolol (trade name Tenormin) can be used to treat cardiovascular diseases such as hypertension, coronary heart disease, arrhythmias, and treatment of myocardial infarction after the acute event. Patients with compensated congestive heart failure may be treated with atenolol as a co medication (usually together with an ACE inhibitor, a diuretic and a digitalis-glycoside, if indicated). In patients with congestive heart failure, it reduces the need for and the consumption of oxygen of the heart muscle. It is very important to start with low doses, as atenolol reduces also the muscular power of the heart, which is an undesired effect in congestive heart failure. |
FRCD ID | F04843 |
CAS Number | 29122-68-7 |
PubChem CID | 2249 |
Formula | C14H22N2O3 |
IUPAC Name | 2-[4-[2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl]acetamide |
InChI Key | METKIMKYRPQLGS-UHFFFAOYSA-N |
InChI | InChI=1S/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) |
Canonical SMILES | CC(C)NCC(COC1=CC=C(C=C1)CC(=O)N)O |
Isomeric SMILES | CC(C)NCC(COC1=CC=C(C=C1)CC(=O)N)O |
Wikipedia | Atenolol |
Synonyms | atenolol 29122-68-7 Tenormin Tenormine Normiten Blokium Prenormine Tenoblock Atehexal Betablok |
Classifies | Illegal Additives |
Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
Kingdom | Organic compounds |
Superclass | Benzenoids |
Class | Benzene and substituted derivatives |
Subclass | Phenylacetamides |
Intermediate Tree Nodes | Not available |
Direct Parent | Phenylacetamides |
Alternative Parents | |
Molecular Framework | Aromatic homomonocyclic compounds |
Substituents | Phenylacetamide - Phenoxy compound - Phenol ether - Alkyl aryl ether - 1,2-aminoalcohol - Amino acid or derivatives - Carboxamide group - Secondary alcohol - Primary carboxylic acid amide - Carboxylic acid derivative - Secondary amine - Secondary aliphatic amine - Ether - Organic nitrogen compound - Organonitrogen compound - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Carbonyl group - Organopnictogen compound - Amine - Organic oxygen compound - Alcohol - Aromatic homomonocyclic compound |
Description | This compound belongs to the class of organic compounds known as phenylacetamides. These are amide derivatives of phenylacetic acids. |
Properties
Property Name | Property Value |
---|---|
Molecular Weight | 266.341 |
Hydrogen Bond Donor Count | 3 |
Hydrogen Bond Acceptor Count | 4 |
Rotatable Bond Count | 8 |
Complexity | 263 |
Monoisotopic Mass | 266.163 |
Exact Mass | 266.163 |
XLogP | 0.2 |
Formal Charge | 0 |
Heavy Atom Count | 19 |
Defined Atom Stereocenter Count | 0 |
Undefined Atom Stereocenter Count | 1 |
Defined Bond Stereocenter Count | 0 |
Undefined Bond Stereocenter Count | 0 |
Isotope Atom Count | 0 |
Covalently-Bonded Unit Count | 1 |
ADMET
Model | Result | Probability |
---|---|---|
Absorption | ||
Blood-Brain Barrier | BBB- | 0.9505 |
Human Intestinal Absorption | HIA+ | 0.9831 |
Caco-2 Permeability | Caco2- | 0.7922 |
P-glycoprotein Substrate | Substrate | 0.6773 |
P-glycoprotein Inhibitor | Non-inhibitor | 0.9446 |
Non-inhibitor | 0.9856 | |
Renal Organic Cation Transporter | Non-inhibitor | 0.8959 |
Distribution | ||
Subcellular localization | Mitochondria | 0.8513 |
Metabolism | ||
CYP450 2C9 Substrate | Non-substrate | 0.8416 |
CYP450 2D6 Substrate | Substrate | 0.5468 |
CYP450 3A4 Substrate | Non-substrate | 0.6826 |
CYP450 1A2 Inhibitor | Non-inhibitor | 0.9045 |
CYP450 2C9 Inhibitor | Non-inhibitor | 0.9163 |
CYP450 2D6 Inhibitor | Non-inhibitor | 0.9231 |
CYP450 2C19 Inhibitor | Non-inhibitor | 0.9026 |
CYP450 3A4 Inhibitor | Non-inhibitor | 0.9379 |
CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9537 |
Excretion | ||
Toxicity | ||
Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9960 |
Non-inhibitor | 0.8861 | |
AMES Toxicity | Non AMES toxic | 0.9132 |
Carcinogens | Non-carcinogens | 0.8691 |
Fish Toxicity | High FHMT | 0.6122 |
Tetrahymena Pyriformis Toxicity | High TPT | 0.7120 |
Honey Bee Toxicity | Low HBT | 0.6965 |
Biodegradation | Not ready biodegradable | 0.8969 |
Acute Oral Toxicity | III | 0.7976 |
Carcinogenicity (Three-class) | Non-required | 0.7116 |
Model | Value | Unit |
---|---|---|
Absorption | ||
Aqueous solubility | -2.0111 | LogS |
Caco-2 Permeability | 0.5609 | LogPapp, cm/s |
Distribution | ||
Metabolism | ||
Excretion | ||
Toxicity | ||
Rat Acute Toxicity | 2.0932 | LD50, mol/kg |
Fish Toxicity | 2.0488 | pLC50, mg/L |
Tetrahymena Pyriformis Toxicity | -0.4589 | pIGC50, ug/L |
References
Title | Journal | Date | Pubmed ID |
---|---|---|---|
Hypertension's 3 Dilemmas and 3 Solutions: Pharmacology of the Kidney inHypertension. | J Cardiovasc Pharmacol | 2017 Mar | 28267687 |
An analysis of the dissipation of pharmaceuticals under thirteen different soilconditions. | Sci Total Environ | 2016 Feb 15 | 26657382 |
Pharmacological characteristics of Artemisia vulgaris L. in isolated porcinebasilar artery. | J Ethnopharmacol | 2016 Apr 22 | 26875644 |
Reactivity of β-blockers/agonists with aqueous permanganate. Kinetics and transformation products of salbutamol. | Water Res | 2015 Aug 1 | 25965887 |
A new approach to predict human intestinal absorption using porcine intestinaltissue and biorelevant matrices. | Eur J Pharm Sci | 2014 Oct 15 | 25046168 |
Assessment of ABCG2-mediated transport of xenobiotics across the blood-milk barrier of dairy animals using a new MDCKII in vitro model. | Arch Toxicol | 2013 Sep | 23652544 |
Effect of pharmaceuticals exposure on acetylcholinesterase (AchE) activity and on the expression of AchE gene in the monogonont rotifer, Brachionus koreanus. | Comp Biochem Physiol C Toxicol Pharmacol | 2013 Nov | 24028855 |
Update on treatment of essential tremor. | Curr Treat Options Neurol | 2013 Aug | 23881742 |
Pharmaco-nutrient interactions - a systematic review of zinc and antihypertensivetherapy. | Int J Clin Pract | 2013 Aug | 23279674 |
Emerging pollutants in sewage, surface and drinking water in Galicia (NW Spain). | Chemosphere | 2012 Mar | 22189380 |
Runoff of pharmaceuticals and personal care products following application of dewatered municipal biosolids to an agricultural field. | Sci Total Environ | 2009 Aug 1 | 19464726 |
Use of toxicity assays for enantiomeric discrimination of pharmaceutical substances. | Chirality | 2009 Aug | 18989896 |
[Arterial hypertension in pregnancy]. | Rev Med Brux | 2008 Sep | 18949985 |
A pharmacodynamic study on clenbuterol-induced toxicity: beta1- and beta2-adrenoceptors involvement in guinea-pig tachycardia in an in vitro model. | Food Chem Toxicol | 2007 Sep | 17449161 |
A pilot study of open label sesame oil in hypertensive diabetics. | J Med Food | 2006 Fall | 17004907 |
Perinatal MSG treatment attenuates fasting-induced bradycardia and metabolicsuppression. | Physiol Behav | 2005 Oct 15 | 16153669 |
Atenolol developmental toxicity: animal-to-human comparisons. | Birth Defects Res A Clin Mol Teratol | 2003 Mar | 12797460 |
Capillary isotachophoresis/NMR: extension to trace impurity analysis and improvedinstrumental coupling. | Anal Chem | 2002 May 15 | 12038755 |
Dietary Mg(2+) supplementation restores impaired vasoactive responses in isolatedrat aorta induced by chronic ethanol consumption. | Eur J Pharmacol | 2002 May 10 | 12065078 |
Trial of antihypertensive intervention and management: greater efficacy withweight reduction than with a sodium-potassium intervention. | J Am Diet Assoc | 1993 Apr | 8454808 |
Targets
- General Function:
- Protein homodimerization activity
- Specific Function:
- Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately 30-fold greater affinity than it does norepinephrine.
- Gene Name:
- ADRB2
- Uniprot ID:
- P07550
- Molecular Weight:
- 46458.32 Da
References
- Nuttall SL, Routledge HC, Kendall MJ: A comparison of the beta1-selectivity of three beta1-selective beta-blockers. J Clin Pharm Ther. 2003 Jun;28(3):179-86. [12795776 ]
- General Function:
- Receptor signaling protein activity
- Specific Function:
- Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately equal affinity. Mediates Ras activation through G(s)-alpha- and cAMP-mediated signaling.
- Gene Name:
- ADRB1
- Uniprot ID:
- P08588
- Molecular Weight:
- 51322.1 Da
- Mechanism of Action:
- Like metoprolol, atenolol competes with sympathomimetic neurotransmitters such as catecholamines for binding at beta(1)-adrenergic receptors in the heart and vascular smooth muscle, inhibiting sympathetic stimulation. This results in a reduction in resting heart rate, cardiac output, systolic and diastolic blood pressure, and reflex orthostatic hypotension. Higher doses of atenolol also competitively block beta(2)-adrenergic responses in the bronchial and vascular smooth muscles.
References
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [11752352 ]