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29122-68-7 molecular structure
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2-(4-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}phenyl)acetamide

ChemBase ID: 219
Molecular Formular: C14H22N2O3
Molecular Mass: 266.33608
Monoisotopic Mass: 266.16304257
SMILES and InChIs

SMILES:
O(CC(O)CNC(C)C)c1ccc(cc1)CC(=O)N
Canonical SMILES:
OC(COc1ccc(cc1)CC(=O)N)CNC(C)C
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)
InChIKey:
METKIMKYRPQLGS-UHFFFAOYSA-N

Cite this record

CBID:219 http://www.chembase.cn/molecule-219.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
2-(4-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}phenyl)acetamide
IUPAC Traditional name
atenolol
Brand Name
Aircrit
Alinor
Altol
Anselol
Antipressan
Apo-Atenolol
Atcardil
Atecard
Atehexal
Atenblock
Atendol
Atenet
Ateni
Atenil
Atenol
Atenol 1A Pharma
Atenol Acis
Atenol AL
Atenol Atid
Atenol Cophar
Atenol CT
Atenol Fecofar
Atenol Gador
Atenol Genericon
Atenol GNR
Atenol Heumann
Atenol MSD
Atenol NM Pharma
Atenol Nordic
Atenol PB
Atenol Quesada
Atenol Stada
Atenol Tika
Atenol Trom
Atenol Von CT
Atenol-Mepha
Atenol-Ratiopharm
Atenol-Wolff
Atenolin
Atenomel
Atereal
Aterol
Betablok
Betacard
Betasyn
Betatop GE
Blocotenol
Blokium
Cardaxen
Cardiopress
Corotenol
Cuxanorm
Duraatenolol
Duratenol
Evitocor
Farnormin
Felo-Bits
Hipres
Hypoten
Ibinolo
Internolol
Jenatenol
Juvental
Lo-Ten
Loten
Lotenal
Myocord
Normalol
Normiten
Noten
Oraday
Ormidol
Panapres
Plenacor
Premorine
Prenolol
Prenormine
Prinorm
Scheinpharm Atenol
Seles Beta
Selobloc
Serten
Servitenol
Stermin
Tenidon
Teno-Basan
Tenobloc
Tenoblock
Tenolol
Tenoprin
Tenormin
Tenormine
Tensimin
Tredol
Unibloc
Uniloc
Vascoten
Vericordin
Wesipin
Xaten
Synonyms
2-{4-[2-Hydroxy-3-(isopropylamino)propoxy]-phenyl}acetamide
4-[2-Hydroxy-3-[(1-methylethyl)amino]propoxyl]benzeneacetamide
2-[p-[2-Hydroxy-3-(isopropylamino)propoxy]phenyl]acetamide
(RS)-Atenolol
(+/-)-Atenolol
ICI-66082
Atehexal
Atenol
Cuxanorm
Myocord
Normalol
Normiten
Uniloc
Vericordin
Wesipin
Xaten
dl-Atenolol
Atenolol
(±)-4-[2-Hydroxy-3-[(1-methylethyl)amino]propoxy]benzeneacetamide
4-[2′-Hydroxy-3′-(isopropylamino)propoxy]phenylacetamide
Atenolol
2-(4-(2-hydroxy-3-(isopropylamino)propoxy)phenyl)acetamide
2-(4-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}phenyl)acetamide
CAS Number
29122-68-7
EC Number
249-451-7
MDL Number
MFCD00057645
PubChem SID
160963682
24277748
46506915
PubChem CID
2249

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 14.078504  H Acceptors
H Donor LogD (pH = 5.5) -2.7682068 
LogD (pH = 7.4) -1.8002133  Log P 0.42502484 
Molar Refractivity 73.5053 cm3 Polarizability 29.0903 Å3
Polar Surface Area 84.58 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 0.57  LOG S -2.79 
Solubility (Water) 4.29e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
13.5 mg/mL expand Show data source
Acetic Acid expand Show data source
Dimethyl Sulfoxide expand Show data source
DMSO: soluble18 mg/mL expand Show data source
ethanol: soluble3.4 mg/mL expand Show data source
H2O: soluble0.3 mg/mL expand Show data source
Methanol expand Show data source
Apperance
Crystalline Solid expand Show data source
white to off-white powder expand Show data source
Melting Point
146-148°C expand Show data source
148 - 152°C expand Show data source
Hydrophobicity(logP)
-0.109 expand Show data source
0.5 expand Show data source
Storage Condition
-20°C Freezer expand Show data source
Storage Warning
IRRITANT expand Show data source
RTECS
AC3600000 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
2 expand Show data source
TSCA Listed
false expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Gene Information
human ... ADRB1(153)rat ... Adrb1(24925) expand Show data source
Purity
≥98% (TLC) expand Show data source
95% expand Show data source
97% expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank - DB00335 external link
Item Information
Drug Groups approved
Description A cardioselective beta-adrenergic blocker possessing properties and potency similar to propranolol, but without a negative inotropic effect. [PubChem]
Indication For the management of hypertention and long-term management of patients with angina pectoris
Pharmacology Atenolol, a competitive beta(1)-selective adrenergic antagonist, has the lowest lipid solubility of this drug class. Although it is similar to metoprolol, atenolol differs from pindolol and propranolol in that it does not have intrinsic sympathomimetic properties or membrane-stabilizing activity. Atenolol is used alone or with chlorthalidone in the management of hypertension and edema.
Toxicity LD50=2000-3000 mg/kg(orally in mice). Symptoms of an atenolol overdose include a slow heart beat, shortness of breath, fainting, dizziness, weakness, confusion, nausea, and vomiting.
Affected Organisms
Humans and other mammals
Biotransformation Hepatic (minimal)
Absorption Approximately 50% of an oral dose is absorbed from the gastrointestinal tract, the remainder being excreted unchanged in the feces.
Half Life 6-7 hours
Protein Binding Plasma protein binding is 6-16%
Elimination Approximately 50% of an oral dose is absorbed from the gastrointestinal tract, the remainder being excreted unchanged in the feces. Unlike propranolol or metoprolol, but like nadolol, atenolol undergoes little or no metabolism by the liver, and the absorbed portion is eliminated primarily by renal excretion.
External Links
Wikipedia
RxList
Drugs.com
Sigma Aldrich - A7655 external link
Biochem/physiol Actions
Selective β1-adrenoceptor antagonist; antihypertensive; antianginal; antiarrhythmic.
Other Notes
Shelf-life of the solid is at least three years.
Application
Atenolol is a β-adrenergic blocker and used in the management of hypertension. Atenolol has antianginal and antiarrhythmic properties.
Toronto Research Chemicals - A790075 external link
Cardioselective β-adrenergic blocker. Antihypertensive, antianginal, antiarrhythmic (class II).

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Caplar, V., et al.: Anal. Profiles Drug Subs., 13, 1 (1984)
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PATENTS

PATENTS

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INTERNET

INTERNET

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