Atenolol

TENORMIN · (RS)-ATENOLOL · Seles · Aterol · Tenolol · ici66082 · dl-Atenolol · (RS)-4-[2-HYDROXY-3-[(1-METHYLETHYL)AMINO]PROPOXY]BENZENEACETAMIDE

https://huagongshe.com/en/chemical/2249

Identifiers & Physical Properties

CAS No.	29122-68-7
Molecular formula	C14H22N2O3
Average molar mass	266.34 g/mol
Monoisotopic mass	266.16304257 g/mol
SMILES	CC(C)NCC(O)COc1ccc(CC(N)=O)cc1
InChIKey	METKIMKYRPQLGS-UHFFFAOYSA-N
PubChem CID	2249
ChEMBL	CHEMBL24
ChEBI	CHEBI:2904
EC No.	249-451-7
DTXSID	DTXSID2022628

Chemical & Physical Properties

XLogP	0.2
Topological polar surface area	84.6
Hydrogen bond donors	3
Hydrogen bond acceptors	4
Rotatable bonds	8
Heavy atoms	19
Formal charge	0
Complexity	263
LogP (partition coefficient)	0.16log Kow= 0.16
Color/Form	White, crystalline powderCrystals from ethyl acetateColorless crystals
Solubility	13300Freely soluble in methanolsoluble in acetic acid, DMSOsparingly soluble in 96% ethanolslightly soluble in isopropanolvery slightly soluble in acetone, dioxanepractically insoluble in acetonitrile, ethyl acetatechloroformFreely soluble in 1 N HCl (300 mg/ml @ 25 °C)less soluble in chloroform (3 mg/ml @ 25 °C)In water, 1.33X10+4 mg/l @ 25 °C13.3 mg/mL at 25 °C>40 [ug/mL] (The mean of the results at pH 7.4)H2O: 0.3 mg/mL13.5mg/L(25 ºC)
Melting point	158-160146 - 148 °C147 °C154°C
Caco2 Permeability	-6.44
Physical Description	Solid
Ionization Efficiency	Positive4.952.7Agilent XCTElectrospray ionizationformic acid (5.3nM)
Dissociation Constants	9.589.549.6pKa = 9.6
Collision Cross Section	157.8 Å² [M+H]+ [CCS Type: DTBuffer gas: N2Ionization: ESI+Dataset: TOXCASTSource Identifier: DTXSID2022628]157.9 Å² [M+H]+ [CCS Type: DTIonization: APCI+164.2 Å² [M+Na]+ [CCS Type: DT155.32 Å² [M+H-H2O]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]158.38 Å² [M+H]+ [CCS Type: TW165.83 Å² [M+K]+ [CCS Type: TW163.26 Å² [M+Na]+ [CCS Type: TW159.5 Å² [M+H]+ [CCS Type: TWMethod: Major Mix IMS/Tof Calibration Kit (Waters)]159 Å² [M+H]+ [CCS Type: TW
Other Experimental Properties	Dipole moment 5.71 D @ 20 °C in propionic acid
Boiling point	409.54°C (rough estimate)
Density	1.0807 (rough estimate)
Refractive index	1.5110 (estimate)
Flash point	2℃
Storage conditions	2-8°C
Physical state	powder
pKa (acidity coefficient)	9.6(at 25℃)
Color	white to off-white
Merck	14,859
BCS Class	3
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
SMILES	N(C(C)C)CC(O)COc1ccc(cc1)CC(=O)N
CAS DataBase Reference	29122-68-7(CAS DataBase Reference)
FDA UNII	50VV3VW0TI
Proposition 65 List	Atenolol
NCI Drug Dictionary	atenolol
ATC code	C07AB03
NIST Chemistry Reference	Atenolol(29122-68-7)
EPA Substance Registry System	Benzeneacetamide, 4-[2-hydroxy-3-[(1-methylethyl)amino]propoxy]- (29122-68-7)
UNSPSC Code	41116107
NACRES	NA.77
Protein binding	3%
Excreted unchanged in urine	>90%
Volume of distribution	1.1(L/kg)
Biological half-life	6-7 / 15-35
GHS pictogram	GHS02,GHS07
Signal word	Danger
GHS hazard statements	H225-H302+H312+H332-H319
GHS precautionary statements	P210-P261-P302+P352+P312-P304+P340+P312-P337+P313-P403+P235
Hazard symbols	Xn,F
Risk statements (R)	22-36/37/38-20/21/22-36-11
Safety statements (S)	22-24/25-36-26-36/37-16
UN transport number	UN 1648 3 / PGII
Water hazard class (WGK)	2
RTECS number	AC3600000
Hazard class	IRRITANT
Customs code	29242995
Storage class	11 - Combustible Solids
Hazardous substances data	29122-68-7(Hazardous Substances Data)
Toxicity	LD50 in mice, rats (mg/kg): 2000, 3000 orally98.7, 59.24 i.v. (Fitzgerald)

Safety & Regulations

GHS classification	This chemical does not meet GHS hazard criteria for 3.4% (3 of 89) of reports.WarningH302 (79.8%): Harmful if swallowed [Warning Acute toxicity, oral]H319 (67.4%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H351 (64%): Suspected of causing cancer [Warning Carcinogenicity]H362 (74.2%): May cause harm to breast-fed children [Reproductive toxicity, effects on or via lactation]P203, P260, P263, P264, P264+P265, P270, P280, P301+P317, P305+P351+P338, P318, P330, P337+P317, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 89 reports by companies from 24 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Reported as not meeting GHS hazard criteria per 3 of 89 reports by companies.There are 22 notifications provided by 86 of 89 reports by companies with hazard statement code(s).Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
Regulatory information	Hazard Traits - Developmental ToxicityAuthoritative List - Prop 65Report - regardless of intended function of ingredient in the productAtenolol: Does not have an individual approval but may be used under an appropriate group standard
Other safety information	IMAP assessments - Benzeneacetamide, 4-[2-hydroxy-3-[(1-methylethyl)amino]propoxy]-: Human health tier I assessmentIMAP assessments - Benzeneacetamide, 4-[2-hydroxy-3-[(1-methylethyl)amino]propoxy]-: Environment tier I assessment
FDA requirements	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.

Applications & Uses

Uses

β-blockers. Clinical application in the treatment of hypertension, angina and arrhythmia.

Uses

Selective b1 adrenergic receptor agonist, anti-hypertensive, anti-anginal, anti-arrhythmic

Uses

Atenolol is 2-[4′[2-hydroxy-3-(iso-propylamino)propoxy]phenyl]acetamide (12.1.7) [11–13].Atenolol is a selective β1-adrenoblocker, or in other words, a cardioblocker. Like acebutol, atenolol possesses antianginal, antihypotensive, and antiarrhythmic action. It is used for arterial hypotension, preventing attacks of angina, sinus tachycardia, and preventing supraventricular tachyarrhythmia.

Uses

It is used for preventing angina pectoris.

General Description

Pharmaceutical secondary standards for application in quality control provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards