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Chemistry

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Also known as: 29122-68-7, Tenormin, Blokium, Myocord, Normiten, Prenormine
Molecular Formula
C14H22N2O3
Molecular Weight
266.34  g/mol
InChI Key
METKIMKYRPQLGS-UHFFFAOYSA-N
FDA UNII
50VV3VW0TI

Atenolol
A cardioselective beta-1 adrenergic blocker possessing properties and potency similar to PROPRANOLOL, but without a negative inotropic effect.
Atenolol is a beta-Adrenergic Blocker. The mechanism of action of atenolol is as an Adrenergic beta-Antagonist.
1 2D Structure

Atenolol

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-[4-[2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl]acetamide
2.1.2 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)
2.1.3 InChI Key
METKIMKYRPQLGS-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC(C)NCC(COC1=CC=C(C=C1)CC(=O)N)O
2.2 Other Identifiers
2.2.1 UNII
50VV3VW0TI
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Ici 66082

2. Ici-66082

3. Ici66082

4. Tenormin

5. Tenormine

2.3.2 Depositor-Supplied Synonyms

1. 29122-68-7

2. Tenormin

3. Blokium

4. Myocord

5. Normiten

6. Prenormine

7. Tenormine

8. (rs)-atenolol

9. Duraatenolol

10. Betacard

11. Corotenol

12. Tenoblock

13. Atehexal

14. Betablok

15. Cuxanorm

16. Juvental

17. Selobloc

18. Antipressan

19. Atcardil

20. Atenblock

21. Evitocor

22. Farnormin

23. Internolol

24. Normalol

25. Premorine

26. Prenolol

27. Tenoprin

28. Tensimin

29. Vascoten

30. Vericordin

31. Alinor

32. Anselol

33. Atecard

34. Atendol

35. Atenet

36. Atenil

37. Atereal

38. Aterol

39. Hipres

40. Hypoten

41. Ibinolo

42. Lotenal

43. Oraday

44. Serten

45. Stermin

46. Tenidon

47. Tenolol

48. Tredol

49. Uniloc

50. Wesipin

51. Altol

52. Ateni

53. Noten

54. Xaten

55. Seles Beta

56. Apo-atenolol

57. Felo-bits

58. Lo-ten

59. Atenolin

60. Atenomel

61. Blocotenol

62. Cardaxen

63. Cardiopress

64. Jenatenol

65. Panapres

66. Plenacor

67. Servitenol

68. Tenobloc

69. Aircrit

70. Betasyn

71. Ormidol

72. Prinorm

73. Unibloc

74. Loten

75. Atenol Acis

76. Atenol Cophar

77. Atenol Fecofar

78. Atenol Heumann

79. Atenol Nordic

80. Atenol Quesada

81. Atenol Gador

82. Atenol Stada

83. Atenol-mepha

84. Atenol-wolff

85. Atenol Atid

86. Atenol Ct

87. Atenol Tika

88. Atenol Trom

89. Atenol Genericon

90. Betatop Ge

91. Atenol Von Ct

92. Atenol-ratiopharm

93. Atenol Al

94. Atenol Pb

95. Atenol Gnr

96. Atenol Msd

97. Atenol Nm Pharma

98. Scheinpharm Atenol

99. Atenol 1a Pharma

100. Atenololum

101. 2-(4-(2-hydroxy-3-(isopropylamino)propoxy)phenyl)acetamide

102. Tenormine [french]

103. (r,s)-atenolol

104. Atenololum [inn-latin]

105. Ici 66082

106. 2-[4-[2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl]acetamide

107. Tenormin (tn)

108. Ici-66082

109. Novaten

110. 1-p-carbamoylmethylphenoxy-3-isopropylamino-2-propanol

111. Ici 66,082

112. 2-[4-(2-hydroxy-3-isopropylaminopropoxy)phenyl]acetamide

113. 2-(p-(2-hydroxy-3-(isopropylamino)propoxy)phenyl)acetamide

114. 4-(2-hydroxy-3-((1-methylethyl)amino)propoxy)benzeneacetamide

115. 2-(4-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}phenyl)acetamide

116. Benzeneacetamide, 4-[2-hydroxy-3-[(1-methylethyl)amino]propoxy]-

117. C07ab03

118. Chembl24

119. Duratenol

120. Nsc-757832

121. Benzeneacetamide, 4-(2-hydroxy-3-((1-methylethyl)amino)propoxy)-

122. 50vv3vw0ti

123. Mls000069622

124. Chebi:2904

125. Atenolol Bp

126. 60966-51-0

127. Smr000036768

128. Atenol

129. 2-{4-[2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl}acetamide

130. Acetamide, 2-(p-(2-hydroxy-3-(isopropylamino)propoxy)phenyl)-

131. Teno-basan

132. Neatenol

133. Tensotin

134. Atcard

135. Dl-atenolol

136. Ccris 4196

137. (+/-)-atenolol

138. Hsdb 6526

139. Sr-01000000159

140. Einecs 249-451-7

141. Einecs 262-544-7

142. Mfcd00057645

143. Unii-50vv3vw0ti

144. Brn 2739235

145. 2-(4-[2-hydroxy-3-(isopropylamino)propoxy]phenyl)acetamide

146. Artrenolol

147. 2-(4-(2-hydroxy-3-(isopropylamino)propoxy)phenyl)ethanamide

148. 4-(2-hydroxy-3-[(1-methylethyl)amino]propoxy)benzeneacetamide

149. 2-(4-(2-hydroxy-3-isopropylaminopropoxy)phenyl)acetamid

150. Phenyl)acetamide

151. Atenolol [usan:ban:inn:jan]

152. (y)-atenolol

153. Atenalol (rs)

154. Atenolol,(s)

155. (?)-atenolol

156. Atenolol [usan:usp:inn:ban:jan]

157. (a+/-)-atenolol

158. Tenoretic (salt/mix)

159. Atenolol (jan/usp)

160. Spectrum_001364

161. Atenolol [hsdb]

162. Atenolol [usan]

163. Atenolol [inn]

164. Atenolol [jan]

165. Atenolol [mi]

166. Atenolol [vandf]

167. Opera_id_1283

168. Spectrum2_001411

169. Spectrum3_001448

170. Spectrum4_000435

171. Spectrum5_001509

172. Atenolol [mart.]

173. Dsstox_cid_2628

174. Atenolol [usp-rs]

175. Atenolol [who-dd]

176. Atenolol [who-ip]

177. A 7655

178. Schembl4362

179. Dsstox_rid_76663

180. Dsstox_gsid_22628

181. Lopac0_000121

182. Oprea1_448775

183. Bspbio_002915

184. Gtpl548

185. Kbiogr_000790

186. Kbioss_001844

187. Mls001066372

188. Mls001074163

189. Mls001304038

190. Divk1c_000057

191. Spectrum1501127

192. Atenolol (jp17/usp/inn)

193. Spbio_001482

194. Atenolol [orange Book]

195. Atenolol [ep Monograph]

196. Atenolol [usp Impurity]

197. Atenolol [usp Monograph]

198. Dtxsid2022628

199. Bdbm25753

200. Hms500c19

201. Kbio1_000057

202. Kbio2_001844

203. Kbio2_004412

204. Kbio2_006980

205. Kbio3_002415

206. Metkimkyrpqlgs-uhfffaoysa-

207. Polycap Component Atenolol

208. Atenololum [who-ip Latin]

209. Ninds_000057

210. S-atenolol-d7 (iso-propyl-d7)

211. 2-{4-[2-hydroxy-3-(isopropylamino)propoxy]-phenyl}acetamide

212. Hms1569l13

213. Hms1921h09

214. Hms2090i19

215. Hms2092d19

216. Hms2233e06

217. Hms3259k08

218. Hms3260i04

219. Hms3266k13

220. Hms3369b14

221. Hms3369d20

222. Hms3369p20

223. Hms3411g21

224. Hms3675g21

225. Hms3886g03

226. Pharmakon1600-01501127

227. ( Inverted Question Mark)-atenolol

228. Tenoretic Component Atenolol

229. Bcp12899

230. Atenolol 1.0 Mg/ml In Acetonitrile

231. Atenolol, >=98% (tlc), Powder

232. Tox21_302426

233. Tox21_500121

234. 2-[4-({2-hydroxy-3-[(1-methylethyl)amino]propyl}oxy)phenyl]acetamide

235. Atenolol 100 Microg/ml In Methanol

236. Bbl009276

237. Ccg-39010

238. Geo-03413

239. Nsc757832

240. S4817

241. Stk528649

242. Akos005111050

243. Atenolol Component Of Tenoretic

244. Ac-8245

245. Atenolol, Analytical Reference Material

246. Db00335

247. Ks-5341

248. Lp00121

249. Nc00548

250. Nsc 757832

251. Sdccgsbi-0050109.p004

252. Idi1_000057

253. Mrf-0000571

254. Ncgc00015007-06

255. Ncgc00015007-07

256. Ncgc00015007-08

257. Ncgc00015007-09

258. Ncgc00015007-10

259. Ncgc00015007-11

260. Ncgc00015007-13

261. Ncgc00015007-24

262. Ncgc00024566-03

263. Ncgc00024566-04

264. Ncgc00024566-05

265. Ncgc00024566-06

266. Ncgc00024566-07

267. Ncgc00255122-01

268. Ncgc00260806-01

269. Ba166036

270. Hy-17498

271. Sbi-0050109.p003

272. Cas-29122-68-7

273. Db-072177

274. Db-079552

275. Eu-0100121

276. Ft-0662315

277. Ft-0662316

278. Ft-0693045

279. 2-(4-(2-hydroxy-3-(isopropylamino)propoxy)

280. Bim-0050109.0001

281. D00235

282. O10469

283. Ab00052208-13

284. Ab00052208-15

285. Ab00052208_16

286. 122a687

287. L000116

288. Q411325

289. Q-200656

290. Sr-01000000159-2

291. Sr-01000000159-4

292. Sr-01000000159-5

293. Sr-01000000159-8

294. Brd-a20239487-001-02-5

295. Brd-a20239487-001-15-7

296. Atenolol, European Pharmacopoeia (ep) Reference Standard

297. Z1541638518

298. Atenolol, United States Pharmacopeia (usp) Reference Standard

299. (+)-4-[2-hydroxy-3-[(1-methylethyl)amino]propoxy]benzeneacetamide

300. (rs)-4-[2-hydroxy-3-[(1-methylethyl)amino]propoxy]benzeneacetamide

301. 2-(p-(hydroxy-3-(isopropylamino)propoxy)phenyl)acetamide

302. (+/-)-4-(2-hydroxy-3-[(1-methylethyl)amino]propoxy)benzeneacetamide

303. 2-(4-{[(2s)-2-hydroxy-3-(propan-2-ylamino)propyl]oxy}phenyl)acetamide

304. Atenolol, Pharmaceutical Secondary Standard; Certified Reference Material

305. 2-(p-(2-hydroxy-3-(isopropylamino)propoxy)phenyl)acetamide (racemate)

306. 2-[4-({(2r)-2-hydroxy-3-[(1-methylethyl)amino]propyl}oxy)phenyl]acetamide

307. Atenolol Solution, 1.0 Mg/ml In Acetonitrile, Ampule Of 1 Ml, Certified Reference Material

308. 106020-65-9

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 266.34 g/mol
Molecular Formula C14H22N2O3
XLogP30.2
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count4
Rotatable Bond Count8
Exact Mass266.16304257 g/mol
Monoisotopic Mass266.16304257 g/mol
Topological Polar Surface Area84.6 Ų
Heavy Atom Count19
Formal Charge0
Complexity263
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 4  
Drug NameAtenolol
PubMed HealthAtenolol
Drug ClassesAntianginal, Antiarrhythmic, Group II, Antihypertensive, Antimigraine, Cardiovascular Agent
Drug LabelAtenolol, a synthetic, beta1-selective (cardioselective) adrenoreceptor blocking agent, may be chemically described as benzeneacetamide, 4 -[2'-hydroxy-3'-[(1- methylethyl) amino] propoxy]-. The molecular formula is C14H22N2O3 and its structural
Active IngredientAtenolol
Dosage FormTablet
RouteOral
Strength25mg; 100mg; 50mg
Market StatusPrescription
CompanyIpca Labs; Mutual Pharm; Teva; Ipr; Aurobindo Pharma; Sun Pharm Inds; Zydus Pharms Usa; Northstar Hlthcare; Unique Pharm Labs; Sandoz; Mylan; Dava Pharms

2 of 4  
Drug NameTenormin
PubMed HealthAtenolol
Drug ClassesAntianginal, Antiarrhythmic, Group II, Antihypertensive, Antimigraine, Cardiovascular Agent
Drug LabelTENORMIN (atenolol), a synthetic, beta1-selective (cardioselective) adrenoreceptor blocking agent, may be chemically described as benzeneacetamide, 4 -[2'-hydroxy-3'-[(1- methylethyl) amino] propoxy]-. The molecular and structural formulas are:
Active IngredientAtenolol
Dosage FormTablet
RouteOral
Strength25mg; 100mg; 50mg
Market StatusPrescription
CompanyAstrazeneca

3 of 4  
Drug NameAtenolol
PubMed HealthAtenolol
Drug ClassesAntianginal, Antiarrhythmic, Group II, Antihypertensive, Antimigraine, Cardiovascular Agent
Drug LabelAtenolol, a synthetic, beta1-selective (cardioselective) adrenoreceptor blocking agent, may be chemically described as benzeneacetamide, 4 -[2'-hydroxy-3'-[(1- methylethyl) amino] propoxy]-. The molecular formula is C14H22N2O3 and its structural
Active IngredientAtenolol
Dosage FormTablet
RouteOral
Strength25mg; 100mg; 50mg
Market StatusPrescription
CompanyIpca Labs; Mutual Pharm; Teva; Ipr; Aurobindo Pharma; Sun Pharm Inds; Zydus Pharms Usa; Northstar Hlthcare; Unique Pharm Labs; Sandoz; Mylan; Dava Pharms

4 of 4  
Drug NameTenormin
PubMed HealthAtenolol
Drug ClassesAntianginal, Antiarrhythmic, Group II, Antihypertensive, Antimigraine, Cardiovascular Agent
Drug LabelTENORMIN (atenolol), a synthetic, beta1-selective (cardioselective) adrenoreceptor blocking agent, may be chemically described as benzeneacetamide, 4 -[2'-hydroxy-3'-[(1- methylethyl) amino] propoxy]-. The molecular and structural formulas are:
Active IngredientAtenolol
Dosage FormTablet
RouteOral
Strength25mg; 100mg; 50mg
Market StatusPrescription
CompanyAstrazeneca

4.2 Therapeutic Uses

Adrenergic beta-Antagonists; Anti-Arrhythmia Agents; Antihypertensive Agents; Sympatholytics

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)


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.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 1739


Atenolol ... /is/ indicated in the treatment of classic angina pectoris, also referred to as "effort-associated angina". /Included in US product labeling/

MICROMEDEX Thomson Health Care. USPDI - Drug Information for the Health Care Professional. 23rd ed. Volume 1. MICROMEDEX Thomson Health Care, Greenwood Village, CO. 2003. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc., p. 550


Atenolol /is/ used in the treatment of mitral value prolapse syndrome. /NOT included in US product labeling/

MICROMEDEX Thomson Health Care. USPDI - Drug Information for the Health Care Professional. 23rd ed. Volume 1. MICROMEDEX Thomson Health Care, Greenwood Village, CO. 2003. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc., p. 551


For more Therapeutic Uses (Complete) data for ATENOLOL (12 total), please visit the HSDB record page.


4.3 Drug Warning

Atenolol should be used with caution and in reduced dosage in patients with impaired renal function, especially when creatinine clearance is less than 35 ml/minute per 1.73 sq m. ... Patients receiving atenolol after hemodialysis /should/ be administered the drug under close supervision in a hospital setting, since marked hypotension may occur.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 1742


Atenolol is contraindicated in patients with sinus bradycardia, AV block greater than first degree, cardiogenic shock, and overt cardiac failure.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 1742


Atenolol should be used with caution in patients undergoing major surgery involving general anesthesia. The necessity of withdrawing beta-adrenergic blocking therapy prior to major surgery is controversial. Severe, protracted hypotension and difficulty in restarting or maintaining a heart beat have occurred during surgery in some patients who have received beta-adrenergic blocking agents.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 1742


Abrupt withdrawal of atenolol may exacerbate angina symptoms and/or precipitate myocardial infarction and venticular arrhythmias in patients with coronary artery disease, or may precipitate thyroid storm in patients with thyrotoxicosis. Therefore, patients receiving atenolol (especially those with ischemic heart disease) should be warned not to interrupt or discontinue therapy without consulting their physician.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 1741


For more Drug Warnings (Complete) data for ATENOLOL (12 total), please visit the HSDB record page.


4.4 Drug Indication

**Indicated** for: 1) Management of hypertension alone and in combination with other antihypertensives. 2) Management of angina pectoris associated with coronary atherosclerosis. 3) Management of acute myocardial infarction in hemodynamically stable patients with a heart rate greater than 50 beats per minutes and a systolic blood pressure above 100 mmHg. **Off-label** uses include: 1) Secondary prevention of myocardial infarction. 2) Management of heart failure. 3) Management of atrial fibrillation. 4) Management of supraventricular tachycardia. 5) Management of ventricular arrythmias such as congenital long-QT and arrhythmogenic right ventricular cardiomyopathy. 6) Management of symptomatic thyrotoxicosis in combination with [methimazole]. 7) Prophylaxis of migraine headaches. 8) Management of alcohol withdrawal.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Atenolol is a cardio-selective beta-blocker and as such exerts most of its effects on the heart. It acts as an antagonist to sympathetic innervation and prevents increases in heart rate, electrical conductivity, and contractility in the heart due to increased release of norepinephrine from the peripheral nervous system. Together the decreases in contractility and rate produce a reduction in cardiac output resulting in a compensatory increase in peripheral vascular resistance in the short-term. This response later declines to baseline with long-term use of atenolol. More importantly, this reduction in the work demanded of the myocardium also reduces oxygen demand which provides therapeutic benefit by reducing the mismatch of oxygen supply and demand in settings where coronary blood flow is limited, such as in coronary atherosclerosis. Reducing oxygen demand, particularly due to exercise, can reduce the frequency of angina pectoris symptoms and potentially improve survival of the remaining myocardium after myocardial infarction. The decrease in rate of sinoatrial node potentials, electrical conduction, slowing of potentials traveling through the atrioventricular node, and reduced frequency of ectopic potentials due to blockade of adrenergic beta receptors has led to benefit in arrhythmic conditions such as atrial fibrillation by controlling the rate of action potential generation and allowing for more effective coordinated contractions. Since a degree of sympathetic activity is necessary to maintain cardiac function, the reduced contractility induced by atenolol may precipitate or worsen heart failure, especially during volume overload. The effects of atenolol on blood pressure have been established, although it is less effective than alternative beta-blockers, but the mechanism has not yet been characterized. As a 1 selective drug, it does not act via the vasodilation produced by non-selective agents. Despite this there is a sustained reduction in peripheral vascular resistance, and consequently blood pressure, alongside a decrease in cardiac output. It is thought that atenolol's antihypertensive activity may be related to action on the central nervous system (CNS) or it's inhibition of the renin-aldosterone-angiotensin system rather than direct effects on the vasculature. Atenolol produces CNS effects similar to other beta-blockers, but does so to a lesser extent due to reduces ability to cross the blood-brain barrier. It has the potential to produce fatigue, depression, and sleep disturbances such as nightmares or insomnia. The exact mechanisms behind these have not been characterized but their occurrence must be considered as they represent clinically relevant adverse effects. Atenolol exerts some effects on the respiratory system although to a much lesser extent than non-selective beta-blockers. Interaction with 2 receptors in the airways can produce bronchoconstriction by blocking the relaxation of bronchial smooth muscle mediated by the sympathetic nervous system. The same action can interfere with -agonist therapies used in asthma and chronic obstructive pulmonary disease. Unlike some other beta-blocker drugs, atenolol does not have intrinsic sympathomimetic or membrane stabilizing activity nor does it produce changes in glycemic control.


5.2 MeSH Pharmacological Classification

Anti-Arrhythmia Agents

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 prolong