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NCGC00024690-04

Synopsis, Chemistry

APIs // Active Pharmaceutical Ingredients

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4 Drug(s) in Development

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CAPSULE, EXTENDED RELEASE;ORAL - 120MG, CAPSULE, EXTENDED RELEASE;ORAL - 160MG, CAPSULE, EXTENDED RELEASE;ORAL - 60MG, CAPSULE, EXTENDED RELEASE;ORAL - 80MG, CAPSULE, EXTENDED RELEASE;ORAL - 120MG, CAPSULE, EXTENDED RELEASE;ORAL - 80MG

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18 APIs, 7 DOSSIERS // FDF

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NCGC00024690-04
Chemistry
Full Screen View

Also known as: 318-98-9, Propranolol hcl, Inderal, Avlocardyl, Dociton, Inderalici

Molecular Formula

C₁₆H₂₂ClNO₂

Molecular Weight

295.80 g/mol

InChI Key

ZMRUPTIKESYGQW-UHFFFAOYSA-N

FDA UNII

F8A3652H1V

A widely used non-cardioselective beta-adrenergic antagonist. Propranolol has been used for MYOCARDIAL INFARCTION; ARRHYTHMIA; ANGINA PECTORIS; HYPERTENSION; HYPERTHYROIDISM; MIGRAINE; PHEOCHROMOCYTOMA; and ANXIETY but adverse effects instigate replacement by newer drugs.

1 2D Structure

2D Structure

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

1-naphthalen-1-yloxy-3-(propan-2-ylamino)propan-2-ol;hydrochloride

2.1.2 InChI

InChI=1S/C16H21NO2.ClH/c1-12(2)17-10-14(18)11-19-16-9-5-7-13-6-3-4-8-15(13)16;/h3-9,12,14,17-18H,10-11H2,1-2H3;1H

2.1.3 InChI Key

ZMRUPTIKESYGQW-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC(C)NCC(COC1=CC=CC2=CC=CC=C21)O.Cl

2.2 Other Identifiers

2.2.1 UNII

F8A3652H1V

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Anaprilin

2. Anapriline

3. Avlocardyl

4. Ay 20694

5. Ay-20694

6. Ay20694

7. Betadren

8. Dexpropranolol

9. Dociton

10. Hydrochloride, Propranolol

11. Inderal

12. Obsidan

13. Obzidan

14. Propanolol

15. Propranolol

16. Rexigen

2.3.2 Depositor-Supplied Synonyms

1. 318-98-9

2. Propranolol Hcl

3. Inderal

4. Avlocardyl

5. Dociton

6. Inderalici

7. Anaprilin

8. Caridolol

9. 3506-09-0

10. Berkolol

11. Herzbase

12. Indobloc

13. Naprilin

14. Pronovan

15. Pylapron

16. Sloprolol

17. Apsolol

18. Beprane

19. Deralin

20. Ikopal

21. Obsidan

22. Tesnol

23. Kemi

24. Propranolol.hcl

25. Beta Neg

26. Innopran Xl

27. Propranolol Chloride

28. Inderex

29. Nsc-91523

30. Hemangeol

31. Innopran

32. Propranolol (hydrochloride)

33. Propanolol Hydrochloride

34. Ici 45520

35. 1-(isopropylamino)-3-(1-naphthyloxy)-2-propanol Hydrochloride

36. Ay 64043

37. 1-(isopropylamino)-3-(naphthalen-1-yloxy)propan-2-ol Hydrochloride

38. Ici-45520

39. Propranolol Hydrochloride (+/-)

40. Ay-64043

41. I 2065

42. 1-naphthalen-1-yloxy-3-(propan-2-ylamino)propan-2-ol;hydrochloride

43. (s)-propranolol (hydrochloride)

44. 1-(isopropylamino)-3-(1-naphthoxy)-propan-2-ol Hydrochloride

45. (+/-)-propranolol Hydrochloride

46. F8a3652h1v

47. Hemangiol

48. Bedranol

49. Inderol

50. Pranolol

51. Sumial

52. Indermigran

53. Proprahexal

54. Propranovitan

55. Angilol

56. Arcablock

57. Artensol

58. Biocard

59. Blocaryl

60. Cardinol

61. Corbeta

62. Detensol

63. Dibudinate

64. Dumopranol

65. Efectolol

66. Emforal

67. Farprolol

68. Frekven

69. Hemipralon

70. Kidoral

71. Nelderal

72. Noloten

73. Novopranol

74. Panolol

75. Prandol

76. Propabloc

77. Propadex

78. Propalong

79. Propayerst

80. Prophylux

81. Propral

82. Propranur

83. Rapynogen

84. Sagittol

85. Sawatol

86. Scandrug

87. Sudenol

88. Tensiflex

89. Tiperal

90. Acifol

91. Cinlol

92. Ciplar

93. Elbrol

94. Herzul

95. Oposim

96. Pranix

97. Procor

98. Prosin

99. Nedis

100. Sinal

101. Tonum

102. 1-naphthalen-1-yloxy-3-(propan-2-ylamino)propan-2-ol Hydrochloride

103. 318-98-9 (hcl)

104. Half-inderal

105. Prano-puren

106. Propra Vt Ct

107. Dsstox_cid_1198

108. Inderal Hydrochloride

109. Inderal La

110. Proberta La

111. Pur-bloka

112. Beta-neg

113. Dsstox_rid_76007

114. Dsstox_gsid_21198

115. (s)-propranolol Hydrochloride

116. 1-isopropylamino-3-(1-naphthoxy)-propan-2-ol-hydrochloride

117. Dl-propranolol Hydrochloride

118. 1-(1-naphthyloxy)-2-hydroxy-3-isopropylaminopropane Hydrochloride

119. R+c5989educor

120. (+-)-1-(isopropylamino)-3-(1-naphthyloxy)-2-propanol Hydrochloride

121. 2-propanol, 1-((1-methylethyl)amino)-3-(1-naphthalenyloxy)-, Hydrochloride

122. Propraratiopharm

123. Beta-tablinen

124. Beta-timelets

125. Dl-anapriline

126. (+/-)-1-(isopropylamino)-3-(1-naphthyloxy)-2-propanol Hydrochloride

127. [2-hydroxy-3-(naphthalen-1-yloxy)propyl](propan-2-yl)amine Hydrochloride

128. 1-[(1-methylethyl)amino]-3-(naphthalen-1-yloxy)propan-2-ol Hydrochloride

129. Chebi:8500

130. Smr000059167

131. Nsc91523

132. Ccris 1105

133. Hsdb 3176

134. Sr-01000075285

135. (r)-propranolol Hydrochloride

136. Einecs 206-268-7

137. Mfcd00012558

138. D,l-propranolol Hydrochloride

139. Servanolol

140. Efektolol

141. Migrastat

142. Unii-f8a3652h1v

143. Propranolol Hydrochloride Intensol

144. Dl-propranolol Hcl

145. Relax-b

146. Einecs 222-501-5

147. Inderal (tn)

148. Nsc 91523

149. Betacap

150. Monoprolol

151. Innopran Xl (tn)

152. (r)-(+)-propanolol Hydrochloride

153. (r)-propranolol Hcl

154. Propranolol Hydrochloride [usan:usp:jan]

155. Propranolon Hydrochloride

156. 1-(isopropylamino)-3-(1-naphthyloxy)propan-2-ol Hydrochloride

157. 1-(isopropylamino)-3-(alpha-naphthoxy)-2-propanol Hydrochloride

158. Cas-318-98-9

159. Chembl1671

160. Schembl41688

161. (y)-propranolol Hydrochloride

162. Mls000859628

163. Mls001055449

164. Mls001056753

165. Mls002222321

166. Mls002548855

167. (?)-propranolol Hydrochloride

168. Spectrum1505270

169. Propranolol Hydrochloride, 99%

170. Dtxsid3021198

171. (2-hydroxy-3-(naphthyloxy)propyl)isopropylammonium Chloride

172. Hms1570p06

173. Hms1571g12

174. Hms1571i04

175. Hms1922p19

176. Pharmakon1600-01505270

177. Act02695

178. Bcp15350

179. Bcp16675

180. Eur-1000

181. Hy-b0573

182. Kdm-1102

183. Rac-propranolol Hydrochloride

184. Tox21_201886

185. Tox21_302905

186. Tox21_500896

187. 2-propanol, 1-(isopropylamino)-3-(1-naphthyloxy)-, Hydrochloride

188. Ccg-39239

189. Ccg-39447

190. Ncs-91523

191. Nsc758950

192. S4076

193. Propranalol Hydrochloride, Dl-

194. Propranolol Hydrochloride [mi]

195. 1-(naphthalen-1-yloxy)-3-[(propan-2-yl)amino]propan-2-ol Hydrochloride

196. 2-propanol, 1-(isopropylamino)-3-(1-naphthyloxy)-, Hydrochloride, (+-)-

197. Akos005267141

198. Propranolol Hydrochloride (jp17/usp)

199. (s)-2-fmoc-6-chlorhex-4-ynoic Acid

200. Ks-1097

201. Lp00896

202. Nc00687

203. Nsc-758950

204. Propranolol Hydrochloride [jan]

205. 2-propanol, 1-((1-methylethyl)amino)-3-(1-naphthalenyloxy)-, Hydrochloride, (+-)-

206. Propranolol Hydrochloride [hsdb]

207. Propranolol Hydrochloride [usan]

208. Ncgc00024690-04

209. Ncgc00091932-01

210. Ncgc00094212-01

211. Ncgc00094212-02

212. Ncgc00094212-03

213. Ncgc00094212-04

214. Ncgc00094212-05

215. Ncgc00256554-01

216. Ncgc00259435-01

217. Ncgc00261581-01

218. Propranolol Hydrochloride [mart.]

219. Propranolol Hydrochloride [vandf]

220. Propranolol Hydrochloride [usp-rs]

221. Propranolol Hydrochloride [who-dd]

222. Propranolol Hydrochloride [who-ip]

223. Db-018092

224. Eu-0100896

225. Ft-0603377

226. Ft-0635178

227. Ft-0636788

228. P0995

229. Sw219414-1

230. Wln: L66j Bo1yq1my1 & 1 & Gh

231. Bim-0050871.0001

232. D00483

233. H10708

234. P 0884

235. Propranolol Hydrochloride [ep Monograph]

236. Propranolol Hydrochloride [orange Book]

237. Propranolol Hydrochloride [usp Monograph]

238. Propranolol Hydrochloride 100 Microg/ml In Water

239. Propranololi Hydrochloridum [who-ip Latin]

240. ( Inverted Question Mark)-propranolol Hydrochloride

241. Q-201632

242. Sr-01000075285-1

243. Sr-01000075285-3

244. W-109142

245. Q27108095

246. Z90121066

247. (+/-)-propranolol Hydrochloride, >=99% (tlc), Powder

248. (+/-)-propranolol, Hydrochloride - Cas 3506-09-0

249. (+/-)-propranolol Hydrochloride, Analytical Reference Material

250. 1-(isopropylamino)-3-(1-napthyloxy)-2-propanol Hydrochloride

251. Propranolol Hydrochloride 1.0 Mg/ml In Methanol (as Free Base)

252. (+/-)-[2-hydroxy-3-(naphthyloxy)propyl]isopropylammonium Chloride

253. 1-(1-naphthyloxy)-2-hydroxy-3-(isopropylamino)propane Hydrochloride

254. 1-(1-naphthyloxy)-2-hydroxy-3-isopropylaminopropanehydrochloride

255. 1-(alpha-naphthoxy)-3-(iso-propylamino)-2-propanol Hydrochloride

256. 1-(alpha-naphthoxy)-3-(isopropylamino)-2-propanol Hydrochloride

257. 1-(isopropylamino)-3-(.alpha.-naphthoxy)-2-propanol Hydrochloride

258. Propranolol Hydrochloride, European Pharmacopoeia (ep) Reference Standard

259. ( Inverted Question Mark)-1-(isopropylamino)-3-(1-naphthyloxy)-2-propanol Hydrochloride

260. (rs)-1-[(1-methylethyl)amino]-3-(1-naphthalenyloxy)-2-propanol Hydrochloride

261. (rs)-1-[(1-methylethyl)amino]-3-(1-naphthalenyloxy)-2-propanolhydrochloride

262. Propranolol Hydrochloride, Pharmaceutical Secondary Standard; Certified Reference Material

263. Propranolol Hydrochloride, United States Pharmacopeia (usp) Reference Standard

264. 2-propanol, 1-((1-methylethyl)amino)-3-(1-naphthalenyloxy)-, Hydrochloride, (+/-)-

265. Propranolol Hydrochloride For Performance Test, European Pharmacopoeia (ep) Reference Standard

266. Propranolol Hydrochloride Solution, 1.0 Mg/ml In Methanol (as Free Base), Ampule Of 1 Ml, Certified Reference Material

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₁₆H₂₂ClNO₂
Molecular Weight	295.80 g/mol
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	6
Exact Mass	295.1339066 g/mol
Monoisotopic Mass	295.1339066 g/mol
Topological Polar Surface Area	41.5 Å²
Heavy Atom Count	20
Formal Charge	0
Complexity	257
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	2

4 Drug and Medication Information

4.1 Drug Information

1 of 10
Drug Name	Inderal
PubMed Health	Propranolol (By mouth)
Drug Classes	Antianginal, Antiarrhythmic, Group II, Antihypertensive, Antimigraine, Cardiovascular Agent
Drug Label	Inderal (propranolol hydrochloride) is a synthetic beta-adrenergic receptor-blocking agent chemically described as 2-Propanol, 1-[(1-methylethyl)amino]-3-(1-naphthalenyloxy)-, hydrochloride,()-. Its molecular and structural formulae are: C16H21NO...
Active Ingredient	Propranolol hydrochloride
Dosage Form	Tablet
Route	oral
Strength	60mg; 10mg; 80mg; 40mg; 20mg
Market Status	Prescription
Company	Akrimax Pharms

2 of 10
Drug Name	Inderal la
PubMed Health	Somatropin, E coli Derived (Injection)
Drug Classes	Endocrine-Metabolic Agent
Drug Label	Inderal (propranolol hydrochloride) is a synthetic beta-adrenergic receptor-blocking agent chemically described as 2-Propanol, 1-[(1-methylethyl)amino]-3-(1-naphthalenyloxy)-, hydrochloride,()-. Its molecular and structural formulae are: C16H21NO...
Active Ingredient	Propranolol hydrochloride
Dosage Form	Capsule, extended release
Route	Oral
Strength	160mg; 120mg; 60mg; 80mg
Market Status	Prescription
Company	Akrimax Pharms

3 of 10
Drug Name	Innopran xl
PubMed Health	Propranolol
Drug Classes	Antianginal, Antiarrhythmic, Group II, Antihypertensive, Antimigraine, Cardiovascular Agent
Drug Label	INNOPRAN XL (propranolol hydrochloride) is a nonselective, beta-adrenergic receptor-blocking agent for oral administration, available as an extended release product. INNOPRAN XL is available as 80-mg and 120-mg capsules which contain sustained-releas...
Active Ingredient	Propranolol hydrochloride
Dosage Form	Capsule, extended release
Route	Oral
Strength	120mg; 80mg
Market Status	Prescription
Company	Glaxosmithkline

4 of 10
Drug Name	Propranolol hydrochloride
PubMed Health	Propranolol (Injection)
Drug Classes	Antianginal, Antiarrhythmic, Group II, Antihypertensive, Antimigraine, Cardiovascular Agent
Drug Label	hydrochloride(Propranolol is a synthetic beta-adrenergic receptor blocking agent chemically described as 2-Propanol, 1-[(1-methylethyl)amino]-3-(1-naphthalenyloxy)-, hydrochloride,()-. Its molecular and structural formulae are:C16H21NO2.HClPropr...
Active Ingredient	Propranolol hydrochloride
Dosage Form	Tablet; Injectable; Capsule, extended release; Solution
Route	Injection; Oral
Strength	1mg/ml; 160mg; 40mg/5ml; 120mg; 60mg; 10mg; 20mg/5ml; 80mg; 40mg; 20mg
Market Status	Prescription
Company	Vintage Pharms; Upsher Smith; Bedford; Aptalis Pharmatech; Hikma Farmaceutica; Northstar Hlthcare; Sandoz; Roxane; Watson Labs; Glatt Air; Actavis Elizabeth; Baxter Hlthcare; Fresenius Kabi Usa; Ipca Labs; Zydus Pharms Usa; Pliva; Mylan

5 of 10
Drug Name	Tev-tropin
Active Ingredient	Somatropin recombinant
Dosage Form	Injectable
Route	Injection
Strength	5mg/vial
Market Status	Prescription
Company	Ferring

6 of 10
Drug Name	Inderal
PubMed Health	Propranolol (By mouth)
Drug Classes	Antianginal, Antiarrhythmic, Group II, Antihypertensive, Antimigraine, Cardiovascular Agent
Drug Label	Inderal (propranolol hydrochloride) is a synthetic beta-adrenergic receptor-blocking agent chemically described as 2-Propanol, 1-[(1-methylethyl)amino]-3-(1-naphthalenyloxy)-, hydrochloride,()-. Its molecular and structural formulae are: C16H21NO...
Active Ingredient	Propranolol hydrochloride
Dosage Form	Tablet
Route	oral
Strength	60mg; 10mg; 80mg; 40mg; 20mg
Market Status	Prescription
Company	Akrimax Pharms

7 of 10
Drug Name	Inderal la
PubMed Health	Somatropin, E coli Derived (Injection)
Drug Classes	Endocrine-Metabolic Agent
Drug Label	Inderal (propranolol hydrochloride) is a synthetic beta-adrenergic receptor-blocking agent chemically described as 2-Propanol, 1-[(1-methylethyl)amino]-3-(1-naphthalenyloxy)-, hydrochloride,()-. Its molecular and structural formulae are: C16H21NO...
Active Ingredient	Propranolol hydrochloride
Dosage Form	Capsule, extended release
Route	Oral
Strength	160mg; 120mg; 60mg; 80mg
Market Status	Prescription
Company	Akrimax Pharms

8 of 10
Drug Name	Innopran xl
PubMed Health	Propranolol
Drug Classes	Antianginal, Antiarrhythmic, Group II, Antihypertensive, Antimigraine, Cardiovascular Agent
Drug Label	INNOPRAN XL (propranolol hydrochloride) is a nonselective, beta-adrenergic receptor-blocking agent for oral administration, available as an extended release product. INNOPRAN XL is available as 80-mg and 120-mg capsules which contain sustained-releas...
Active Ingredient	Propranolol hydrochloride
Dosage Form	Capsule, extended release
Route	Oral
Strength	120mg; 80mg
Market Status	Prescription
Company	Glaxosmithkline

9 of 10
Drug Name	Propranolol hydrochloride
PubMed Health	Propranolol (Injection)
Drug Classes	Antianginal, Antiarrhythmic, Group II, Antihypertensive, Antimigraine, Cardiovascular Agent
Drug Label	hydrochloride(Propranolol is a synthetic beta-adrenergic receptor blocking agent chemically described as 2-Propanol, 1-[(1-methylethyl)amino]-3-(1-naphthalenyloxy)-, hydrochloride,()-. Its molecular and structural formulae are:C16H21NO2.HClPropr...
Active Ingredient	Propranolol hydrochloride
Dosage Form	Tablet; Injectable; Capsule, extended release; Solution
Route	Injection; Oral
Strength	1mg/ml; 160mg; 40mg/5ml; 120mg; 60mg; 10mg; 20mg/5ml; 80mg; 40mg; 20mg
Market Status	Prescription
Company	Vintage Pharms; Upsher Smith; Bedford; Aptalis Pharmatech; Hikma Farmaceutica; Northstar Hlthcare; Sandoz; Roxane; Watson Labs; Glatt Air; Actavis Elizabeth; Baxter Hlthcare; Fresenius Kabi Usa; Ipca Labs; Zydus Pharms Usa; Pliva; Mylan

10 of 10
Drug Name	Tev-tropin
Active Ingredient	Somatropin recombinant
Dosage Form	Injectable
Route	Injection
Strength	5mg/vial
Market Status	Prescription
Company	Ferring

4.2 Therapeutic Uses

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

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

/SRP: Former use/: Propranolol has proven to be effective in numerous cases in which digitalis, with or without quinidine and/or procainamide, failed to reduce ventricular rate, and in cases of paroxysmal atrial tachycardia attributed to digitalis toxicity.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 700

Propranolol is also used in hypertrophic obstructive cardiomyopathies. In these conditions forceful contraction of myocardium along a ventricular outflow tract can greatly increase outflow resistance, particularly during exercise. .../It/ is sometimes useful in management of tachycardia and arrhythmias in patient with pheochromocytoma.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 552

Medication (Vet): ...Atropine in conjunction with propranolol /was found/ to be useful in treatment of oleander poisoning.

Clarke, E.G., and M. L. Clarke. Veterinary Toxicology. Baltimore, Maryland: The Williams and Wilkins Company, 1975., p. 275

For more Therapeutic Uses (Complete) data for PROPRANOLOL HYDROCHLORIDE (25 total), please visit the HSDB record page.

4.3 Drug Warning

.../Propranolol/ is relatively contraindicated in ...hay fever, cardiogenic shock, congestive heart failure, right ventricular failure secondary to pulmonary hypertension, and when myocardial depressant anesthetics, tricyclic antidepressants, or oral hypoglycemics are used.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 835

Propranolol (1% solution) used as eye-drops .../per 1 report/, caused intense pain lasting as long as 15 min and induced hyperemia and slight miosis, but according to others these eye-drops have been well tolerated by most patients in use up to 4 times/day for 3-4 months, causing burning sensations and conjunctival hyperemia in only 8/47 eyes.

Grant, W.M. Toxicology of the Eye. 3rd ed. Springfield, IL: Charles C. Thomas Publisher, 1986., p. 768

Contraindicated in patients with cardiogenic shock, sinus bradycardia and greater than first degree block, bronchial asthma, and congestive heart failure. Adverse reactions include weakness, light headedness, depression, bradycardia, paresthesia of hands, arterial insufficiency (e.g., Raynaud type), nausea, and diarrhea. Use is best avoided in patients with bronchospastic diseases and therapy in diabetic patients must be closely monitored.

Hussar, D.A. (ed.). Modell's Drugs in Current Use and New Drugs. 38th ed. New York, NY: Springer Publishing Co., 1992., p. 140

After sudden cessation of propranolol therapy in some patients treated for angina, increased frequency, duration, and severity of angina episodes have occurred, often within 24 hr. These episodes are unstable and are not relieved by nitroglycerin. Acute and sometimes fatal myocardial infarction and sudden death have also occurred after abrupt withdrawal of propranolol therapy in some patients treated for angina. In hypertensive patients, sudden cessation of propranolol has produced a syndrome similar to florid thyrotoxicosis, characterized by tenseness, anxiety, tachycardia, and excessive perspiration; these symptoms occurred within one week of cessation of the drug and were relieved by reinstituting propranolol therapy.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 1782

For more Drug Warnings (Complete) data for PROPRANOLOL HYDROCHLORIDE (31 total), please visit the HSDB record page.

4.4 Drug Indication

Hemangiol is indicated in the treatment of proliferating infantile haemangioma requiring systemic therapy:

- Life- or function-threatening haemangioma,

- Ulcerated haemangioma with pain and/or lack of response to simple wound care measures,

- Haemangioma with a risk of permanent scars or disfigurement.

It is to be initiated in infants aged 5 weeks to 5 months.

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Adrenergic beta-Antagonists

Drugs that bind to but do not activate beta-adrenergic receptors thereby blocking the actions of beta-adrenergic agonists. Adrenergic beta-antagonists are used for treatment of hypertension, cardiac arrhythmias, angina pectoris, glaucoma, migraine headaches, and anxiety. (See all compounds classified as Adrenergic beta-Antagonists.)

Antihypertensive Agents

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. (See all compounds classified as Antihypertensive Agents.)

Vasodilator Agents

Drugs used to cause dilation of the blood vessels. (See all compounds classified as Vasodilator Agents.)

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 prolongation, or calcium channel blockade. (See all compounds classified as Anti-Arrhythmia Agents.)

5.2 FDA Pharmacological Classification

5.2.1 Pharmacological Classes

beta-Adrenergic Blocker [EPC]; Adrenergic beta-Antagonists [MoA]

5.3 ATC Code

C07AA05

5.4 Absorption, Distribution and Excretion

Studies in man and experimental animals indicate that rapid hepatic clearance is responsible for appearance of only trace amount of unmetabolized propranolol in blood after small oral doses. With larger doses, blood levels are linearly related to dose, suggesting saturation of hepatic metabolic system.

The Chemical Society. Foreign Compound Metabolism in Mammals Volume 3. London: The Chemical Society, 1975., p. 144

Propranolol is almost completely absorbed from the GI tract; however, plasma concentrations attained are quite variable among individuals. There is no difference in the rate of absorption of the 2 isomers of propranolol. Propranolol appears in the plasma within 30 min, and peak plasma concentrations are reached about 60-90 min after oral administration of the conventional tablets. The time when peak plasma concentrations are reached may be delayed, but concentrations are not necessarily lowered, when the drug is administered with food. Oral bioavailability of the drug may be increased in children with Down's syndrome; higher than expected plasma propranolol concentrations have been observed in such children. Bioavailability of a single 40-mg oral dose of propranolol hydrochloride as a conventional tablet or oral solution reportedly is equivalent in adults.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 1785-6

Propranolol hydrochloride is slowly absorbed following administration of the drug as extended release capsules, and peak blood concentrations are reached about 6 hr after administration. When measured at steady state over a 24 hr period, the area under the plasma concentration time curve for the extended release capsules is about 60-65% of the plasma concentration time curve for a comparable divided daily dose of the conventional tablets. The lower plasma concentration time curve is probably caused by the slower rate of absorption of the drug from the extended release capsules with resultant greater hepatic metabolism. After administration of a single dose of propranolol as the extended release capsules, blood concentrations are fairly constant for about 12 hr and then decline exponentially during the following 12 hr.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 1785-6

Following iv administration of propranolol, the onset of action is almost immediate. Animal studies indicate that propranolol is rapidly absorbed after im administration.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 1786

For more Absorption, Distribution and Excretion (Complete) data for PROPRANOLOL HYDROCHLORIDE (12 total), please visit the HSDB record page.

5.5 Metabolism/Metabolites

Besides ... 4-hydroxypropranolol and naphthoxylacetic acid, 6 new urinary metabolites have... been identified... /which are/ n-deisopropylpropranolol; 1-(alpha-naphthoxy)-2,3-propyleneglycol; ring hydroxylated 1-(alpha-naphthoxy)-2,3-propyleneglycol; alpha-naphthoxyacetic acid; alpha-naphthol and 1,4-dihydroxynaphthalene.

The Chemical Society. Foreign Compound Metabolism in Mammals Volume 3. London: The Chemical Society, 1975., p. 215

Isopropylamine and hexadeuteriated isopropylamine have been identified as urinary metabolites of propranolol and hexadeuteriated propranolol, respectively; this is believed to be 1st recorded example of single-step oxidative deamination of n-isopropylamine compound.

The Chemical Society. Foreign Compound Metabolism in Mammals Volume 3. London: The Chemical Society, 1975., p. 217

During initial oral therapy (but not during iv or chronic oral therapy), an active metabolite, 4-hydroxypropranolol, is formed. 4-Hydroxypropranolol has about the same beta-adrenergic blocking potency as does propranolol and may be present in plasma in amounts about equal to propranolol. This metabolite is eliminated more rapidly than propranolol and is virtually absent from the plasma 6 hr after oral administration of the drug. Results of one study indicate that after iv administration or chronic oral administration of propranolol, 4-hydroxypropranolol is not formed to a substantial extent, and beta-adrenergic blocking activity is more closely reflected by propranolol concentrations. Individual variations in ability to hydroxylate propranolol to the active metabolite may also exist. In addition, some other metabolites of propranolol may possess antiarrhythmic activity without beta-adrenergic blocking activity.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 1786

Propranolol is almost completely metabolized in the liver and at least 8 metabolites have been identified in urine. Only 1-4% of an oral or iv dose of the drug appears in feces as unchanged drug and metabolites.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 1786

5.6 Biological Half-Life

When usual therapeutic doses of propranolol are administered chronically, the half-life ranges from 3.4-6 hr. Single dose studies generally have shown a shorter half-life of 2-3 hr.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 1786

5.7 Mechanism of Action

Propranolol is a nonselective beta-adrenergic blocking agent. Propranolol inhibits response to adrenergic stimuli by competitively blocking, beta-adrenergic receptors within the myocardium and within bronchial and vascular smooth muscle. Only the l-isomer of propranolol has substantial beta-adrenergic blocking activity. Propranolol has no intrinsic sympathomimetic activity.