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Chemistry

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Also known as: Isoprenaline, Novodrin, Isopropydrin, Asmalar, 7683-59-2, Bellasthman
Molecular Formula
C11H17NO3
Molecular Weight
211.26  g/mol
InChI Key
JWZZKOKVBUJMES-UHFFFAOYSA-N
FDA UNII
L628TT009W

Isoproterenol Hydrochloride
Isopropyl analog of EPINEPHRINE; beta-sympathomimetic that acts on the heart, bronchi, skeletal muscle, alimentary tract, etc. It is used mainly as bronchodilator and heart stimulant.
Isoproterenol is a beta-Adrenergic Agonist. The mechanism of action of isoproterenol is as an Adrenergic beta-Agonist.
1 2D Structure

Isoproterenol Hydrochloride

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
4-[1-hydroxy-2-(propan-2-ylamino)ethyl]benzene-1,2-diol
2.1.2 InChI
InChI=1S/C11H17NO3/c1-7(2)12-6-11(15)8-3-4-9(13)10(14)5-8/h3-5,7,11-15H,6H2,1-2H3
2.1.3 InChI Key
JWZZKOKVBUJMES-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC(C)NCC(C1=CC(=C(C=C1)O)O)O
2.2 Other Identifiers
2.2.1 UNII
L628TT009W
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 4-(1-hydroxy-2-((1-methylethyl)amino)ethyl)-1,2-benzenediol

2. Euspiran

3. Hydrochloride, Isoproterenol

4. Isadrin

5. Isadrine

6. Isoprenaline

7. Isopropyl Noradrenaline

8. Isopropylarterenol

9. Isopropylnoradrenaline

10. Isopropylnorepinephrine

11. Isoproterenol Hydrochloride

12. Isoproterenol Sulfate

13. Isuprel

14. Izadrin

15. Noradrenaline, Isopropyl

16. Norisodrine

17. Novodrin

18. Sulfate, Isoproterenol

2.3.2 Depositor-Supplied Synonyms

1. Isoprenaline

2. Novodrin

3. Isopropydrin

4. Asmalar

5. 7683-59-2

6. Bellasthman

7. Isoprenalin

8. Norisodrine

9. Aludrine

10. Asiprenol

11. Assiprenol

12. Respifral

13. Neodrenal

14. Proternol

15. Neo-epinine

16. Isopropylarterenol

17. Saventrine

18. Aludrin

19. Isadrine

20. Isonorin

21. Isorenin

22. N-isopropylnoradrenaline

23. Isonorene

24. Isopropyladrenaline

25. Lomupren

26. N-isopropylnorepinephrine

27. Isopropylnorepinephrine

28. Vapo-n-iso

29. Isupren

30. Isopropylnoradrenaline

31. Isopropyl Noradrenaline

32. Racemic Isoprenaline

33. Dl-isadrine

34. Racemic Isoproterenol

35. (+-)-isoproterenol

36. Epinephrine Isopropyl Homolog

37. Isoprenalinum

38. Aleudrin

39. Aleudrine

40. (+-)-isoprenaline

41. Dl-isoproterenol

42. Isoprenalina

43. 4-[1-hydroxy-2-(propan-2-ylamino)ethyl]benzene-1,2-diol

44. Dihydroxyphenylethanolisopropylamine

45. Win 5162

46. 1-(3,4-dihydroxyphenyl)-2-(isopropylamino)ethanol

47. Ici 46399

48. 1-(3,4-dihydroxyphenyl)-2-isopropylaminoethanol

49. Alpha-(isopropylaminomethyl)protocatechuyl Alcohol

50. 1,2-benzenediol, 4-[1-hydroxy-2-[(1-methylethyl)amino]ethyl]-

51. 149-53-1

52. N-isopropyl-beta-dihydroxyphenyl-beta-hydroxyethylamine

53. Isoprenaline (inn)

54. Isoprenaline [inn]

55. 4-(1-hydroxy-2-((1-methylethyl)amino)ethyl)-1,2-benzenediol

56. 1,2-benzenediol, 4-(1-hydroxy-2-((1-methylethyl)amino)ethyl)-

57. Nsc-9975

58. Nsc-33791

59. Chembl434

60. 4-(1-hydroxy-2-(isopropylamino)ethyl)benzene-1,2-diol

61. 3,4-dihydroxy-alpha-((isopropylamino)methyl)benzyl Alcohol

62. Isoproterenolum

63. Chebi:64317

64. Isopropylaminomethyl(3,4-dihydroxyphenyl)carbinol

65. L628tt009w

66. 7683-59-2 (free)

67. Nsc33791

68. 3,4-dihydroxy-alpha-[(isopropylamino)methyl]benzyl Alcohol

69. Ncgc00015558-06

70. 3,4-dihydroxy-.alpha.-(isopropylaminomethyl)-benzyl Alcohol

71. A-21

72. Isoproterenol [jan]

73. Protocatechuyl Alcohol,-

74. Dsstox_cid_3175

75. Dl(+-)-isoproterenol

76. L-isoproterenol; Levisoprenaline; Proternol L

77. Dsstox_rid_76904

78. Dsstox_gsid_23175

79. Isoprenalinum [inn-latin]

80. .alpha.-(isopropylaminomoethyl)protocatechuyl Alcohol

81. Isoprenalina [inn-spanish]

82. Isoproterenol Chloride

83. Wln: Qr Bq Dyq1my1&1

84. 3,4-dihydroxy-.alpha.-[(isopropylamino)methyl]benzyl Alcohol

85. 4-{1-hydroxy-2-[(1-methylethyl)amino]ethyl}benzene-1,2-diol

86. 4-[1-hydroxy-2-(isopropylamino)ethyl]-1,2-benzenediol

87. Cas-7683-59-2

88. Isoprop

89. Ccris 3081

90. Nsc 9975

91. 1, 4-[1-hydroxy-2-[(1-methylethyl)amino]ethyl]-

92. Einecs 231-687-7

93. Nsc 33791

94. Isopropylaminomethyl-3,4-dihydroxyphenyl Carbinol

95. 4-[1-hydroxy-2-(isopropylamino)ethyl]benzene-1,2-diol

96. Brn 2213857

97. Benzyl Alcohol,4-dihydroxy-.alpha.-[(isopropylamino)methyl]-

98. Isoproterenol-l

99. Isoproterenol;

100. Unii-l628tt009w

101. 3,4-dihydroxy-.alpha.-((isopropylamino)methyl)benzyl Alcohol

102. Isoproterenol (-)

103. Isoproterenol,(+)

104. Protocatechuyl Alcohol, Alpha-(isopropylaminomethyl)-

105. Isoproteronol

106. Isoproterenol Dl-form

107. Isuprel (salt/mix)

108. Izadrin (salt/mix)

109. Euspiran (salt/mix)

110. (+/-)-isoprenaline

111. (+/-)-isoproterenol

112. Spectrum_000949

113. Prestwick0_001097

114. Prestwick1_001097

115. Prestwick2_001097

116. Spectrum2_001061

117. Spectrum3_000474

118. Spectrum4_000024

119. Spectrum5_000880

120. (.+/-.)-isoprenaline

121. Isoproterenol [mi]

122. (.+/-.)-isoproterenol

123. Schembl4165

124. Dl(.+/-.)-isoproterenol

125. Lopac0_000711

126. Oprea1_009434

127. Bspbio_002208

128. Gtpl536

129. Isoprenaline [mart.]

130. Isoproterenol [vandf]

131. Kbiogr_000427

132. Kbioss_001429

133. 3-13-00-02387 (beilstein Handbook Reference)

134. Divk1c_000894

135. Isoprenaline [who-dd]

136. Spbio_001042

137. Spbio_003057

138. Sgcut00015

139. 4-(1-hydroxy-2(isopropylamino)ethyl)-benzene 1,2-diol

140. Dtxsid4023175

141. Bdbm25392

142. Kbio1_000894

143. Kbio2_001429

144. Kbio2_003997

145. Kbio2_006565

146. Kbio3_001428

147. Nsc9975

148. Ninds_000894

149. 4-{1-hydroxy-2-[(propan-2-yl)amino]ethyl}benzene-1,2-diol

150. Hms2089a12

151. Hms3742a11

152. Isoproterenol Dl-form [mi]

153. Bcp09043

154. Benzyl Alcohol, 3,4-dihydroxy-alpha-((isopropylamino)methyl)-

155. To_000062

156. (a+/-)-isoproterenol Hydrochloride

157. Tox21_110172

158. Pdsp1_001425

159. Pdsp2_001409

160. Stl558077

161. Akos015913894

162. Tox21_110172_1

163. Ccg-204727

164. Ccg-204796

165. Db01064

166. Sdccgsbi-0050620.p003

167. Sdccgsbi-0050689.p005

168. Idi1_000894

169. Ncgc00015558-04

170. Ncgc00015558-05

171. Ncgc00015558-07

172. Ncgc00015558-08

173. Ncgc00015558-09

174. Ncgc00015558-10

175. Ncgc00015558-11

176. Ncgc00015558-12

177. Ncgc00015558-14

178. Ncgc00015558-25

179. Ncgc00016665-02

180. Ncgc00025274-03

181. Ncgc00025274-04

182. Ncgc00162220-01

183. Sbi-0050689.p004

184. Hy-108353

185. Cs-0028436

186. Ft-0724367

187. C07056

188. D08090

189. Ab00053487-09

190. Ab00053487-10

191. Ab00053487_11

192. Ab00053487_12

193. 683i592

194. Ag-219/03618046

195. L000936

196. Q415550

197. .alpha.-(isopropylaminomethyl)protocatechuyl Alcohol

198. Protocatechuyl Alcohol,.alpha.-(isopropylamino-methyl),-

199. 4-[1-hydroxy-2-(isopropylamino)ethyl]-1,2-benzenediol #

200. N-isopropyl-.beta.-dihydroxyphenyl-.beta.-hydroxyethylamine

201. 4-[1-hydroxy-2-(isopropylamino)ethyl]pyrocatechol;hydrochloride

202. 4-{1-hydroxy-2-[(propan-2-yl)amino]ethyl}benzene-1,2-diol, 2

203. Benzyl Alcohol, 3,4-dihydroxy-.alpha.-((isopropylamino)methyl)-

204. 114-45-4

205. Iso

2.3.3 Other Synonyms

1. Isoproterenol Sulfate

2. Isoprenaline Sulfate

3. Isoprenaline Sulphate

4. Isopropylarterenol Sulfate

5. Schembl41841

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 211.26 g/mol
Molecular Formula C11H17NO3
XLogP3-0.6
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count4
Rotatable Bond Count4
Exact Mass211.12084340 g/mol
Monoisotopic Mass211.12084340 g/mol
Topological Polar Surface Area72.7 Ų
Heavy Atom Count15
Formal Charge0
Complexity187
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 2  
Drug NameIsuprel
PubMed HealthIsoproterenol (Injection)
Drug ClassesBronchodilator, Vasopressor
Drug LabelIsoproterenol hydrochloride is 3,4-Dihydroxy--[(isopropylamino)methyl] benzyl alcohol hydrochloride, a synthetic sympathomimetic amine that is structurally related to epinephrine but acts almost exclusively on beta receptors. The molecular formula...
Active IngredientIsoproterenol hydrochloride
Dosage FormInjectable
RouteInjection
Strength0.2mg/ml
Market StatusPrescription
CompanyHospira

2 of 2  
Drug NameIsuprel
PubMed HealthIsoproterenol (Injection)
Drug ClassesBronchodilator, Vasopressor
Drug LabelIsoproterenol hydrochloride is 3,4-Dihydroxy--[(isopropylamino)methyl] benzyl alcohol hydrochloride, a synthetic sympathomimetic amine that is structurally related to epinephrine but acts almost exclusively on beta receptors. The molecular formula...
Active IngredientIsoproterenol hydrochloride
Dosage FormInjectable
RouteInjection
Strength0.2mg/ml
Market StatusPrescription
CompanyHospira

4.2 Drug Indication

Isoprenaline is indicated to treat mild or transient episodes of heart block not requiring electric shock or pacemakers, serious episodes of heart block and Adams-Stokes attacks not caused by ventricular tachycardia or fibrillation, and bronchospasm during anesthesia. Isoprenaline is also indicated for cases of cardiac arrest until preferable treatments like electric shock and pacemakers are available. Isoprenaline is also indicated as an adjunct therapy to fluid and electrolyte replacement therapy in hypovolemic shock, septic shock, hypoperfusion, congestive heart failure, and cardiogenic shock.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Isoprenaline is a non-selective beta adrenergic receptor agonist used in a number of indications for the heart, as well as bronchospasm in anesthesia. Isoprenaline has a short duration of action as it is rapidly cleared, and a wide therapeutic index. Patients should be counselled regarding the risks of isoprenaline in the treatment of cardiogenic shock following myocardial infarction, paradoxical worsening of heart block, or precipitation of Adams-Stokes attacks.


5.2 MeSH Pharmacological Classification

Adrenergic beta-Agonists

Drugs that selectively bind to and activate beta-adrenergic receptors. (See all compounds classified as Adrenergic beta-Agonists.)


Bronchodilator Agents

Agents that cause an increase in the expansion of a bronchus or bronchial tubes. (See all compounds classified as Bronchodilator Agents.)


Sympathomimetics

Drugs that mimic the effects of stimulating postganglionic adrenergic sympathetic nerves. Included here are drugs that directly stimulate adrenergic receptors and drugs that act indirectly by provoking the release of adrenergic transmitters. (See all compounds classified as Sympathomimetics.)


Cardiotonic Agents

Agents that have a strengthening effect on the heart or that can increase cardiac output. They may be CARDIAC GLYCOSIDES; SYMPATHOMIMETICS; or other drugs. They are used after MYOCARDIAL INFARCT; CARDIAC SURGICAL PROCEDURES; in SHOCK; or in congestive heart failure (HEART FAILURE). (See all compounds classified as Cardiotonic Agents.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
ISOPROTERENOL
5.3.2 FDA UNII
L628TT009W
5.3.3 Pharmacological Classes
Established Pharmacologic Class [EPC] - beta-Adrenergic Agonist
5.4 ATC Code

C01CA02

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355


C - Cardiovascular system

C01 - Cardiac therapy

C01C - Cardiac stimulants excl. cardiac glycosides

C01CA - Adrenergic and dopaminergic agents

C01CA02 - Isoprenaline


R - Respiratory system

R03 - Drugs for obstructive airway diseases

R03A - Adrenergics, inhalants

R03AB - Non-selective beta-adrenoreceptor agonists

R03AB02 - Isoprenaline


R - Respiratory system

R03 - Drugs for obstructive airway diseases

R03C - Adrenergics for systemic use

R03CB - Non-selective beta-adrenoreceptor agonists

R03CB01 - Isoprenaline


5.5 Absorption, Distribution and Excretion

Absorption

Data regarding absorption kinetics of isoprenaline are not readily available.


Route of Elimination

Isoprenaline is 12.2-27.0% recovered in the feces and 59.1-106.8% recovered in the urine after 48 hours. The majority of the recovered dose in the urine is conjugated isoprenaline, with 6.5-16.2% free isoprenaline, and 2.6-11.4% 3-O-methylisoprenaline and conjugates.


Volume of Distribution

In pediatric patients, the volume of distribution was 216 57 mL/kg.


Clearance

In pediatric patients, the clearance of isoprenaline was 42.5 5.0 mL/kg/min.


5.6 Metabolism/Metabolites

Isoprenaline is predominantly metabolized to glucuronide conjugates. Isoprenaline can also be O-methylated by catechol O-methyltransferase to the metabolite 3-O-methylisoprenaline, which can also be further glucuronidated.


5.7 Biological Half-Life

The half life of intravenous isoprenaline is 2.5-5 minutes. Oral isoprenaline has a half life of 40 minutes.


5.8 Mechanism of Action

Isoprenaline is a non-selective beta adrenergic receptor agonist. Agonism of beta-1 and beta-2 adrenergic receptors causes the alpha subunit of G-protein coupled receptors to exchange GMP for GTP, activating them, and allowing the alpha subunit to dissociate from the beta and gamma subunits. Dissociation of the alpha subunit activates adenylate cyclase, converting ATP to cyclic AMP. Cyclic AMP activates protein kinase A (PKA), which phosphorylates cardiac L-type calcium channels such as Cav1.2. These channels depolarize cells by inward active transport of calcium ions. Agonism of beta-1 adrenergic receptors lead to increased strength of contractility, conduction of nerve impulses, speed of relaxation, and rate in the heart. Agonism of beta-2 adrenergic receptors leads to glycogenolysis in the liver, glucagon release from the pancreas, and activation of the renin-angiotensin-aldosterone system. In the alveoli, agonism of beta-2 adrenergic receptors, activates similar pathways to the heart, however the end result is regulation of sodium channels, the cystic fibrosis transmembrane conductance regulator (CFTR), and sodium potassium ATPase. PKA phosphorylates scaffolding proteins and sodium channels, increasing the number of sodium channels on the apical side of alveolar cells and increasing active transport of sodium ions into cells. Agonism of beta-2 adrenergic receptors can also increase chloride ion transport across CFTR. Together, these actions lead to passive transport of water out of the alveoli, and the clearance of alveolar fluid.


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26-Jun-2021
24-Sep-2024
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Quantity (KGS) & Unit rate (USD/KGS) over time

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