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Prestwick3_000276
Also known as: 28395-03-1, 3-(butylamino)-4-phenoxy-5-sulfamoylbenzoic acid, Bumex, Burinex, Fordiuran, Lunetoron
Molecular Formula
C17H20N2O5S
Molecular Weight
364.4  g/mol
InChI Key
MAEIEVLCKWDQJH-UHFFFAOYSA-N
FDA UNII
0Y2S3XUQ5H

A sulfamyl diuretic.
Bumetanide is a Loop Diuretic. The physiologic effect of bumetanide is by means of Increased Diuresis at Loop of Henle.
1 2D Structure

Prestwick3_000276

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
3-(butylamino)-4-phenoxy-5-sulfamoylbenzoic acid
2.1.2 InChI
InChI=1S/C17H20N2O5S/c1-2-3-9-19-14-10-12(17(20)21)11-15(25(18,22)23)16(14)24-13-7-5-4-6-8-13/h4-8,10-11,19H,2-3,9H2,1H3,(H,20,21)(H2,18,22,23)
2.1.3 InChI Key
MAEIEVLCKWDQJH-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCCCNC1=C(C(=CC(=C1)C(=O)O)S(=O)(=O)N)OC2=CC=CC=C2
2.2 Other Identifiers
2.2.1 UNII
0Y2S3XUQ5H
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Bumedyl

2. Bumethanide

3. Bumex

4. Burinex

5. Drenural

6. Fordiuran

7. Miccil

8. Pf 1593

9. Pf-1593

10. Pf1593

2.3.2 Depositor-Supplied Synonyms

1. 28395-03-1

2. 3-(butylamino)-4-phenoxy-5-sulfamoylbenzoic Acid

3. Bumex

4. Burinex

5. Fordiuran

6. Lunetoron

7. Fontego

8. Segurex

9. Ro 10-6338

10. Bumetanida

11. Bumetanidum

12. Bumetanidum [inn-latin]

13. Pf 1593

14. Bumetanida [inn-spanish]

15. 3-(aminosulfonyl)-5-(butylamino)-4-phenoxybenzoic Acid

16. Benzoic Acid, 3-(aminosulfonyl)-5-(butylamino)-4-phenoxy-

17. Bumetanide (ro 10-6338)

18. 0y2s3xuq5h

19. Ro-10-6338

20. Mls000028457

21. Chebi:3213

22. Aquazone

23. Butinat

24. Cambiex

25. Diurama

26. Yurinex

27. Benzoic Acid, 3-(butylamino)-4-phenoxy-5-sulfamoyl-

28. Burine

29. 3-butylamino-4-phenoxy-5-sulfamoyl-benzoic Acid

30. 3-butylamino-4-(phenoxy)-5-sulfamoylbenzoic Acid

31. Lixil-leo

32. Ro-106338

33. Ncgc00015149-02

34. Smr000058418

35. Lixil

36. Cas-28395-03-1

37. Ro 10-6338;pf 1593

38. Dsstox_cid_2699

39. 3-butylamino-4-phenoxy-5-sulfamoylbenzoic Acid

40. Dsstox_rid_76695

41. Dsstox_gsid_22699

42. S95008.

43. S-95008.

44. Bufenox

45. Bumex (tn)

46. Sr-01000003062

47. Einecs 249-004-6

48. Unii-0y2s3xuq5h

49. Brn 2185351

50. Bumetanide In Bulk

51. 82u

52. Prestwick_679

53. Mfcd00078949

54. Bumetanide [usan:usp:inn:ban:jan]

55. Spectrum_001317

56. Bumetanide, >=98%

57. Bumetanide [mi]

58. Bumetanide [inn]

59. Bumetanide [jan]

60. Opera_id_1734

61. Prestwick0_000276

62. Prestwick1_000276

63. Prestwick2_000276

64. Prestwick3_000276

65. Spectrum2_001050

66. Spectrum3_001481

67. Spectrum4_000030

68. Spectrum5_001212

69. Bumetanide [usan]

70. Lopac-b-3023

71. Bumetanide [vandf]

72. B 3023

73. Bumetanide [mart.]

74. Cid_2471

75. Bumetanide [usp-rs]

76. Bumetanide [who-dd]

77. Chembl1072

78. Lopac0_000162

79. Schembl27525

80. Bspbio_000152

81. Bspbio_001508

82. Bspbio_003061

83. Kbiogr_000228

84. Kbiogr_000439

85. Kbioss_000228

86. Kbioss_001797

87. 3-(butylamino)-4-phenoxy-5-sulfamoyl-benzoic Acid

88. Mls001148265

89. Divk1c_000034

90. Spectrum1502004

91. Spbio_000980

92. Spbio_002371

93. Bpbio1_000168

94. Bumetanide (jp17/usp/inn)

95. Gtpl4837

96. Bumetanide [ep Impurity]

97. Bumetanide [orange Book]

98. Dtxsid5022699

99. Bdbm25903

100. Hms500b16

101. Kbio1_000034

102. Kbio2_000228

103. Kbio2_001797

104. Kbio2_002796

105. Kbio2_004365

106. Kbio2_005364

107. Kbio2_006933

108. Kbio3_000455

109. Kbio3_000456

110. Kbio3_002561

111. Bumetanide [ep Monograph]

112. Ninds_000034

113. 3-(aminosulfonyl)-5-(butylamino)-4-(phenyloxy)benzoic Acid

114. Bio1_000421

115. Bio1_000910

116. Bio1_001399

117. Bio2_000228

118. Bio2_000708

119. Bumetanide [usp Monograph]

120. Hms1361l10

121. Hms1568h14

122. Hms1791l10

123. Hms1921b20

124. Hms1989l10

125. Hms2089p13

126. Hms2092n03

127. Hms2095h14

128. Hms2230p15

129. Hms3259o08

130. Hms3260b05

131. Hms3374e02

132. Hms3402l10

133. Hms3654b13

134. Hms3712h14

135. Hms3873c13

136. Pharmakon1600-01502004

137. Bcp28485

138. Zinc3813061

139. Tox21_110088

140. Tox21_500162

141. Ccg-40125

142. Nsc758145

143. S1287

144. Akos015896600

145. Tox21_110088_1

146. Ac-8115

147. Cs-1821

148. Db00887

149. Ks-5211

150. Lp00162

151. Nc00550

152. Nsc 758145

153. Nsc-758145

154. Sdccgsbi-0050150.p004

155. Idi1_000034

156. Idi1_033978

157. Smp1_000049

158. Ncgc00015149-01

159. Ncgc00015149-03

160. Ncgc00015149-04

161. Ncgc00015149-05

162. Ncgc00015149-06

163. Ncgc00015149-07

164. Ncgc00015149-08

165. Ncgc00015149-09

166. Ncgc00015149-10

167. Ncgc00015149-11

168. Ncgc00015149-12

169. Ncgc00015149-13

170. Ncgc00015149-15

171. Ncgc00015149-16

172. Ncgc00015149-26

173. Ncgc00022072-03

174. Ncgc00022072-04

175. Ncgc00022072-05

176. Ncgc00022072-06

177. Ncgc00022072-07

178. Ncgc00022072-08

179. Ncgc00260847-01

180. Hy-17468

181. Sbi-0050150.p003

182. Ab00052253

183. Eu-0100162

184. Sw196834-3

185. D00247

186. 3-butylamino-4-phenoxy-5-sulphamyl-benzoic Acid

187. Ab00052253-15

188. Ab00052253-16

189. Ab00052253_17

190. Ab00052253_18

191. 3-n-butylamino-4-phenoxy-5-sulfamyl-benzoic Acid

192. 3-n-butylamino-4-phenoxy-5-sulphamyl-benzoic Acid

193. 395b031

194. A819434

195. Q275926

196. J-017055

197. Sr-01000003062-2

198. Sr-01000003062-4

199. Sr-01000003062-7

200. Brd-k38197229-001-06-7

201. Brd-k38197229-001-17-4

202. 3-(aminosulfonyl)-5-(butylamino)-4-phenoxy-benzoic Acid

203. Z1550648769

204. 3-(butylamino)-4-phenoxy-5-sulfamoylbenzoic Acid.

205. Bumetanide, British Pharmacopoeia (bp) Reference Standard

206. Bumetanide, European Pharmacopoeia (ep) Reference Standard

207. Bumetanide, United States Pharmacopeia (usp) Reference Standard

208. Ro 10-6338; Pf 1593 Pound>>ro-10-6338; Pf1593 Pound>>ro10-6338; Pf-1593

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 364.4 g/mol
Molecular Formula C17H20N2O5S
XLogP32.8
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count7
Rotatable Bond Count8
Exact Mass364.10929292 g/mol
Monoisotopic Mass364.10929292 g/mol
Topological Polar Surface Area127 Ų
Heavy Atom Count25
Formal Charge0
Complexity528
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
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 NameBumetanide
PubMed HealthBumetanide
Drug ClassesCardiovascular Agent, Diuretic, Loop
Drug LabelBumetanide is a loop diuretic, available as scored tablets, 0.5 mg (light green), 1 mg (yellow) and 2 mg (peach) for oral administration; each tablet also contains: anhydrous lactose, magnesium stearate, microcrystalline cellulose, corn starch and ta...
Active IngredientBumetanide
Dosage FormInjectable; Tablet
RouteInjection; Oral
Strength0.5mg; 2mg; 1mg; 0.25mg/ml
Market StatusPrescription
CompanyBedford; Ivax Sub Teva Pharms; Hospira; Hikma Maple; Sandoz

2 of 2  
Drug NameBumetanide
PubMed HealthBumetanide
Drug ClassesCardiovascular Agent, Diuretic, Loop
Drug LabelBumetanide is a loop diuretic, available as scored tablets, 0.5 mg (light green), 1 mg (yellow) and 2 mg (peach) for oral administration; each tablet also contains: anhydrous lactose, magnesium stearate, microcrystalline cellulose, corn starch and ta...
Active IngredientBumetanide
Dosage FormInjectable; Tablet
RouteInjection; Oral
Strength0.5mg; 2mg; 1mg; 0.25mg/ml
Market StatusPrescription
CompanyBedford; Ivax Sub Teva Pharms; Hospira; Hikma Maple; Sandoz

4.2 Drug Indication

For the treatment of edema associated with congestive heart failure, hepatic and renal disease including the nephrotic syndrome.


FDA Label


Treatment of autism spectrum disorder


5 Pharmacology and Biochemistry
5.1 Pharmacology

Bumetanide is a loop diuretic of the sulfamyl category to treat heart failure. It is often used in patients in whom high doses of furosemide are ineffective. There is however no reason not to use bumetanide as a first choice drug. The main difference between the two substances is in bioavailability. Bumetanide has more predictable pharmacokinetic properties as well as clinical effect. In patients with normal renal function, bumetanide is 40 times more effective than furosemide.


5.2 MeSH Pharmacological Classification

Sodium Potassium Chloride Symporter Inhibitors

Agents that inhibit SODIUM-POTASSIUM-CHLORIDE SYMPORTERS which are concentrated in the thick ascending limb at the junction of the LOOP OF HENLE and KIDNEY TUBULES, DISTAL. They act as DIURETICS. Excess use is associated with HYPOKALEMIA and HYPERGLYCEMIA. (See all compounds classified as Sodium Potassium Chloride Symporter Inhibitors.)


Diuretics

Agents that promote the excretion of urine through their effects on kidney function. (See all compounds classified as Diuretics.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
BUMETANIDE
5.3.2 FDA UNII
0Y2S3XUQ5H
5.3.3 Pharmacological Classes
Loop Diuretic [EPC]; Increased Diuresis at Loop of Henle [PE]
5.4 ATC Code

C03CA02

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

C03 - Diuretics

C03C - High-ceiling diuretics

C03CA - Sulfonamides, plain

C03CA02 - Bumetanide


5.5 Absorption, Distribution and Excretion

Absorption

Bumetanide is completely absorbed (80%), and the absorption is not altered when taken with food. Bioavailability is almost complete.


Route of Elimination

Oral administration of carbon-14 labeled Bumex to human volunteers revealed that 81% of the administered radioactivity was excreted in the urine, 45% of it as unchanged drug. Biliary excretion of Bumex amounted to only 2% of the administered dose.


Clearance

0.2 - 1.1 mL/min/kg [preterm and full-term neonates with respiratory disorders]

2.17 mL/min/kg [neonates receiving bumetanide for volume overload]

1.8 +/- 0.3 mL/min/kg [geriatric subjects]

2.9 +/- 0.2 mL/min/kg [younger subjects]


5.6 Metabolism/Metabolites

45% is secreted unchanged. Urinary and biliary metabolites are formed by oxidation of the N-butyl side chain.


5.7 Biological Half-Life

60-90 minutes


5.8 Mechanism of Action

Bumetanide interferes with renal cAMP and/or inhibits the sodium-potassium ATPase pump. Bumetanide appears to block the active reabsorption of chloride and possibly sodium in the ascending loop of Henle, altering electrolyte transfer in the proximal tubule. This results in excretion of sodium, chloride, and water and, hence, diuresis.


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