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    Chemistry

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    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
    Bumetanide
    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

    Bumetanide

    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.

    API Reference Price

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    19-Jan-2021
    24-Oct-2024
    KGS
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