Bumetanide (CED0003712)

Record Information
Version1.0
Creation Date2016-05-22 03:38:05 UTC
Update Date2026-08-19 20:37:54 UTC
Accession NumberCHEM016596
Identification
Common NameBumetanide
ClassSmall Molecule
Description
Bumetanide is an organic compound with the formula C17H20N2O5S and an average molecular weight of 364.42 g/mol. Bumetanide belongs to the diphenylethers, a subclass of benzene and substituted derivatives within the organic compounds. It functions biologically as a diuretic (PMC8766311). The compound is recorded as being found in or released from 15 sources, including healthcare, pharmaceuticals & veterinary products such as gynecologicals and diuretics; food, food processing & cookware specifically for food preservation; household cleaning & consumer products including soap detergents, perfumes within detergents and soaps, cigar cigarettes, other smoking requisites, and non electric simulated smoking devices; and electrical & electronic equipment including antennas, conductors or conductive bodies characterised by the conductive materials, electrodes, electric hearing aids, and electrically stimulated smoking devices. Recorded exposure routes include oral, nasal, intravenous, and intramuscular administration. Bumetanide acts on five recorded protein targets, serving as an antagonist/inhibitor of the solute carrier family 12 member 1 (SLC12A1), solute carrier family 12 member 2 (SLC12A2), solute carrier family 12 member 4 (SLC12A4), and the cystic fibrosis transmembrane conductance regulator (CFTR), along with one other protein. Regarding health effects, the compound is associated with loss of appetite (PMC8766311) and has a therapeutic effect on epilepsy (PMC8766311).
Contaminant Type
  • Human Neurotoxin
Chemical Structure
Synonyms
ValueSource
3-(Aminosulfonyl)-5-(butylamino)-4-phenoxybenzoic acidChEBI
3-Butylamino-4-(phenoxy)-5-sulfamoylbenzoic acidChEBI
3-Butylamino-4-phenoxy-5-sulfamoyl-benzoic acidChEBI
3-Butylamino-4-phenoxy-5-sulfamoylbenzoic acidChEBI
BumetanidaChEBI
BumetanidumChEBI
BumexKegg
3-(Aminosulfonyl)-5-(butylamino)-4-phenoxybenzoateGenerator
3-(Aminosulphonyl)-5-(butylamino)-4-phenoxybenzoateGenerator
3-(Aminosulphonyl)-5-(butylamino)-4-phenoxybenzoic acidGenerator
3-Butylamino-4-(phenoxy)-5-sulfamoylbenzoateGenerator
3-Butylamino-4-(phenoxy)-5-sulphamoylbenzoateGenerator
3-Butylamino-4-(phenoxy)-5-sulphamoylbenzoic acidGenerator
3-Butylamino-4-phenoxy-5-sulfamoyl-benzoateGenerator
3-Butylamino-4-phenoxy-5-sulphamoyl-benzoateGenerator
3-Butylamino-4-phenoxy-5-sulphamoyl-benzoic acidGenerator
3-Butylamino-4-phenoxy-5-sulfamoylbenzoateGenerator
3-Butylamino-4-phenoxy-5-sulphamoylbenzoateGenerator
3-Butylamino-4-phenoxy-5-sulphamoylbenzoic acidGenerator
Atlantis brand OF bumetanideHMDB
BumedylHMDB
Bumetanide astrazeneca brandHMDB
BumethanideHMDB
FordiuranHMDB
Senosiain brand OF bumetanideHMDB
Bumetanide farmacusi brandHMDB
Bumetanide leo brandHMDB
Bumetanide atlantis brandHMDB
Bumetanide senosiain brandHMDB
DrenuralHMDB
Farmacusi brand OF bumetanideHMDB
Leo brand OF bumetanideHMDB
Roche brand OF bumetanideHMDB
AstraZeneca brand OF bumetanideHMDB
Bumetanide grossmann brandHMDB
Bumetanide roche brandHMDB
BurinexHMDB
Grossmann brand OF bumetanideHMDB
MiccilHMDB
Chemical FormulaC17H20N2O5S
Average Molecular Mass364.416 g/mol
Monoisotopic Mass364.109 g/mol
CAS Registry Number28395-03-1
IUPAC Name3-(butylamino)-4-phenoxy-5-sulfamoylbenzoic acid
Traditional Namebumetanide
SMILESCCCCNC1=C(OC2=CC=CC=C2)C(=CC(=C1)C(O)=O)S(N)(=O)=O
InChI IdentifierInChI=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)
InChI KeyMAEIEVLCKWDQJH-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as diphenylethers. These are aromatic compounds containing two benzene rings linked to each other through an ether group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassDiphenylethers
Direct ParentDiphenylethers
Alternative Parents
Substituents
  • Diphenylether
  • Aminobenzenesulfonamide
  • Diaryl ether
  • Aminobenzoic acid
  • Aminobenzoic acid or derivatives
  • Benzenesulfonamide
  • Benzoic acid or derivatives
  • Benzenesulfonyl group
  • Benzoic acid
  • Phenoxy compound
  • Benzoyl
  • Phenol ether
  • Aniline or substituted anilines
  • Phenylalkylamine
  • Secondary aliphatic/aromatic amine
  • Organosulfonic acid amide
  • Organosulfonic acid or derivatives
  • Organic sulfonic acid or derivatives
  • Aminosulfonyl compound
  • Sulfonyl
  • Amino acid
  • Amino acid or derivatives
  • Secondary amine
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organosulfur compound
  • Organic nitrogen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.026 g/LALOGPS
logP3.44ALOGPS
logP2.42ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)4.69ChemAxon
pKa (Strongest Basic)2.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area118.72 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity95.78 m³·mol⁻¹ChemAxon
Polarizability37.21 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-000w-7198000000-9c32fd3e7109756cbcbbNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-00dj-9034300000-5a798c87f87ef51b1527Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00lu-1694000000-dbf4d76ea1a12ee57935Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00lu-0594000000-78579410f8f6799b400bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0009000000-2a72173931dce5701622Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0119000000-4abf1963718d72f73f59Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-9351000000-b43658e112020008b9f9Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-9100000000-4d303174266311856c28Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-9000000000-2d120289f52c86515beaNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0009000000-97827d479a3470c40d42Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-015c-0396000000-5edaaa0fcc7cd3681c24Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000x-0980000000-0b360ca9bf4e58649db7Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-053s-0910000000-c5fc710abfdf5947bc62Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4j-0900000000-368c9661bc6dfd8a8d83Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000x-0291000000-134f42a8645c2f1b9bc5Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0009000000-e4d18d4c63310d0528dbNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000x-0390000000-abfea32acc207ff88b1fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-053r-0930000000-cc33040126bfe7cb08faNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a5a-0910000000-42b9627a1135073b6ce1Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0ars-0900000000-d22f5ff182cd71ced792Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00lu-0594000000-78579410f8f6799b400bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00lu-1694000000-dbf4d76ea1a12ee57935Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-053s-2920000000-ecd6db66d16ce8f483b8Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a5a-0910000000-72ae7a783a63a8ce732eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-053r-0920000000-0364ad9fda8b80cf0d02Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0ars-0900000000-d22f5ff182cd71ced792Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0ars-0900000000-b7842b9702685f387d87Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000x-0390000000-abfea32acc207ff88b1fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0009000000-e4d18d4c63310d0528dbNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-053r-0920000000-b294fafa0f5d5d0d6217Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a5a-0910000000-42b9627a1135073b6ce1Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-053r-0930000000-cc33040126bfe7cb08faNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-1009000000-09e85edf114cc804bbf1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0aor-5079000000-0fed70d52a46e216c387Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0r00-8490000000-249e2af61c2ace14276bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-4009000000-a4f63b404f4b2683d366Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0404-7479000000-109242300f7a6e750327Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01t9-9410000000-89f0a65fb708b0eac550Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0009000000-ded63bdc4b3d4467073bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0009000000-ec7654788555574d3910Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-08i0-2097000000-ff0861dea9a66a3fe5e3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0009000000-37cbefeac48e794b0b6aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01t9-9013000000-8f6db57778d09a5c4b7dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-002f-9141000000-b878ddcd942a742ef696Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
5314.0Log mg/kg[3000:9500]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
epilepsyhas_therapeutic_effect_onNot AvailablePMC8766311
loss of appetiteassociated_withNot AvailablePMC8766311
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
290DiureticsHealthcare, pharmaceuticals & veterinary productsNot Available
316GynecologicalsHealthcare, pharmaceuticals & veterinary productsNot Available
506AntennasElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
516Electric Hearing AidsElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
545Food PreservationFood, food processing & cookwareNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
583Anchoring EquipmentMarine, shipping & aquacultureNot Available
596AcaricidesAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
Pathways
4 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)15.492
Solute carrier family 12 member 2 structureClick to view 3D structureSolute carrier family 12 member 2P55011HumansPredicted (SEA)0.0778492
Click to view 3D structureSolute carrier family 22 member 6O35956Rattus norvegicusPredicted (SEA)0.0778492
Click to view 3D structureIntracellular chorismate mutaseP9WIC1Mycobacterium tuberculosisPredicted (SEA)0.155698
Secreted chorismate mutase structureClick to view 3D structureSecreted chorismate mutaseP9WIB9Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)Predicted (SEA)0.544945
Carbonic anhydrase 7 structureClick to view 3D structureCarbonic anhydrase 7P43166HumansPredicted (SEA)63.6028
Carbonic anhydrase 12 structureClick to view 3D structureCarbonic anhydrase 12O43570HumansPredicted (SEA)94.6646
Carbonic anhydrase 6 structureClick to view 3D structureCarbonic anhydrase 6P23280HumansPredicted (SEA)33.553
Carbonic anhydrase 14 structureClick to view 3D structureCarbonic anhydrase 14Q9ULX7HumansPredicted (SEA)45.6196
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansPredicted (SEA)113.738
Click to view 3D structureCarbonic anhydrase 5A, mitochondrialP35218HumansPredicted (SEA)47.0988
Carbonic anhydrase 13 structureClick to view 3D structureCarbonic anhydrase 13Q8N1Q1HumansPredicted (SEA)16.8933
Carbonic anhydrase 3 structureClick to view 3D structureCarbonic anhydrase 3P07451HumansPredicted (SEA)15.1806
Carbonic anhydrase 9 structureClick to view 3D structureCarbonic anhydrase 9Q16790HumansPredicted (SEA)156.01
Click to view 3D structureCarbonic anhydrase 5B, mitochondrialQ9Y2D0HumansPredicted (SEA)59.399
UDP-3-O-acyl-N-acetylglucosamine deacetylase structureClick to view 3D structureUDP-3-O-acyl-N-acetylglucosamine deacetylaseO67648Aquifex aeolicus (strain VF5)Predicted (SEA)22.4984
Click to view 3D structureAquaporin-4P47863Rattus norvegicusPredicted (SEA)2.41333
Cytochrome P450 2C9 structureClick to view 3D structureCytochrome P450 2C9P11712HumansPredicted (SEA)995.302
72 kDa type IV collagenase structureClick to view 3D structure72 kDa type IV collagenaseP08253HumansPredicted (SEA)346.974
Interstitial collagenase structureClick to view 3D structureInterstitial collagenaseP03956HumansPredicted (SEA)264.999
Collagenase 3 structureClick to view 3D structureCollagenase 3P45452HumansPredicted (SEA)264.142
Click to view 3D structureCyclic nucleotide-gated channel alpha-1Q00194Bos taurusPredicted (SEA)2.88042
Click to view 3D structureOrganic anion transporter 3O88909Mus musculusPredicted (SEA)8.48557
Click to view 3D structureAcidic phospholipase A2 CM-IP00602Naja mossambicaPredicted (SEA)16.1148
Beta-ketoacyl-[acyl-carrier-protein] synthase III structureClick to view 3D structureBeta-ketoacyl-[acyl-carrier-protein] synthase IIIQ820T1Enterococcus faecalis (strain ATCC 700802 / V583)Predicted (SEA)16.1926
Concentrations
Not Available
External Links
DrugBank IDDB00887
HMDB IDHMDB0015024
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkBumetanide
Chemspider ID2377
ChEBI ID3213
PubChem Compound ID2471
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=18374572
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=19454284
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=28166217
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=3989818