Record Information
Version1.0
Creation date2010-04-08 22:04:46 UTC
Update date2015-10-09 22:31:19 UTC
Primary IDFDB000956
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameFrusemide
DescriptionPotential contaminant in cow's milk arising from its use in dairy cattle for the treatment of physiological parturient edema Additionally, furosemide is a noncompetitive subtype-specific blocker of GABA-A receptors. Furosemide has been reported to reversibly antagonize GABA-evoked currents of alpha6 beta2 gamma2 receptors at microM concentrations, but not alpha1 beta2 gamma2 receptors. During development, the alpha6 beta2 gamma2 receptor increases in expression in cerebellar granule neurons, corresponding to increased sensitivity to furosemide.; An antibiotic isolated from the fermentation broth of Fusidium coccineum. (From Merck Index, 11th ed) It acts by inhibiting translocation during protein synthesis.; Furosemide (INN) or frusemide (former BAN) is a loop diuretic used in the treatment of congestive heart failure and edema. It is most commonly marketed by Sanofi-Aventis under the brand name Lasix. It has also been used to prevent thoroughbred and standardbred race horses from bleeding through the nose during races.; Furosemide or frusemide is a loop diuretic used in the treatment of congestive heart failure and edema. It is most commonly marketed by Aventis Pharma under the brand name Lasix. It has also been used to prevent thoroughbred race horses from bleeding through the nose during races.; Furosemide, a sulfonamide-type loop diuretic structurally related to bumetanide, is used to manage hypertension and edema associated with congestive heart failure, cirrhosis, and renal disease, including the nephrotic syndrome.
CAS Number54-31-9
Structure
Thumb
Synonyms
SynonymSource
2-Furfurylamino-4-chloro-5-sulfamoylbenzoic acidChEBI
4-Chloro-5-sulfamoyl-N-furfuryl-anthranilic acidChEBI
4-Chloro-N-(2-furylmethyl)-5-sulfamoylanthranilic acidChEBI
4-Chloro-N-furfuryl-5-sulfamoylanthranilic acidChEBI
FrusemideChEBI
LasixChEBI
2-Furfurylamino-4-chloro-5-sulfamoylbenzoateGenerator
2-Furfurylamino-4-chloro-5-sulphamoylbenzoateGenerator
2-Furfurylamino-4-chloro-5-sulphamoylbenzoic acidGenerator
4-Chloro-5-sulfamoyl-N-furfuryl-anthranilateGenerator
4-Chloro-5-sulphamoyl-N-furfuryl-anthranilateGenerator
4-Chloro-5-sulphamoyl-N-furfuryl-anthranilic acidGenerator
4-Chloro-N-(2-furylmethyl)-5-sulfamoylanthranilateGenerator
4-Chloro-N-(2-furylmethyl)-5-sulphamoylanthranilateGenerator
4-Chloro-N-(2-furylmethyl)-5-sulphamoylanthranilic acidGenerator
4-Chloro-N-furfuryl-5-sulfamoylanthranilateGenerator
4-Chloro-N-furfuryl-5-sulphamoylanthranilateGenerator
4-Chloro-N-furfuryl-5-sulphamoylanthranilic acidGenerator
Acetic acid potassium saltHMDB
AisemideHMDB
AldalixHMDB
AldicHMDB
AluzineHMDB
AnfuramaideHMDB
Apo-frusemideHMDB
Apo-furosemideHMDB
AquaridHMDB
AquasinHMDB
ArasemideHMDB
BeronaldHMDB
BioreticHMDB
CetasixHMDB
DepixHMDB
DesalHMDB
DesdeminHMDB
DirineHMDB
DisalHMDB
DiscoidHMDB
DisemideHMDB
DiuralHMDB
DiurapidHMDB
Diuretic saltHMDB
DiurinHMDB
DiurolasaHMDB
DiusemideHMDB
DiusilHMDB
DiuzolHMDB
DranexHMDB
DryptalHMDB
DurafuridHMDB
EdemidHMDB
EdenolHMDB
EliurHMDB
EnduralHMDB
ErrolonHMDB
EutensinHMDB
FarsixHMDB
FluidrolHMDB
FlussHMDB
FranylHMDB
FrumexHMDB
FrumideHMDB
FrumilHMDB
FrusedanHMDB
FrusemaHMDB
FrusemidHMDB
FruseminHMDB
FrusenexHMDB
FruseticHMDB
FrusidHMDB
FulsixHMDB
FuluvamideHMDB
FuluvamineHMDB
FuranthrilHMDB
FuranthrylHMDB
FurantrilHMDB
FuranturilHMDB
FuresisHMDB
FureticHMDB
FurexHMDB
FurfanHMDB
FurixHMDB
FurmidHMDB
Furo-basanHMDB
Furo-purenHMDB
FurobetaHMDB
FurocotHMDB
FurodiurolHMDB
FurodrixHMDB
FuromenHMDB
FuromexHMDB
Furomide m.d.HMDB
FuroreseHMDB
FurosanHMDB
FuroseHMDB
FurosedonHMDB
FurosemidHMDB
FurosemidaHMDB
Furosemide "mita"HMDB
FurosemiduHMDB
FurosemidumHMDB
FurosemixHMDB
FurosideHMDB
FurosifarHMDB
FurosixHMDB
FuroterHMDB
FuroviteHMDB
FursemidHMDB
FursemidaHMDB
FursemideHMDB
FursolHMDB
FusidHMDB
Fusidic acidHMDB
GolanHMDB
HissufluxHMDB
HydrexHMDB
HydroHMDB
Hydro-rapidHMDB
HydroledHMDB
ImpuganHMDB
JenafusidHMDB
KatlexHMDB
KofuzonHMDB
KolkinHMDB
KutrixHMDB
LasemidHMDB
LasexHMDB
LasilettenHMDB
LasilixHMDB
Lasix retardHMDB
LaxurHMDB
LazixHMDB
Less diurHMDB
LisideHMDB
LogireneHMDB
LowpstonHMDB
LowpstronHMDB
LuscekHMDB
MacasiroolHMDB
MarsemideHMDB
MirfatHMDB
MitaHMDB
MoilarorinHMDB
NadisHMDB
NelsixHMDB
Neo-renalHMDB
NephronHMDB
NicorolHMDB
NovosemideHMDB
Octan draselnyHMDB
OdemaseHMDB
OdemexHMDB
OedemexHMDB
OsyrolHMDB
Polysquall aHMDB
PrefeminHMDB
ProfeminHMDB
PromedesHMDB
PromideHMDB
ProtargenHMDB
PuresisHMDB
RadisemideHMDB
RadonnaHMDB
RadounaHMDB
RetepHMDB
RosemideHMDB
RosisHMDB
RusydeHMDB
Sal diureticumHMDB
SalinexHMDB
SalixHMDB
SalurexHMDB
SaluridHMDB
SegurilHMDB
SelectofurHMDB
SigasalurHMDB
SpirofurHMDB
SynephronHMDB
TransitHMDB
TrofuritHMDB
UremideHMDB
UresixHMDB
UrexHMDB
Urex-mHMDB
UrianHMDB
UridonHMDB
UritolHMDB
UrosemideHMDB
VesixHMDB
YidoliHMDB
ZafimidaHMDB
FurantralHMDB
Furosemide monohydrochlorideHMDB
Salix (brand OF furosemide)HMDB
Furosemide monosodium saltHMDB
4-chloro-5-Sulfamoyl-N-furfuryl-anthranilateGenerator
4-chloro-5-Sulphamoyl-N-furfuryl-anthranilateGenerator
4-chloro-5-Sulphamoyl-N-furfuryl-anthranilic acidGenerator
4-chloro-N-(2-Furylmethyl)-5-sulfamoylanthranilateGenerator
4-chloro-N-(2-Furylmethyl)-5-sulphamoylanthranilateGenerator
4-chloro-N-(2-Furylmethyl)-5-sulphamoylanthranilic acidGenerator
4-chloro-N-Furfuryl-5-sulfamoylanthranilateGenerator
4-chloro-N-Furfuryl-5-sulphamoylanthranilateGenerator
4-chloro-N-Furfuryl-5-sulphamoylanthranilic acidGenerator
5-(Aminosulfonyl)-4-chloro-2-[2-(furanylmethyl)amino]benzoic acid, 9CIdb_source
Anthranilic acid, 4-chloro-N-furfuryl-5-sulfamoyl-biospider
Bio-furosemidebiospider
Dom-furosemidebiospider
Froopdb_source
Frumaxdb_source
Frusemide, BANdb_source
Frusoldb_source
Furosemide 40mgbiospider
Furosemide specialbiospider
Furosemide(usan)biospider
hydro-RapidHMDB
Lasix specialbiospider
MITAbiospider
PMS-furosemidebiospider
Tenkafrusedb_source
Predicted Properties
PropertyValueSource
Water Solubility0.12 g/LALOGPS
logP2.71ALOGPS
logP1.75ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)4.25ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area122.63 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity77.47 m³·mol⁻¹ChemAxon
Polarizability30.55 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC12H11ClN2O5S
IUPAC name4-chloro-2-{[(furan-2-yl)methyl]amino}-5-sulfamoylbenzoic acid
InChI IdentifierInChI=1S/C12H11ClN2O5S/c13-9-5-10(15-6-7-2-1-3-20-7)8(12(16)17)4-11(9)21(14,18)19/h1-5,15H,6H2,(H,16,17)(H2,14,18,19)
InChI KeyZZUFCTLCJUWOSV-UHFFFAOYSA-N
Isomeric SMILESNS(=O)(=O)C1=C(Cl)C=C(NCC2=CC=CO2)C(=C1)C(O)=O
Average Molecular Weight330.744
Monoisotopic Molecular Weight330.007719869
Classification
Description belongs to the class of organic compounds known as aminobenzenesulfonamides. These are organic compounds containing a benzenesulfonamide moiety with an amine group attached to the benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzenesulfonamides
Direct ParentAminobenzenesulfonamides
Alternative Parents
Substituents
  • Aminobenzenesulfonamide
  • 4-halobenzoic acid or derivatives
  • Aminobenzoic acid
  • Aminobenzoic acid or derivatives
  • Halobenzoic acid or derivatives
  • 4-halobenzoic acid
  • Halobenzoic acid
  • Benzenesulfonyl group
  • Benzoic acid
  • Benzoic acid or derivatives
  • Aniline or substituted anilines
  • Phenylalkylamine
  • Benzoyl
  • Aralkylamine
  • Secondary aliphatic/aromatic amine
  • Halobenzene
  • Chlorobenzene
  • Organosulfonic acid amide
  • Aryl chloride
  • Aryl halide
  • Furan
  • Heteroaromatic compound
  • Sulfonyl
  • Organosulfonic acid or derivatives
  • Organic sulfonic acid or derivatives
  • Aminosulfonyl compound
  • Vinylogous amide
  • Amino acid or derivatives
  • Amino acid
  • Oxacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organopnictogen compound
  • Organosulfur compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 43.58%; H 3.35%; Cl 10.72%; N 8.47%; O 24.19%; S 9.69%DFC
Melting PointMp 206°DFC
Boiling PointNot Available
Experimental Water Solubility0.0731 mg/mL at 30 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP2.03SANGSTER (1993)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0gxa-6293000000-f457e26eb77dd682fe06View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0089-9005000000-e4a5fbc3253373e3940fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-03dr-0090000000-da505a3f09285d049f34View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-0f89-2190000000-53c91100e89c81f0fa30View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-01ox-9660000000-83d8486cbca0dd3487c9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-000i-0090000000-f3a3dcb92cfcdff9f7dcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-0019000000-946089b12d2ab6fd05a4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-000i-0090000000-04af1dec204d462d4bc4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-1090000000-1af70d23e1a0ebaa0878View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-9770000000-0c5cd578b5b69a1a61d4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-9800000000-3303b20f9b23e24ae312View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-9400000000-23cfec716ac8fbcb092fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-0019000000-e73aa1d969ab4255732bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-000i-0090000000-33053544119c01ac6b45View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-1090000000-7029ab63efa73a3ff88dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-9670000000-4bad8928bbcfc85f431fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-9800000000-2193e38e314f2b18be26View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-9600000000-e703f7ab6221182df156View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-000i-0090000000-f3645e993869ff3886baView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-000i-0090000000-18400153a811f7100a2fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0f79-0090000000-7e491b92dab050fb81c0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0029000000-8dad548395d661a23aebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q0-0095000000-9350244c3603284fb554View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05o0-0290000000-6f3a7c51c8cbbf91e9a0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004r-1097000000-a65ddeb1624425b6a0b7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004r-4091000000-73474c5bbe697da9eb13View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9010000000-611ee6d1e47c2cd8a7d8View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID3322
ChEMBL IDCHEMBL35
KEGG Compound IDC07017
Pubchem Compound ID3440
Pubchem Substance IDNot Available
ChEBI ID5198
Phenol-Explorer IDNot Available
DrugBank IDDB00695
HMDB IDHMDB01933
CRC / DFC (Dictionary of Food Compounds) IDBNM41-Q:BNM41-Q
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDFUN
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDFurosemide
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
6-phosphogluconate dehydrogenase, decarboxylatingPGDP52209
Pathways
NameSMPDB LinkKEGG Link
Furosemide PathwaySMP00115 Not Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference