Furosemide (Frusemide) (CHEM016006)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-20 16:10:25 UTC
Update Date2016-10-28 10:03:38 UTC
Accession NumberCHEM016006
Identification
Common NameFurosemide (Frusemide)
ClassSmall Molecule
DescriptionFurosemide is a potent loop diuretic that acts on the kidneys to ultimately increase water loss from the body. It is an anthranilic acid derivative. Furosemide is used for edema secondary to various clinical conditions, such as congestive heart failure exacerbation, liver failure, renal failure, and high blood pressure. It mainly works by inhibiting electrolyte reabsorption from the kidneys and enhancing the excretion of water from the body. Furosemide has a fast onset and short duration of action and has been used safely and effectively in both pediatric and adult patients. The use of furosemide is particularly beneficial in clinical settings that require a drug with a higher diuretic potential. In addition to oral formulations, the solution for intravenous and intramuscular administration is also available, which is typically limited to patients who are unable to take oral medication or for patients in emergency clinical situations.
Contaminant Sources
  • FooDB Chemicals
  • IARC Carcinogens Group 3
  • STOFF IDENT Compounds
  • Suspected Compounds
  • Suspected Compounds - Waste Water
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
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
Chemical FormulaC12H11ClN2O5S
Average Molecular Mass330.744 g/mol
Monoisotopic Mass330.008 g/mol
CAS Registry Number54-31-9
IUPAC Name4-chloro-2-{[(furan-2-yl)methyl]amino}-5-sulfamoylbenzoic acid
Traditional Namefurosemide
SMILESNS(=O)(=O)C1=C(Cl)C=C(NCC2=CC=CO2)C(=C1)C(O)=O
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
Chemical Taxonomy
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.12 g/LALOGPS
logP2.71ALOGPS
logP1.75ChemAxon
logS-3.4ALOGPS
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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0gxa-6293000000-f457e26eb77dd682fe06Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0089-9005000000-e4a5fbc3253373e3940fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-03dr-0090000000-da505a3f09285d049f34Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-0f89-2190000000-53c91100e89c81f0fa30Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-01ox-9660000000-83d8486cbca0dd3487c9Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-000i-0090000000-f3a3dcb92cfcdff9f7dcSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-0019000000-946089b12d2ab6fd05a4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-000i-0090000000-04af1dec204d462d4bc4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-1090000000-1af70d23e1a0ebaa0878Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-9770000000-0c5cd578b5b69a1a61d4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-9800000000-3303b20f9b23e24ae312Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-9400000000-23cfec716ac8fbcb092fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-0019000000-e73aa1d969ab4255732bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-000i-0090000000-33053544119c01ac6b45Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-1090000000-7029ab63efa73a3ff88dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-9670000000-4bad8928bbcfc85f431fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-9800000000-2193e38e314f2b18be26Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-9600000000-e703f7ab6221182df156Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-000i-0090000000-f3645e993869ff3886baSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-000i-0090000000-18400153a811f7100a2fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0f79-0090000000-7e491b92dab050fb81c0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0029000000-8dad548395d661a23aebSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q0-0095000000-9350244c3603284fb554Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05o0-0290000000-6f3a7c51c8cbbf91e9a0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004r-1097000000-a65ddeb1624425b6a0b7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004r-4091000000-73474c5bbe697da9eb13Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9010000000-611ee6d1e47c2cd8a7d8Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB00695
HMDB IDHMDB0001933
FooDB IDFDB000956
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID2981
PDB IDNot Available
Wikipedia LinkFurosemide
Chemspider ID3322
ChEBI ID47426
PubChem Compound ID3440
Kegg Compound IDC07017
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Humke U, Siemer S, Uder M, Ziegler M: [Long-term outcome of conservative surgery for kidney cancer: survival, blood pressure, and renal function]. Ann Urol (Paris). 2002 Dec;36(6):349-53.
2. Schonfelder EM, Knuppel T, Tasic V, Miljkovic P, Konrad M, Wuhl E, Antignac C, Bakkaloglu A, Schaefer F, Weber S: Mutations in Uroplakin IIIA are a rare cause of renal hypodysplasia in humans. Am J Kidney Dis. 2006 Jun;47(6):1004-12.
3. Albqami N, Janetschek G: Laparoscopic partial nephrectomy. Curr Opin Urol. 2005 Sep;15(5):306-11.
4. Reyes L, Manalich R: Long-term consequences of low birth weight. Kidney Int Suppl. 2005 Aug;(97):S107-11.
5. Wilson FH, Disse-Nicodeme S, Choate KA, Ishikawa K, Nelson-Williams C, Desitter I, Gunel M, Milford DV, Lipkin GW, Achard JM, Feely MP, Dussol B, Berland Y, Unwin RJ, Mayan H, Simon DB, Farfel Z, Jeunemaitre X, Lifton RP: Human hypertension caused by mutations in WNK kinases. Science. 2001 Aug 10;293(5532):1107-12.
6. Delakas D, Karyotis I, Daskalopoulos G, Terhorst B, Lymberopoulos S, Cranidis A: Nephron-sparing surgery for localized renal cell carcinoma with a normal contralateral kidney: a European three-center experience. Urology. 2002 Dec;60(6):998-1002.
7. Moog R, Becmeur F, Dutson E, Chevalier-Kauffmann I, Sauvage P, Brunot B: Functional evaluation by quantitative dimercaptosuccinic Acid scintigraphy after kidney trauma in children. J Urol. 2003 Feb;169(2):641-4.
8. Korpi ER, Kuner T, Seeburg PH, Luddens H: Selective antagonist for the cerebellar granule cell-specific gamma-aminobutyric acid type A receptor. Mol Pharmacol. 1995 Feb;47(2):283-9.
9. Tia S, Wang JF, Kotchabhakdi N, Vicini S: Developmental changes of inhibitory synaptic currents in cerebellar granule neurons: role of GABA(A) receptor alpha 6 subunit. J Neurosci. 1996 Jun 1;16(11):3630-40.
10. Wafford KA, Thompson SA, Thomas D, Sikela J, Wilcox AS, Whiting PJ: Functional characterization of human gamma-aminobutyric acidA receptors containing the alpha 4 subunit. Mol Pharmacol. 1996 Sep;50(3):670-8.
11. Rais-Bahrami K, Majd M, Veszelovszky E, Short BL: Use of furosemide and hearing loss in neonatal intensive care survivors. Am J Perinatol. 2004 Aug;21(6):329-32.
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=15286542
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=18701232