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Record Information
Version3.6
Creation Date2006-05-18 08:52:05 UTC
Update Date2016-02-11 01:05:07 UTC
HMDB IDHMDB01933
Secondary Accession NumbersNone
Metabolite Identification
Common NameFurosemide
DescriptionFurosemide 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. An antibiotic isolated from the fermentation broth of Fusidium coccineum. (From Merck Index, 11th ed) It acts by inhibiting translocation during protein synthesis.
Structure
Thumb
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
Chemical FormulaC12H11ClN2O5S
Average Molecular Weight330.744
Monoisotopic Molecular Weight330.007719869
IUPAC Name4-chloro-2-[(furan-2-ylmethyl)amino]-5-sulfamoylbenzoic acid
Traditional Namefurosemide
CAS Registry Number54-31-9
SMILES
NS(=O)(=O)C1=C(Cl)C=C(NCC2=CC=CO2)C(=C1)C(O)=O
InChI Identifier
InChI=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 KeyInChIKey=ZZUFCTLCJUWOSV-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Halobenzoic acid
  • 4-halobenzoic acid
  • 4-halobenzoic acid or derivatives
  • Aminobenzoic acid or derivatives
  • Aminobenzoic acid
  • Benzoic acid
  • Benzoic acid or derivatives
  • Phenylalkylamine
  • Substituted aniline
  • Benzoyl
  • Aralkylamine
  • Secondary aliphatic/aromatic amine
  • Halobenzene
  • Chlorobenzene
  • Aniline
  • Aryl halide
  • Aryl chloride
  • Heteroaromatic compound
  • Vinylogous amide
  • Aminosulfonyl compound
  • Sulfonyl
  • Sulfonic acid derivative
  • Sulfonamide
  • Furan
  • Oxacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Protein component
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point295 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0731 mg/mL at 30 °CNot Available
LogP2.03SANGSTER (1993)
Predicted Properties
PropertyValueSource
Water Solubility0.12 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity77.47 m3·mol-1ChemAxon
Polarizability30.55 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
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
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue Location
  • Kidney
Pathways
NameSMPDB LinkKEGG Link
Furosemide PathwaySMP00115Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00695
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB000956
KNApSAcK IDNot Available
Chemspider ID3322
KEGG Compound IDC07017
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkFurosemide
NuGOwiki LinkHMDB01933
Metagene LinkHMDB01933
METLIN ID2981
PubChem Compound3440
PDB IDFUN
ChEBI ID5198
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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. [11498583 ]
  2. 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. [12611132 ]
  3. 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. [16731295 ]
  4. Albqami N, Janetschek G: Laparoscopic partial nephrectomy. Curr Opin Urol. 2005 Sep;15(5):306-11. [16093853 ]
  5. Reyes L, Manalich R: Long-term consequences of low birth weight. Kidney Int Suppl. 2005 Aug;(97):S107-11. [16014086 ]
  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. [12475657 ]
  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. [12544333 ]
  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. [7870036 ]
  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. [8642407 ]
  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. [8794909 ]
  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. [15311369 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative decarboxylation of 6-phosphogluconate to ribulose 5-phosphate and CO(2), with concomitant reduction of NADP to NADPH (By similarity).
Gene Name:
PGD
Uniprot ID:
P52209
Molecular weight:
53139.56
References
  1. Akkemik E, Budak H, Ciftci M: Effects of some drugs on human erythrocyte 6-phosphogluconate dehydrogenase: an in vitro study. J Enzyme Inhib Med Chem. 2010 Aug;25(4):476-9. [20235752 ]
  2. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [10592235 ]
General function:
Involved in ATP binding
Specific function:
This is the catalytic component of the active enzyme, which catalyzes the hydrolysis of ATP coupled with the exchange of sodium and potassium ions across the plasma membrane. This action creates the electrochemical gradient of sodium and potassium ions, providing the energy for active transport of various nutrients.
Gene Name:
ATP1A1
Uniprot ID:
P05023
Molecular weight:
112895.01
General function:
Involved in carbonate dehydratase activity
Specific function:
Essential for bone resorption and osteoclast differentiation (By similarity). Reversible hydration of carbon dioxide. Can hydrate cyanamide to urea. Involved in the regulation of fluid secretion into the anterior chamber of the eye.
Gene Name:
CA2
Uniprot ID:
P00918
Molecular weight:
29245.895
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [10592235 ]

Transporters

General function:
Involved in ion transmembrane transporter activity
Specific function:
Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Also relative uptake activity ratio of carnitine to TEA is 11.3
Gene Name:
SLC22A5
Uniprot ID:
O76082
Molecular weight:
62751.1
References
  1. Ohashi R, Tamai I, Yabuuchi H, Nezu JI, Oku A, Sai Y, Shimane M, Tsuji A: Na(+)-dependent carnitine transport by organic cation transporter (OCTN2): its pharmacological and toxicological relevance. J Pharmacol Exp Ther. 1999 Nov;291(2):778-84. [10525100 ]
General function:
Involved in ATP binding
Specific function:
Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter
Gene Name:
ABCC2
Uniprot ID:
Q92887
Molecular weight:
174205.6
References
  1. Bakos E, Evers R, Sinko E, Varadi A, Borst P, Sarkadi B: Interactions of the human multidrug resistance proteins MRP1 and MRP2 with organic anions. Mol Pharmacol. 2000 Apr;57(4):760-8. [10727523 ]
General function:
Involved in transporter activity
Specific function:
Mediates saturable uptake of estrone sulfate, dehydroepiandrosterone sulfate and related compounds
Gene Name:
SLC22A11
Uniprot ID:
Q9NSA0
Molecular weight:
59970.9
References
  1. Cha SH, Sekine T, Kusuhara H, Yu E, Kim JY, Kim DK, Sugiyama Y, Kanai Y, Endou H: Molecular cloning and characterization of multispecific organic anion transporter 4 expressed in the placenta. J Biol Chem. 2000 Feb 11;275(6):4507-12. [10660625 ]
General function:
Involved in transport
Specific function:
Mediates electroneutral potassium-chloride cotransport in mature neurons. Transport occurs under isotonic conditions, but is activated 20-fold by cell swelling. Important for Cl(-) homeostasis in neurons
Gene Name:
SLC12A5
Uniprot ID:
Q9H2X9
Molecular weight:
126182.5
General function:
Involved in transport
Specific function:
Electrically silent transporter system. Mediates sodium and chloride reabsorption. Plays a vital role in the regulation of ionic balance and cell volume
Gene Name:
SLC12A1
Uniprot ID:
Q13621
Molecular weight:
121449.1
References
  1. Brater DC: Pharmacology of diuretics. Am J Med Sci. 2000 Jan;319(1):38-50. [10653443 ]
  2. Davies DL, Wilson GM: Diuretics: mechanism of action and clinical application. Drugs. 1975;9(3):178-226. [1092541 ]
  3. Vormfelde SV, Sehrt D, Toliat MR, Schirmer M, Meineke I, Tzvetkov M, Nurnberg P, Brockmoller J: Genetic variation in the renal sodium transporters NKCC2, NCC, and ENaC in relation to the effects of loop diuretic drugs. Clin Pharmacol Ther. 2007 Sep;82(3):300-9. Epub 2007 Apr 25. [17460608 ]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [11752352 ]
General function:
Not Available
Specific function:
May mediate the release of newly synthesized prostaglandins from cells, the transepithelial transport of prostaglandins, and the clearance of prostaglandins from the circulation. Transports PGD2, as well as PGE1, PGE2 and PGF2A
Gene Name:
SLCO2A1
Uniprot ID:
Q92959
Molecular weight:
70117.0
References
  1. Kanai N, Lu R, Satriano JA, Bao Y, Wolkoff AW, Schuster VL: Identification and characterization of a prostaglandin transporter. Science. 1995 May 12;268(5212):866-9. [7754369 ]
General function:
Involved in ion transmembrane transporter activity
Specific function:
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS). Mediates the sodium-independent uptake of p- aminohippurate (PAH), ochratoxin (OTA), acyclovir (ACV), 3'-azido- 3-'deoxythymidine (AZT), cimetidine (CMD), 2,4-dichloro- phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS) and 3-carboxy-4-methyl-5-propyl-2- furanpropionate (CMPF), cidofovir, adefovir, 9-(2- phosphonylmethoxyethyl) guanine (PMEG), 9-(2- phosphonylmethoxyethyl) diaminopurine (PMEDAP) and edaravone sulfate. PAH uptake is inhibited by p- chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), sulindac, diclofenac, carprofen, glutarate and okadaic acid. PAH uptake is inhibited by benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, furosemide, indomethacin, bumetamide, losartan, probenecid, phenol red, urate, and alpha-ketoglutarate
Gene Name:
SLC22A6
Uniprot ID:
Q4U2R8
Molecular weight:
61815.8
References
  1. Kim GH, Na KY, Kim SY, Joo KW, Oh YK, Chae SW, Endou H, Han JS: Up-regulation of organic anion transporter 1 protein is induced by chronic furosemide or hydrochlorothiazide infusion in rat kidney. Nephrol Dial Transplant. 2003 Aug;18(8):1505-11. [12897087 ]
  2. Hosoyamada M, Sekine T, Kanai Y, Endou H: Molecular cloning and functional expression of a multispecific organic anion transporter from human kidney. Am J Physiol. 1999 Jan;276(1 Pt 2):F122-8. [9887087 ]
  3. Lu R, Chan BS, Schuster VL: Cloning of the human kidney PAH transporter: narrow substrate specificity and regulation by protein kinase C. Am J Physiol. 1999 Feb;276(2 Pt 2):F295-303. [9950961 ]
  4. Uwai Y, Saito H, Hashimoto Y, Inui KI: Interaction and transport of thiazide diuretics, loop diuretics, and acetazolamide via rat renal organic anion transporter rOAT1. J Pharmacol Exp Ther. 2000 Oct;295(1):261-5. [10991988 ]