FUN

5-(AMINOSULFONYL)-4-CHLORO-2-[(2-FURYLMETHYL)AMINO]BENZOIC ACID

Created: 2005-09-13
Last modified:  2021-03-01

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Chemical Details

Formal Charge0
Atom Count32
Chiral Atom Count0
Bond Count33
Aromatic Bond Count11
2D diagram of FUN

Chemical Component Summary

Name5-(AMINOSULFONYL)-4-CHLORO-2-[(2-FURYLMETHYL)AMINO]BENZOIC ACID
SynonymsFurosemide
Systematic Name (OpenEye OEToolkits)4-chloro-2-(furan-2-ylmethylamino)-5-sulfamoyl-benzoic acid
FormulaC12 H11 Cl N2 O5 S
Molecular Weight330.744
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs12.01O=S(=O)(N)c1c(Cl)cc(c(C(=O)O)c1)NCc2occc2
SMILESCACTVS3.370N[S](=O)(=O)c1cc(C(O)=O)c(NCc2occc2)cc1Cl
SMILESOpenEye OEToolkits1.7.0c1cc(oc1)CNc2cc(c(cc2C(=O)O)S(=O)(=O)N)Cl
Canonical SMILESCACTVS3.370 N[S](=O)(=O)c1cc(C(O)=O)c(NCc2occc2)cc1Cl
Canonical SMILESOpenEye OEToolkits1.7.0 c1cc(oc1)CNc2cc(c(cc2C(=O)O)S(=O)(=O)N)Cl
InChIInChI1.03 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)
InChIKeyInChI1.03 ZZUFCTLCJUWOSV-UHFFFAOYSA-N

Drug Info: DrugBank

DrugBank IDDB00695 
NameFurosemide
Groups
  • approved
  • vet_approved
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.[L7958] Furosemide is used for edema secondary to various clinical conditions, such as congestive heart failure exacerbation, liver failure, renal failure, and high blood pressure.[L7961] 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.[A182495] 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.[L7958]
Synonyms
  • 4-Chloro-5-sulfamoyl-N-furfuryl-anthranilic acid
  • Furosemida
  • Furosemide sodium
  • 4-Chloro-N-(2-furylmethyl)-5-sulfamoylanthranilic acid
  • Frusemide
Brand Names
  • Lasix Special
  • Furosemide 40mg Tablets
  • Furosemide Injection, USP
  • Lasix Tab 80mg
  • Lasix
IndicationFurosemide is indicated for the treatment of edema associated with congestive heart failure, cirrhosis of the liver, and renal disease, including the nephrotic syndrome, in adults and pediatric patients.[L7958] Oral furosemide is indicated alone for the management of mild to moderate hypertension or severe hypertension in combination with other antihypertensive medications.[L9659] Intravenous furosemide is indicated as adjunctive therapy in acute pulmonary edema when a rapid onset of diuresis is desired.[L7958] Subcutaneous furosemide is indicated for the treatment of congestion due to fluid overload in adults with NYHA Class II/III chronic heart failure. This drug formulation is not indicated for emergency situations or in patients with acute pulmonary edema.[L43408]
Categories
  • Acids, Carbocyclic
  • Amides
  • Amines
  • Aminobenzoates
  • Aniline Compounds
ATC-Code
  • C03EB01
  • C03CA01
  • G01AE10
  • C03CB01
CAS number54-31-9

Drug Targets

NameTarget SequencePharmacological ActionActions
Solute carrier family 12 member 1MSLNNSSNVFLDSVPSNTNRFQVSVINENHESSAAADDNTDPPHYEETSF...unknowninhibitor
Carbonic anhydrase 2MSHHWGYGKHNGPEHWHKDFPIAKGERQSPVDIDTHTAKYDPSLKPLSVS...unknowninhibitor
G-protein coupled receptor 35MNGTYNTCGSSDLTWPPAIKLGFYAYLGVLLVLGLLLNSLALWVFCCRMQ...unknownagonist
6-phosphogluconate dehydrogenase, decarboxylatingMAQADIALIGLAVMGQNLILNMNDHGFVVCAFNRTVSKVDDFLANEAKGT...unknowninhibitor
UDP-glucuronosyltransferase 1-1MAVESQGGRPLVLGLLLCVLGPVVSHAGKILLIPVDGSHWLSMLGAIQQL...unknownsubstrate
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL35
PubChem 3440, 118985385
ChEMBL CHEMBL35
ChEBI CHEBI:47426
CCDC/CSD FURSEM03, XUDYED, TARPOU, BOKHAM02, BOKHAM01, LODFUH, YASGOQ03, BOKHUG, LOFLID, IWERUY, LOFLAV, BOKHIU, BOKJAO, BOKHAM, LODGAO, ESAWEC, YASGOQ04, BOKHEQ, YASGOQ02, YASGOQ01, TARPIO, VARGAZ, YASGOQ, TARPIO02, NOLBEY, ESAVIF, LODGAO02, FURSEM18, FURSEM16, FURSEM17, FURSEM14, FEFYIA, BOKHOA, LUTBOU, NOLBIC, FURSEM13, FURSEM01, ESAWAY, FEFYAS, ESAWIG, FEFYEW, XIFRAH, BUQTEP, SARQUB, SARQOV
COD 4509860, 4509862, 4509913, 4509914, 4509915, 4502989, 4502992, 4502990, 4502991, 7119123, 7218156, 7218157, 7218158, 1551859, 1551858, 1551860