Showing Compound Frusemide (FDB000956)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:46 UTC

Update date

2015-10-09 22:31:19 UTC

Primary ID

FDB000956

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Frusemide

Description

Potential 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 Number

54-31-9

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
2-Furfurylamino-4-chloro-5-sulfamoylbenzoic acid	ChEBI
4-Chloro-5-sulfamoyl-N-furfuryl-anthranilic acid	ChEBI
4-Chloro-N-(2-furylmethyl)-5-sulfamoylanthranilic acid	ChEBI
4-Chloro-N-furfuryl-5-sulfamoylanthranilic acid	ChEBI
Frusemide	ChEBI
Lasix	ChEBI
2-Furfurylamino-4-chloro-5-sulfamoylbenzoate	Generator
2-Furfurylamino-4-chloro-5-sulphamoylbenzoate	Generator
2-Furfurylamino-4-chloro-5-sulphamoylbenzoic acid	Generator
4-Chloro-5-sulfamoyl-N-furfuryl-anthranilate	Generator
4-Chloro-5-sulphamoyl-N-furfuryl-anthranilate	Generator
4-Chloro-5-sulphamoyl-N-furfuryl-anthranilic acid	Generator
4-Chloro-N-(2-furylmethyl)-5-sulfamoylanthranilate	Generator
4-Chloro-N-(2-furylmethyl)-5-sulphamoylanthranilate	Generator
4-Chloro-N-(2-furylmethyl)-5-sulphamoylanthranilic acid	Generator
4-Chloro-N-furfuryl-5-sulfamoylanthranilate	Generator
4-Chloro-N-furfuryl-5-sulphamoylanthranilate	Generator
4-Chloro-N-furfuryl-5-sulphamoylanthranilic acid	Generator
Acetic acid potassium salt	HMDB
Aisemide	HMDB
Aldalix	HMDB
Aldic	HMDB
Aluzine	HMDB
Anfuramaide	HMDB
Apo-frusemide	HMDB
Apo-furosemide	HMDB
Aquarid	HMDB
Aquasin	HMDB
Arasemide	HMDB
Beronald	HMDB
Bioretic	HMDB
Cetasix	HMDB
Depix	HMDB
Desal	HMDB
Desdemin	HMDB
Dirine	HMDB
Disal	HMDB
Discoid	HMDB
Disemide	HMDB
Diural	HMDB
Diurapid	HMDB
Diuretic salt	HMDB
Diurin	HMDB
Diurolasa	HMDB
Diusemide	HMDB
Diusil	HMDB
Diuzol	HMDB
Dranex	HMDB
Dryptal	HMDB
Durafurid	HMDB
Edemid	HMDB
Edenol	HMDB
Eliur	HMDB
Endural	HMDB
Errolon	HMDB
Eutensin	HMDB
Farsix	HMDB
Fluidrol	HMDB
Fluss	HMDB
Franyl	HMDB
Frumex	HMDB
Frumide	HMDB
Frumil	HMDB
Frusedan	HMDB
Frusema	HMDB
Frusemid	HMDB
Frusemin	HMDB
Frusenex	HMDB
Frusetic	HMDB
Frusid	HMDB
Fulsix	HMDB
Fuluvamide	HMDB
Fuluvamine	HMDB
Furanthril	HMDB
Furanthryl	HMDB
Furantril	HMDB
Furanturil	HMDB
Furesis	HMDB
Furetic	HMDB
Furex	HMDB
Furfan	HMDB
Furix	HMDB
Furmid	HMDB
Furo-basan	HMDB
Furo-puren	HMDB
Furobeta	HMDB
Furocot	HMDB
Furodiurol	HMDB
Furodrix	HMDB
Furomen	HMDB
Furomex	HMDB
Furomide m.d.	HMDB
Furorese	HMDB
Furosan	HMDB
Furose	HMDB
Furosedon	HMDB
Furosemid	HMDB
Furosemida	HMDB
Furosemide "mita"	HMDB
Furosemidu	HMDB
Furosemidum	HMDB
Furosemix	HMDB
Furoside	HMDB
Furosifar	HMDB
Furosix	HMDB
Furoter	HMDB
Furovite	HMDB
Fursemid	HMDB
Fursemida	HMDB
Fursemide	HMDB
Fursol	HMDB
Fusid	HMDB
Fusidic acid	HMDB
Golan	HMDB
Hissuflux	HMDB
Hydrex	HMDB
Hydro	HMDB
Hydro-rapid	HMDB
Hydroled	HMDB
Impugan	HMDB
Jenafusid	HMDB
Katlex	HMDB
Kofuzon	HMDB
Kolkin	HMDB
Kutrix	HMDB
Lasemid	HMDB
Lasex	HMDB
Lasiletten	HMDB
Lasilix	HMDB
Lasix retard	HMDB
Laxur	HMDB
Lazix	HMDB
Less diur	HMDB
Liside	HMDB
Logirene	HMDB
Lowpston	HMDB
Lowpstron	HMDB
Luscek	HMDB
Macasirool	HMDB
Marsemide	HMDB
Mirfat	HMDB
Mita	HMDB
Moilarorin	HMDB
Nadis	HMDB
Nelsix	HMDB
Neo-renal	HMDB
Nephron	HMDB
Nicorol	HMDB
Novosemide	HMDB
Octan draselny	HMDB
Odemase	HMDB
Odemex	HMDB
Oedemex	HMDB
Osyrol	HMDB
Polysquall a	HMDB
Prefemin	HMDB
Profemin	HMDB
Promedes	HMDB
Promide	HMDB
Protargen	HMDB
Puresis	HMDB
Radisemide	HMDB
Radonna	HMDB
Radouna	HMDB
Retep	HMDB
Rosemide	HMDB
Rosis	HMDB
Rusyde	HMDB
Sal diureticum	HMDB
Salinex	HMDB
Salix	HMDB
Salurex	HMDB
Salurid	HMDB
Seguril	HMDB
Selectofur	HMDB
Sigasalur	HMDB
Spirofur	HMDB
Synephron	HMDB
Transit	HMDB
Trofurit	HMDB
Uremide	HMDB
Uresix	HMDB
Urex	HMDB
Urex-m	HMDB
Urian	HMDB
Uridon	HMDB
Uritol	HMDB
Urosemide	HMDB
Vesix	HMDB
Yidoli	HMDB
Zafimida	HMDB
Furantral	HMDB
Furosemide monohydrochloride	HMDB
Salix (brand OF furosemide)	HMDB
Furosemide monosodium salt	HMDB
4-chloro-5-Sulfamoyl-N-furfuryl-anthranilate	Generator
4-chloro-5-Sulphamoyl-N-furfuryl-anthranilate	Generator
4-chloro-5-Sulphamoyl-N-furfuryl-anthranilic acid	Generator
4-chloro-N-(2-Furylmethyl)-5-sulfamoylanthranilate	Generator
4-chloro-N-(2-Furylmethyl)-5-sulphamoylanthranilate	Generator
4-chloro-N-(2-Furylmethyl)-5-sulphamoylanthranilic acid	Generator
4-chloro-N-Furfuryl-5-sulfamoylanthranilate	Generator
4-chloro-N-Furfuryl-5-sulphamoylanthranilate	Generator
4-chloro-N-Furfuryl-5-sulphamoylanthranilic acid	Generator
5-(Aminosulfonyl)-4-chloro-2-[2-(furanylmethyl)amino]benzoic acid, 9CI	db_source
Anthranilic acid, 4-chloro-N-furfuryl-5-sulfamoyl-	biospider
Bio-furosemide	biospider
Dom-furosemide	biospider
Froop	db_source
Frumax	db_source
Frusemide, BAN	db_source
Frusol	db_source
Furosemide 40mg	biospider
Furosemide special	biospider
Furosemide(usan)	biospider
hydro-Rapid	HMDB
Lasix special	biospider
MITA	biospider
PMS-furosemide	biospider
Tenkafruse	db_source

Predicted Properties

Property	Value	Source
Water Solubility	0.12 g/L	ALOGPS
logP	2.71	ALOGPS
logP	1.75	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	4.25	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	122.63 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	77.47 m³·mol⁻¹	ChemAxon
Polarizability	30.55 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C12H11ClN2O5S

IUPAC name

4-chloro-2-{[(furan-2-yl)methyl]amino}-5-sulfamoylbenzoic acid

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 Key

ZZUFCTLCJUWOSV-UHFFFAOYSA-N

Isomeric SMILES

NS(=O)(=O)C1=C(Cl)C=C(NCC2=CC=CO2)C(=C1)C(O)=O

Average Molecular Weight

330.744

Monoisotopic Molecular Weight

330.007719869

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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzenesulfonamides

Direct Parent

Aminobenzenesulfonamides

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 Framework

Aromatic heteromonocyclic compounds

External Descriptors

sulfonamide (CHEBI:47426 )
furans (CHEBI:47426 )
chlorobenzoic acid (CHEBI:47426 )

Ontology

Disposition

Biological location:

Organ and components:

Kidney

Role

Industrial application:

Drug

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 43.58%; H 3.35%; Cl 10.72%; N 8.47%; O 24.19%; S 9.69%	DFC
Melting Point	Mp 206°	DFC
Boiling Point	Not Available
Experimental Water Solubility	0.0731 mg/mL at 30 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP	2.03	SANGSTER (1993)
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Frusemide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0gxa-6293000000-f457e26eb77dd682fe06	Spectrum
Predicted GC-MS	Frusemide, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0089-9005000000-e4a5fbc3253373e3940f	Spectrum
Predicted GC-MS	Frusemide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)	splash10-03dr-0090000000-da505a3f09285d049f34	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)	splash10-0f89-2190000000-53c91100e89c81f0fa30	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)	splash10-01ox-9660000000-83d8486cbca0dd3487c9	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-000i-0090000000-f3a3dcb92cfcdff9f7dc	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-004i-0019000000-946089b12d2ab6fd05a4	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-000i-0090000000-04af1dec204d462d4bc4	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0udi-1090000000-1af70d23e1a0ebaa0878	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-004i-9770000000-0c5cd578b5b69a1a61d4	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-004i-9800000000-3303b20f9b23e24ae312	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-004i-9400000000-23cfec716ac8fbcb092f	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-004i-0019000000-e73aa1d969ab4255732b	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-000i-0090000000-33053544119c01ac6b45	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0udi-1090000000-7029ab63efa73a3ff88d	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-004i-9670000000-4bad8928bbcfc85f431f	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-004i-9800000000-2193e38e314f2b18be26	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-004i-9600000000-e703f7ab6221182df156	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-000i-0090000000-f3645e993869ff3886ba	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-000i-0090000000-18400153a811f7100a2f	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0f79-0090000000-7e491b92dab050fb81c0	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0029000000-8dad548395d661a23aeb	2017-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01q0-0095000000-9350244c3603284fb554	2017-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05o0-0290000000-6f3a7c51c8cbbf91e9a0	2017-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004r-1097000000-a65ddeb1624425b6a0b7	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004r-4091000000-73474c5bbe697da9eb13	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9010000000-611ee6d1e47c2cd8a7d8	2017-07-26	View Spectrum

NMR

Type	Description		View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)		Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)		Spectrum