CAS 54-31-9|4-chloro-2-[(furan-2-ylmethyl)amino]-5-sulfamoylbenzoic acid|furosemide|5-(AMINOSULFONYL)-4-CHLORO-2-[(2-FURYLMETHYL)AMINO]BENZOIC ACID|5-(Aminosulphonyl)-4-chloro-2-[(2-furanylmethyl)am...

General Information

Structure

Molecular Formula

C₁₂H₁₁ClN₂O₅S

Molecular Mass

330.74414

Exact Mass

330.00772014

Charge

InChI

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)

InChIKey

ZZUFCTLCJUWOSV-UHFFFAOYSA-N

Canonic Smiles

OC(=O)c1cc(c(cc1NCc1ccco1)Cl)S(=O)(=O)N

Isomeric Smiles

Clc1c(S(=O)(=O)N)cc(c(NCc2occc2)c1)C(=O)O

Calculated Properties

JChem

Acid pKa

4.251508

H Acceptors

H Donor

LogD (pH = 5.5)

0.47831637

LogD (pH = 7.4)

-1.250643

Log P

1.748402

Molar Refractivity

77.4742

Polarizability

29.503298

Polar Surface Area

122.63

Rotatable Bonds

Lipinski's Rule of Five

true

ALOGPS 2.1

Log P

2.71

LOG S

-3.45

Solubility (Water)

1.18e-01 g/l

Data Source

Names and Identifiers

IUPAC name

4-chloro-2-[(furan-2-ylmethyl)amino]-5-sulfamoylbenzoic acid

IUPAC Traditional name

furosemide 4-chloro-2-[(furan-2-ylmethyl)amino]-5-sulfamoylbenzoic acid

Synonyms

5-(AMINOSULFONYL)-4-CHLORO-2-[(2-FURYLMETHYL)AMINO]BENZOIC ACID5-(Aminosulphonyl)-4-chloro-2-[(2-furanylmethyl)amino]benzoic acidFurosemide5-[Aminosulfonyl]-4-chloro-2-[(2-furanylmethyl)-amino]benzoic acid4-Chloro-N-furfuryl-5-sulfamoylanthranilic acidFurosemideMethforylthiazidineFurosemida [INN-Spanish]FrusemidDihydroflumethiazideFurosemidFursemideMetflorylthiazidineFurosemidum [INN-Latin]FursemidFrusemideFurosemidu [Polish]FursemidaLasix呋塞米5-(氨基磺酰基)-4-氯-2-([2-呋喃甲基]氨基)苯甲酸FurosemideFurosemide(Lasix)4-氯-N-呋喃基-5-氨磺酰邻氨基苯甲酸4-chloro-2-((furan-2-ylmethyl)amino)-5-sulfamoylbenzoic acid5-(Aminosulfonyl)-4-chloro-2-([2-furanylmethyl]amino)benzoic acidFrusidFrusemideFrusolTenkafruseFrumaxDryptalDiurapidRusydeFroopPromedesRadonnaDisemidePromideDiscoidDiuralRadisemide5-(Aminosulfonyl)-4-chloro-2-[(2-furanyl-methyl)amino]benzoic Acid2-Furfurylamino-4-chloro-5-sulfamoylbenzoic Acid4-Chloro-N-(2-furylmethyl)-5-sulfamoylanthranilic AcidZafuridaDisal

Brand Name

SalurexTransitRadonnaSelectofurNadisPrefeminHydroledLazixRadounaRodiuranAquasinCetasixVesixFursolFurixFurosemixUrexRusydeAquaridSegurilRadisemideSalinexFuroterFuroviteKutrixLasilixFuranturilPromedesSynephronFusidHydrenoxFuromide M.D.RosemideMirfatHissufluxHydrexSisurilSalixMacasiroolMyrosemideZafimidaMarsemideNovosemideFurosifarSal DiureticumLogireneNeo-RenalFurosanFuro-BasanLowpstronLuscekLaxurBristurinUresixUrianProfeminSaluridJenafusidYidoliSpirofurLasemidTrofuritOdemaseImpuganLasix RetardLisideHydroPolysquall ALasilettenLowpstonFurosixUrex-MVergonilDesalDi-AdemilUrosemideNelsixPromidePuresisUremideProtargenOctan DraselnyKolkinLess DiurSigasalurUritolUridonHydro-RapidFuroreseFurosideLasexGolanHydolSaluronFurantrilDisalArasemideAisemideApo-FurosemideDisemideFruseticFrumexFinuretDiscoidFurobetaDurafuridEnduralFurexDiurolasaFurodrixFuroseFuranthrilDiuretic SaltOedemexLasix SpecialEdenolFuro-PurenFlussFarsixEutensinRosisFrusedanFruseminDiurapidEdemidAldicAluzineBeronaldKofuzonFuranthrylFuresisFurfanBioreticMoilarorinFureticAnfuramaideFrusemaDiusilFrusidMitaDiurinFurosedonDryptalEliurDiuralOdemexFulsixElodrineKatlexFrumilFrusenexBristabFuromexFuluvamideApo-FrusemideLeodrineFranylDiusemideAldalixDepixFurmidErrolonDiumide-KOlmagranRetepRontylFluidrolFurocotFrumideDirineDiuzolDranexDesdeminDiucardinLasixFuromenFurodiurolFuluvamine

Names and Identifiers

Registration numbers

PubChem SID

4650677916096404024277714

CAS Number

PubChem CID

EC Number

MDL Number

CHEMBL

Chemspider ID

CHEBI ID

DailyMed ID

KEGG ID

Wikipedia Title

ATC CODE

Unique Ingredient Identifier

7LXU5N7ZO5

DrugBank ID

DB00695

Registration numbers

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

DrugBank

DB00695

Drug Groups

approved

Description

A benzoic-sulfonamide-furan. It is a diuretic with fast onset and short duration that is used for edema and chronic renal insufficiency. [PubChem]

Indication

For the treatment of edema associated with congestive heart failure, cirrhosis of the liver, and renal disease, including the nephrotic syndrome. Also for the treatment of hypertension alone or in combination with other antihypertensive agents.

Pharmacology

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.

Toxicity

Profound diuresis may cause fluid and electrolyte depletion. Excessive dehydration and potassium depletion may occur. Excessive diuresis may cause rapid weight loss, orthostatic hypotension or acute hypotensive episodes. May also cause tinnitus, reversible or permanent hearing loss or reversible deafness.

Affected Organisms

Humans and other mammals

Biotransformation

Only a small amount is hepatically metabolized to the defurfurylated derivative, 4-chloro-5-sulfamoylanthranilic acid.

Absorption

60% absorbed in patients with normal renal function

Half Life

2 hours

Protein Binding

95% bound to plasma proteins

Elimination

Furosemide is excreted in urine. Significantly more furosemide is excreted in urine following the I.V. injection than after the tablet or oral solution.

References

• 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. [Pubmed]

• 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. [Pubmed]

• 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. [Pubmed]

• 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. [Pubmed]

External Links

• [Wikipedia]

• [RxList]

• [Drugs.com]

DB07799

Drug information: experimental

Selleck Chemicals

S1603

Research Area: Cardiovascular Disease
Biological Activity:
Furosemide(Lasix) is a loop diuretic used in the treatment of congestive heart failure and edema. Furosemide acts by inhibiting the Na-K-2Cl symporter in the thick ascending limb of the loop of Henle. The action on the distal tubules is independent of any inhibitory effect on carbonic anhydrase or aldosterone; it also abolishes the corticomedullary osmotic gradient and blocks negative as well as positive free water clearance. [1]

Crystalline

F4381

Biochem/physiol Actions
抑制肾脏中离子的协同运输。
"High ceiling" diuretic that strongly affects renal tubular action by increasing renal blood flow; antihypertensive.

257753

Biochem/physiol Actions
Inhibits ion co-transport in the kidney.

09205

Biochem/physiol Actions
Inhibits ion co-transport in the kidney.

TRC

F865000

Furosemide inhibits ion co-transport in the kidney. Furosemide is used as a diuretic.

Molecule Details

References

PubChem Literature

From Data Sources

• 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. Pubmed

• 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. Pubmed

• http://en.wikipedia.org/wiki/Furosemide

• Benet, L.Z.: J. Pharmacokinet. Biopharm., 7, 1 (1979)

• Goldenthal, E.I.: Toxicol. Appl. Pharmacol., 18, 185 (1971)

• Brater, D.C., Annu. Rev. Pharmacol. Toxicol., 1983, 23, 45, (rev, pharmacol)

• Al-Obaid, A.M. et al., Anal. Profiles Drug Subst., 1989, 18, 153, (rev)

• Ponto, L.L.B. et al., Clin. Pharmacokinet., 1990, 18, 460, (rev, pharmacol)

• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 871

• Prandota, J. et al., Eur. J. Drug Metab. Pharmacokinet., 1976, 1, 177, (rev, metab)

• Lamotte, J. et al., Acta Cryst. B, 1978, 34, 1657, (cryst struct)

• Negwer, M., Organic-Chemical Drugs and their Synonyms, 7th edn., Akademie-Verlag, 1994, 2766, (synonyms)

• Du Souich, P. et al., Prog. Pharmacol. Clin. Pharmacol., 1992, 9, 147, (rev)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, CHJ750

• Sturm, K. et al., Chem. Ber., 1966, 99, 328; 345, (synth, props)

• IARC Monog., 1990, 50, 277, (rev, tox)

• Stanker, L.H. et al., J. Agric. Food Chem., 1996, 44, 2455-2459, (occur)

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 41C, (nmr)

• Rupp, W. et al., Arch. Int. Pharmacodyn. Ther., Suppl., 1980, 119, (rev, pharmacol)

• Aspects of Diuretic Therapy with Furosemide: an Update, Wells Medical, 1993, (book)

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 591A, (ir)

• Benet, L.Z., J. Pharmacokinet. Biopharm., 1979, 7, 1, (rev)

References

Bioactivity

PubChem BioAssay

Bioactivity