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

基本信息

化学结构

分子式

C₁₂H₁₁ClN₂O₅S

分子量

330.74414

精确质量

330.00772014

电荷

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

计算属性

JChem

Acid pKa

4.251508

质子受体

质子供体

LogD (pH = 5.5)

0.47831637

LogD (pH = 7.4)

-1.250643

Log P

1.748402

摩尔折射率

77.4742

极化性

29.503298

极化表面积

122.63

可自由旋转的化学键

里宾斯基五规则

true

ALOGPS 2.1

Log P

2.71

LOG S

-3.45

溶解度

1.18e-01 g/l

数据来源

名称和标识

别名

5-(AMINOSULFONYL)-4-CHLORO-2-[(2-FURYLMETHYL)AMINO]BENZOIC ACIDFurosemide5-(Aminosulphonyl)-4-chloro-2-[(2-furanylmethyl)amino]benzoic acidFurosemide5-[Aminosulfonyl]-4-chloro-2-[(2-furanylmethyl)-amino]benzoic acid4-Chloro-N-furfuryl-5-sulfamoylanthranilic acidFrusemideDihydroflumethiazideFurosemidFurosemidu [Polish]MethforylthiazidineFurosemida [INN-Spanish]FursemidFursemidaFurosemidum [INN-Latin]FursemideMetflorylthiazidineFrusemidLasix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 acidFrusemideTenkafruseFrusidFrusolFroopFrumaxRusydeDiurapidDryptalDisemideDiscoidPromedesRadonnaPromideDiuralRadisemide4-Chloro-N-(2-furylmethyl)-5-sulfamoylanthranilic AcidDisalZafurida5-(Aminosulfonyl)-4-chloro-2-[(2-furanyl-methyl)amino]benzoic Acid2-Furfurylamino-4-chloro-5-sulfamoylbenzoic Acid

IUPAC标准名

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

IUPAC传统名

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

商标名

NelsixSalinexTransitFurosideMarsemideKolkinLasilettenSigasalurUritolUremideZafimidaSaluridSaluronDesalDi-AdemilProtargenLaxurHissufluxSegurilPromideOdemaseFuromide M.D.ProfeminFurixNadisGolanUrianFuroreseLuscekMirfatAquasinVesixNeo-RenalFurosanVergonilLisideHydrenoxRosemideSalurexPuresisFuroterFuroviteKutrixSelectofurHydroledLazixOctan DraselnyUrosemideSalixUridonFuro-BasanNovosemideLasexFurosifarSal DiureticumCetasixYidoliFurosemixLogirenePrefeminHydro-RapidRadounaLasemidFuranturilTrofuritRadonnaSynephronPolysquall ALowpstronJenafusidUrex-MMacasiroolRusydeMyrosemideRodiuranHydolBristurinUresixFursolUrexPromedesLasix RetardFusidAquaridSpirofurRadisemideLasilixImpuganHydroLess DiurLowpstonFurosixHydrexSisurilApo-FurosemideFuroseFurantrilFuranthrilFrumexFurodrixDiurolasaDiuretic SaltDisalFinuretFurobetaDisemideEnduralAisemideArasemideDiscoidFruseticFurexDurafuridFurocotDiuralFluidrolLasixRetepMoilarorinDesdeminDiurapidDiurinEdemidFrumideFureticAnfuramaideAluzineApo-FrusemideMitaFranylDranexErrolonDiusilRosisFruseminKatlexFlussFuresisFurodiurolFrusemaEutensinBioreticAldalixFurosedonFrusenexDiumide-KOedemexOlmagranRontylFrusidLeodrineElodrineDiusemideDepixFurmidFarsixEliurFulsixEdenolFuro-PurenFrumilFuluvamideDirineDiuzolFuranthrylFrusedanDiucardinAldicBeronaldKofuzonFurfanFuluvamineOdemexLasix SpecialFuromenBristabFuromexDryptal

名称和标识

数据登录号

CAS号

54-31-9

PubChem SID

4650677916096404024277714

PubChem CID

3440

EC号

200-203-6

MDL号

MFCD00010549

CHEMBL

Chemspider ID

CHEBI ID

DailyMed ID

ATC码

维基百科标题

KEGG ID

美国药典/FDA物质标识码

DrugBank ID

数据登录号

化合物性质

分子相关蛋白质

暂无数据

点击上传数据

分子图谱

暂无数据

点击上传数据

描述信息

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
抑制肾脏中离子的协同运输。

09205

Biochem/physiol Actions
抑制肾脏中离子的协同运输。

TRC

F865000

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

描述信息

参考文献

PubChem文献

数据源提供

• 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)

参考文献

生物活性

PubChem BioAssay

生物活性