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

• ChemBase ID: 577
• Molecular Formular: C12H11ClN2O5S
• Molecular Mass: 330.74414
• Monoisotopic Mass: 330.00772014
• SMILES: Clc1c(S(=O)(=O)N)cc(c(NCc2occc2)c1)C(=O)O
• Canonical SMILES: OC(=O)c1cc(c(cc1NCc1ccco1)Cl)S(=O)(=O)N
• 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

NAMES AND DATABASE IDS

Names

• 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
• Brand Name: Aisemide; Aldalix; Aldic; Aluzine; Anfuramaide; Apo-Frusemide; Apo-Furosemide; Aquarid; Aquasin; Arasemide; Beronald; Bioretic; Bristab; Bristurin; Cetasix; Depix; Desal; Desdemin; Di-Ademil; Dirine; Disal; Discoid; Disemide; Diucardin; Diumide-K; Diural; Diurapid; Diuretic Salt; Diurin; Diurolasa; Diusemide; Diusil; Diuzol; Dranex; Dryptal; Durafurid; Edemid; Edenol; Eliur; Elodrine; Endural; Errolon; Eutensin; Farsix; Finuret; Fluidrol; Fluss; Franyl; Frumex; Frumide; Frumil; Frusedan; Frusema; Frusemin; Frusenex; Frusetic; Frusid; Fulsix; Fuluvamide; Fuluvamine; Furanthril; Furanthryl; Furantril; Furanturil; Furesis; Furetic; Furex; Furfan; Furix; Furmid; Furo-Basan; Furo-Puren; Furobeta; Furocot; Furodiurol; Furodrix; Furomen; Furomex; Furomide M.D.; Furorese; Furosan; Furose; Furosedon; Furosemix; Furoside; Furosifar; Furosix; Furoter; Furovite; Fursol; Fusid; Golan; Hissuflux; Hydol; Hydrenox; Hydrex; Hydro; Hydro-Rapid; Hydroled; Impugan; Jenafusid; Katlex; Kofuzon; Kolkin; Kutrix; Lasemid; Lasex; Lasiletten; Lasilix; Lasix; Lasix Retard; Lasix Special; Laxur; Lazix; Leodrine; Less Diur; Liside; Logirene; Lowpston; Lowpstron; Luscek; Macasirool; Marsemide; Mirfat; Mita; Moilarorin; Myrosemide; Nadis; Nelsix; Neo-Renal; Novosemide; Octan Draselny; Odemase; Odemex; Oedemex; Olmagran; Polysquall A; Prefemin; Profemin; Promedes; Promide; Protargen; Puresis; Radisemide; Radonna; Radouna; Retep; Rodiuran; Rontyl; Rosemide; Rosis; Rusyde; Sal Diureticum; Salinex; Salix; Salurex; Salurid; Saluron; Seguril; Selectofur; Sigasalur; Sisuril; Spirofur; Synephron; Transit; Trofurit; Uremide; Uresix; Urex; Urex-M; Urian; Uridon; Uritol; Urosemide; Vergonil; Vesix; Yidoli; Zafimida
• Synonyms: Frusemide; Frusemid; Dihydroflumethiazide; Furosemida [INN-Spanish]; Furosemidu [Polish]; Furosemidum [INN-Latin]; Furosemid; Fursemid; Fursemida; Fursemide; Metflorylthiazidine; Methforylthiazidine; Furosemide; Furosemide; 5-(Aminosulfonyl)-4-chloro-2-([2-furanylmethyl]amino)benzoic acid; 5-(Aminosulfonyl)-4-chloro-2-[(2-furanyl-methyl)amino]benzoic Acid; 2-Furfurylamino-4-chloro-5-sulfamoylbenzoic Acid; 4-Chloro-N-(2-furylmethyl)-5-sulfamoylanthranilic Acid; Disal; Discoid; Disemide; Diural; Promedes; Promide; Radisemide; Radonna; Zafurida; 4-chloro-2-((furan-2-ylmethyl)amino)-5-sulfamoylbenzoic acid; 5-[Aminosulfonyl]-4-chloro-2-[(2-furanylmethyl)-amino]benzoic acid; 4-Chloro-N-furfuryl-5-sulfamoylanthranilic acid; Lasix; Furosemide(Lasix); Furosemide; 5-(Aminosulphonyl)-4-chloro-2-[(2-furanylmethyl)amino]benzoic acid; 5-(AMINOSULFONYL)-4-CHLORO-2-[(2-FURYLMETHYL)AMINO]BENZOIC ACID; Diurapid; Froop; Frumax; Frusid; Frusol; Dryptal; Rusyde; Tenkafruse; Frusemide; 4-氯-N-呋喃基-5-氨磺酰邻氨基苯甲酸; 5-(氨基磺酰基)-4-氯-2-([2-呋喃甲基]氨基)苯甲酸; 呋塞米

Database IDs

• CAS Number: 54-31-9
• EC Number: 200-203-6
• MDL Number: MFCD00010549
• PubChem SID: 160964040; 46506779; 24277714
• PubChem CID: 3440
• CHEBI ID: 47426
• ATC CODE: C03CA01
• CHEMBL: 35
• Chemspider ID: 3322
• DailyMed ID: 3940
• DrugBank ID: DB00695
• KEGG ID: D00331
• Unique Ingredient Identifier: 7LXU5N7ZO5
• Wikipedia Title: Furosemide

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.251508
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 0.47831637
• LogD (pH = 7.4): -1.250643
• Log P: 1.748402
• Molar Refractivity: 77.4742 cm^3
• Polarizability: 29.503298 Å^3
• Polar Surface Area: 122.63 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.71
• LOG S: -3.45
• Solubility (Water): 1.18e-01 g/l

PROPERTIES

Physical Property

• Solubility: 0.006 mg/mL; Methanol
• Apperance: Off-White Solid
• Melting Point: >205°C (dec.); 206; 220 °C (dec.)(lit.); 220(dec.)°C
• Hydrophobicity(logP): 1.4

Safety Information

• Storage Condition: -20°C; -20°C Freezer; Room Temperature (15-30°C)
• RTECS: CB2625000
• European Hazard Symbols: Toxic (T); Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 61; R:61
• Safety Statements: 53-22-36/37/39-45; S:22-36/37/39-45
• GHS Pictograms: GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H360
• GHS Precautionary statements: P201-P308 + P313
• Personal Protective Equipment: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges

Pharmacology Properties

• Target: Metabolic Disease
• Admin Routes: Oral, IV, IM
• Bioavailability: 43-69%
• Excretion: renal 66%, biliary 33%
• Half Life: up to 100 minutes
• Metabolism: hepatic and renal glucuronidation
• Legal Status: Rx-only
• Pregnancy Category: C (Australia); C (US)
• Gene Information: human ... ALB(213), CYP1A2(1544), SLC12A1(6557); human ... SLC12A1(6557)
• Mechanism of Action: Inhibitor of carbonic anhydrase,; subtype-specific blocker of GABA-A receptors

Product Information

• Purity: 99%
• Salt Data: Free Base
• Application(s): Antihypertensive; Diuretic; Used for treatment of cirrhotic patients with ascites.; Used in conjunction with Spironolactone HJR81-N for prophylaxis of hypokalaemia and hepatic encephalopathy or in treatment of hyperaldosteronism
• Pharmacopeia Traceability: traceable to BP 547; traceable to PhEur F0700000; traceable to USP 1287008
• Empirical Formula (Hill Notation): C12H11ClN2O5S

DETAILS

MP Biomedicals - 02158210

Crystalline

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

DrugBank - 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]

Sigma Aldrich - 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.

Sigma Aldrich - 257753

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

Sigma Aldrich - 09205

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

Toronto Research Chemicals - F865000

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

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
• http://en.wikipedia.org/wiki/Furosemide
• Goldenthal, E.I.: Toxicol. Appl. Pharmacol., 18, 185 (1971)
• Benet, L.Z.: J. Pharmacokinet. Biopharm., 7, 1 (1979)
• 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)
• IARC Monog., 1990, 50, 277, (rev, tox)
• Du Souich, P. et al., Prog. Pharmacol. Clin. Pharmacol., 1992, 9, 147, (rev)
• Aspects of Diuretic Therapy with Furosemide: an Update, Wells Medical, 1993, (book)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 7th edn., Akademie-Verlag, 1994, 2766, (synonyms)
• Stanker, L.H. et al., J. Agric. Food Chem., 1996, 44, 2455-2459, (occur)
• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 871
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, CHJ750
• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 591A, (ir)
• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 41C, (nmr)
• Sturm, K. et al., Chem. Ber., 1966, 99, 328; 345, (synth, props)
• 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)
• Benet, L.Z., J. Pharmacokinet. Biopharm., 1979, 7, 1, (rev)
• Rupp, W. et al., Arch. Int. Pharmacodyn. Ther., Suppl., 1980, 119, (rev, pharmacol)