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

• ChemBase编号: 577
• 分子式: C12H11ClN2O5S
• 平均质量: 330.74414
• 单一同位素质量: 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

名称和登记号

名称

• 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: 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
• 别名: 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; 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

登记号

• CAS号: 54-31-9
• EC号: 200-203-6
• MDL号: MFCD00010549
• PubChem SID: 24277714; 46506779; 160964040
• PubChem CID: 3440
• CHEBI ID: 47426
• ATC码: C03CA01
• CHEMBL: 35
• Chemspider ID: 3322
• DailyMed ID: 3940
• DrugBank ID: DB00695
• KEGG ID: D00331
• 美国药典/FDA物质标识码: 7LXU5N7ZO5
• 维基百科标题: Furosemide

理论计算性质

JChem

• Acid pKa: 4.251508
• 质子受体: 5
• 质子供体: 3
• LogD (pH = 5.5): 0.47831637
• LogD (pH = 7.4): -1.250643
• Log P: 1.748402
• 摩尔折射率: 77.4742 cm^3
• 极化性: 29.503298 Å^3
• 极化表面积: 122.63 Å^2
• 可自由旋转的化学键: 5
• 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

分子性质

理化性质

• 溶解度: 0.006 mg/mL; Methanol
• 外观: Off-White Solid
• 熔点: >205°C (dec.); 206; 220 °C (dec.)(lit.); 220(dec.)°C
• 疏水性(logP): 1.4

安全信息

• 保存条件: -20°C; -20°C Freezer; Room Temperature (15-30°C)
• RTECS编号: CB2625000
• 欧盟危险性物质标志: 有毒(Toxic) (T); 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 61; R:61
• 安全公开号: 53-22-36/37/39-45; S:22-36/37/39-45
• GHS危险品标识: GHS08
• GHS警示词: Danger
• GHS危险声明: H360
• GHS警示性声明: P201-P308 + P313
• 个人保护装置: 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

药理学性质

• 作用靶点: Metabolic Disease
• 给药途径: Oral, IV, IM
• 生物利用度: 43-69%
• 排泄: renal 66%, biliary 33%
• 半衰期: up to 100 minutes
• 代谢: hepatic and renal glucuronidation
• 法定药品分级: Rx-only
• 妊娠期药物分类: C (Australia); C (US)
• 相关基因信息: human ... ALB(213), CYP1A2(1544), SLC12A1(6557); human ... SLC12A1(6557)
• 生物活性机理: Inhibitor of carbonic anhydrase,; subtype-specific blocker of GABA-A receptors

产品相关信息

• 纯度: 99%
• 成盐信息: Free Base
• 应用领域: 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

详细说明

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
抑制肾脏中离子的协同运输。

Sigma Aldrich - 09205

Biochem/physiol Actions
抑制肾脏中离子的协同运输。

Toronto Research Chemicals - F865000

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

参考文献

• 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
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