Furosemide

Base Information

• Chemical Name: Furosemide
• CAS No.: 54-31-9
• Molecular Formula: C12H11ClN2O5S
• Molecular Weight: 330.749
• Hs Code.: 2935904000
• European Community (EC) Number: 200-203-6
• NSC Number: 757039,269420
• UNII: 7LXU5N7ZO5
• DSSTox Substance ID: DTXSID6020648
• Nikkaji Number: J1.913E
• Wikipedia: Furosemide
• Wikidata: Q388801
• NCI Thesaurus Code: C515
• RXCUI: 4603
• Pharos Ligand ID: A5RF13NLPV8J
• Metabolomics Workbench ID: 37940
• ChEMBL ID: CHEMBL35
• Mol file: 54-31-9.mol

Synonyms:Frumide;Urex-M;Diurin;Uritol;Frusedan;Prefemin;5-(Aminosulfonyl)-4-chloro-2-[(2-furanylmethyl)amino]benzoic acid;Depix;Mirfat;Furosix;Aquarid;Chlor-N- (2-furylmethyl)-5-sulfamylanthranilsaeure;Bioretic;4-chloro-2-(2-furylmethylamino)-5-sulfamoyl-benzoic acid;Neo-renal;Furosifar;Puresis;Furosan;Furex;Rusyde;Jenafusid;Aldic;Urian;Furanthril;

Chemical Property of Furosemide

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Melting Point: 220 °C
• Refractive Index: 1.6580 (estimate)
• Boiling Point: 582.1 °C at 760 mmHg
• PKA: pKa 3.8 (Uncertain)
• Flash Point: 305.9 °C
• PSA: 131.01000
• Density: 1.606 g/cm³
• LogP: 3.74480
• Storage Temp.: 2-8°C
• Solubility.: Practically insoluble in water, soluble in acetone, sparingly soluble in ethanol (96 per cent), practically insoluble in methylene chloride. It dissolves in dilute solutions of alkali hydroxides.
• Water Solubility.: Soluble in acetone, DMF or methanol. Slightly soluble in water
• XLogP3: 2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 330.0077203
• Heavy Atom Count: 21
• Complexity: 481

Purity/Quality:

99% ^*data from raw suppliers

Furosemide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T, F, Xi
• Hazard Codes: T,F,Xi
• Statements: 61-39/23/24/25-23/24/25-11-36/37/38
• Safety Statements: 7-16-36/37-45-53-36/37/39-22-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=COC(=C1)CNC2=CC(=C(C=C2C(=O)O)S(=O)(=O)N)Cl
• Recent ClinicalTrials: Furosemide Use to Fill the Bladder of Pediatric Females Awaiting Pelvic Ultrasound
• Recent EU Clinical Trials: Withdrawal of pharmacological treatment in patients responding to cardiac resynchronization therapy: Open and randomized study
• Recent NIPH Clinical Trials: Effect of Long-Acting vs. Short-Acting Loop Diuretics and Neurohormonal Agents on Patients' Quality-of-Life Among Patients with Heart Failure
• Uses: The diuretic effect of this product is a strong and short,it is a potent diuretic for the treatment of edema caused by heart, liver, kidney and other diseases, in particular, the base cases which other diuretics are invalid to;it can be used to treat acute pulmonary edema, brain edema , acute renal failure and high blood pressure and other diseases; in combination with fluid infusion, the product can promote poison excretion. Rat oral LD50 is 2600-2820mg/kg. diuretic, antihypertensive Furosemide inhibits ion co-transport in the kidney. Furosemide is used as a diuretic. This compound belongs to the aminobenzenesulfonamides. These are organic compounds containing a benzenesulfonamide moiety with an amine group attached to the benzene ring. An inhibitor of NKCC and a GABAA receptor antagonist.
• production method: 2,4-dichlorobenzoic acid (see 12740) by sulfochlorination,ammoniation, acidification ,dichloro-5-sulfamoyl-benzoic acid is obtained. Then after condensation with the chaff amine , furosemide is produced.
• Description: Furosemide (Item No. 26298) is an analytical reference standard categorized as a diuretic. Formulations containing diuretics, including furosemide, have been misused in sports for weight reduction and as masking agents in humans and to prevent exercise-induced pulmonary hemorrhage in racehorses. This product is intended for use in analytical forensic applications. This product is also available as a general research tool .
• Therapeutic Function: Diuretic
• Clinical Use: Furosemide has a saluretic effect 8- to 10-fold that of the thiazide diuretics; however, it has a shorter duration of action (~6–8 hours). Furosemide causes a marked excretion of sodium, chloride, potassium, calcium, magnesium, and bicarbonate ions, with as much as 25% of the filtered load of sodium excreted in response to initial treatment. It is effective for the treatment of edemas connected with cardiac, hepatic, and renal sites. Because it lowers the blood pressure similar to the thiazide derivatives, one of its uses is in the treatment of hypertension.
• Drug interactions: Potentially hazardous interactions with other drugs Analgesics: increased risk of nephrotoxicity with NSAIDs; antagonism of diuretic effect with NSAIDs. Anti-arrhythmics: risk of cardiac toxicity with anti-arrhythmics if hypokalaemia occurs; effects of lidocaine and mexiletine antagonised. Antibacterials: increased risk of ototoxicity with aminoglycosides, polymyxins and vancomycin; avoid with lymecycline. Antidepressants: increased risk of hypokalaemia with reboxetine; enhanced hypotensive effect with MAOIs; increased risk of postural hypotension with tricyclics. Antiepileptics: increased risk of hyponatraemia with carbamazepine; effects antagonised by phenytoin. Antifungals: increased risk of hypokalaemia with amphotericin. Antihypertensives: enhanced hypotensive effect; increased risk of first dose hypotensive effect with alpha-blockers; increased risk of ventricular arrhythmias with sotalol if hypokalaemia occurs. Antipsychotics: increased risk of ventricular arrhythmias with amisulpride or pimozide (avoid with pimozide) if hypokalaemia occurs; enhanced hypotensive effect with phenothiazines. Atomoxetine: hypokalaemia increases risk of ventricular arrhythmias. Cardiac glycosides: increased toxicity if hypokalaemia occurs. Ciclosporin: variable reports of increased nephrotoxicity, ototoxicity and hepatotoxicity. Cytotoxics: concentration of furosemide increased by dasabuvir, ombitasvir and paritaprevir - reduce furosemide dose; increased risk of ventricular arrhythmias due to hypokalaemia with arsenic trioxide; increased risk of nephrotoxicity and ototoxicity with platinum compounds. Lithium: risk of toxicity.

Technology Process of Furosemide

There total 19 articles about Furosemide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

→ DL-lysine salt of furosemide (135334-21-3) + 4-chloro-2-furfurylamino-5-sulfamoyl-benzoic acid (54-31-9)

Guidance literature:

Reference yield: 97.0%

2-Chloromethylfuran (617-88-9) + 4-chloro-5-sulfamoylanthranilic acid (3086-91-7) → 4-chloro-2-furfurylamino-5-sulfamoyl-benzoic acid (54-31-9)

Guidance literature:

With potassium bromide; In N,N-dimethyl-formamide; at 120 ℃; for 24h; Reagent/catalyst; Solvent; Temperature;

Reference yield: 94.0%

→ 4-chloro-2-furfurylamino-5-sulfamoyl-benzoic acid (54-31-9)

Guidance literature:

upstream raw materials:

Furosemide glucuronide

2,4-dichloro-5-sulfamoylbenzoic acid

4-chloro-N-(2-furfuryl)-5-sulfamoylanthranilic acid sodium salt

2-Chloromethylfuran

Downstream raw materials:

4-Chloro-2-[(furan-2-ylmethyl)-amino]-5-sulfamoyl-benzoic acid 2,2-dimethyl-propionyloxymethyl ester

acetyloxymethyl-4-chloro-N-furfuryl-5-sulfamoyl anthranitrilate

4-Chloro-2-[(furan-2-ylmethyl)-amino]-5-sulfamoyl-benzoic acid isobutyryloxymethyl ester

4-Chloro-2-[(furan-2-ylmethyl)-amino]-5-sulfamoyl-benzoic acid butyryloxymethyl ester

Refernces

• 1、 Shi, Zhiyuan,Wu, Jingnan,Song, Qingchuan,G?stl, Robert,Herrmann, Andreas. "Toward Drug Release Using Polymer Mechanochemical Disulfide Scission". . p. 14725 - 14732. Retrieved 2020.
• 2、 -. "Furosemide and purification method thereof". Page/Page column 0035-0036; 0038. . Retrieved 2021/06/23.