Bumetanide

Base Information

• Chemical Name: Bumetanide
• CAS No.: 28395-03-1
• Molecular Formula: C17H20N2O5S
• Molecular Weight: 364.422
• Hs Code.: 2935904000
• European Community (EC) Number: 249-004-6
• NSC Number: 758145
• UNII: 0Y2S3XUQ5H
• DSSTox Substance ID: DTXSID5022699
• Nikkaji Number: J3.168B
• Wikipedia: Bumetanide
• Wikidata: Q275926
• NCI Thesaurus Code: C28875
• RXCUI: 1808
• Pharos Ligand ID: VCWU19G4S4YZ
• Metabolomics Workbench ID: 43161
• ChEMBL ID: CHEMBL1072
• Mol file: 28395-03-1.mol

Synonyms:Bumedyl;Bumetanide;Bumethanide;Bumex;Burinex;Drenural;Fordiuran;Miccil;PF 1593;PF-1593;PF1593

Chemical Property of Bumetanide

Chemical Property:

• Appearance/Colour: crystalline solid
• Vapor Pressure: 6.89E-14mmHg at 25°C
• Melting Point: 230-231 °C
• Refractive Index: 1.612
• Boiling Point: 571.2 °C at 760 mmHg
• PKA: pK1 3.6, pK2 7.7(at 25℃)
• Flash Point: 299.3 °C
• PSA: 127.10000
• Density: 1.347 g/cm³
• LogP: 4.89060
• Storage Temp.: Store at RT
• Solubility.: Practically insoluble in water, soluble in acetone and in alcohol, slightly soluble in methylene chloride. It dissolves in dilute solutions of alkali hydroxides.
• Water Solubility.: Soluble in ethanol (10 mg/ml), DMSO (25 mg/ml), acetone, benzene, methanol, propylene glycol, and water (<1 mg/ml).
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 8
• Exact Mass: 364.10929292
• Heavy Atom Count: 25
• Complexity: 528

Purity/Quality:

99%-101% ^*data from raw suppliers

Bumetanide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCCNC1=C(C(=CC(=C1)C(=O)O)S(=O)(=O)N)OC2=CC=CC=C2
• Recent ClinicalTrials: Mechanisms of Diuretic Resistance in Heart Failure, Aim 1
• Recent EU Clinical Trials: Diuretic Treatment in Acute Heart Failure with Volume Overload Guided by Serial Spot Urine Sodium Assessment
• Uses: antineoplastic, alkylating agent Bumetanide is used for relieving edema associated with cardiac insufficiency, for liver and kidney diseases including nephrotic syndrome, for ascites, and hypertension.
• Therapeutic Function: Diuretic
• Clinical Use: A diuretic structurally related to furosemide is bumetanide. This compound also functions as a high-ceiling diuretic in the ascending limb of the loop of Henle. It has a duration of action of approximately 4 hours. The uses of this compound are similar to those described for furosemide. The dose of bumetanide is 0.5 to 2 mg/day given as a single dose.
• 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. 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 if hypokalaemia occurs - avoid with pimozide; enhanced hypotensive effect with phenothiazines. Atomoxetine: increased risk of ventricular arrhythmias if hypokalaemia occurs. Cardiac glycosides: increased toxicity if hypokalaemia occurs. Cytotoxics: 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 Bumetanide

There total 5 articles about Bumetanide 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: 95.8%

3-amino-5-(aminosulfonyl)-4-phenoxybenzoic acid (28328-54-3) + butan-1-ol (71-36-3) → Bumetanide (28395-03-1)

Guidance literature:

With iron(III) chloride; boron trifluoride diethyl etherate; at 20 ℃; for 6h; Reagent/catalyst;

Reference yield: 87.0%

butyl 3-aminosulfonyl-5-butylamino-4-phenoxybenzoate (32643-00-8) → Bumetanide (28395-03-1)

Guidance literature:

butyl 3-aminosulfonyl-5-butylamino-4-phenoxybenzoate; With sodium hydroxide; water; for 0.75h; Heating / reflux;

With hydrogenchloride; In water; pH=2.5 - 3;

Reference yield:

sodium tetrahydroborate (16940-66-2) + sodium 3-n-butyrylamino-4-phenoxy-5-sulfamyl-benzoate → Bumetanide (28395-03-1)

Guidance literature:

With hydrogenchloride; aluminium trichloride; In methanol; diethylene glycol dimethyl ether; ammonia; water;

upstream raw materials:

sodium tetrahydroborate

methyl 3-(butylamino)-4-phenoxy-5-sulfamoylbenzoate

butyl 3-aminosulfonyl-5-butylamino-4-phenoxybenzoate

3-amino-5-(aminosulfonyl)-4-phenoxybenzoic acid

Downstream raw materials:

methyl 3-(butylamino)-4-phenoxy-5-sulfamoylbenzoate

PF-1712

Refernces

• 1、 -. "SUBSTITUTED ANTHRANILIC ACIDS". Page/Page column 29. . Retrieved 2008/12/04.
• 2、 -. "2,3-dihydrobenzofuran-5-sulfonamide derivatives useful as antihypertensive diuretic agents". . . Retrieved 2008/06/13.