3-(butylamino)-4-phenoxy-5-sulfamoylbenzoic acid

• ChemBase ID: 764
• Molecular Formular: C17H20N2O5S
• Molecular Mass: 364.4161
• Monoisotopic Mass: 364.10929275
• SMILES: S(=O)(=O)(N)c1c(Oc2ccccc2)c(NCCCC)cc(c1)C(=O)O
• Canonical SMILES: CCCCNc1cc(cc(c1Oc1ccccc1)S(=O)(=O)N)C(=O)O
• InChI: InChI=1S/C17H20N2O5S/c1-2-3-9-19-14-10-12(17(20)21)11-15(25(18,22)23)16(14)24-13-7-5-4-6-8-13/h4-8,10-11,19H,2-3,9H2,1H3,(H,20,21)(H2,18,22,23)
• InChIKey: MAEIEVLCKWDQJH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(butylamino)-4-phenoxy-5-sulfamoylbenzoic acid
• IUPAC Traditional name: bumetanide
• Brand Name: Bumex; Burine; Burinex; Fontego; Fordiuran; Lixil; Lunetoron; Segurex
• Synonyms: 3-(Aminosulfonyl)-5-(butylamino)-4-phenoxybenzoic acid; Bumetanide; 3-(Aminosulfonyl)-5-(butylamino)-4-phenoxy-benzoic Acid; 3-(Butylamino)-4-phenoxy-5-sulfamoylbenzoic Acid; Bufenox; Burinex; Fordiuran; Lixil; Lunetoron; PF 1593; 3-(butylamino)-4-phenoxy-5-sulfamoylbenzoic acid; Bumetanida [INN-Spanish]; Bumetanidum [INN-Latin]; Bumetanide; Bumex; Ro 10-6338

Database IDs

• CAS Number: 28395-03-1
• EC Number: 249-004-6
• MDL Number: MFCD00078949
• PubChem SID: 46508147; 160964227; 24278265
• PubChem CID: 2471

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.6927853
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 1.6518241
• LogD (pH = 7.4): -0.1262592
• Log P: 2.4234617
• Molar Refractivity: 95.7803 cm^3
• Polarizability: 36.81077 Å^3
• Polar Surface Area: 118.72 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.44
• LOG S: -4.15
• Solubility (Water): 2.57e-02 g/l

PROPERTIES

Physical Property

• Solubility: >20 mg/mL (in base); Acetone; Benzene; Ethanol; Methanol; Propylene Glycol
• Apperance: White Solid
• Melting Point: 230-231°C
• Hydrophobicity(logP): 2.6; 3.372

Safety Information

• Storage Condition: -20°C; 2-8°C; Refrigerator
• RTECS: DG4910000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98%; 95%; 97%; 99%
• Salt Data: Free Base

DETAILS

MP Biomedicals - 02154263

(Ro 10-6338) White micronized solid Purity: 99% An inhibitor of sodium and potassium cotransport.

DrugBank - DB00887

• Drug Groups: approved
• Description: A sulfamyl diuretic. [PubChem]
• Indication: For the treatment of edema associated with congestive heart failure, hepatic and renal disease including the nephrotic syndrome.
• Pharmacology: Bumetanide is a loop diuretic of the sulfamyl category to treat heart failure. It is often used in patients in whom high doses of furosemide are ineffective. There is however no reason not to use bumetanide as a first choice drug. The main difference between the two substances is in bioavailability. It is said to be a more predictable diuretic, meaning that the predictable absorption is reflected in a more predictable effect. Bumetanide is 40 times more potent than furosemide (for patients with normal renal function).
• Toxicity: Overdosage can lead to acute profound water loss, volume and electrolyte depletion, dehydration, reduction of blood volume and circulatory collapse with a possibility of vascular thrombosis and embolism. Electrolyte depletion may be manifested by weakness, dizziness, mental confusion, anorexia, lethargy, vomiting and cramps. Treatment consists of replacement of fluid and electrolyte losses by careful monitoring of the urine and electrolyte output and serum electrolyte levels.
• Affected Organisms: Humans and other mammals
• Biotransformation: 45% is secreted unchanged. Urinary and biliary metabolites are formed by oxidation of the N-butyl side chain.
• Absorption: Bumetanide is completely absorbed (80%), and the absorption is not altered when taken with food. Bioavailability is almost complete.
• Half Life: 60-90 minutes
• Protein Binding: 97%
• Elimination: Oral administration of carbon-14 labeled Bumex to human volunteers revealed that 81% of the administered radioactivity was excreted in the urine, 45% of it as unchanged drug. Biliary excretion of Bumex amounted to only 2% of the administered dose.
• Clearance: * 0.2 - 1.1 mL/min/kg [preterm and full-term neonates with respiratory disorders]; * 2.17 mL/min/kg [neonates receiving bumetanide for volume overload]; * 1.8 +/- 0.3 mL/min/kg [geriatric subjects]; * 2.9 +/- 0.2 mL/min/kg [younger subjects]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Selleck Chemicals - S1287

Research Area: Cardiovascular Disease
Biological Activity:
Bumetanide (Bumex) is a loop diuretic of the sulfamyl category to treat heart failure. Bumetanide is 40 times more potent than furosemide (for patients with normal renal function). [1]

Sigma Aldrich - B3023

Biochem/physiol Actions
Inhibitor of Na+/K+/Cl- cotransporter.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. B3023.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - B689550

Bumetanide is a diuretic.

REFERENCES

• http://en.wikipedia.org/wiki/Bumetanide
• Ward, A., et al.: Drugs, 28, 426 (1984)
• Gradeen, C.Y, et al.: J. Anal. Toxicol., 14, 123 (1984)
• Tata, P.N.V., et al.: Anal. Profiles Drug Subs. Excip., 22, 107 (1984)