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Azosemide

Azosemide structure

CAS No:
27589-33-9
Formula:
C12H11ClN6O2S2
Chemical Name:
Azosemide
Synonyms:
Benzenesulfonamide,2-chloro-5-(2H-tetrazol-5-yl)-4-[(2-thienylmethyl)amino]-;Sulfanilamide,2-chloro-5-(1H-tetrazol-5-yl)-N4-2-thenyl-;Benzenesulfonamide,2-chloro-5-(1H-tetrazol-5-yl)-4-[(2-thienylmethyl)amino]-;2-Chloro-5-(2H-tetrazol-5-yl)-4-[(2-thienylmethyl)amino]benzenesulfonamide;5-(4-Chloro-5-sulfamoyl-2-thenylaminophenyl)tetrazole;Ple 1053;Azosemide;2-Chloro-5-(1H-tetrazol-5-yl)-4-[(2-thienylmethyl)amino]benzenesulfonamide;SK 110 (pharmaceutical);SK 110;Luret;Diart;Diurapid;2-Chloro-5-(2H-tetrazol-5-yl)-4-(thiophen-2-ylmethylamino)benzenesulfonamide
Categories:
Active Pharmaceutical Ingredients > Urinary System Drugs

Description

Azosemide, a sulfonamide loop diuretic, is a potent NKCC1 inhibitor with IC50s of 0.246 µM and 0.197 µM for hNKCC1A and NKCC1B, respectively[1].

Solid

Azosemide is a sulfonamide that is benzenesulfonamide which is substituted at positions 2, 4, and 5 by chlorine, (2-thienylmethyl)amino and 1H-tetrazol-5-yl groups, respectively. It is a diuretic that has been used in the management of oedema and hypertension. It has a role as a loop diuretic. It is a member of tetrazoles, a member of monochlorobenzenes, a sulfonamide and a member of thiophenes.|Azosemide is a loop diuretic used to treat hypertension, edema, and ascites.|Azosemide is a monosulfamyl belonging to the class of loop diuretics. Azosemide inhibits sodium and chloride reabsorption throughout the thick ascending limb of the loop of Henle.

Azosemide Basic Attributes

Molecular Weight：

370.84

Exact Mass：

370.84

EC Number：

248-549-7

UNII：

MR40VT1L8Z

DSSTox ID：

DTXSID7046910

NCI Thesaurus Code：

C77515

HScode：

2935009090

Characteristics

PSA：

163

XLogP3：

1.5

Appearance：

Density：

1.661g/cm3

Melting Point：

219.5 °C

Boiling Point：

671.1°C at 760 mmHg

Flash Point：

359.6ºC

Refractive Index：

1.709

Vapor Pressure：

7.19E-18mmHg at 25°C

Toxicity：

Oral-rat LD50: 2545 mg/kg; Oral-Mouse LD50: 6350 mg/kg

Flammability characteristics：

Flammable; burning produces toxic nitrogen oxides, sulfur oxides and chloride fumes

Safety Information

Storage features：

Ventilated, low temperature and dry

Toxicity

Toxicity class：

moderately

Protein Binding：

> 95% 4% protein binding to 4% human serum albumin at azosemide concentrations of 10-100ug/ml, using equilibrium dialysis.

Drug Information

Pharmacology：

Diuretic affects upon oral administration match those of furosemide. However, upon intravenous administration azosemide displays 5.5 to 8 times greater effect.

MeSH：

Agents that promote the excretion of urine through their effects on kidney function. (See all compounds classified as Diuretics.)

Absorption：

Peak plasma concentrations are achieved in 3-4 hours when azosemide is administered to healthy humans in a fasting state. There is an absorption lag time of approximately 1 hour. Oral bioavailability estimated to be 20.4%|Total body clearance 112ml/min. Renal clearance 41.6ml/min. Actively secreted in the renal proximal tubule of humans. This may or may not involve a nonspecific organic acid secretory pathway. There is thus a potential for disease states and other organic acids such as NSAIDs which affect the organic acid transport pathway to affect the efficacy of azosemide.|Poor affinity for human tissue. Small apparent post-pseudodistribution Vd of 0.262 l/kg.

Metabolism/Metabolites：

Considerable first pass metabolism which makes parentral administration more effective than oral administration. Eleven metabolites of azosemide were found in rats, but only azosemide and its glucuronide were detected in humans.

Biological Half-Life：

Terminal half life 2-3 hours.

Mechanism of Action：

Exact mechanism of action is unclear. However, it acts primarily on the loop of Henle, in both the medullary and cortical segments of the thick ascending limb.

MeSH Entry Terms：

5-(4-chloro-5-sulfamyl-2-thienylaminophenyl)tetrazole

Azosemide Use and Manufacturing

Used as pharmaceutical intermediate Diuretics. It has the effect of inhibiting the reabsorption of salts, and its hypotensive effect is weak. Used for edema of heart, liver and kidney.

Computed Properties

Molecular Weight:370.8
XLogP3:1.5
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:5
Exact Mass:370.0073437
Monoisotopic Mass:370.0073437
Topological Polar Surface Area:163
Heavy Atom Count:23
Complexity:504
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

Benzonitrile

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