Azosemide

Identification

Generic Name

Azosemide

DrugBank Accession Number

DB08961

Background

Azosemide is a loop diuretic used to treat hypertension, edema, and ascites.

Type

Small Molecule

Groups

Investigational

Structure

Similar Structures

Weight: Average: 370.838
Monoisotopic: 370.007342713
Chemical Formula: C₁₂H₁₁ClN₆O₂S₂

Synonyms

2-chloro-5-(1H-tetrazol-5-yl)-N4-2-thenylsulfanilamide
5-(4'-chloro-5'-sulfamoyl-2'-thenylaminophenyl)tetrazole
azosemida
azosémide
Azosemide
azosemidum

Pharmacology

Indication: Not Available
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Pharmacodynamics: Diuretic affects upon oral administration match those of furosemide. However, upon intravenous administration azosemide displays 5.5 to 8 times greater effect.
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.
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%
Volume of distribution: Poor affinity for human tissue. Small apparent post-pseudodistribution Vd of 0.262 l/kg.
Protein binding: > 95% 4% protein binding to 4% human serum albumin at azosemide concentrations of 10-100ug/ml, using equilibrium dialysis.
Metabolism: 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.
Route of elimination: 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.
Half-life: Terminal half life 2-3 hours.
Clearance: Not Available
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Toxicity: Not Available
Pathways: Not Available
Pharmacogenomic Effects/ADRs: Not Available

Interactions

Drug Interactions

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

Drug	Interaction
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Abacavir	Azosemide may increase the excretion rate of Abacavir which could result in a lower serum level and potentially a reduction in efficacy.
Acarbose	The therapeutic efficacy of Acarbose can be increased when used in combination with Azosemide.
Aceclofenac	The therapeutic efficacy of Azosemide can be decreased when used in combination with Aceclofenac.
Acemetacin	The therapeutic efficacy of Azosemide can be decreased when used in combination with Acemetacin.
Acetaminophen	Azosemide may increase the excretion rate of Acetaminophen which could result in a lower serum level and potentially a reduction in efficacy.
Acetohexamide	The therapeutic efficacy of Acetohexamide can be increased when used in combination with Azosemide.
Acetyldigitoxin	The risk or severity of adverse effects can be increased when Azosemide is combined with Acetyldigitoxin.
Acetylsalicylic acid	Acetylsalicylic acid may decrease the excretion rate of Azosemide which could result in a higher serum level.
Aclidinium	Azosemide may increase the excretion rate of Aclidinium which could result in a lower serum level and potentially a reduction in efficacy.
Acrivastine	Azosemide may increase the excretion rate of Acrivastine which could result in a lower serum level and potentially a reduction in efficacy.

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Food Interactions

Not Available

Chemical Identifiers

UNII: MR40VT1L8Z
CAS number: 27589-33-9
InChI Key: HMEDEBAJARCKCT-UHFFFAOYSA-N
InChI: InChI=1S/C12H11ClN6O2S2/c13-9-5-10(15-6-7-2-1-3-22-7)8(12-16-18-19-17-12)4-11(9)23(14,20)21/h1-5,15H,6H2,(H2,14,20,21)(H,16,17,18,19)
IUPAC Name: 2-chloro-5-(2H-1,2,3,4-tetrazol-5-yl)-4-{[(thiophen-2-yl)methyl]amino}benzene-1-sulfonamide
SMILES: NS(=O)(=O)C1=C(Cl)C=C(NCC2=CC=CS2)C(=C1)C1=NNN=N1

References

General References

Not Available

External Links

Human Metabolome Database: HMDB0041831
PubChem Compound: 2273
PubChem Substance: 347827814
ChemSpider: 2186
RxNav: 18651
ChEBI: 31248
ChEMBL: CHEMBL1097235
ZINC: ZINC000005843546
PDBe Ligand: IWE
Wikipedia: Azosemide

PDB Entries

7zl5 / 7zl6

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
4	Completed	Treatment	Congestive Heart Failure (CHF)	1

Pharmacoeconomics

Manufacturers: Not Available
Packagers: Not Available
Dosage Forms: Not Available
Prices: Not Available
Patents: Not Available

Properties

State

Solid

Experimental Properties

Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0929 mg/mL	ALOGPS
logP	2.36	ALOGPS
logP	2.38	Chemaxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	5.84	Chemaxon
pKa (Strongest Basic)	-0.77	Chemaxon
Physiological Charge	-1	Chemaxon
Hydrogen Acceptor Count	6	Chemaxon
Hydrogen Donor Count	3	Chemaxon
Polar Surface Area	126.65 Å²	Chemaxon
Rotatable Bond Count	5	Chemaxon
Refractivity	102.08 m³·mol^-1	Chemaxon
Polarizability	34.56 Å³	Chemaxon
Number of Rings	3	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	Yes	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Not Available

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available

Drug created at May 30, 2014 15:41 / Updated at February 21, 2021 18:52

Azosemide

Identification

Structure for Azosemide (DB08961)

Pharmacology

Interactions

Categories

Chemical Identifiers

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra