NAV

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
3D
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
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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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

Adverse Effects
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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.
DrugInteraction
Integrate drug-drug
interactions in your software
AbacavirAzosemide may increase the excretion rate of Abacavir which could result in a lower serum level and potentially a reduction in efficacy.
AcarboseThe therapeutic efficacy of Acarbose can be increased when used in combination with Azosemide.
AceclofenacThe therapeutic efficacy of Azosemide can be decreased when used in combination with Aceclofenac.
AcemetacinThe therapeutic efficacy of Azosemide can be decreased when used in combination with Acemetacin.
AcetaminophenAzosemide may increase the excretion rate of Acetaminophen which could result in a lower serum level and potentially a reduction in efficacy.
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as phenyltetrazoles and derivatives. These are compounds containing a phenyltetrazole skeleton, which consists of a tetrazole bound to a phenyl group.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Azoles
Sub Class
Tetrazoles
Direct Parent
Phenyltetrazoles and derivatives
Alternative Parents
Aminobenzenesulfonamides / Benzenesulfonyl compounds / Phenylalkylamines / Aniline and substituted anilines / Secondary alkylarylamines / Chlorobenzenes / Organosulfonamides / Aryl chlorides / Thiophenes / Aminosulfonyl compounds
show 6 more
Substituents
Amine / Aminobenzenesulfonamide / Aminosulfonyl compound / Aniline or substituted anilines / Aralkylamine / Aromatic heteromonocyclic compound / Aryl chloride / Aryl halide / Azacycle / Benzenesulfonamide
show 24 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
sulfonamide, thiophenes, tetrazoles, monochlorobenzenes (CHEBI:31248)
Affected organisms
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
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
PhaseStatusPurposeConditionsCount
4CompletedTreatmentCongestive 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
PropertyValueSource
Water Solubility0.0929 mg/mLALOGPS
logP2.36ALOGPS
logP2.38Chemaxon
logS-3.6ALOGPS
pKa (Strongest Acidic)5.84Chemaxon
pKa (Strongest Basic)-0.77Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area126.65 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity102.08 m3·mol-1Chemaxon
Polarizability34.56 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-002f-3179000000-ab9cce02c68a2faedfa5
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0009000000-9104aebf2c4d1d4c85bd
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0009000000-a398003d13d3a936aaa9
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0fk9-0009000000-2c0f60c9b56a6736fbfd
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-01t9-5009000000-19f0cb84120e6b2e8748
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-1029000000-63a4cda4fcc14dda415e
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9062000000-5c901c404e222eec42cf
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-183.3477341
predicted
DarkChem Lite v0.1.0
[M-H]-167.31078
predicted
DeepCCS 1.0 (2019)
[M+H]+184.2274341
predicted
DarkChem Lite v0.1.0
[M+H]+169.66878
predicted
DeepCCS 1.0 (2019)
[M+Na]+184.2967341
predicted
DarkChem Lite v0.1.0
[M+Na]+176.76927
predicted
DeepCCS 1.0 (2019)

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