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
- 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
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.
- 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 Integrate drug-drug
interactions in your softwareAbacavir 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. Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - 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
- External Links
- Human Metabolome Database
- HMDB0041831
- PubChem Compound
- 2273
- PubChem Substance
- 347827814
- ChemSpider
- 2186
- 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