Azosemide

Identification

Name
Azosemide
Accession Number
DB08961
Type
Small Molecule
Groups
Investigational
Description

Azosemide is a loop diuretic used to treat hypertension, edema, and ascites [1,2].

Structure
Thumb
Synonyms
  • 2-chloro-5-(1H-tetrazole-5-yl)-N^4-(2-thenyl)
Product Ingredients
IngredientUNIICASInChI Key
Azosemide phosphateNot AvailableNot AvailableNot applicable
Categories
UNII
MR40VT1L8Z
CAS number
27589-33-9
Weight
Average: 370.838
Monoisotopic: 370.007342713
Chemical Formula
C12H11ClN6O2S2
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-ylmethyl)amino]benzene-1-sulfonamide
SMILES
NS(=O)(=O)C1=C(Cl)C=C(NCC2=CC=CS2)C(=C1)C1=NNN=N1

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics

Diuretic affects upon oral administration match those of furosemide. However, upon intravenous administration azosemide displays 5.5-8 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. [1]

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. [1] Oral bioavailability estimated to be 20.4% [1]

Volume of distribution

Poor affinity for human tissue. Small apparent post-pseudodistribution Vd of 0.262 l/kg. [1]

Protein binding

> 95% 4% protein binding to 4% human serum albumin at azosemide concentrations of 10-100ug/ml, using equilibrium dialysis. [1]

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. [1]

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. [1] 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. [1]

Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AlfentanilThe risk or severity of adverse effects can be increased when Alfentanil is combined with Azosemide.Approved, Illicit
AlphacetylmethadolThe risk or severity of adverse effects can be increased when Alphacetylmethadol is combined with Azosemide.Experimental, Illicit
AlphaprodineThe risk or severity of adverse effects can be increased when Alphaprodine is combined with Azosemide.Illicit
BezitramideThe risk or severity of adverse effects can be increased when Bezitramide is combined with Azosemide.Experimental, Illicit, Withdrawn
BuprenorphineThe risk or severity of adverse effects can be increased when Buprenorphine is combined with Azosemide.Approved, Illicit, Investigational, Vet Approved
ButorphanolThe risk or severity of adverse effects can be increased when Butorphanol is combined with Azosemide.Approved, Illicit, Vet Approved
CarfentanilThe risk or severity of adverse effects can be increased when Carfentanil is combined with Azosemide.Illicit, Vet Approved
CodeineThe risk or severity of adverse effects can be increased when Codeine is combined with Azosemide.Approved, Illicit
DexketoprofenThe risk or severity of adverse effects can be increased when Dexketoprofen is combined with Azosemide.Approved
DextromoramideThe risk or severity of adverse effects can be increased when Dextromoramide is combined with Azosemide.Experimental, Illicit
DextropropoxypheneThe risk or severity of adverse effects can be increased when Dextropropoxyphene is combined with Azosemide.Approved, Illicit, Withdrawn
DezocineThe risk or severity of adverse effects can be increased when Dezocine is combined with Azosemide.Approved
DihydrocodeineThe risk or severity of adverse effects can be increased when Dihydrocodeine is combined with Azosemide.Approved, Illicit
DihydroetorphineThe risk or severity of adverse effects can be increased when Dihydroetorphine is combined with Azosemide.Experimental, Illicit
DihydromorphineThe risk or severity of adverse effects can be increased when Dihydromorphine is combined with Azosemide.Experimental, Illicit
DiphenoxylateThe risk or severity of adverse effects can be increased when Diphenoxylate is combined with Azosemide.Approved, Illicit
DPDPEThe risk or severity of adverse effects can be increased when DPDPE is combined with Azosemide.Investigational
EthylmorphineThe risk or severity of adverse effects can be increased when Ethylmorphine is combined with Azosemide.Approved, Illicit
EtorphineThe risk or severity of adverse effects can be increased when Etorphine is combined with Azosemide.Illicit, Vet Approved
FentanylThe risk or severity of adverse effects can be increased when Fentanyl is combined with Azosemide.Approved, Illicit, Investigational, Vet Approved
HeroinThe risk or severity of adverse effects can be increased when Heroin is combined with Azosemide.Approved, Illicit
HydrocodoneThe risk or severity of adverse effects can be increased when Hydrocodone is combined with Azosemide.Approved, Illicit
HydromorphoneThe risk or severity of adverse effects can be increased when Hydromorphone is combined with Azosemide.Approved, Illicit
KetobemidoneThe risk or severity of adverse effects can be increased when Ketobemidone is combined with Azosemide.Approved
Levomethadyl AcetateThe risk or severity of adverse effects can be increased when Levomethadyl Acetate is combined with Azosemide.Approved
LevorphanolThe risk or severity of adverse effects can be increased when Levorphanol is combined with Azosemide.Approved
LofentanilThe risk or severity of adverse effects can be increased when Lofentanil is combined with Azosemide.Illicit
MecamylamineThe risk or severity of adverse effects can be increased when Azosemide is combined with Mecamylamine.Approved
MeptazinolThe risk or severity of adverse effects can be increased when Meptazinol is combined with Azosemide.Experimental
MethadoneThe risk or severity of adverse effects can be increased when Methadone is combined with Azosemide.Approved
Methadyl AcetateThe risk or severity of adverse effects can be increased when Methadyl Acetate is combined with Azosemide.Approved, Illicit
MorphineThe risk or severity of adverse effects can be increased when Morphine is combined with Azosemide.Approved, Investigational
NalbuphineThe risk or severity of adverse effects can be increased when Nalbuphine is combined with Azosemide.Approved
NicomorphineThe risk or severity of adverse effects can be increased when Nicomorphine is combined with Azosemide.Experimental
NormethadoneThe risk or severity of adverse effects can be increased when Normethadone is combined with Azosemide.Approved, Illicit
OpiumThe risk or severity of adverse effects can be increased when Opium is combined with Azosemide.Approved, Illicit
OxycodoneThe risk or severity of adverse effects can be increased when Oxycodone is combined with Azosemide.Approved, Illicit, Investigational
OxymorphoneThe risk or severity of adverse effects can be increased when Oxymorphone is combined with Azosemide.Approved, Investigational, Vet Approved
PentazocineThe risk or severity of adverse effects can be increased when Pentazocine is combined with Azosemide.Approved, Vet Approved
PethidineThe risk or severity of adverse effects can be increased when Pethidine is combined with Azosemide.Approved
PhenazocineThe risk or severity of adverse effects can be increased when Phenazocine is combined with Azosemide.Experimental
PhenoperidineThe risk or severity of adverse effects can be increased when Phenoperidine is combined with Azosemide.Experimental
PiritramideThe risk or severity of adverse effects can be increased when Piritramide is combined with Azosemide.Investigational
RemifentanilThe risk or severity of adverse effects can be increased when Remifentanil is combined with Azosemide.Approved
Sodium phosphateAzosemide may increase the nephrotoxic activities of Sodium phosphate.Approved
SufentanilThe risk or severity of adverse effects can be increased when Sufentanil is combined with Azosemide.Approved, Investigational
TapentadolThe risk or severity of adverse effects can be increased when Tapentadol is combined with Azosemide.Approved
TilidineThe risk or severity of adverse effects can be increased when Tilidine is combined with Azosemide.Experimental
TramadolThe risk or severity of adverse effects can be increased when Tramadol is combined with Azosemide.Approved, Investigational
Food Interactions
Not Available

References

Synthesis Reference
Not Available
General References
Not Available
External Links
Human Metabolome Database
HMDB41831
ChemSpider
2186
ChEBI
31248
ChEMBL
CHEMBL1097235
ATC Codes
Not Available
AHFS Codes
Not Available
PDB Entries
Not Available
FDA label
Not Available
MSDS
Not Available

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)7.38ChemAxon
pKa (Strongest Basic)-0.77ChemAxon
Physiological Charge0ChemAxon
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-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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
Aminobenzenesulfonamide / Phenyltetrazole / Benzenesulfonamide / Benzenesulfonyl group / Aniline or substituted anilines / Phenylalkylamine / Chlorobenzene / Halobenzene / Secondary aliphatic/aromatic amine / Aralkylamine
show 24 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
sulfonamide, thiophenes, tetrazoles, monochlorobenzenes (CHEBI:31248)

Drug created on May 30, 2014 09:41 / Updated on October 02, 2017 06:11