Azosemide
PubChem CID
2273
Structure
Molecular Formula
Synonyms
- azosemide
- 27589-33-9
- Azosemid
- Azosemida
- Diart
Molecular Weight
370.8 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
- Create:2005-03-25
- Modify:2025-01-25
Description
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.
Chemical Structure Depiction
2-chloro-5-(2H-tetrazol-5-yl)-4-(thiophen-2-ylmethylamino)benzenesulfonamide
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)
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)
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
HMEDEBAJARCKCT-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
C1=CSC(=C1)CNC2=CC(=C(C=C2C3=NNN=N3)S(=O)(=O)N)Cl
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)
C12H11ClN6O2S2
Computed by PubChem 2.2 (PubChem release 2021.10.14)
- 2-chloro-5-(1H-tetrazol-5-yl)-N(sup 4)-2-thenylsulfanilamide
- 5-(4-chloro-5-sulfamyl-2-thienylaminophenyl)tetrazole
- azosemid
- azosemide
- benzenesulfonamide, 2-chloro-5-(1H-tetrazol-5-yl)-4-((2-thienylmethyl)amino)-
- BM 02.001
- Ple 1053
- azosemide
- 27589-33-9
- Azosemid
- Azosemida
- Diart
- Azosemidum
- 2-chloro-5-(2H-tetrazol-5-yl)-4-((thiophen-2-ylmethyl)amino)benzenesulfonamide
- Luret
- PLE 1053
- 2-chloro-5-(2H-tetrazol-5-yl)-4-(thiophen-2-ylmethylamino)benzenesulfonamide
- 2-Chloro-5-(1H-tetrazol-5-yl)-N(sup 4)-2-thenylsulfanilamide
- MR40VT1L8Z
- Benzenesulfonamide, 2-chloro-5-(2H-tetrazol-5-yl)-4-[(2-thienylmethyl)amino]-
- DTXSID7046910
- CHEBI:31248
- Sulfanilamide, 2-chloro-5-(1H-tetrazol-5-yl)-N(sup 4)-2-thenyl-
- Benzenesulfonamide, 2-chloro-5-(1H-tetrazol-5-yl)-4-((2-thienylmethyl)amino)-
- 5-(4'-chloro-5'-sulfamoyl-2'-thenylaminophenyl)tetrazole
- NCGC00181340-01
- 2-chloro-5-(1H-tetrazol-5-yl)-4-[(thiophen-2-ylmethyl)amino]benzenesulfonamide
- DTXCID5026910
- C12H11ClN6O2S2
- 2-Chloro-5-(1H-tetrazol-5-yl)-N4-2-thenylsulfanilamide
- Azosemidum [INN-Latin]
- Azosemida [INN-Spanish]
- Azosemide [USAN:INN:JAN]
- CAS-27589-33-9
- EINECS 248-549-7
- SK-110
- UNII-MR40VT1L8Z
- BRN 1178491
- 2-Chloro-5-(1H-tetrazol-5-yl)-4-((thiophen-2-ylmethyl)amino)benzenesulfonamide
- IWE
- MFCD00867321
- Diart (TN)
- 5-(4'-Chloro-5'-sulfamoyl-2'-thenylaminophenyl)-tetrazole
- AZOSEMIDE [INN]
- AZOSEMIDE [JAN]
- AZOSEMIDE [MI]
- AZOSEMIDE [USAN]
- AZOSEMIDE [MART.]
- AZOSEMIDE [WHO-DD]
- SCHEMBL48976
- Azosemide (JP17/USAN/INN)
- CHEMBL1097235
- EX-A1266
- Tox21_112799
- AC-096
- MFCD30541344
- SK 110
- AKOS015961824
- Tox21_112799_1
- DB08961
- NCGC00181340-02
- AS-12235
- SY288607
- DB-047249
- HY-107321
- CS-0028137
- NS00002746
- C74435
- D01323
- Q4832859
- BRD-K68770713-001-01-8
- 5-(4-chloro-5-sulfamoyl-2-thenylaminophenyl)-tetrazole
- 2-chloro-5-(1H-tetrazol-5-yl)-N(4)-2-thenylsulfanilamide
- 2-chloro-5-(1H-tetrazol-5-yl)-4-(thiophen-2-ylmethylamino)benzenesulfonamide
- 2-chloranyl-5-(1~{H}-1,2,3,4-tetrazol-5-yl)-4-(thiophen-2-ylmethylamino)benzenesulfonamide
- 2-chloro-5-(2H-1,2,3,4-tetrazol-5-yl)-4-[(thiophen-2-ylmethyl)amino]benzene-1-sulfonamide
Property Name
Property Value
Reference
Property Name
Molecular Weight
Property Value
370.8 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
1.5
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
8
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
370.0073437 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
370.0073437 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
163 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
23
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
504
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)
Solid
219.5 °C
Pharmaceuticals -> Listed in ZINC15
S55 | ZINC15PHARMA | Pharmaceuticals from ZINC15 | DOI:10.5281/zenodo.3247749
Follow these links to do a live 2D search or do a live 3D search for this compound, sorted by annotation score. This section is deprecated (see here for details), but these live search links provide equivalent functionality to the table that was previously shown here.
Same Parent, Exact Count
Mixtures, Components, and Neutralized Forms Count
Similar Compounds (2D)
Similar Conformers (3D)
Diuretic affects upon oral administration match those of furosemide. However, upon intravenous administration azosemide displays 5.5 to 8 times greater effect.
Diuretics
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%
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.
Volume of Distribution
Poor affinity for human tissue. Small apparent post-pseudodistribution Vd of 0.262 l/kg.
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.
Terminal half life 2-3 hours.
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.
Membrane
> 95% 4% protein binding to 4% human serum albumin at azosemide concentrations of 10-100ug/ml, using equilibrium dialysis.
Patents are available for this chemical structure:
https://patentscope.wipo.int/search/en/result.jsf?inchikey=HMEDEBAJARCKCT-UHFFFAOYSA-N
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- PATENTSCOPE (WIPO)SID 388421517https://pubchem.ncbi.nlm.nih.gov/substance/388421517
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