Azosemide (HCID 2273)

Overview

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 thiophenes, a sulfonamide, a member of tetrazoles and a member of monochlorobenzenes.

Names & identifiers

Preferred name: Azosemide
IUPAC: 2-chloro-5-(2H-tetrazol-5-yl)-4-(thiophen-2-ylmethylamino)benzenesulfonamide
English name: Azosemide
Molecular formula: C12H11ClN6O2S2
Molecular weight: 370.84

Names & synonyms

azosemide27589-33-9AzosemidDiartAzosemidaAzosemidumLuretDTXSID7046910MR40VT1L8Z2-Chloro-5-(1H-tetrazol-5-yl)-N(sup 4)-2-thenylsulfanilamideBenzenesulfonamide, 2-chloro-5-(1H-tetrazol-5-yl)-4-((2-thienylmethyl)amino)-5-(4'-chloro-5'-sulfamoyl-2'-thenylaminophenyl)tetrazole

Show more names

SK-110ple1053DiurapidAZOSEMIDE HPLCAzosemide USP/EP/BP

DTXCID5026910CHEBI:312482-chloro-5-(2H-1,2,3,4-tetrazol-5-yl)-4-((thiophen-2-ylmethyl)amino)benzene-1-sulfonamide2-chloro-5-(2H-1,2,3,4-tetrazol-5-yl)-4-[(thiophen-2-ylmethyl)amino]benzene-1-sulfonamide5-(4-chloro-5-sulfamyl-2-thienylaminophenyl)tetrazoleRefChem:5606092-Chloro-5-(1H-tetrazol-5-yl)-4-((thien-2-ylmethyl)amino)benzenesulfonamide248-549-7

Database identifiers

CAS: 27589-33-9
PubChem CID: 2273
DTXSID: DTXSID7046910
ChEMBL: CHEMBL1097235
ChEBI: CHEBI:31248
UNII: MR40VT1L8Z
EC Number: 248-549-7
Nikkaji: J10.727A

Properties

Computed structural properties

XLogP: 1.5
Topological polar surface area: 163 Å²
Hydrogen bond donors: 3
Hydrogen bond acceptors: 8
Rotatable bonds: 5
Heavy atoms: 23
Formal charge: 0
Complexity: 504

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15

Melting Point219.5 °C

Physical DescriptionSolid

Physicochemical properties

Melting point: 218 · 218-221°
Boiling point: 221 °C · 221°C (rough estimate)
Density: 1.6843 · 1.6843 (rough estimate)
refractive index: 1.61 · 1.6100 (estimate)
storage temp.: 2 · under inert gas (nitrogen or Argon) at 2–8 °C
solubility: DMSO (Slightly), Methanol (Slightly, Heated)
form: Solid
pka: 3.58 · 3.58±0.10(Predicted)
color: Crystals
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)
InChIKey: HMEDEBAJARCKCT-UHFFFAOYSA-N
SMILES: C1(S(N)(=O)=O)=CC(C2=NNN=N2)=C(NCC2SC=CC=2)C=C1Cl
CAS DataBase Reference: 27589 · 27589-33-9(CAS DataBase Reference)
FDA UNII: 40 VT1L8Z · MR40VT1L8Z
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302+H312+H332-H315-H319-H227
Precautionary statements: 501 · P501-P261-P270-P210-P271-P264-P280-P370+P378-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330-P302+P352+P312-P304+P340+P312-P403+P235
Toxicity: 50 orl-rat: · LD50 orl-rat: 2545 mg/kg IYKEDH 18,666,87

Safety & regulation

Safety data

Toxicity: LD50 orl-rat: 2545 mg/kg IYKEDH 18,666,87
Signal word: Warning
Symbol(GHS): GHS07
Hazard statements: H302+H312+H332-H315-H319-H227
Precautionary statements: P501-P261-P270-P210-P271-P264-P280-P370+P378-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330-P302+P352+P312-P304+P340+P312-P403+P235

Chemistry & industry

Pharmacology

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

PharmacodynamicsDiuretic affects upon oral administration match those of furosemide. However, upon intravenous administration azosemide displays 5.5 to 8 times greater effect.

Mechanism of ActionExact 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.

Biological Half-LifeTerminal half life 2-3 hours.

Metabolism/MetabolitesConsiderable 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.

MeSH Pharmacological ClassificationAgents that promote the excretion of urine through their effects on kidney function.

Applications · 3 items

DescriptionAzosemide is a high-ceiling diuretic similiar in structure and profile to furosemide, albeit somewhat less potent and less bioavailable. It is useful in the treatment of congestive heart failure and similar edematous conditions.

UsesDiuretic.

UsesAzosemide is a high-ceiling diuretic agent. It is used in the treatment of edematous states and hypertension.

Upstream & downstream products

Upstream raw materials

Suppliers50 total

Hebei Zhuanglai Chemical Trading Co Ltd+86-16264648883 · [email protected]

杭州品高化工有限公司0571-87658025 · [email protected]

陕西缔都新材料有限公司029-63373950 17392216152 · [email protected]

河北展药生物科技有限公司15369953316 +8615369953316 · [email protected]

Hebei Yanxi Chemical Co., Ltd.+86-17531190177 · [email protected]

Additional notes · 1 item

DefinitionChEBI: 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 hyp rtension.