Basic information
- Standard SMILES
NS(=O)(=O)c1cc(C(=O)O)cc(N2CCCC2)c1Oc1ccccc1- InChIKey
UJEWTUDSLQGTOA-UHFFFAOYSA-N- Molecular formula
- C17H18N2O5S
- Average molar mass
- 362.4 g/mol
- Monoisotopic mass
- 362.09364285
Names & identifiers
- Preferred name
- Piretanide
- IUPAC
- 4-phenoxy-3-pyrrolidin-1-yl-5-sulfamoylbenzoic acid
- English name
- Piretanide
- Molecular formula
- C17H18N2O5S
- Molecular weight
- 362.4
Names & synonyms
Show more names
Database identifiers
- CAS
55837-27-9- PubChem CID
- 4849
- DTXSID
DTXSID2023488- ChEMBL
CHEMBL349803- ChEBI
CHEBI:32015- UNII
- DQ6KK6GV93
- EC Number
- 259-852-9
- Nikkaji
- J3.520C
Properties
Computed structural properties
- XLogP
- 2.2
- Topological polar surface area
- 118 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 5
- Heavy atoms
- 25
- Formal charge
- 0
- Complexity
- 564
Experimental & physicochemical properties
Physicochemical properties
- Melting point
- 225 · 225-227°
- Boiling point
- 253 °C · 253°C (rough estimate)
- Density
- 1.3049 · 1.3049 (rough estimate)
- refractive index
- 1.651 · 1.6510 (estimate)
- storage temp.
- 2 · 2-8°C
- solubility
- Very slightly soluble in water, sparingly soluble in anhydrous ethanol. It shows polymorphism (5.9).
- pka
- 10.22 · 10.22±0.60(Predicted)
- form
- Solid
- color
- Pale-yellow platelets from MeOH (aq)
- Major Application
- pharmaceutical (small molecule)
- InChI
- 1S/C17H18N2O5S/c18-25(22,23)15-11-12(17(20)21)10-14(19-8-4-5-9-19)16(15)24-13-6-2-1-3-7-13/h1-3,6-7,10-11H,4-5,8-9H2,(H,20,21)(H2,18,22,23)
- InChIKey
- UJEWTUDSLQGTOA-UHFFFAOYSA-N
- SMILES
- [S](=O)(=O)(N)c1c(c(cc(c1)C(=O)O)N3CCCC3)Oc2ccccc2
- CAS DataBase Reference
- 55837 · 55837-27-9(CAS DataBase Reference)
- FDA UNII
- 6 KK6GV93 · DQ6KK6GV93
- ATC code
- 3 CA03 · C03CA03
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Hazard statements
- 412 · H412
- Precautionary statements
- 273 · P273-P501
- WGK Germany
- 3 · WGK 3
- Storage Class
- 11 · 11 - Combustible Solids
- Toxicity
- 50 in · LD50 in rats, mice (mg/kg): 5601, 3672 orally (Merkel)
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 33.3% (1 of 3) of reports.
H412 (66.7%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]
P273, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 3 reports by companies from 2 notifications to the ECHA C&L Inventory.;Reported as not meeting GHS hazard criteria per 1 of 3 reports by companies.;There is 1 notification provided by 2 of 3 reports by companies with hazard statement code(s).;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
Hazard information
Safety data
- wgk
- WGK 3
- Toxicity
- LD50 in rats, mice (mg/kg): 5601, 3672 orally (Merkel)
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H412
- Precautionary statements
- P273-P501
Chemistry & industry
Pharmacology
ATC Code
C - Cardiovascular system;C03 - Diuretics;C03C - High-ceiling diuretics;C03CA - Sulfonamides, plain;C03CA03 - Piretanide
QC - Cardiovascular system;QC03 - Diuretics;QC03C - High-ceiling diuretics;QC03CA - Sulfonamides, plain;QC03CA03 - Piretanide
MeSH Pharmacological Classification
Agents that promote the excretion of urine through their effects on kidney function.
Agents that inhibit SODIUM-POTASSIUM-CHLORIDE SYMPORTERS which are concentrated in the thick ascending limb at the junction of the LOOP OF HENLE and KIDNEY TUBULES, DISTAL. They act as DIURETICS. Excess use is associated with HYPOKALEMIA and HYPERGLYCEMIA.
Uses & manufacturing
Applications
UsesHigh-ceiling loop diuretic; structurally related to Bumetanide (B689550). Diuretic.
Upstream & downstream products
Upstream raw materials
Suppliers36 total
Additional notes
DefinitionChEBI: Piretanide is an aromatic ether.
Related reactions
Linked notes
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