Piretanide

HCID 4849CAS 55837-27-9

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

piretanide55837-27-94-phenoxy-3-(pyrrolidin-1-yl)-5-sulfamoylbenzoic acidHOE 118Arlix4-phenoxy-3-pyrrolidin-1-yl-5-sulfamoylbenzoic acidPiretanidumHoe-118PiretanidaDTXSID2023488S 73 4118DQ6KK6GV93
Show more names
DiuMaxTaulizEurelixS 734118
Benzoic acid, 3-(aminosulfonyl)-4-phenoxy-5-(1-pyrrolidinyl)-S-73-4118DTXCID703488S-734118RefChem:863638C03CA03259-852-9Arelix

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

Experimental & physicochemical properties

LogP3.92

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).

Safety & regulation

GHS classification

GHS Classification · 4 items

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

Hazard Classes and CategoriesAquatic Chronic 3 (66.7%)

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 · 2 items

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 · 2 items

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

UsesUse (kg; approx.) in Germany (2009): >250;Consumption (g per capita; approx.) in Germany (2009): 0.00305;Calculated removal (%): 42.7
Use ClassificationPharmaceuticals

Applications

UsesHigh-ceiling loop diuretic; structurally related to Bumetanide (B689550). Diuretic.

Upstream & downstream products

Suppliers36 total

湖北威德利化学试剂有限公司17771473825 13385289472 · [email protected]
安耐吉化学&3A(安徽泽升科技有限公司)021-58432009 400-005-6266 · [email protected]
西安泽邦生物科技有限公司[email protected]
InvivoChem中国13549236410 · [email protected]
佛山宝诺生物科技有限公司0757-85921206 18520245316 · [email protected]

Additional notes

DefinitionChEBI: Piretanide is an aromatic ether.

Related reactions

22 records

Linked notes

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