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Piretanide

Piretanide structure

CAS No:
55837-27-9
Formula:
C17H18N2O5S
Chemical Name:
Piretanide
Synonyms:
Benzoic acid,3-(aminosulfonyl)-4-phenoxy-5-(1-pyrrolidinyl)-;3-(Aminosulfonyl)-4-phenoxy-5-(1-pyrrolidinyl)benzoic acid;Piretanide;HOE 118;Arelix;S 73-4118;Diumax;Tauliz;Eurelix;Arlix
Categories:
Analytical Chemistry > Standard

Description

Pale Yellow Solid

Piretanide is an aromatic ether.|Piretanide (INN, trade names Arelix, Eurelix, Tauliz) has been synthesized in 1973 at Hoechst AG (Germany) as a loop diuretic compound by using a then-new method for introducing cyclic amine residues in an aromatic nucleus in the presence of other aromatically bonded functional groups.|Piretanide is a sulfamoylbenzoic acid belonging to the class of loop diuretics. Piretanide is structurally related to furosemide and bumetanide.

Piretanide Basic Attributes

Molecular Weight：

362.4

Exact Mass：

362.40

EC Number：

259-852-9

UNII：

DQ6KK6GV93

DSSTox ID：

DTXSID2023488

NCI Thesaurus Code：

C66419

ATC Code：

C - Cardiovascular system

HScode：

2935009090

Characteristics

PSA：

118

XLogP3：

3.92

Appearance：

Pale yellow powder.

Density：

1.415 g/cm3

Melting Point：

225-227 °C

Boiling Point：

597.7ºC at 760 mmHg

Flash Point：

315.3ºC

Refractive Index：

1.64

Toxicity：

LD50 in rats, mice (mg/kg): 5601, 3672 orally (Merkel)

Safety Information

Precautionary statement(s)：

P273, P501

Hazard Statements：

H412

GHS Classification：

H412 (100%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]|P273, and P501|Aggregated GHS information provided by 3 companies from 2 notifications to the ECHA C&L Inventory.

Drug Information

MeSH：

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. (See all compounds classified as Sodium Potassium Chloride Symporter Inhibitors.)|Agents that promote the excretion of urine through their effects on kidney function. (See all compounds classified as Diuretics.)

MeSH Entry Terms：

4-phenoxy-3-pyrrolidin-1-yl-5-sulfamoylbenzoic acid

Piretanide Use and Manufacturing

Uses

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

Use Classification：

Pharmaceuticals

Computed Properties

Molecular Weight:362.4
XLogP3:2.2
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:5
Exact Mass:362.09364285
Monoisotopic Mass:362.09364285
Topological Polar Surface Area:118
Heavy Atom Count:25
Complexity:564
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes