4-phenoxy-3-[(2,2,5,5-2H4)pyrrolidin-1-yl]-5-sulfamoylbenzoic acid

• ChemBase ID: 176787
• Molecular Formular: C17H18N2O5S
• Molecular Mass: 362.40022
• Monoisotopic Mass: 362.09364269
• SMILES: c1c(c(c(cc1C(=O)O)S(=O)(=O)N)Oc1ccccc1)N1CCCC1
• Canonical SMILES: OC(=O)c1cc(N2CCCC2)c(c(c1)S(=O)(=O)N)Oc1ccccc1
• InChI: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-phenoxy-3-[(2,2,5,5-^2H₄)pyrrolidin-1-yl]-5-sulfamoylbenzoic acid
• IUPAC Traditional name: 4-phenoxy-3-[(2,2,5,5-^2H₄)pyrrolidin-1-yl]-5-sulfamoylbenzoic acid
• Synonyms: 3-(Aminosulfonyl)-4-phenoxy-5-(1-pyrrolidinyl-d4)benzoic Acid; Arelix-d4; Arlix-d4; Diumax-d4; Eurelix-d4; HOE 118-d4; S 73-4118-d4; Tauliz-d4; Piretanide-d4 (Major)

Database IDs

• CAS Number: 1246816-90-9
• PubChem SID: 164232697
• PubChem CID: 71751694

CALCULATED PROPERTIES

• Acid pKa: 4.6754136
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.3666213
• LogD (pH = 7.4): -0.4132289
• Log P: 2.250988
• Molar Refractivity: 93.6825 cm^3
• Polarizability: 36.09539 Å^3
• Polar Surface Area: 109.93 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Pale Yellow Solid
• Melting Point: 219-221-2°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - P508702

Labelled Piretanide (P508700). High-ceiling loop diuretic; structurally related to Bumetanide (B689550). Diuretic.

REFERENCES

• Merkel, W., et al.: Eur. J. Med. Chem., 11, 399 (1976)
• Pozet, N., et al.: Br. J. Clin. Pharmacol., 9, 577 (1976)
• Clissold, S.P., et al.: Drugs, 29, 489 (1976)