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55837-27-9 molecular structure
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4-phenoxy-3-(pyrrolidin-1-yl)-5-sulfamoylbenzoic acid

ChemBase ID: 2635
Molecular Formular: C17H18N2O5S
Molecular Mass: 362.40022
Monoisotopic Mass: 362.09364269
SMILES and InChIs

SMILES:
NS(=O)(=O)c1cc(cc(N2CCCC2)c1Oc1ccccc1)C(=O)O
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

Cite this record

CBID:2635 http://www.chembase.cn/molecule-2635.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
4-phenoxy-3-(pyrrolidin-1-yl)-5-sulfamoylbenzoic acid
IUPAC Traditional name
piretanide
Brand Name
Piretanide (JAN)
Arelix (TN)
Synonyms
Piretanide
3-(Aminosulfonyl)-4-phenoxy-5-(1-pyrrolidinyl)benzoic Acid
Arelix
Arlix
Diumax
Eurelix
HOE 118
S 73-4118
Tauliz
CAS Number
55837-27-9
PubChem SID
46507197
160966084
PubChem CID
4849

DATA SOURCES

DATA SOURCES

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Data Source Data ID Price
TRC
P508700 external link Add to cart Please log in.

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 4.6754136  H Acceptors
H Donor LogD (pH = 5.5) 1.3666213 
LogD (pH = 7.4) -0.4132289  Log P 2.250988 
Molar Refractivity 93.6825 cm3 Polarizability 36.094254 Å3
Polar Surface Area 109.93 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 2.2  LOG S -3.6 
Solubility (Water) 9.14e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
DMSO expand Show data source
Methanol expand Show data source
Apperance
Pale Yellow Solid expand Show data source
Melting Point
219-221°C (dec.) expand Show data source
Storage Condition
-20°C Freezer expand Show data source
MSDS Link
Download expand Show data source
Certificate of Analysis
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DETAILS

DETAILS

DrugBank DrugBank TRC TRC
DrugBank - DB02925 external link
Drug information: experimental
Toronto Research Chemicals - P508700 external link
High-ceiling loop diuretic; structurally related to Bumetanide (B689550). Diuretic.

REFERENCES

REFERENCES

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  • • 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)
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PATENTS

PATENTS

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INTERNET

INTERNET

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