Details of the Drug

General Information of Drug (ID: DM0SCDR)

Drug Name
Piretanide
Synonyms
piretanide; 55837-27-9; Tauliz; Arlix; 4-phenoxy-3-(pyrrolidin-1-yl)-5-sulfamoylbenzoic acid; Piretanido [Spanish]; HOE 118; Piretanidum [INN-Latin]; Piretanido [INN-Spanish]; UNII-DQ6KK6GV93; Arelix (TN); C17H18N2O5S; EINECS 259-852-9; Hoe-118; BRN 5633965; DQ6KK6GV93; 4-phenoxy-3-pyrrolidin-1-yl-5-sulfamoylbenzoic acid; 4-Phenoxy-3-(1-pyrrolidinyl)-5-sulfamoylbenzoic acid; S 734118; S 73 4118; NCGC00016878-01; 3-(Aminosulfonyl)-4-phenoxy-5-(1-pyrrolidinyl)-benzoic acid; Benzoic acid, 3-(aminosulfonyl)-4-phenoxy-5-(1-pyrrolidin
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
ATC Code
C03CA03: Piretanide
C03CA: Sulfonamides, plain
C03C: HIGH-CEILING DIURETICS
C03: DIURETICS
C: CARDIOVASCULAR SYSTEM
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 362.4
Logarithm of the Partition Coefficient (xlogp) 2.2
Rotatable Bond Count (rotbonds) 5
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 7
ADMET Property
Bioavailability
92% of drug becomes completely available to its intended biological destination(s) [2]
Clearance
The drug present in the plasma can be removed from the body at the rate of 3.1 mL/min/kg [3]
Half-life
The concentration or amount of drug in body reduced by one-half in 1.3 hours [3]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 0.55187 micromolar/kg/day [4]
Unbound Fraction
The unbound fraction of drug in plasma is 0.058% [3]
Vd
Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 0.17 L/kg [3]
Chemical Identifiers
Formula
C17H18N2O5S
IUPAC Name
4-phenoxy-3-pyrrolidin-1-yl-5-sulfamoylbenzoic acid
Canonical SMILES
C1CCN(C1)C2=C(C(=CC(=C2)C(=O)O)S(=O)(=O)N)OC3=CC=CC=C3
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
Cross-matching ID
PubChem CID
4849
ChEBI ID
CHEMBL349803
CAS Number
55837-27-9
UNII
DQ6KK6GV93
DrugBank ID
DB02925
TTD ID
D09NNS
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug Pharmacogenomic Perturbation (DPP)NEW Click to Jump to the Detailed DPP Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Solute carrier family 12 member 1 (SLC12A1) TTS087L S12A1_HUMAN Blocker [5]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Solute carrier family 12 member 2 (SLC12A2) OT3ZJ3LH S12A2_HUMAN Gene/Protein Processing [6]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 4742).
2 Critical Evaluation of Human Oral Bioavailability for Pharmaceutical Drugs by Using Various Cheminformatics Approaches
3 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
4 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
5 Peripheral and central antinociceptive action of Na+-K+-2Cl- cotransporter blockers on formalin-induced nociception in rats. Pain. 2005 Mar;114(1-2):231-8.
6 Azosemide is more potent than bumetanide and various other loop diuretics to inhibit the sodium-potassium-chloride-cotransporter human variants hNKCC1A and hNKCC1B. Sci Rep. 2018 Jun 29;8(1):9877. doi: 10.1038/s41598-018-27995-w.