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]
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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)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

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: CHEBI:32015
CAS Number: 55837-27-9
DrugBank ID: DB02925
TTD ID: D09NNS

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]

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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]

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Molecular Interaction Atlas (MIA)

MIA Detail

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.