Pentamidine isethionate

Base Information

• Chemical Name: Pentamidine isethionate
• CAS No.: 140-64-7
• Molecular Formula: C19H24N4O2^.2(C2H6O4S)
• Molecular Weight: 592.692
• Hs Code.: 2925294500
• European Community (EC) Number: 205-424-1
• UNII: V2P3K60DA2
• DSSTox Substance ID: DTXSID5023796
• Wikidata: Q26841221
• NCI Thesaurus Code: C29349
• RXCUI: 7995
• ChEMBL ID: CHEMBL361506
• Mol file: 140-64-7.mol

Synonyms:Diamidine;Lomidine;NebuPent;Pentacarinat;Pentam;Pentamidin;Pentamidine;Pentamidine Isethionate;Pentamidine Mesylate

Chemical Property of Pentamidine isethionate

Chemical Property:

• Appearance/Colour: COA
• Melting Point: 188-194 °C(lit.)
• Boiling Point: 539.4 °C at 760 mmHg
• Flash Point: 280 °C
• PSA: 284.16000
• LogP: 4.37750
• Storage Temp.: −20°C
• Solubility.: Freely soluble in water, sparingly soluble in ethanol (96 per cent), practically insoluble in methylene chloride.
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 14
• Exact Mass: 592.18728571
• Heavy Atom Count: 39
• Complexity: 493

Purity/Quality:

99% ^*data from raw suppliers

Pentamidine isethionate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-43
• Safety Statements: 26-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Uses -> Pharmaceuticals
• Canonical SMILES: C1=CC(=CC=C1C(=N)N)OCCCCCOC2=CC=C(C=C2)C(=N)N.C(CS(=O)(=O)O)O.C(CS(=O)(=O)O)O
• Recent ClinicalTrials: Hypertrophic Scar Prevention by Novel Topical Gel Application
• Recent EU Clinical Trials: A Phase IIa Exploratory Study of OCZ103-OS in Combination with Platinum-Gemcitabine based Doublet First Line Therapy in Stage IV Non-Small Cell Lung Cancer (NSCLC) Patients
• Uses: Pentamidine isethionate salt has been used:as a positive control for anti-leishmanial, anti-plasmodial and cytotoxic assaysas a prototypical compound to analyse the inhibitor effect on human ether-a-go-go-related gene (HERG) K+ channel traffickingas an anti-leishmanial agent in promastigotes Antiparasitic
• Therapeutic Function: Antiprotozoal
• Clinical Use: 4,4’-(Pentamethylenedioxy)dibenzamidine diisethionate(NebuPent, Pentam 300) is a water-soluble crystalline saltthat is stable to light and air. The principal use of pentamidineis for the treatment of pneumonia caused by the opportunisticpathogenic protozoan P. carinii, a frequent secondaryinvader associated with AIDS. The drug may beadministered by slow intravenous infusion or by deep intramuscularinjection for PCP. An aerosol form of pentamidineis used by inhalation for the prevention of PCP inhigh-risk patients infected with HIV who have a previoushistory of PCP infection or a low peripheral CD4+ lymphocytecount.Pentamidine has been used for the prophylaxis and treatmentof African trypanosomiasis. It also has some value fortreating visceral leishmaniasis. Pentamidine rapidly disappearsfrom the plasma after intravenous injection and is distributedto the tissues, where it is stored for a long period.This property probably contributes to the usefulness of thedrug as a prophylactic agent.
• Drug interactions: Potentially hazardous interactions with other drugs Anti-arrhythmics: increased risk of ventricular arrhythmias with amiodarone - avoid; possible increased risk of ventricular arrhythmias with disopyramide. Antibacterials: increased risk of ventricular arrhythmias with delamanid, moxifloxacin and parenteral erythromycin - avoid with moxifloxacin; increased risk of ventricular arrhythmias with parenteral pentamidine and telithromycin. Antidepressants: increased risk of ventricular arrhythmias with tricyclics; increased risk of ventricular arrhythmias with citalopram and escitalopram - avoid. Antimalarials: increased risk of ventricular arrhythmias with piperaquine with artenimol - avoid. Antipsychotics: increased risk of ventricular arrhythmias with amisulpride, droperidol and phenothiazines - avoid with amisulpride and droperidol. Antivirals: increased risk of hypocalcaemia with parenteral pentamidine and foscarnet; increased risk of ventricular arrhythmias with saquinavir - avoid. Cytotoxics: increased risk of ventricular arrhythmias with vandetanib - avoid. Ivabradine: increased risk of ventricular arrhythmias.

Technology Process of Pentamidine isethionate

There total 1 articles about Pentamidine isethionate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 83.0%

4,4'-pentanediyldioxy-bis-benzimidic acid diethyl ester (1252-44-4) + isethionic acid ammonium salt (57267-78-4) → pentamidine isothionate (140-64-7)

Guidance literature:

In ethanol; water; at 45 - 50 ℃; for 24h;

Reference yield:

pentamidine isothionate (140-64-7) → pentamidine hydrochloride

Guidance literature:

With hydrogenchloride; In water; Heating;

Reference yield:

C97H136N6O15 + pentamidine isothionate (140-64-7) → C97H136N6O15*C19H24N4O2*2C2H6O4S

Guidance literature:

In chloroform-d1; d⁽⁴⁾-methanol; at 24.84 ℃;

DOI:10.1039/c6ra08202e

upstream raw materials:

4,4'-pentanediyldioxy-bis-benzimidic acid diethyl ester

isethionic acid ammonium salt

Refernces