140-64-7

Basic information

• Product Name: Pentamidine isethionate
• Synonyms: 1,5-BIS(P-AMIDINOPHENOXY)PENTANE BIS(2-HYDROXYETHANESULFONATE SALT);1,5-BIS[P-AMIDINOPHENOXY]PENTANE BIS[2-HYDROXYETHANESULFONATE SALT] ISETHIONATE SALT;4,4'-(PENTAMETHYLENEDIOXY)DIBENZAMIDE BIS(2-HYDROXYETHANESULFONATE);4,4'-(PENTAMETHYLENEDIOXY)DIBENZAMIDINE, BIS-2-HYDROXYETHANESULFONATE;PENTAMIDINE ISETHIONATE;PENTAMIDINE ISETHIONATE SALT;4,4'-(pentamethylenedioxy)dibenzamidine bis(2-hyd;pentamidine isetionate
• CAS NO: 140-64-7
• Molecular Formula: 2C₂H₆O₄S*C₁₉H₂₄N₄O₂
• Molecular Weight: 592.68
• EINECS: 205-424-1
• Product Categories: API;HIV/AIDS/Related Products;Amines;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 140-64-7.mol
• Article Data: 1

Chemical Properties

• Melting Point: 188-194 °C(lit.)
• Boiling Point: 539.4 °C at 760 mmHg
• Flash Point: 280 °C
• Appearance: /powder
• Storage Temp.: −20°C
• Solubility: Freely soluble in water, sparingly soluble in ethanol (96 per cent), practically insoluble in methylene chloride.
• Stability: Hygroscopic
• Merck: 13,7192
• CAS DataBase Reference: Pentamidine isethionate(CAS DataBase Reference)
• NIST Chemistry Reference: Pentamidine isethionate(140-64-7)
• EPA Substance Registry System: Pentamidine isethionate(140-64-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-43
• Safety Statements: 26-36/37
• RIDADR: 3249
• WGK Germany: 3
• RTECS: CV6500000
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 140-64-7(Hazardous Substances Data)

Usage

Chemical Properties

White or almost white powder or colourless crystals, hygroscopic.

Uses

Different sources of media describe the Uses of 140-64-7 differently. You can refer to the following data:
1. 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
2. Antiparasitic

Definition

ChEBI: An organosulfonate salt obtained by reaction of pentamidine with two equivalents of 2-hydroxyethylsulfonic acid.

Therapeutic Function

Antiprotozoal

General Description

Odorless white or almost white crystals or powder. Odor also reported as a slight butyric odor. Very bitter taste. pH (5% aqueous solution) 4.5-6.5.

Air & Water Reactions

Hygroscopic. May be sensitive to prolonged exposure to air. Aqueous solutions deteriorate on storage. Water soluble.

Reactivity Profile

Can decompose on prolonged exposure to light.

Fire Hazard

Flash point data for Pentamidine isethionate are not available; however, Pentamidine isethionate is probably combustible.

Biological Activity

Antimicrobial. Neuroprotective; inhibits constitutive nitric oxide synthase in the brain and acts as a NMDA glutamate receptor antagonist.

Biochem/physiol Actions

Neuroprotective; inhibits constitutive nitric oxide synthase in the brain; NMDA glutamate receptor antagonist.

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.

Metabolism

Extensively hepatically metabolised. Renal clearance accounts for <5% of the plasma clearance of pentamidine.

Synthetic route

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

Conditions	Yield
In ethanol; water at 45 - 50℃; for 24h;	83%

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

Conditions	Yield
With hydrogenchloride In water Heating;

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

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

Upstream product

• 1252-44-4 4,4'-pentanediyldioxy-bis-benzimidic acid diethyl ester 
• 57267-78-4 isethionic acid ammonium salt 

Related news

Monitoring the response of patients with cutaneous leishmaniasis to treatment with Pentamidine isethionate (cas 140-64-7) by quantitative real‐time PCR, and identification of Leishmania parasites not responding to therapy09/29/2019

Background Leishmania (Viannia) guyanensis is believed to be the principal cause of cutaneous leishmaniasis (CL) in Suriname. This disease is treated with pentamidine isethionate (PI), but treatment failure has increasingly been reported.Aim To evaluate PI for its clinical efficacy, to compare p...detailed

Physical characterization of Pentamidine isethionate (cas 140-64-7) during freeze‐drying—relevance to development of stable lyophilized product10/01/2019

The purpose of this study was to perform physical characterization of pentamidine isethionate (PI) in frozen and freeze‐dried systems and to monitor the phase behavior during all the stages of freeze‐drying. Frozen aqueous PI solutions as well as the final lyophiles were characterized by diffe...detailed

Relevant articles and documents

Synthesis, Spectroscopic Properties and Antileishmanial Screening of some Pentamidine Analogues

Pentamidine, the diamidine drug of choice is used for the treatment of antimony resistant leishmanial infection.A modified method for preparation of the water-soluble isethionate salt of pentamidine has been developed using p-hydroxybenzaldehyde as starting material.Beside the synthesis of the dimethoxy analogues of pentamidine hydrochloride and pentamidine isethionate, two compounds have been prepared by substitution of amidino groups of pentamidine and its dimethoxy analogue by imidazoline moieties.Cmr spectral data of the compounds have been assigned and the in vitro antileishmanial activity of the analogues were compared with pentamidine isethionate using Leishmania donovani UR-6 strain.