| Identification | More | [Name]
Pentamidine isethionate | [CAS]
140-64-7 | [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
PENTAMIDINE ISETHIONATE NMDA ANTAGONIST, NEUR
Pentamide Isethionate
PENTAMIDINE DIISETHIONATE
PENTAMINIDE ISETIONATE
PENTAMINE ISETHIONATE
p,p'-[Pentamethylenedioxy] dibenzamidine bis[β-hydroxyethanesulfonate]
4,4μ-(Pentamethylenedioxy)dibenzamidine bis(2-hydroxyethanesulfonate), 1,5-Bis(p-amidinophenoxy)pentane bis(2-hydroxyethanesulfonate salt)
Benambax
Benzamidine, 4,4'-(pentamethylenedioxy)di-, bis(beta-hydroxyethanesulfonate)
Diamidine
Pentacarinat
2512RP | [EINECS(EC#)]
205-424-1 | [Molecular Formula]
C23H36N4O10S2 | [MDL Number]
MFCD00079213 | [Molecular Weight]
592.68 | [MOL File]
140-64-7.mol |
| Chemical Properties | Back Directory | [Appearance]
White or almost white powder or colourless crystals, hygroscopic. | [Melting point ]
188-194 °C(lit.)
| [storage temp. ]
−20°C
| [solubility ]
Freely soluble in water, sparingly soluble in ethanol (96 per cent), practically insoluble in methylene chloride. | [form ]
powder
| [color ]
White to Off-White | [Merck ]
13,7192 | [Stability:]
Hygroscopic | [InChIKey]
YBVNFKZSMZGRAD-UHFFFAOYSA-N | [CAS DataBase Reference]
140-64-7(CAS DataBase Reference) | [EPA Substance Registry System]
140-64-7(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R43:May cause sensitization by skin contact. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37:Wear suitable protective clothing and gloves . | [RIDADR ]
3249 | [WGK Germany ]
3
| [RTECS ]
CV6500000
| [HazardClass ]
6.1(b) | [PackingGroup ]
III | [HS Code ]
2925294500 | [Toxicity]
LD50 intraperitoneal in mouse: 63mg/kg |
| Hazard Information | Back Directory | [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. | [Reactivity Profile]
Can decompose on prolonged exposure to light. | [Air & Water Reactions]
Hygroscopic. May be sensitive to prolonged exposure to air. Aqueous solutions deteriorate on storage. Water soluble. | [Fire Hazard]
Flash point data for this chemical are not available; however, PENTAMIDINE ISETHIONATE is probably combustible. | [Chemical Properties]
White or almost white powder or colourless crystals, hygroscopic. | [Originator]
Nebupent,Fujisawa Healthcare Inc ,USA | [Uses]
Antiparasitic | [Uses]
Has been widely used as a drug to treat protozoal diseases, such as malaria, amoebic dysentery and trypanosomiasis. It has also been shown to be effective for both prophylaxis of pneumocystic carinii pneumonia (PCC). | [Definition]
ChEBI: An organosulfonate salt obtained by reaction of pentamidine with two equivalents of 2-hydroxyethylsulfonic acid. | [Manufacturing Process]
2.5 g of p,p'-dicyano-1,5-diphenoxy-pentane (obtained by the interaction of phydroxybenzonitrile and pentamethylene-dibromide in aqueous alkaline solution, melting point 114°C) are dissolved in 15 cc of nitrobenzene and 2.5 cc of absolute ethyl alcohol added. The solution is saturated with dry hydrochloric acid gas at 0°C and allowed to stand for 48 h. It is then diluted with dry ether and the precipitated 1,5-diphenoxypentane, 4,4'di(ethoxycarbonimidoyl) dihydrochlorid is filtered and washed with ether.
4 g of 1,5-diphenoxypentane, 4,4'-di(ethoxycarbonimidoyl) dihydrochloride are mixed with 30 cc. of 6 % ethyl alcoholic ammonia and heated in a closed vessel at 50°C for 5 h. The alcohol is removed and the residual 1,5diphenoxypentane, 4,4'-diamidino dihydrochloride is twice recrystallised fromdilute hydrochloric acid and finally purifled by dissolving in water and precipitating with acetone. Its melts at 236°C, dec.
Pentamidine isetionate salt may be produced by the reaction pentamidine base with isethionic acid. | [Therapeutic Function]
Antiprotozoal | [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. |
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