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Merck

P0547

Pentamidine isethionate salt

NMDA glutamate receptor antagonist, powder

Synonym(s):

1,5-Bis(p-amidinophenoxy)pentane bis(2-hydroxyethanesulfonate salt), 4,4′-(Pentamethylenedioxy)dibenzamidine bis(2-hydroxyethanesulfonate)

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About This Item

Linear Formula:
CH2[CH2CH2OC6H4C(=NH)NH2]2·2HOCH2CH2SO3H
CAS Number:
140-64-7
Molecular Weight:
592.68
NACRES:
NA.77
PubChem Substance ID:
24277999
UNSPSC Code:
12352200
EC Number:
205-424-1
MDL number:
MFCD00079213

Product Name

Pentamidine isethionate salt, powder

InChI key

YBVNFKZSMZGRAD-UHFFFAOYSA-N

InChI

1S/C19H24N4O2.2C2H6O4S/c20-18(21)14-4-8-16(9-5-14)24-12-2-1-3-13-25-17-10-6-15(7-11-17)19(22)23;2*3-1-2-7(4,5)6/h4-11H,1-3,12-13H2,(H3,20,21)(H3,22,23);2*3H,1-2H2,(H,4,5,6)

SMILES string

OCCS(O)(=O)=O.OCCS(O)(=O)=O.NC(=N)c1ccc(OCCCCCOc2ccc(cc2)C(N)=N)cc1

form

powder

mp

188-194 °C (lit.)

antibiotic activity spectrum

fungi

mode of action

enzyme | inhibits

originator

Celgene

storage temp.

−20°C

Quality Level

100

Gene Information

human ... GRIN1(2902), GRIN2A(2903), GRIN2B(2904), GRIN2C(2905), GRIN2D(2906), GRINA(2907), NOS1(4842), NOS2(4843), NOS2B(201288), NOS2C(645740), NOS3(4846)

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Application

Antimicrobial against Pneumocystis carinii.
Pentamidine isethionate salt has been used:
  • as a positive control for anti-leishmanial, anti-plasmodial and cytotoxic assays
  • as a prototypical compound to analyse the inhibitor effect on human ether-a-go-go-related gene (HERG) K+ channel trafficking
  • as an anti-leishmanial agent in promastigotes

Biochem/physiol Actions

Neuroprotective; inhibits constitutive nitric oxide synthase in the brain; NMDA glutamate receptor antagonist.
Pentamidine isethionate is used as a second line drug for leishmaniasis.

Features and Benefits

This compound was developed by Celgene. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

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Certificates of Analysis (COA)

Lot/Batch Number
0000274391
0000274392
0000274393
0000274394
0000274392

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I J Reynolds et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 12(3), 970-975 (1992-03-01)
Acquired immunodeficiency syndrome (AIDS) is frequently associated with dementia. The wide spectrum of neurological abnormalities associated with this dementia may involve a neurotoxin that activates the NMDA subtype of glutamate receptor in neurons. We have found that the antimicrobial agent
Anti-leishmanial lindenane sesquiterpenes from Hedyosmum angustifolium
Acebey L, et al.
Planta Medica, 76(04), 365-368 (2010)
Drug-induced functional cardiotoxicity screening in stem cell-derived human and mouse cardiomyocytes: effects of reference compounds
Himmel HM
Journal of Pharmacological and Toxicological Methods, 68(1), 97-111 (2013)
Reduced Antimony Accumulation in ARM58-Overexpressing Leishmania infantum.
Schafer C, et al.
Antimicrobial Agents and Chemotherapy, 58(3), 1565-1574 (2014)
Lucia Acebey et al.
Planta medica, 76(4), 365-368 (2009-10-16)
The aim of this work is the isolation of anti-leishmanial compounds from the ethyl acetate extracts of the bark of HEDYOSMUM ANGUSTIFOLIUM. We have successfully isolated and characterized five sesquiterpenes: one new compound (oxyonoseriolide, 1), one compound isolated for the
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