PROPAMIDINE ISETHIONATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C17H20N4O2.2C2H6O4S
Molecular Weight	564.63
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OCCS(O)(=O)=O.OCCS(O)(=O)=O.NC(=N)C1=CC=C(OCCCOC2=CC=C(C=C2)C(N)=N)C=C1

InChI

InChIKey=WSOSYBUSMXEYDO-UHFFFAOYSA-N

InChI=1S/C17H20N4O2.2C2H6O4S/c18-16(19)12-2-6-14(7-3-12)22-10-1-11-23-15-8-4-13(5-9-15)17(20)21;2*3-1-2-7(4,5)6/h2-9H,1,10-11H2,(H3,18,19)(H3,20,21);2*3H,1-2H2,(H,4,5,6)

HIDE SMILES / InChI

Description
Sources: http://www.chemistwarehouse.com.au/buy/1688/Brolene-Eye-Drops-10ml

Propamidine, an aromatic diamidine compound, is widely used as an antimicrobial agent. Propamidine isethionate, the salt of propamidine with isethionic acid, is used in the treatment of Acanthamoeba infection. Diseases caused by Acanthamoeba include keratitis and granulomatous amoebic encephalitis.

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Mild short-term conjunctivitis 2 Sources: http://www.chemistwarehouse.com.au/buy/1688/Brolene-Eye-Drops-10ml	Curative		Basic research	Brolene Approved Use Unknown

PubMed

Title	Date	PubMed
Structure-activity relationships of analogs of pentamidine against Plasmodium falciparum and Leishmania mexicana amazonensis.	1990 Jul	2201254
Treatment of experimental pneumocystosis: review of 7 years of experience and development of a new system for classifying antimicrobial drugs.	1992 Sep	1416885
The accumulation of pentamidine and the toxic effects of the drug, its selected analogues and metabolites on isolated alveolar cells.	1993 Jun 4	8322368
Susceptibility of Encephalitozoon cuniculi to several drugs in vitro.	1995 Jun	7574513
1,5-Bis(4-amidinophenoxy)pentane (pentamidine) is a potent inhibitor of [3H]idazoxan binding to imidazoline I2 binding sites.	1998 Jul 17	9721046
Anti-Pneumocystis activities of aromatic diamidoxime prodrugs.	1998 Mar	9517949
Structure-in vitro activity relationships of pentamidine analogues and dication-substituted bis-benzimidazoles as new antifungal agents.	1998 Oct	9756747
Sequence specific recognition of ligand-DNA complexes studied by NMR.	2001 Apr	11281842
[Painless acanthamoeba keratitis].	2001 Aug	11573159
Aromatic polyamidines inhibiting the Tat-induced HIV-1 transcription recognize structured TAR-RNA.	2001 Aug	11572598
Encystation in Acanthamoeba castellanii: development of biocide resistance.	2001 Jan-Feb	11249185
Persistence of a clone of methicillin-resistant Staphylococcus aureus in a burns unit.	2001 Jun	11393293
Genetic analysis of methicillin-resistant Staphylococcus aureus expressing high- and low-level mupirocin resistance.	2001 Oct	11599741
[Acanthamoeba keratitis treated with propamidine and polyhexamethyl biguanide (PHMB)].	2002 Apr	12090104
Polyhydroxylated azepanes as new motifs for DNA minor groove binding agents.	2002 Jan 21	11755363
Progressive ulcerative keratitis related to the use of topical chlorhexidine gluconate (0.02%).	2002 Mar	11862106
Bilateral Acanthamoeba keratitis with late recurrence of the infection in a corneal graft: a case report.	2003 Apr	12747654
Treatment of Acanthamoeba keratitis.	2003 Aug	15482114
An atypical presentation of Acanthamoeba keratitis in a noncontact lens wearer.	2003 Jan	12769151
Antibacterial resistance and their genetic location in MRSA isolated in Kuwait hospitals, 1994-2004.	2006 Nov 25	17125522
Acanthamoeba keratitis due to Acanthamoeba genotype T4 in a non-contact-lens wearer in Turkey.	2007 Jan	17013653
[Painless acanthamoeba keratitis].	2007 May	17318475
Good visual outcome after prompt treatment of acanthamoeba keratitis associated with overnight orthokeratology lens wear.	2007 Nov	17993830
Acanthamoeba keratitis and contact lens wear.	2007 Sep	17697181
Multicomponent reactions in fungicide research: the discovery of mandipropamid.	2008 Feb 1	17962029
Evaluation of Antioxidant and Wound Healing Effects of Alcoholic and Aqueous Extract of Ocimum sanctum Linn in Rats.	2008 Mar	18317555
Medical management approach to infectious keratitis.	2008 May-Jun	18417822
Prognostic factors affecting visual outcome in Acanthamoeba keratitis.	2008 Nov	18571729
Enucleation following treatment with intravenous pentamidine for Acanthamoeba sclerokeratitis.	2010 Oct 5	20957062

Patents

Sample Use Guides

In Vivo Use Guide

1-2 drops in the affected eye 3-4 times daily, for not more than 1 week

Route of Administration: Topical

In Vitro Use Guide

There was compared the amoebicidal activity of the Brolene (propamidine isethionate, commercial product), propamidine isethionate and pentamidine isethionate (Pentam) in vitro against three different species of Acanthamoeba, and the drugs' corresponding biocompatibility with rabbit corneal epithelial and endothelial cell cultures. The results indicated that there were significant species differences in drug sensitivity. Propamidine (> 1,000 micrograms/ml) was clearly less effective than pentamidine (> 125 micrograms/ml) against A. castellanii, although equivalent potency (> 250 micrograms/ml) was observed against A. polyphaga. On the other hand, propamidine (> 31.25 micrograms/ml) was slightly more effective than pentamidine (> 62.5 micrograms/ml) against A. hatchetti.

Name

Type

Language

PROPAMIDINE ISETHIONATE

Common Name

English

PROPAMIDINE ISETHIONATE [MI]

Common Name

English

M&B 782

Code

English

M&B-782

Code

English

Propamidine isetionate [WHO-DD]

Common Name

English

PROPAMIDINE DIISETHIONATE

Common Name

English

BENZAMIDINE, 4,4'-(TRIMETHYLENEDIOXY)DI-, BIS(2-HYDROXYETHANESULFONATE)

Common Name

English

PROPAMIDINE ISETIONATE

Common Name

English

ETHANESULFONIC ACID, 2-HYDROXY-, COMPD. WITH 4,4'-(1,3-PROPANEDIYLBIS(OXY))BIS(BENZENECARBOXIMIDAMIDE) (2:1)

Common Name

English

PROPAMIDINE ISETIONATE [MART.]

Common Name

English

BROLENE DROPS

Brand Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

27288