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

Molecular Formula	C2H6O4S
Molecular Weight	126.132
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C17H20N4O2
Molecular Weight	312.3663
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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
Analogues of 1,5-bis(4-amidinophenoxy)pentane (pentamidine) in the treatment of experimental Pneumocystis carinii pneumonia.	1990 Apr	2319567
Treatment of experimental pneumocystosis: review of 7 years of experience and development of a new system for classifying antimicrobial drugs.	1992 Sep	1416885
Structure-in vitro activity relationships of pentamidine analogues and dication-substituted bis-benzimidazoles as new antifungal agents.	1998 Oct	9756747
[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
Uptake of pentamidine in Trypanosoma brucei brucei is mediated by three distinct transporters: implications for cross-resistance with arsenicals.	2001 Mar	11179454
Genetic analysis of methicillin-resistant Staphylococcus aureus expressing high- and low-level mupirocin resistance.	2001 Oct	11599741
Atypical presentation of Acanthamoeba keratitis.	2001 Oct	11588431
[Acanthamoeba keratitis, a possible dibromo propamidine isethionate resistance].	2002 May	12023748
[Treatment of Acanthamoeba keratitis: possibilities, problems, and new approaches].	2003	15508774
Persistently culture positive acanthamoeba keratitis: in vivo resistance and in vitro sensitivity.	2003 Aug	12917179
Bilateral microsporidial keratoconjunctivitis in an immunocompetent non-contact lens wearer.	2003 May	12792484
A chromosomal location of the mupA gene in Staphylococcus aureus expressing high-level mupirocin resistance.	2003 May	12668579
Mechanisms of arsenical and diamidine uptake and resistance in Trypanosoma brucei.	2003 Oct	14555482
Persistent acanthamoeba keratitis in a non-contact lens wearer following exposure to bird seed dust.	2005 Mar	15722327
Acanthamoeba keratitis associated with misuse of daily disposable contact lenses.	2006 Dec	16945570
Good visual outcome after prompt treatment of acanthamoeba keratitis associated with overnight orthokeratology lens wear.	2007 Nov	17993830
Bilateral acanthamoeba keratitis.	2008 Feb	18222188
Prognostic factors affecting visual outcome in Acanthamoeba keratitis.	2008 Nov	18571729
Phenotypic and molecular characterization of Staphylococcus aureus isolates expressing low- and high-level mupirocin resistance in Nigeria and South Africa.	2009 Jan 28	19175912

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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:58:42 GMT 2023` Edited by `admin` on `Fri Dec 15 15:58:42 GMT 2023`
Record UNII	7T9IJ84C42
Record Status	`Validated (UNII)`
Record Version

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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