PROPAMIDINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C17H20N4O2
Molecular Weight	312.3663
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC(=N)C1=CC=C(OCCCOC2=CC=C(C=C2)C(N)=N)C=C1

InChI

InChIKey=WTFXJFJYEJZMFO-UHFFFAOYSA-N

InChI=1S/C17H20N4O2/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/h2-9H,1,10-11H2,(H3,18,19)(H3,20,21)

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
Treatment of experimental pneumocystosis: review of 7 years of experience and development of a new system for classifying antimicrobial drugs.	1992 Sep	1416885
New drug developments for opportunistic infections in immunosuppressed patients: Pneumocystis carinii.	1995 Nov 24	7490723
1,5-Bis(4-amidinophenoxy)pentane (pentamidine) is a potent inhibitor of [3H]idazoxan binding to imidazoline I2 binding sites.	1998 Jul 17	9721046
Structure-in vitro activity relationships of pentamidine analogues and dication-substituted bis-benzimidazoles as new antifungal agents.	1998 Oct	9756747
Atypical presentation of Acanthamoeba keratitis.	2001 Oct	11588431
Persistently culture positive acanthamoeba keratitis: in vivo resistance and in vitro sensitivity.	2003 Aug	12917179
Mechanisms of arsenical and diamidine uptake and resistance in Trypanosoma brucei.	2003 Oct	14555482
Are cataract and iris atrophy toxic complications of medical treatment of acanthamoeba keratitis?	2004 Apr	15043548
Methicillin-resistant Staphylococcus aureus clones, Western Australia.	2006 Feb	16494749
Antibacterial resistance and their genetic location in MRSA isolated in Kuwait hospitals, 1994-2004.	2006 Nov 25	17125522
Bilateral acanthamoeba keratitis.	2008 Feb	18222188
Evaluation of Antioxidant and Wound Healing Effects of Alcoholic and Aqueous Extract of Ocimum sanctum Linn in Rats.	2008 Mar	18317555
Rapidly progressive cataract and iris atrophy during treatment of Acanthamoeba keratitis.	2008 May	18452764
Medical management approach to infectious keratitis.	2008 May-Jun	18417822
Medical treatment for combined Fusarium and Acanthamoeba keratitis.	2009 Mar	18507727
The dissemination of ST80-SCCmec-IV community-associated methicillin resistant Staphylococcus aureus clone in Kuwait hospitals.	2010 Nov 4	21050425
A retrospective study of nine cases of Acanthamoeba keratitis.	2010 Oct 21	21060670
First report of a mixed infection due to Acanthamoeba genotype T3 and Vahlkampfia in a cosmetic soft contact lens wearer in Iran.	2010 Sep	19857491

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

Official Name

English

4,4'-(TRIMETHYLENEDIOXY)DIBENZAMIDINE

Systematic Name

English

M&B 782 FREE BASE

Code

English

propamidine [INN]

Common Name

English

4,4'-(TRIMETHYLEDEDIOXY)DIBENZAMIDINE

Common Name

English

M&B-782 FREE BASE

Code

English

Propamidine [WHO-DD]

Common Name

English

PROPAMIDINE [MI]

Common Name

English

4,4'-(1,3-PROPANEDIYLBIS(OXY)BIS(BENZENECARBOXIMIDAMIDE)

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C277