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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 of PROPAMIDINE

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
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

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

Unknown
139594
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Basic research
Brolene

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Analogues of 1,5-bis(4-amidinophenoxy)pentane (pentamidine) in the treatment of experimental Pneumocystis carinii pneumonia.
1990 Apr
Structure-activity relationships of analogs of pentamidine against Plasmodium falciparum and Leishmania mexicana amazonensis.
1990 Jul
Treatment of experimental pneumocystosis: review of 7 years of experience and development of a new system for classifying antimicrobial drugs.
1992 Sep
The accumulation of pentamidine and the toxic effects of the drug, its selected analogues and metabolites on isolated alveolar cells.
1993 Jun 4
DNA-binding activity and biological effects of aromatic polyamidines.
1994 Feb 11
Susceptibility of Encephalitozoon cuniculi to several drugs in vitro.
1995 Jun
New drug developments for opportunistic infections in immunosuppressed patients: Pneumocystis carinii.
1995 Nov 24
1,5-Bis(4-amidinophenoxy)pentane (pentamidine) is a potent inhibitor of [3H]idazoxan binding to imidazoline I2 binding sites.
1998 Jul 17
Anti-Pneumocystis activities of aromatic diamidoxime prodrugs.
1998 Mar
Structure-in vitro activity relationships of pentamidine analogues and dication-substituted bis-benzimidazoles as new antifungal agents.
1998 Oct
Resistance of Acanthamoeba castellanii cysts to physical, chemical, and radiological conditions.
2002 Jun
[Treatment of Acanthamoeba keratitis: possibilities, problems, and new approaches].
2003
Bilateral Acanthamoeba keratitis with late recurrence of the infection in a corneal graft: a case report.
2003 Apr
Treatment of Acanthamoeba keratitis.
2003 Aug
Persistently culture positive acanthamoeba keratitis: in vivo resistance and in vitro sensitivity.
2003 Aug
An atypical presentation of Acanthamoeba keratitis in a noncontact lens wearer.
2003 Jan
Bilateral microsporidial keratoconjunctivitis in an immunocompetent non-contact lens wearer.
2003 May
A chromosomal location of the mupA gene in Staphylococcus aureus expressing high-level mupirocin resistance.
2003 May
Mechanisms of arsenical and diamidine uptake and resistance in Trypanosoma brucei.
2003 Oct
Laser in situ keratomileusis treatment for myopia after Acanthamoeba keratitis.
2004 Apr
Are cataract and iris atrophy toxic complications of medical treatment of acanthamoeba keratitis?
2004 Apr
Modelling bound ligands in protein crystal structures.
2004 Dec
Chronic microsporidial stromal keratitis in an immunocompetent, non-contact lens wearer.
2005 Jun
Persistent acanthamoeba keratitis in a non-contact lens wearer following exposure to bird seed dust.
2005 Mar
Diagnosis and management of Acanthamoeba keratitis.
2006 Aug
Acanthamoeba keratitis associated with misuse of daily disposable contact lenses.
2006 Dec
Methicillin-resistant Staphylococcus aureus clones, Western Australia.
2006 Feb
Antibacterial resistance and their genetic location in MRSA isolated in Kuwait hospitals, 1994-2004.
2006 Nov 25
Acanthamoeba keratitis due to Acanthamoeba genotype T4 in a non-contact-lens wearer in Turkey.
2007 Jan
[Painless acanthamoeba keratitis].
2007 May
Good visual outcome after prompt treatment of acanthamoeba keratitis associated with overnight orthokeratology lens wear.
2007 Nov
Acanthamoeba keratitis and contact lens wear.
2007 Sep
Bilateral acanthamoeba keratitis.
2008 Feb
Multicomponent reactions in fungicide research: the discovery of mandipropamid.
2008 Feb 1
Evaluation of Antioxidant and Wound Healing Effects of Alcoholic and Aqueous Extract of Ocimum sanctum Linn in Rats.
2008 Mar
Rapidly progressive cataract and iris atrophy during treatment of Acanthamoeba keratitis.
2008 May
Medical management approach to infectious keratitis.
2008 May-Jun
Prognostic factors affecting visual outcome in Acanthamoeba keratitis.
2008 Nov
Phenotypic and molecular characterization of Staphylococcus aureus isolates expressing low- and high-level mupirocin resistance in Nigeria and South Africa.
2009 Jan 28
The prevalence of antimicrobial resistance and carriage of virulence genes in Staphylococcus aureus isolated from food handlers in Kuwait City restaurants.
2009 Jun 16
Medical treatment for combined Fusarium and Acanthamoeba keratitis.
2009 Mar
A case of descemet's membrane rupture in a patient affected by Acanthamoeba Keratitis.
2009 Nov
Major role for cysteine proteases during the early phase of Acanthamoeba castellanii encystment.
2010 Apr
Drug-resistant severe Acanthamoeba keratitis caused by rare T5 Acanthamoeba genotype.
2010 May
Bilateral Acanthamoeba keratitis in Synergeyes contact lens wear: clinical and confocal microscopy findings.
2010 May
The dissemination of ST80-SCCmec-IV community-associated methicillin resistant Staphylococcus aureus clone in Kuwait hospitals.
2010 Nov 4
A retrospective study of nine cases of Acanthamoeba keratitis.
2010 Oct 21
Enucleation following treatment with intravenous pentamidine for Acanthamoeba sclerokeratitis.
2010 Oct 5
Propamidine decreas mitochondrial complex III activity of Botrytis cinerea.
2010 Sep
First report of a mixed infection due to Acanthamoeba genotype T3 and Vahlkampfia in a cosmetic soft contact lens wearer in Iran.
2010 Sep
Patents

Patents

CN101965843
2
US2804463
2

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 15:09:50 GMT 2023
Edited
by admin
on Fri Dec 15 15:09:50 GMT 2023
Record UNII
G20G12V769
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PROPAMIDINE
INN   MI   WHO-DD  
INN  
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
Created by admin on Fri Dec 15 15:09:50 GMT 2023 , Edited by admin on Fri Dec 15 15:09:50 GMT 2023
WHO-ATC S01AX15
Created by admin on Fri Dec 15 15:09:50 GMT 2023 , Edited by admin on Fri Dec 15 15:09:50 GMT 2023
WHO-VATC QS01AX15
Created by admin on Fri Dec 15 15:09:50 GMT 2023 , Edited by admin on Fri Dec 15 15:09:50 GMT 2023
WHO-VATC QD08AC03
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WHO-ATC D08AC03
Created by admin on Fri Dec 15 15:09:50 GMT 2023 , Edited by admin on Fri Dec 15 15:09:50 GMT 2023
Code System Code Type Description
CHEBI
87462
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PRIMARY
ECHA (EC/EINECS)
203-195-2
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PRIMARY
SMS_ID
100000081130
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PRIMARY
EVMPD
SUB10095MIG
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PRIMARY
DRUG CENTRAL
3493
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PRIMARY
INN
4182
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PRIMARY
EPA CompTox
DTXSID6048674
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PRIMARY
PUBCHEM
64949
Created by admin on Fri Dec 15 15:09:50 GMT 2023 , Edited by admin on Fri Dec 15 15:09:50 GMT 2023
PRIMARY
WIKIPEDIA
PROPAMIDINE
Created by admin on Fri Dec 15 15:09:50 GMT 2023 , Edited by admin on Fri Dec 15 15:09:50 GMT 2023
PRIMARY
RXCUI
34633
Created by admin on Fri Dec 15 15:09:50 GMT 2023 , Edited by admin on Fri Dec 15 15:09:50 GMT 2023
PRIMARY RxNorm
CAS
104-32-5
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PRIMARY
MESH
C005555
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PRIMARY
ALANWOOD
propamidine
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PRIMARY
ChEMBL
CHEMBL23013
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PRIMARY
NCI_THESAURUS
C82250
Created by admin on Fri Dec 15 15:09:50 GMT 2023 , Edited by admin on Fri Dec 15 15:09:50 GMT 2023
PRIMARY
FDA UNII
G20G12V769
Created by admin on Fri Dec 15 15:09:50 GMT 2023 , Edited by admin on Fri Dec 15 15:09:50 GMT 2023
PRIMARY
MERCK INDEX
m9181
Created by admin on Fri Dec 15 15:09:50 GMT 2023 , Edited by admin on Fri Dec 15 15:09:50 GMT 2023
PRIMARY Merck Index
DRUG BANK
DB13296
Created by admin on Fri Dec 15 15:09:50 GMT 2023 , Edited by admin on Fri Dec 15 15:09:50 GMT 2023
PRIMARY
Related Record Type Details
Structure of PROPAMIDINE ISETHIONATE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of PROPAMIDINE
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