U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
149124
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Basic research
Brolene

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
The dissemination of ST80-SCCmec-IV community-associated methicillin resistant Staphylococcus aureus clone in Kuwait hospitals.
2010-11-04
A retrospective study of nine cases of Acanthamoeba keratitis.
2010-10-21
Enucleation following treatment with intravenous pentamidine for Acanthamoeba sclerokeratitis.
2010-10-05
Propamidine decreas mitochondrial complex III activity of Botrytis cinerea.
2010-09
First report of a mixed infection due to Acanthamoeba genotype T3 and Vahlkampfia in a cosmetic soft contact lens wearer in Iran.
2010-09
Drug-resistant severe Acanthamoeba keratitis caused by rare T5 Acanthamoeba genotype.
2010-05
Bilateral Acanthamoeba keratitis in Synergeyes contact lens wear: clinical and confocal microscopy findings.
2010-05
Major role for cysteine proteases during the early phase of Acanthamoeba castellanii encystment.
2010-04
A case of descemet's membrane rupture in a patient affected by Acanthamoeba Keratitis.
2009-11
The prevalence of antimicrobial resistance and carriage of virulence genes in Staphylococcus aureus isolated from food handlers in Kuwait City restaurants.
2009-06-16
Medical treatment for combined Fusarium and Acanthamoeba keratitis.
2009-03
Phenotypic and molecular characterization of Staphylococcus aureus isolates expressing low- and high-level mupirocin resistance in Nigeria and South Africa.
2009-01-28
Prognostic factors affecting visual outcome in Acanthamoeba keratitis.
2008-11
Rapidly progressive cataract and iris atrophy during treatment of Acanthamoeba keratitis.
2008-05
Medical management approach to infectious keratitis.
2008-04-18
Evaluation of Antioxidant and Wound Healing Effects of Alcoholic and Aqueous Extract of Ocimum sanctum Linn in Rats.
2008-03
Multicomponent reactions in fungicide research: the discovery of mandipropamid.
2008-02-01
Bilateral acanthamoeba keratitis.
2008-02
Good visual outcome after prompt treatment of acanthamoeba keratitis associated with overnight orthokeratology lens wear.
2007-11
Acanthamoeba keratitis and contact lens wear.
2007-09
[Painless acanthamoeba keratitis].
2007-05
Acanthamoeba keratitis due to Acanthamoeba genotype T4 in a non-contact-lens wearer in Turkey.
2007-01
Acanthamoeba keratitis associated with misuse of daily disposable contact lenses.
2006-12
Antibacterial resistance and their genetic location in MRSA isolated in Kuwait hospitals, 1994-2004.
2006-11-25
Diagnosis and management of Acanthamoeba keratitis.
2006-08
Methicillin-resistant Staphylococcus aureus clones, Western Australia.
2006-02
Chronic microsporidial stromal keratitis in an immunocompetent, non-contact lens wearer.
2005-06
Persistent acanthamoeba keratitis in a non-contact lens wearer following exposure to bird seed dust.
2005-03
Modelling bound ligands in protein crystal structures.
2004-12
Laser in situ keratomileusis treatment for myopia after Acanthamoeba keratitis.
2004-04
Are cataract and iris atrophy toxic complications of medical treatment of acanthamoeba keratitis?
2004-04
Mechanisms of arsenical and diamidine uptake and resistance in Trypanosoma brucei.
2003-10
Treatment of Acanthamoeba keratitis.
2003-08
Persistently culture positive acanthamoeba keratitis: in vivo resistance and in vitro sensitivity.
2003-08
Bilateral microsporidial keratoconjunctivitis in an immunocompetent non-contact lens wearer.
2003-05
A chromosomal location of the mupA gene in Staphylococcus aureus expressing high-level mupirocin resistance.
2003-05
Bilateral Acanthamoeba keratitis with late recurrence of the infection in a corneal graft: a case report.
2003-04
An atypical presentation of Acanthamoeba keratitis in a noncontact lens wearer.
2003-01
[Treatment of Acanthamoeba keratitis: possibilities, problems, and new approaches].
2003
Resistance of Acanthamoeba castellanii cysts to physical, chemical, and radiological conditions.
2002-06
Structure-in vitro activity relationships of pentamidine analogues and dication-substituted bis-benzimidazoles as new antifungal agents.
1998-10
1,5-Bis(4-amidinophenoxy)pentane (pentamidine) is a potent inhibitor of [3H]idazoxan binding to imidazoline I2 binding sites.
1998-07-17
Anti-Pneumocystis activities of aromatic diamidoxime prodrugs.
1998-03
New drug developments for opportunistic infections in immunosuppressed patients: Pneumocystis carinii.
1995-11-24
Susceptibility of Encephalitozoon cuniculi to several drugs in vitro.
1995-06
DNA-binding activity and biological effects of aromatic polyamidines.
1994-02-11
The accumulation of pentamidine and the toxic effects of the drug, its selected analogues and metabolites on isolated alveolar cells.
1993-06-04
Treatment of experimental pneumocystosis: review of 7 years of experience and development of a new system for classifying antimicrobial drugs.
1992-09
Structure-activity relationships of analogs of pentamidine against Plasmodium falciparum and Leishmania mexicana amazonensis.
1990-07
Analogues of 1,5-bis(4-amidinophenoxy)pentane (pentamidine) in the treatment of experimental Pneumocystis carinii pneumonia.
1990-04
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 Mon Mar 31 17:48:39 GMT 2025
Edited
by admin
on Mon Mar 31 17:48:39 GMT 2025
Record UNII
G20G12V769
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PROPAMIDINE
INN   MI   WHO-DD  
INN  
Official Name English
4,4'-(1,3-PROPANEDIYLBIS(OXY)BIS(BENZENECARBOXIMIDAMIDE)
Preferred 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
Classification Tree Code System Code
NCI_THESAURUS C277
Created by admin on Mon Mar 31 17:48:39 GMT 2025 , Edited by admin on Mon Mar 31 17:48:39 GMT 2025
WHO-ATC S01AX15
Created by admin on Mon Mar 31 17:48:39 GMT 2025 , Edited by admin on Mon Mar 31 17:48:39 GMT 2025
WHO-VATC QS01AX15
Created by admin on Mon Mar 31 17:48:39 GMT 2025 , Edited by admin on Mon Mar 31 17:48:39 GMT 2025
WHO-VATC QD08AC03
Created by admin on Mon Mar 31 17:48:39 GMT 2025 , Edited by admin on Mon Mar 31 17:48:39 GMT 2025
WHO-ATC D08AC03
Created by admin on Mon Mar 31 17:48:39 GMT 2025 , Edited by admin on Mon Mar 31 17:48:39 GMT 2025
Code System Code Type Description
CHEBI
87462
Created by admin on Mon Mar 31 17:48:39 GMT 2025 , Edited by admin on Mon Mar 31 17:48:39 GMT 2025
PRIMARY
ECHA (EC/EINECS)
203-195-2
Created by admin on Mon Mar 31 17:48:39 GMT 2025 , Edited by admin on Mon Mar 31 17:48:39 GMT 2025
PRIMARY
SMS_ID
100000081130
Created by admin on Mon Mar 31 17:48:39 GMT 2025 , Edited by admin on Mon Mar 31 17:48:39 GMT 2025
PRIMARY
EVMPD
SUB10095MIG
Created by admin on Mon Mar 31 17:48:39 GMT 2025 , Edited by admin on Mon Mar 31 17:48:39 GMT 2025
PRIMARY
DRUG CENTRAL
3493
Created by admin on Mon Mar 31 17:48:39 GMT 2025 , Edited by admin on Mon Mar 31 17:48:39 GMT 2025
PRIMARY
INN
4182
Created by admin on Mon Mar 31 17:48:39 GMT 2025 , Edited by admin on Mon Mar 31 17:48:39 GMT 2025
PRIMARY
EPA CompTox
DTXSID6048674
Created by admin on Mon Mar 31 17:48:39 GMT 2025 , Edited by admin on Mon Mar 31 17:48:39 GMT 2025
PRIMARY
PUBCHEM
64949
Created by admin on Mon Mar 31 17:48:39 GMT 2025 , Edited by admin on Mon Mar 31 17:48:39 GMT 2025
PRIMARY
WIKIPEDIA
PROPAMIDINE
Created by admin on Mon Mar 31 17:48:39 GMT 2025 , Edited by admin on Mon Mar 31 17:48:39 GMT 2025
PRIMARY
RXCUI
34633
Created by admin on Mon Mar 31 17:48:39 GMT 2025 , Edited by admin on Mon Mar 31 17:48:39 GMT 2025
PRIMARY RxNorm
CAS
104-32-5
Created by admin on Mon Mar 31 17:48:39 GMT 2025 , Edited by admin on Mon Mar 31 17:48:39 GMT 2025
PRIMARY
MESH
C005555
Created by admin on Mon Mar 31 17:48:39 GMT 2025 , Edited by admin on Mon Mar 31 17:48:39 GMT 2025
PRIMARY
ALANWOOD
propamidine
Created by admin on Mon Mar 31 17:48:39 GMT 2025 , Edited by admin on Mon Mar 31 17:48:39 GMT 2025
PRIMARY
ChEMBL
CHEMBL23013
Created by admin on Mon Mar 31 17:48:39 GMT 2025 , Edited by admin on Mon Mar 31 17:48:39 GMT 2025
PRIMARY
NCI_THESAURUS
C82250
Created by admin on Mon Mar 31 17:48:39 GMT 2025 , Edited by admin on Mon Mar 31 17:48:39 GMT 2025
PRIMARY
FDA UNII
G20G12V769
Created by admin on Mon Mar 31 17:48:39 GMT 2025 , Edited by admin on Mon Mar 31 17:48:39 GMT 2025
PRIMARY
MERCK INDEX
m9181
Created by admin on Mon Mar 31 17:48:39 GMT 2025 , Edited by admin on Mon Mar 31 17:48:39 GMT 2025
PRIMARY Merck Index
DRUG BANK
DB13296
Created by admin on Mon Mar 31 17:48:39 GMT 2025 , Edited by admin on Mon Mar 31 17:48:39 GMT 2025
PRIMARY
Related Record Type Details
Structure of Propamidine diisethionate
SALT/SOLVATE -> PARENT
Structure of Propamidine diisethionate
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of PROPAMIDINE
ACTIVE MOIETY
NIH
NCATS
PRIVACY NOTICE
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966