ChemicalBook--->CAS DataBase List--->104-32-5

104-32-5

104-32-5 Structure

104-32-5 Structure
IdentificationBack Directory
[Name]

Propamidine
[CAS]

104-32-5
[Synonyms]

DAPP
Brolene
propamidine
4,4'-(1,3-Propanediyl)bis(oxy)bisbenzamidine
4,4'-[1,3-Propanediylbis(oxy)]dibenzenecarboximidamide
4,4'-[1,3-Propanediylbis(oxy)]bis(benzenecarbimidamide)
4,4'-(1,3-Propanediylbis(oxy))bisbenzenecarboximidamide
BenzenecarboxiMidaMide,4,4'-[1,3-propanediylbis(oxy)]bis-
[EINECS(EC#)]

203-195-2
[Molecular Formula]

C17H20N4O2
[MDL Number]

MFCD00866601
[MOL File]

104-32-5.mol
[Molecular Weight]

312.37
Chemical PropertiesBack Directory
[Boiling point ]

497.3±55.0 °C(Predicted)
[density ]

1.25±0.1 g/cm3(Predicted)
[pka]

12.75±0.50(Predicted)
Hazard InformationBack Directory
[Uses]

as isethionate.
[Definition]

ChEBI: A polyether that is the bis(4-guanidinophenyl) ether of propane-1,3-diol. Used (as its isethionate salt) for the treatment of minor eye or eyelid infections, such as conjunctivitis and blepharitis.
[Production Methods]

Commercial production of propamidine follows the classic industrial route for generating aromatic diamidines from dinitrile precursors. Manufacturers begin with a bis substituted aromatic dinitrile, which is converted to the corresponding imidate ester under acidic alcoholysis. This activated intermediate is then reacted with propylamine, producing the bis amidine framework through sequential nucleophilic substitution. The process requires careful control of moisture and temperature to prevent hydrolysis and to ensure full conversion of both nitrile groups. After neutralisation and purification, the technical material is isolated as a stable salt suitable for downstream formulation.
[Pharmaceutical Applications]

A synthetic diamidine formulated as the isethionate or as dibromopropamidine isethionate for topical administration to the eye. Resistant clinical isolates of Acanthamoeba have been identified. It is available over the counter in eye drops.
Its activity against bacterial pathogens is poor, but it exhibits specific activity against Acanthamoeba spp. Reduction in sensitivity of Acanthamoeba during encystation might reflect changes in drug uptake. It is still recommended for aggressive treatment of amebic keratitis (in combination with neomycin or other agents), but is not well tolerated.
[Mechanism of action]

Curative and protectant activity. Acts by disrupting cell membrane and thus causing leakage of essential amino acids from microbes
[Pesticide Type]

Fungicide; Antimicrobial
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