7797. Propamidine

Nomenclature

CAS number: 104-32-5
4,4′-[1,3-Propanediylbis(oxy)]bisbenzenecarboximidamide; 4,4′-(trimethylenedioxy)dibenzamidine; 4,4′-diamidino-α,ω-diphenoxypropane.
C17H20N4O2; mol wt 312.37.
C 65.37%, H 6.45%, N 17.94%, O 10.24%.

Description and references

Prepn: A. J. Ewins et al., GB 507565 (1939 to May & Baker); J. N. Ashley et al., J. Chem. Soc. 1942, 103; of isethionate: G. Newbery, A. P. T. Easson: US 2394003 (1946 to May & Baker). Trypanocidal activity: E. M. Lourie, W. Yorke, Ann. Trop. Med. Parasitol. 33, 289 (1939). Preliminary pharmacology: R. Wien, ibid. 37, 1 (1943). Determn in biological fluids: D. P. Jackson et al., J. Biol. Chem. 167, 377 (1947). Mode of action: M. J. Pine, Biochem. Pharmacol. 17, 75 (1968). Activity in fibrinolytic systems: J. D. Geratz, Thromb. Diath. Haemorrh. 29, 154 (1973). Clinical use in treatment of Acanthamoeba keratitis: D. L. Easty, Br. Med. J. 296, 228 (1988); J. J. Wiens, W. B. Jackson, Can. J. Ophthalmol. 23, 107 (1988). Early review of pharmacology, mode of action and clinical applications: E. B. Schoenbach, E. M. Greenspan, Medicine 27, 327-377 (1948).

Chemical structure

Derivative

Isethionate.

Nomenclature

CAS number: 140-63-6
M & B 782; Brolene Drops (RPR).
C21H32N4O10S2; mol wt 564.63.
C 44.67%, H 5.71%, N 9.92%, O 28.34%, S 11.36%.

Properties

Hygroscopic, very bitter crystals or granular powder, mp ≈235°. Soluble in water (≈1 in 5), glycerol, 95% alcohol (≈1 in 33). Practically insol in ether, chloroform, fixed oils, liquid petrolatum. pH of a 5% w/v soln in water = 4.5 to 6.5.

Therapeutic Category

Antiprotozoal (Trypanosoma); antiamebic.

Therapeutic Category (Veterinary)

Anti-infective (topical). Formerly used as antiprotozoal (Trypanosoma, Babesia).

Keywords

Antiamebic; Antiprotozoal (Trypanosoma)