Octenidine dihydrochloride

Description

The antiseptic agent octenidine dihydrochloride (OCT) was developed by Sterling Winthrop (WIN41464-2) in the 1980s as an alternative to the anti-plaque agent CHX and successfully tested in vitro and in vivo. OCT has a broad spectrum of activity with similar effectiveness against Gram-negative and Gram-positive bacteria, fungi, and yeasts. Moreover, it has been shown that it may effectively interfere with the co-aggregation of dental plaque microbial colonizers without disturbing the normal, healthy oral flora. In a standardized comparison of antimicrobial activity ofthe antiseptic agents triclosan, polyvinylpyrrolidone-iodine, OCT, polyhexamethylene biguanide, and Chlorhexidine digluconat (CHX) using the min-imal effective concentration and minimum bactericidal con-centration, OCT was the most effective active agent of alltested antimicrobial substances. In other studies, the antibacterial and antiplaque efficacy of OCT was equal to or even greater than that of CHX[1].

Uses

Octenidine is an antiseptic (topical). Octenidine is a cationic surfactant and bis-(dihydropyridinyl)-decane derivative.

Uses

Octenidine dihydrochloride is used as a antiseptic for skin, mucous Membranes and wounds.

Application

Octenidine dihydrochloride is a cationic antiseptic that belongs to the bispyridine class of chemicals. Its action is binding to anionic structures of the cell membrane, further bursting the membrane. It has activity against Gram-positive and Gram-negative bacteria. It was effective in oral hygiene, preventing plaque and gingivitis, as a whole body wash for methicillin-resistant S. aureus decolonization and skin disinfection of premature newborn infants. Octenidine concentrations of less than 1.5 μM (0.94 μg/mL) reduced each microbial population by more than 99% within 15 minutes. Staphylococcus epidermidis was the most susceptible of the test organisms, and E. coli and Candida albicans were the least susceptible. Octenidine was more active than chlorhexidine against each test strain. This antiseptic has not been established in veterinary medicine for skin preparation but is used for wound cleansing.

Flammability and Explosibility

Not classified

Synthesis

2162-98-3

64690-19-3

70775-75-6

The general procedure for the synthesis of N,N'-[1,10-decanediylidene-1(4H)-pyridin-4-ylidene]bis(1-octylamine) dihydrochloride from 1,10-dichlorodecane and 4-(octylamino)pyridine was as follows: 6.18 g of 4-(octylamino)pyridine base and 3.15 g of 1,10-dichlorodecane were mixed and slowly heated to 120 °C, and the reaction was exothermic to 180 °C, during which the reaction progress was monitored by thin layer chromatography (TLC). Upon completion of the reaction, 25 mL of dimethylformamide (DMF) was added and heated to completely dissolve the mixture. Subsequently, the mixture was cooled to 0 °C to promote crystal precipitation, the crystals were collected by filtration and dried at 60 °C under reduced pressure. By the above steps, 7.3 g of N,N'-[1,10-decylidenebis-1(4H)-pyridin-4-ylidene]bis(1-octylamine) dihydrochloride was obtained in a yield of 39.0% with a melting point of 215 to 217 °C.

in vivo

References

[1] A. Welk. “Antibacterial and antiplaque efficacy of a commercially available octenidine-containing mouthrinse.” Clinical Oral Investigations 20 1 (2015): 1469–1476.