PHENETHICILLIN POTASSIUM SALT Property

color 

dl-Form: Crystals from acetone

Safety

Hazardous Substances Data

132-93-4(Hazardous Substances Data)

Toxicity

LD50 oral in mouse: > 2gm/kg

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H317May cause an allergic skin reaction

H334May cause allergy or asthma symptoms or breathing difficulties if inhaled

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P272Contaminated work clothing should not be allowed out of the workplace.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P285In case of inadequate ventilation wear respiratory protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P341IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.

P321Specific treatment (see … on this label).

P333+P313IF SKIN irritation or rash occurs: Get medical advice/attention.

P342+P311IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.

P363Wash contaminated clothing before reuse.

P501Dispose of contents/container to..…

PHENETHICILLIN POTASSIUM SALT Chemical Properties,Usage,Production

Originator

Syncillin, Bristol, US ,1959

Definition

ChEBI: Phenethicillin potassium is an organic potassium salt. It contains a phenethicillin(1-).

Application

Phenethicillin was the first member of the semisynthetic penicillin class of antibiotics to be introduced in clinics. This drug was synthesized in 1960 by Bristol-Myers in collaboration with Beecham Research Laboratories starting with 6-aminopenicillanic acid. It is as stable against gastric acid as phenoxymethylpenicillin and is used orally for therapy of gram-positive and Neisseria infections.

Manufacturing Process

Triethylamine (1.5 ml) was added to a cold solution (10°C) of αphenoxypropionic acid (1.66 g, 0.01 mol) in 15 ml of pure dioxane, with stirring and cooling to 5°C to 10°C while isobutyl chloroformate (1.36 g, 0.01 mol) in 5 ml of dioxane was added dropwise. Then the mixture was stirred for ten minutes at 5°C to 8°C. A solution of 6-amino-penicillanic acid (2.16 g, 0.01 mol) in 15 ml of water and 2 ml of triethylamine was then added dropwise while the temperature was maintained below 10°C. The resulting mixture was stirred in the cold for 15 minutes then at room temperature for 30 minutes, diluted with 30 ml of cold water and extracted with ether which was discarded. The cold aqueous solution was then covered with 75 ml of ether and acidified to pH 2 with 5 N H2SO4. After shaking, the ether layer containing the product 6-(α-phenoxypropionamido)penicillanic acid, was dried for ten minutes over anhydrous sodium sulfate and filtered. Addition of 6 ml of dry n-butanol containing 0.373 g/ml of potassium 2-ethylhexanoate precipitated the potassium salt of the product as a colorless oil which crystallized on stirring and scratching and was collected, dried in vacuo and found to weigh 2.75 g, to melt at 217°C to 219°C.

brand name

Chemipen (Bristol-Myers Squibb); Syncillin (Bristol-Myers Squibb) [Name previously used: Phenethicillin.].

Therapeutic Function

Antibacterial

Safety Profile

Poison by intravenous route. Moderately toxic by intraperitoneal route. When heated to decomposition it emits toxic fumes of K2O, SOx, and NOx.