CYCLACILLIN (200 MG) Property

Melting point:

182-183° (anhydrate) (Hou, Poole); mp 156-158° (dec) (Alburn et al.)

alpha 

D25 +268° (water)

Boiling point:

649.6±55.0 °C(Predicted)

Density 

1.40±0.1 g/cm3(Predicted)

solubility 

Aqueous Acid (Slightly), DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

pK1, pK2 in water: 2.68, 7.50; in 50% dioxane: 4.16, 7.04(at 25℃)

color 

White to Off-White

Water Solubility 

32g/L(25 ºC)

Stability:

Hygroscopic

Hazard and Precautionary Statements (GHS)

CYCLACILLIN (200 MG) Chemical Properties,Usage,Production

Description

Ciclacillin was synthesized by Wyeth Laboratories in 1967 in the course of studies on the improvement of oral absorption of ampicillin. Although its antibacterial activity is one-sixteenth to one-half that of ampicillin, it shows a four to tenfold higher oral absorption and higher urinary excretion. Ciclacillin shows less tendency than ampicillin to cause diarrhea and is used for therapy of pyoderma, wound infection, respiratory and urinary tract infections, as well as ear and nose, and other infections caused by Staphylococcus, Streptococcus, Escherichia coli, Citrobacter, Klebsiella, Proteus, and Haemophilus influenzae.

Originator

UItracillin,Gruenenthal,W. Germany,1972

Uses

Antibacterial.

Uses

Cyclacillin is an aminosalicylic semisynthetic penicillin; Antibiotic.

Definition

ChEBI: Cyclacillin is a penicillin. It has a role as an antibacterial drug.

Manufacturing Process

To 21.6 g (0.10 mol) of 6-aminopenicillanic acid (6-APA) and 213 ml of methylene chloride in a dry 500 ml 3-neck flask fitted with stirrer, thermometer, nitrogen inlet and reflux condenser with drying tube, 25.3 g (0.25 mol) of triethylamine and 13.4 g (0.11 mol) of N,N-dimethylaniline were added. After stirring at reflux for one hour, the mixture was cooled and 21.7 g (0.20 mol) of trimethylchlorosilane was added dropwise at 12° to 15°C
The mixture was refluxed for 45 minutes, cooled under nitrogen, and 19.8 g (0.10 mol) of 1-amino-1-cyclohexane-carboxylic acid chloride HCl was added portionwise at -10°C over 20 minutes. The mixture was stirred for an additional hour while the temperature rose to 20°C. The reaction mixture was poured into 200 ml of cold water with stirring and the two-phase mixture clarified by filtration. Dilute sodium hydroxide solution was added to the filtrate at 5° to 10°C to pH 5.4.
After stirring overnight at room temperature, the crystalline product was collected by filtration, washed with water and finally with acetone, and then dried at 45°C; yield of dihydrate, 29.9 g or 79% of theory based on 6-APA; iodometric assay, 922 mcg per mg; bioassay, 921 mcg per mg, as described in US Patent 3,478,018.

brand name

Cyclapen-W (Wyeth).

Therapeutic Function

Antibacterial

Antimicrobial activity

The structure differs from other aminopenicillins in that the benzene ring is completely saturated and the amino substituent is attached directly to it instead of being linked to an adjacent carbon atom. It is less active than ampicillin against staphylococci, streptococci and H. influenzae, but is better absorbed by mouth, peak plasma levels of 10–18 mg/L being reached after a 500 mg oral dose. Its pharmacokinetic properties, side effects and use resemble those of ampicillin. It has limited availability.