Apicycline Chemical Properties

Melting point:

144.5° (dec)

alpha 

D -123° (c = 0.5 in methanol); D -133° (c = 0.5 in water)

Apicycline Usage And Synthesis

Originator

Travert,Baxter

Manufacturing Process

Glyoxylic acid monohydrate (1.96 g, 20 mrnoles) is dissolved in 200 ml of methanol, and a solution of 2.60 g (20 mmoles) of N-(2-hydroxyethyl) piperazine in 50 ml of methanol is slowly added thereto with stirring.
Stirring is maintained for 15 minutes and the medium is cooled to 5°C. There is then added 10.2 g (20 mmoles) of tetracycline base trihydrate and the reaction medium is maintained for 20 hours at 5°C under stirring. After that reaction time, the solution is concentrated up to 50 ml and 0.25 liter of acetone is added for precipitating a yellowish product which is filtered and dried to yield N-[(carboxy)(4-β-hydroxyethylpiperazino)methyl] tetracycline (apicycline).
When tested for antibiotic potency against Bacillus cereus var. mycoides ATCC 9634 (diffusion method), the product is shown to present an antibiotic potency equivalent to 97% of the tetracycline present therein.
Anhydrous tetracycline base (0.90 g, 2 mmoles) is dissolved in 30 ml of nbutanol at about 40°C. There is then added thereto under stirring a solution of 0.26 g (2 mmoles) of N-(2-hydroxyethyl)piperazine in 10 ml of butanol and 0.191 g (2 mmoles) of glyoxylic acid monohydrate. A precipitate appears after a few minutes and the suspension is maintained for six hours under stirring and at room temperature.
After that reaction time, precipitation is completed by addition of 120 ml of ether. The yellowish precipitate is filtered and dried to yield N-[(carboxy)(4-β- hydroxyethylpiperazino)methyl]tetracycline (apicycline). Yellow, amorphous powder with slight amine odor, MP: 144.5°C (dec). Freely solves in water. [α]D =-123° (c = 0.5 in methanol); [α]D =-133° (c = 0.5 in water).
The pH value of a 2% aqueous solution of this product is 6.2. When tested for antibiotic potency against Bacillus cercus var. mycoides ATCC 9634 (diffusion method), the product is shown to present an antibiotic potency equivalent to 95% of the tetracycline present therein.

Therapeutic Function

Antibiotic

Apicycline(15599-51-6)Related Product Information

• N-Methacryloylglycine
• 1-Piperazineaceticacid,4-ethyl-(9CI)
• N-Tigloylglycine
• 1-ACETYL-1-CYCLOHEXENE
• pipacycline
• 2-(PIPERAZIN-1-YL)-ACETIC ACID H2O
• 1,4-BIS(2-HYDROXYETHYL)PIPERAZINE
• N-(ACETOACETYL)GLYCINE,
• 1,2,3,4-TETRAHYDRO-1,5-NAPHTHALENEDIOL
• 4-Methyl-1-tetralone
• Apicycline
• [4-(2-HYDROXY-ETHYL)-PIPERAZIN-1-YL]-ACETIC ACID
• Tetracycline
• (4-METHYL-PIPERAZIN-1-YL)-ACETIC ACID