ROLITETRACYCLINE Property

Melting point:

163.5°C

Boiling point:

608.16°C (rough estimate)

Density 

1.2902 (rough estimate)

refractive index 

1.7120 (estimate)

storage temp. 

-20°C Freezer, Under inert atmosphere

solubility 

DMSO (Slightly), Methanol (Very Slightly)

form 

Solid

pka

pKa 7.4 (Uncertain)

color 

Very Dark Red to Very Dark Brown

Water Solubility 

>20g/L(21 ºC)

Safety

Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

26-36

WGK Germany 

1

RTECS 

QI9150000

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

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

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

ROLITETRACYCLINE Chemical Properties,Usage,Production

Description

Rolitetracycline was synthesized in 1958. Bristol-Myers Laboratories prepared it from tetracycline by introducing a pyrrolidinylmethyl moiety. This antibiotic is very soluble in water and more stable than tetracycline under acidic conditions. Rolitetracycline is used by intravenous injection, and its nitrate is used by both intravenous and intramuscular injections for therapy of the same infections as those treated by tetracycline.

Uses

Rolitetracycline, launched in the late 1950s, was the first of the semi-synthetic tetracyclines. Rolitetracycline is formed by a Mannich condensation of formaldehyde and pyrrolidine with tetracycline. Rolitetracycline is a pro-drug of tetracycline, in which the pyrrolidine moiety improves bioavailability compared with tetracycline. Rolitetracycline has broad spectrum Gram positive activity in vivo, but pH instability limits use to parenteral administration. The intrinsic in vitro activity and SARs for this region of the tetracycline molecule have not been extensively investigated.

Uses

neuromuscular blocker

Uses

Rolitetracycline is a tetracycline antibiotic that may be given intravenously or intramuscularly in serious bacterial infections when oral administration is not practicable.

Definition

ChEBI: A derivative of tetracycline in which the amide function is substituted with a pyrrolidinomethyl group.

brand name

Syntetrin (Bristol-Myers Squibb).

General Description

Rolitetracycline, N-(pyrrolidinomethyl)tetracycline(Syntetrin), was introduced for use by intramuscular or intravenousinjection. This derivative is made by condensingtetracycline with pyrrolidine and formaldehyde in the presenceof tert-butyl alcohol. It is very soluble in water (1 g dissolvesin about 1 mL) and provides a means of injecting theantibiotic in a small volume of solution. It has been recommendedfor cases when the oral dosage forms are not suitable,but it is no longer widely used.

Pharmaceutical Applications

2-N-pyrrolidinomethyl-tetracycline. A semisynthetic derivative of tetracycline supplied as the nitrate sesquihydrate for parenteral use.
It is not absorbed from the gastrointestinal tract. It is highly soluble and therefore can be administered parenterally. Peak plasma concentrations of 4–6 mg/L occur at 0.5–1 h after 350 mg intravenously. The plasma elimination half-life is 5–8 h. About 50% of the dose is excreted in the urine, producing high concentrations.
Intravenous administration is occasionally accompanied by abnormal taste, shivering and rigors, hot flushes, facial reddening, dizziness and, rarely, circulatory collapse. Symptoms of myasthenia gravis have occasionally been exacerbated.