lymecycline Chemical Properties

Melting point:

192.5°C

Boiling point:

648.97°C (rough estimate)

Density 

1.53

refractive index 

1.5500 (estimate)

storage temp. 

Amber Vial, -86°C Freezer, Under inert atmosphere

solubility 

Very soluble in water, slightly soluble in ethanol (96 per cent), practically insoluble in methylene chloride.

pka

2.50±0.24(Predicted)

form 

Solid

color 

Yellow to Dark Brown

Stability:

Light Sensitive, Temperature Sensitive

lymecycline Usage And Synthesis

Chemical Properties

Yellow, hygroscopic powder.

Originator

Armyl,Armour Pharm.

Uses

Labelled Lymecycline. A semi-synthetic antibiotic related to Tetracycline (T291400). Antibacterial.

Definition

ChEBI: A tetracycline-based broad-spectrum antibiotic. It is approximately 5000 times more soluble than tetracycline base and is unique amongst tetracyclines in that it is absorbed by the "active transport" process across the intestinal wall.

Manufacturing Process

Amido-N-(lysinomethyl)tetracycline hydrochloride:
To 18.3 g of L-lysine hydrochloride dissolved in 100 ml of water is added 10 ml of 37% aqueous solution of formaldehyde. To the resultant mixture is added 44.0 g of anhydrous tetracycline dissolved in 500 ml of tetrahydrofuran. After thorough mixing the product forms over a period of about 15 min as an oily layer which after separation from the aqueous phase is added dropwise to 3 L of stirred isopropyl alcohol. The product after recovery by filtration, is reslurried with acetone, filtered and dried at 65°C at reduced pressure.
The product thus obtained has a bioassay of 500 mcg/mg (K. pneumonlae oxytetracyoline assay).

Therapeutic Function

Antibiotic

Pharmaceutical Applications

2-N-lysinomethyl-tetracycline. A water-soluble prodrug of tetracycline available for oral administration.
Its antimicrobial activity is due to the tetracycline content. It is lipophilic, rapidly absorbed from the gastrointestinal tract and widely distributed. Concentrations around 1 mg/kg have been found in maxillary sinus tissue some 3 h after administration of a conventional dose. The half-life is 7–14 h. Approximately 30% of an orally administered dose is excreted as active drug in the urine, where it achieves concentrations of 300 mg/L.
Its untoward effects and clinical uses are those of tetracycline, although it is claimed to be better tolerated.

Clinical Use

Antibacterial agent:
Also used for treatment of acne

Drug interactions

Potentially hazardous interactions with other drugs
Anticoagulants: possibly enhanced anticoagulant effect of coumarins and phenindione.
Oestrogens: possibly reduce contraceptive effects of oestrogens (risk probably small).
Retinoids: possible increased risk of benign intracranial hypertension – avoid.

Metabolism

The tetracyclines are excreted in the urine and in the faeces. Renal clearance is by glomerular filtration. Up to 60% of an intravenous dose, and up to 55% of an oral dose, is eliminated unchanged in the urine. Usually between 40% and 70% of a dose is excreted in the urine; urinary excretion is increased if urine is alkalinised.

lymecycline(992-21-2)Related Product Information

• Pilylysine
• Tetracycline
• lymecycline
• 1,2,3,4-TETRAHYDRO-1,5-NAPHTHALENEDIOL
• 4-Methyl-1-tetralone