lymecycline

lymecycline Basic information
Product Name:lymecycline
Synonyms:N-lysinomethyltetracycline;Armyl;Mucomycin;N6-[[(4S)-4β-(Dimethylamino)-1,4,4aβ,5,5aβ,6,11,12a-octahydro-3,6α,10,12,12aβ-pentahydroxy-6-methyl-1,11-dioxonaphthacen-2-yl]carbonylaminomethyl]-L-lysine;Tetralisal;Tetralysal;(+)-N-(5-Amino-5-carboxypentylaminomethyl)-4-dimethylamino-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxonaphthacene-2-carboxamide;Tertamyl
CAS:992-21-2
MF:C29H38N4O10
MW:602.63
EINECS:213-592-2
Product Categories:Antibacterial;Amines;Intermediates & Fine Chemicals;Pharmaceuticals;Isotope Labelled Compounds
Mol File:992-21-2.mol
lymecycline Structure
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.
pka2.50±0.24(Predicted)
form Solid
color Yellow to Dark Brown
Stability:Light Sensitive, Temperature Sensitive
Safety Information
MSDS Information
lymecycline Usage And Synthesis
Chemical PropertiesYellow, hygroscopic powder.
OriginatorArmyl,Armour Pharm.
UsesLabelled Lymecycline. A semi-synthetic antibiotic related to Tetracycline (T291400). Antibacterial.
DefinitionChEBI: 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 ProcessAmido-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 FunctionAntibiotic
Pharmaceutical Applications2-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 UseAntibacterial agent:
Also used for treatment of acne
Drug interactionsPotentially 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.
MetabolismThe 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 Preparation Products And Raw materials
Raw materialsL-Lysine hydrochloride-->Tetracycline-->Formaldehyde
Pilylysine 4-Methyl-1-tetralone lymecycline Tetracycline 1,2,3,4-TETRAHYDRO-1,5-NAPHTHALENEDIOL

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