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Home > Encyclopedia > Lymecycline

Lymecycline

pharmaceutical raw materials
Lymecycline structure

Lymecycline 

structure
  • CAS No:

    992-21-2

  • Formula:

    C29H38N4O10

  • Chemical Name:

    Lymecycline

  • Synonyms:

    L-Lysine,N6-[[[[(4S,4aS,5aS,6S,12aS)-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenyl]carbonyl]amino]methyl]-;Lysine,N6-[[4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenecarboxamido]methyl]-,L-;L-Lysine,N6-[[[[4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenyl]carbonyl]amino]methyl]-,[4S-(4α,4aα,5aα,6β,12aα)]-;Lysine,N6-[[4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenecarboxamido]methyl]-;N6-[[[[(4S,4aS,5aS,6S,12aS)-4-(Dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenyl]carbonyl]amino]methyl]-L-lysine;Tetracyclinemethylenelysine;2-Naphthacenecarboxamide,4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-,lysinemethylene deriv.;Tetracycline-L-methylenelysine;(+)-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;N2-[[(+)-5-Amino-5-carboxypentylamino]methyl]tetracycline;Lymecycline;Tetralysal;N6-[[4-(Dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenecarboxamido]methyl]lysine;8059-91-4;15302-19-9;31041-50-6

  • Categories:

    Active Pharmaceutical Ingredients  >  Antibiotics

Description

Yellow, hygroscopic powder.


Lymecycline is 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. It has a role as a protein synthesis inhibitor, an antiprotozoal drug, an antibacterial drug and an antimicrobial agent. It is a member of tetracyclines and a tertiary alpha-hydroxy ketone.|Lymecycline is a broad-spectrum second-generation tetracycline antibiotic used for the treatment of acne and other susceptible bacterial infections. It has been proven a cost-effective alternative to treatment with [minocycline] with comparable safety and efficacy. Lymecycline was initially discovered in 1961. It is marketed by Galderma and used in the UK as well as New Zealand in addition to other countries. Lymecycline is not marketed in the USA, however, equivalent drugs are available, such as minocycline and [tetracycline].|A semisynthetic antibiotic related to TETRACYCLINE. It is more readily absorbed than TETRACYCLINE and can be used in lower doses.

Lymecycline Basic Attributes

602.637

602.63

213-592-2

7D6EM3S13P

DTXSID9045344

J - Antiinfectives for systemic use

Characteristics

243

0.3

1.53

192.5°C

840.5ºC at 760 mmHg

462.1ºC

1.693

soluble (at all physiological pH values)

2.50±0.24

Safety Information

P201, P202, P260, P261, P263, P264, P270, P271, P272, P280, P281, P285, P301+P312, P302+P352, P304+P312, P304+P340, P304+P341, P305+P351+P338, P308+P313, P312, P321, P330, P332+P313, P333+P313, P337+P313, P342+P311, P362, P363, P403+P233, P405, P501

H302

|Danger|H302 (50%): Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P260, P261, P263, P264, P270, P271, P272, P280, P281, P285, P301+P312, P302+P352, P304+P312, P304+P340, P304+P341, P305+P351+P338, P308+P313, P312, P321, P330, P332+P313, P333+P313, P337+P313, P342+P311, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 2 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

The oral LD50 of lymecycline in rats is 3200 mg/kg. Overdoses with lymecycline are rare. In the case of an overdose, gastric lavage should be performed immediately. Provide supportive treatment and maintain fluid balance.

Drug Information

Lymecycline is used for the treatment of acne in addition to other susceptible infections; propionibacterium is often the cause of acne. Some of the infections that can be treated with lymecycline include upper respiratory tract infections, urinary tract infections, bronchitis, chlamydial infections, and rickettsial infections.

Lymecycline, like other tetracyclines, exerts bacteriostatic actions on intracellular and extracellular bacteria, treating susceptible bacterial infections. It has been shown to be safe and effective in the treatment of moderate to severe acne. It is important to note that like other tetracyclines, lymecycline may cause esophageal irritation and ulceration, which can be prevented by drinking adequate fluids during administration. It also has the potential to cause photosensitivity. Lymecycline can lead to renal tubular acidosis or hepatic toxicity. It is not recommended to administer this drug in patients with renal disease or severe hepatic disease.

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

Lymecycline is 77-88% absorbed after oral administration with a relative bioavailability of 70%. The Cmax of lymecycline is 2.1 mg/L and is achieved about 3 hours after administration. The AUC is 21.9 ± 4.3 mg·h/L.|Lymecycline is 25% eliminated in the urine. Based on being a member of the tetracycline drug class, fecal elimination is likely another route of elimination.|Lymecycline is lipophilic and easily crosses the cell membrane and passively diffuses through bacterial porin channels. As a second-generation tetracycline, the concentration in the bile ranges from 10 to 25 times higher than plasma concentration. In general, the volume of distribution of tetracyclines ranges from 1.3–1.7 L/kg or 100–130 L.|Lymecycline is partially cleared by the kidneys, like other tetracyclines.

The half-life of lymecycline is approximately 8 hours.

Normally, the ribosome synthesizes proteins through the binding of aminoacyl-tRNA to the mRNA-ribosome complex. Lymecycline binds to the 30S ribosomal subunit, preventing amino-acyl tRNA from binding to the A site of the ribosome, which prevents the elongation of polypeptide chains. This results in bacteriostatic actions, treating various infections.

Hydrochloride, Lymecycline

Lymecycline Use and Manufacturing

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

Computed Properties

Molecular Weight:602.6
XLogP3:-4.4
Hydrogen Bond Donor Count:9
Hydrogen Bond Acceptor Count:13
Rotatable Bond Count:10
Exact Mass:602.25879342
Monoisotopic Mass:602.25879342
Topological Polar Surface Area:243
Heavy Atom Count:43
Complexity:1230
Defined Atom Stereocenter Count:6
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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