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Lymecycline

Lymecycline is a broad-spectrum tetracycline  antibiotic more soluble than tetracycline base and is unique amongst tetracyclines in that it is absorbed by an active transport process across the intestinal wall, making use of the same mechanism by which carbohydrates are absorbed.

Therapeutic use

Lymecycline, like other tetracyclines, is used to treat a range of infections. Its better absorption profile makes it preferable to tetracycline for moderately severe acne and typically prescribed for 8 weeks at a time. It may also be used to treat urinary tract infections, gum disease, and other bacterial infections such as gonorrhea and chlamydia. Lymecycline is also used commonly as a prophylactic treatment for infection by Bacillus anthracis (anthrax). It is also effective against Yersinia pestis and malaria and is also prescribed for the treatment of Lyme disease.

Dosage and Administration

The standard dose is 408 mg (one capsule) daily by mouth. In particularly severe infections this dose may be increased to 12241632 mg (three or four capsules) daily.

Toxicology

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mammal (species unspecified) LD50 unreported 253mg/kg (253mg/kg)   British Medical Journal. Vol. 2, Pg. 106, 1964.
mouse LD50 intravenous 181mg/kg (181mg/kg)   Research Progress in Organic-Biological and Medicinal Chemistry. Vol. 2, Pg. 333, 1970

 

Adverse effects include nausea, vomiting, diarrhoea, glossitis, enterocolitis, dysphagia, dermatitis, hypersensitivity reactions, proctitis, and vaginitis.

Pharmacokinetic

Bioavailability 100%
Metabolism  
Cmax (mg/ml) 2.1
tmax (hrs) 3
Half-life 8hrs
AUC mgh/l (300mg) 21.9 4.3
Eliminiation rate Constant  
Excretion renal (25%)

Absorption

Lymecycline is absorbed by the "active transport" process across the intestinal wall, making use of the same fast and efficient mechanism by which carbohydrates are absorbed.

Distribution

Elimination

Metabolism

Mechanism of Action

Lymecycline inhibits cell growth by inhibiting translation. It binds to the 30S ribosomal subunit and prevents the amino-acyl tRNA from binding to the A site of the ribosome. The binding is reversible in nature. Lymecycline is lipophilic and can easily pass through the cell membrane or passively diffuses through porin channels in the bacterial membrane.

Microbiology

Mechanism of resistance

Cells become resistant to lymecycline by at least two mechanisms: efflux and ribosomal protection. In efflux, a resistance gene encodes a membrane protein that actively pumps lymecycline out of the cell. This is the mechanism of action of the tetracycline resistance gene on the artificial plasmid pBR322. In ribosomal protection, a resistance gene encodes a protein which binds to the ribosome and prevents lymecycline from acting on the ribosome.


Medicinal Chemistry

CAS number: 992-21-2   EINECS:

Molecular Formula: C29H38N4O10

Average mass: 602.632813 Da

Monoisotopic mass: 602.258789 Da

Systematic name: N6-[({[(4S,4aS,5aS,6S,12aS)-4-(Dimethylamino)-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-2-tetracenyl]carbonyl}amino)methyl]-L-lysine

SMILES: OC(=O)[C@@H](N)CCCCNCNC(=O)\C3=C(/O)[C@@H](N(C)C)[C@@H]4C[C@H]2C(\C(=O)c1c(O)cccc1[C@@]2(C)O)=C(\O)[C@]4(O)C3=O

Std. InChI: 1S/C29H38N4O10/c1-28(42)13-7-6-9-17(34)18(13)22(35)19-14(28)11-15-21(33(2)3)23(36)20(25(38)29(15,43)24(19)37)26(39)32-12-31-10-5-4-8-16(30)27(40)41/h6-7,9,14-16,21,31,34,36-37,42-43H,4-5,8,10-12,30H2,1-3H3,(H,32,39)(H,40,41)/t14-,15-,16-,21-,28+,29-/m0/s1

ACD/LogP: -1.696 # of Rule of 5 Violations: 3
ACD/LogD (pH 5.5): -5.66 ACD/LogD (pH 7.4): -4.72
ACD/BCF (pH 5.5): 1.00 ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 5.5): 1.00 ACD/KOC (pH 7.4): 1.00
#H bond acceptors: 14 #H bond donors: 10
#Freely Rotating Bonds: 16 Polar Surface Area: 242.98 2
Index of Refraction: 1.693 Molar Refractivity: 150.438 cm3
Molar Volume: 392.226 cm3 Polarizability: 59.638 10-24cm3
Surface Tension: 91.5510025024414 dyne/cm Density: 1.536 g/cm3
Flash Point: 515.1 C Enthalpy of Vaporization: 141.424 kJ/mol
Boiling Point: 928.106 C at 760 mmHg Vapour Pressure: 0 mmHg at 25C

 

 

 

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