Product Name

Lymecycline

CAS Number

992-21-2

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Product Name:
Lymecycline
CAS Number:
992-21-2
Indication:
For the treatment of infections and to treat acne. 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.
Mode 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. 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.

Pharmacodynamics:

Lymecycline is a tetracycline 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, making use of the same fast and efficient mechanism by which carbohydrates are absorbed. It inhibits cell growth by inhibiting translation.

Toxicity:

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

IUPAC:
(2S)-6-[({[(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-octahydrotetracen-2-yl]formamido}methyl)amino]-2-aminohexanoic acid
ATC:
J01AA04
PubChem:
24757945
DrugBank:
DB00256 (APRD00565, EXPT01049)
Formula:
C16H13ClN2O
Molecular Mass:
602.6328
Synonyms:
7-Chlorotetracycline Chlorotetracycline Chlorotetracycline hydrochloride Chlortetracyclin Chlortetracycline Chlortetracycline hydrochloride Chlortetracyclinium chloride CLTC
SMILES:
CN(C)[C@H]1[C@@H]2C[C@H]3C(=C(O)[C@]2(O)C(=O)C(C(=O)NCNCCCC[C@H](N)C(O)=O)=C1O)C(=O)C1=C(O)C=CC=C1[C@@]3(C)O
InChi:
AHEVKYYGXVEWNO-UEPZRUIBSA-N
General Reference:
General Reference:

  1. Link
  2. Meynadier J, Alirezai M: Systemic antibiotics for acne. Dermatology. 1998;196(1):135-9. Pubmed

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