Chlortetracycline
Chlortetracycline
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Chlortetracycline

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Catalog Number PR57625
CAS 57-62-5
Description Chlortetracycline is a member of the class of tetracyclines with formula C22H23ClN2O8 isolated from Streptomyces aureofaciens. It has a role as an antiprotozoal drug, a fluorescent probe, a calcium ionophore and an antibacterial drug.
Synonyms 7-Chlorotetracycline; Chlorotetracycline
IUPAC Name (4S,4aS,5aS,6S,12aR)-7-chloro-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide
Molecular Weight 478.9
Molecular Formula C22H23ClN2O8
InChI DHPRQBPJLMKORJ-XRNKAMNCSA-N
InChI Key InChI=1S/C22H23ClN2O8/c1-21(32)7-6-8-15(25(2)3)17(28)13(20(24)31)19(30)22(8,33)18(29)11(7)16(27)12-10(26)5-4-9(23)14(12)21/h4-5,7-8,15,26-27,30,32-33H,6H2,1-3H3,(H2,24,31)/t7-,8-,15-,21-,22-/m0/s1
Drug Categories Agents that produce neuromuscular block (indirect); Alimentary Tract and Metabolism; Anti-Bacterial Agents; Anti-Infective Agents; Antibacterials for Systemic Use; Antibiotics for Topical Use; Antiinfectives and Antiseptics for Local Oral Treatment; Antiinfectives for Systemic Use; Antiparasitic Agents; Antiprotozoals; Dermatologicals; Enzyme Inhibitors; Naphthacenes; Ophthalmologicals; Protein Synthesis Inhibitors; Sensory Organs; Stomatological Preparations; Tetracyclines
Drug Interactions Acetylcysteine-The therapeutic efficacy of Acetylcysteine can be decreased when used in combination with Chlortetracycline.
Ambroxol-The risk or severity of methemoglobinemia can be increased when Chlortetracycline is combined with Ambroxol.
Articaine-The risk or severity of methemoglobinemia can be increased when Chlortetracycline is combined with Articaine.
Benzocaine-The risk or severity of methemoglobinemia can be increased when Chlortetracycline is combined with Benzocaine.
Benzyl alcohol-The risk or severity of methemoglobinemia can be increased when Chlortetracycline is combined with Benzyl alcohol.
Half-Life The half-life of Chlortetracycline is 5.6 hours.
Isomeric SMILES C[C@@]1([C@H]2C[C@H]3[C@@H](C(=O)C(=C([C@]3(C(=O)C2=C(C4=C(C=CC(=C41)Cl)O)O)O)O)C(=O)N)N(C)C)O
Type Small Molecule
Therapeutic Category Antibacterials
Pharmacology

Indications

Chlortetracycline is primarily utilized in the formulation of medicated animal feeds. This application is designed to promote growth and prevent disease within livestock populations, ultimately contributing to improved health and productivity in agricultural settings.

Pharmacodynamics

As a member of the tetracycline class of antibiotics, chlortetracycline functions as a bacteriostatic agent. It effectively inhibits bacterial growth and reproduction by interfering with the protein synthesis of susceptible bacteria, thereby limiting the propagation of bacterial infections.

Absorption

When administered orally, chlortetracycline achieves peak plasma concentration approximately three hours post-ingestion. The oral bioavailability of chlortetracycline is relatively low, ranging from 25 to 30%. This indicates that a modest proportion of the drug reaches systemic circulation when taken through this route.

Metabolism

Chlortetracycline is not known to undergo significant metabolic transformation. This characteristic suggests that the drug is excreted largely in its original form, minimizing the impact of metabolic variations on its effectiveness and facilitating predictable pharmacokinetic behavior.

Mechanism of Action

Chlortetracycline operates by targeting the bacterial ribosome, specifically competing for the A site, similar to other tetracyclines. By binding to this site, it prevents the attachment of tRNA molecules that carry amino acids, thereby obstructing their addition to the growing peptide chain. This action effectively disrupts protein synthesis, which is essential for bacterial growth and reproduction, as it hinders the production of necessary proteins.

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