Metacycline hydrochloride
[CAS# 3963-95-9]

Identification

• Classification: API >> Antibiotics >> Tetracycline
• Name: Metacycline hydrochloride
• Synonyms: Methacycline hydrochloride
• Molecular Formula: C₂₂H₂₂N₂O₈.HCl
• Molecular Weight: 478.89
• CAS Registry Number: 3963-95-9
• EC Number: 223-568-3

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319

Discovery and Applications

Metacycline hydrochloride, an antibiotic belonging to the tetracycline class, was discovered during the 1960s as part of efforts to develop derivatives of tetracycline with improved pharmacological properties. Tetracyclines were well-known for their broad-spectrum antibacterial activity, but researchers sought to enhance their efficacy and reduce side effects. Metacycline, synthesized by modifying the chemical structure of tetracycline, demonstrated promising results. The addition of a hydrochloride salt form improved its solubility and stability, making it more effective in clinical settings. Metacycline hydrochloride was subsequently developed and introduced as a therapeutic agent to combat a variety of bacterial infections.

Metacycline hydrochloride is primarily used as an antibiotic for treating a wide range of bacterial infections. Its broad-spectrum activity allows it to inhibit the growth of various Gram-positive and Gram-negative bacteria. This makes it particularly useful in the treatment of respiratory tract infections, urinary tract infections, and skin infections, including acne vulgaris. The ability of metacycline hydrochloride to interfere with bacterial protein synthesis, by binding to the 30S ribosomal subunit, underlies its effectiveness in inhibiting bacterial growth and replication.

In addition to its use in treating common bacterial infections, metacycline hydrochloride has applications in the treatment of certain chronic conditions. For instance, it is used in managing chronic bronchitis and in cases of sexually transmitted infections like chlamydia and gonorrhea. Its efficacy in treating these infections is attributed to its ability to achieve high tissue concentrations, ensuring that it reaches the sites of infection effectively.

Moreover, metacycline hydrochloride is employed in veterinary medicine. It is used to treat infections in livestock and pets, helping to maintain animal health and prevent the spread of bacterial diseases in agricultural settings.

Metacycline hydrochloride also plays a role in scientific research. It is used as a tool in microbiological studies to understand bacterial resistance mechanisms and to develop new antibiotics. By studying how bacteria interact with metacycline, researchers can gain insights into overcoming antibiotic resistance, which is a growing concern in global health.

References

2019. Methacycline displays a strong efficacy in reducing toxicity in a SCA3 Caenorhabditis elegans model. Biochimica et Biophysica Acta (BBA) - General Subjects, 1863(2).
DOI: 10.1016/j.bbagen.2018.10.008

2014. Inhibition of Epithelial-to-Mesenchymal Transition and Pulmonary Fibrosis by Methacycline. American Journal of Respiratory Cell and Molecular Biology, 50(1).
DOI: 10.1165/rcmb.2013-0099oc

2006. Precision study on capillary electrophoresis methods for metacycline. ELECTROPHORESIS, 27(11).
DOI: 10.1002/elps.200500873