Chemical Identity

Property	Value
Chemical Formula	C89H97Cl2N9O33 (major component)
Molecular Weight	1879 Da (average of 5 components)
CAS Number	61036-62-2
Peptide Class	Glycopeptide Antibiotic
Origin	Actinoplanes teichomyceticus

Structure

Teicoplanin is a complex of five closely related glycopeptides (TA2-1 through TA2-5) produced by Actinoplanes teichomyceticus. The core structure consists of a heptapeptide backbone with three fused aromatic rings, similar to vancomycin, but with an additional sugar moiety (N-acetylglucosamine) and a lipophilic acyl side chain that enhances membrane anchoring.

Mechanism of Action

Teicoplanin binds to the D-alanyl-D-alanine terminus of lipid II, blocking peptidoglycan polymerization in gram-positive bacteria. The lipophilic side chain anchors the molecule to the bacterial membrane, increasing local concentration at the site of action. This binding is cooperative and essentially irreversible.

Clinical Applications

• MRSA infections: Bacteremia, endocarditis, pneumonia, skin/soft tissue
• Clostridioides difficile infection: Oral therapy for C. difficile colitis
• Gram-positive prosthetic joint infections: Long-duration therapy
• Endocarditis: Native and prosthetic valve

Pharmacokinetics

• Half-life: 70-100 hours (enables once-daily or thrice-weekly dosing)
• Protein binding: 90-95%
• Elimination: Primarily renal (80% unchanged)
• Loading dose required: Due to long half-life
• Route: IV, IM

Safety and Side Effects

Nephrotoxicity (less than vancomycin), ototoxicity (rare), injection site reactions, fever, rash, and rarely red man syndrome. Thrombocytopenia reported with prolonged use. Less nephrotoxic than vancomycin in comparative studies.

References

• Parenti, F., et al. (1978). Teichomycins, new antibiotics from Actinoplanes teichomyceticus. Journal of Antibiotics, 31, 276-283.
• Wilson, A.P.R. (2000). Clinical pharmacokinetics of teicoplanin. Clinical Pharmacokinetics, 39, 167-183.