Teicoplanin

Overview

Teicoplanin is a glycopeptide antibiotic with a spectrum of activity similar to vancomycin. Its mechanism of action is to inhibit bacterial cell wall peptidoglycan synthesis. It is used in the prophylaxis and treatment of serious infections caused by Gram-positive bacteria, including methicillin-resistant Staphylococcus aureus and Enterococcus faecalis.[1][2] WP

Teicoplanin is widely available in many European, Asian, and South American countries, however it is not currently approved by the US Food and Drug Administration and is not commercially available in the United States. Teicoplanin is marketed by Sanofi-Aventis under the trade name Targocid. Other trade names include Ticocin marketed by Cipla(India).[3][4] WP⚠ Wikipedia itself has flagged this text: citation needed.

Its strength is considered to be due to the length of the hydrocarbon chain.[5] WP

Risks and side effects

Adverse effects

Adverse effects of teicoplanin are usually limited to local effects or hypersensitivity reactions. While there is potential for nephrotoxicity and ototoxicity, the incidence of such organ toxicity is rare if recommended serum concentrations are successfully maintained.[6] WP

Pharmacology

Pharmacokinetics

Due to poor oral absorption, teicoplanin requires intravenous or intramuscular administration for systemic effect. Intramuscular administration achieves approximately 90% bioavailability. The drug exhibits high protein binding (90-95%) and is primarily eliminated through the kidneys unchanged, with minimal liver metabolism (2-3%) via hydroxylation. Clearance is reduced in patients with kidney impairment and is not significantly removed by hemodialysis. Teicoplanin exhibits a long half-life of 45-70 hours, allowing for once-daily dosing after loading doses. Although teicoplanin is primarily approved for intravenous and intramuscular use, several clinical and pharmacokinetic studies have explored its administration via the subcutaneous route. Subcutaneous teicoplanin has been reported as a feasible alternative in selected patients, particularly in outpatient, frail, or palliative care settings. Available evidence suggests that subcutaneous administration achieves pharmacokinetic and pharmacodynamic exposures comparable to intravenous dosing after appropriate loading, with good local tolerability. However, this route of administration remains off-label.[4][6–10] WP

Pharmacodynamics

Teicoplanin is a glycopeptide antibiotic that inhibits bacterial cell wall synthesis. It binds to the D-alanyl-D-alanine (D-Ala-D-Ala) terminus of the peptidoglycan precursor, preventing the transpeptidation reaction necessary for cell wall cross-linking. This binding also interferes with the polymerization of peptidoglycan, ultimately leading to cell death.[4] WP

In addition to its binding to the D-Ala-D-Ala terminus, teicoplanin may also interact with the lipid II substrate in the bacterial cell membrane through its hydrophobic tail. This interaction could facilitate the antibiotic's proximity to the nascent peptidoglycan, enhancing its inhibitory effect. However, this mechanism has not been fully confirmed.[4] WP

Research

Research

Researchers have explored the potential of teicoplanin as an antiviral agent against various viruses, including SARS-CoV-2. Laboratory studies indicate that teicoplanin inhibits cathepsin L, a host cell protease utilized by SARS-CoV-2 for cell entry via the endocytic pathway. In vitro experiments have demonstrated teicoplanin's ability to reduce SARS-CoV-2 infection, with reported IC₅₀ values in the low micromolar range. This suggests potential efficacy against various SARS-CoV-2 variants due to conserved cathepsin L cleavage sites on the SARS-CoV-2 spike protein. Animal studies have also shown a protective effect against SARS-CoV-2 infection with teicoplanin pre-treatment.[4][11][12] WP

History

History

Teicoplanin was first isolated in 1978 from Actinoplanes teichomyceticus (ATCC 31121), a rare species of actinobacteria in the family Micromonosporaceae. The bacteria were obtained from a soil sample collected in Nimodi Village, Indore, India. The chemical structure of teicoplanin was determined and published in 1984.[4][13][14] WP

Teicoplanin was first introduced into clinical use in 1984. Following the publication of studies demonstrating its efficacy against infections such as bone and soft tissue infections, endocarditis, pneumonia, and sepsis in 1986, it received regulatory approval in Europe in 1988.[4][15][16] WP

The biosynthetic pathway leading to teicoplanin, as well as the regulatory circuit governing the biosynthesis, were studied intensively in recent years, allowing for the creation of an integrated model of its biosynthesis.[17] WP

Chemistry

Formula

C89H99Cl2N9O33 PC

Molar mass (g/mol)

1893.7 PC

IUPAC name (computed by PubChem)

(1S,2R,19R,22S,34S,37R,40R,52R)-2-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-22-amino-5,15-dichloro-64-[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-(9-methyldecanoylamino)oxan-2-yl]oxy-26,31,44,49-tetrahydroxy-21,35,38,54,56,59-hexaoxo-47-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-7,13,28-trioxa-20,36,39,53,55,58-hexazaundecacyclo[38.14.2.23,6.214,17.219,34.18,12.123,27.129,33.141,45.010,37.046,51]hexahexaconta-3,5,8,10,12(64),14,16,23(61),24,26,29(60),30,32,41(57),42,44,46(51),47,49,62,65-henicosaene-52-carboxylic acid PC

SMILES

CC(C)CCCCCCCC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@H]1OC2=C3C=C4C=C2OC5=C(C=C(C=C5)[C@H]([C@H]6C(=O)N[C@H](C7=C(C(=CC(=C7)O)O[C@@H]8[C@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)C9=C(C=CC(=C9)[C@H](C(=O)N6)NC(=O)[C@@H]4NC(=O)[C@@H]1C2=CC(=CC(=C2)OC2=C(C=CC(=C2)[C@@H](C(=O)N[C@H](CC2=CC(=C(O3)C=C2)Cl)C(=O)N1)N)O)O)O)C(=O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)NC(=O)C)Cl)CO)O)O PC

InChIKey

FHBQKTSCJKPYIO-OXIGXJDJSA-N PC

PubChem CID

16129712

Harm reduction information

No harm reduction data is on file for this compound yet. That means no dose, timing or combination data from PsychonautWiki or TripSit. Please don't guess a dose from similar compounds. If you have taken it and feel unwell, contact emergency services or a poison control center.

User reports

Pop culture

No references added yet.

Sources

1. Journal / agency Reynolds PE. Structure, biochemistry and mechanism of action of glycopeptide antibiotics. European Journal of Clinical Microbiology & Infectious Diseases. November 1989. doi:10.1007/BF01967563 · PMID 2532132
2. Other Teicoplanin Susceptibility and Minimum Inhibitory Concentration (MIC) Data
3. Journal / agency Murray BE, Arias CA, Nannini EC. Mandell, Douglas, and Bennett's Principles and Practice of Infectious Diseases. 2014
4. Journal / agency Vimberg V. Teicoplanin-A New Use for an Old Drug in the COVID-19 Era?. Pharmaceuticals (Basel, Switzerland). November 2021. doi:10.3390/ph14121227 · PMID 34959628 · PMC8708781
5. Other Gilpin M, Milner P. Resisting changes -- Over the past 40 years the glycopeptide antibiotics have played a crucial role in treating bacterial infections. But how long can it continue?. 1997
6. Journal / agency Campoli-Richards DM, Brogden RN, Faulds D. Teicoplanin. A review of its antibacterial activity, pharmacokinetic properties and therapeutic potential. Drugs. September 1990. doi:10.2165/00003495-199040030-00007 · PMID 2146108
7. Journal / agency Bernareggi A, Borghi A, Borgonovi M, Cavenaghi L, Ferrari P, Vékey K, Zanol M, Zerilli LF. Teicoplanin metabolism in humans. Antimicrobial Agents and Chemotherapy. August 1992. doi:10.1128/AAC.36.8.1744 · PMID 1416858 · PMC192040
8. Journal / agency Wang Y, Yao F, Chen S, Ouyang X, Lan J, Wu Z, Wang Y, Chen J, Wang X, Chen C. Optimal Teicoplanin Dosage Regimens in Critically Ill Patients: Population Pharmacokinetics and Dosing Simulations Based on Renal Function and Infection Type. Drug Design, Development and Therapy. 2023. doi:10.2147/DDDT.S413662 · PMID 37546521 · PMC10404122
9. Journal / agency Pandey A, Nikam AN, Shreya AB, Mutalik SP, Gopalan D, Kulkarni S, Padya BS, Fernandes G, Mutalik S, Prassl R. Potential therapeutic targets for combating SARS-CoV-2: Drug repurposing, clinical trials and recent advancements. Life Sciences. September 2020. doi:10.1016/j.lfs.2020.117883 · PMID 32497632 · PMC7263255
10. Journal / agency Di Bella S, Geremia N, Pea F, Zeitlinger M, Sanson G, Monticelli J, Bergmann F, Motet C, Lambotte-Buffet C, Zerbato V, Gatti M. When and How to Use Subcutaneous Antibiotics. Clinical Infectious Diseases. January 2026. doi:10.1093/cid/ciaf691 · PMID 41556663
11. Journal / agency Yu F, Pan T, Huang F, Ying R, Liu J, Fan H, Zhang J, Liu W, Lin Y, Yuan Y, Yang T, Li R, Zhang X, Lv X, Chen Q, Liang A, Zou F, Liu B, Hu F, Tang X, Li L, Deng K, He X, Zhang H, Zhang Y, Ma X. Glycopeptide Antibiotic Teicoplanin Inhibits Cell Entry of SARS-CoV-2 by Suppressing the Proteolytic Activity of Cathepsin L. Frontiers in Microbiology. 2022. doi:10.3389/fmicb.2022.884034 · PMID 35572668 · PMC9096618
12. Journal / agency Huang J, Ma Q, Su Z, Cheng X. Advancements in the Development of Anti-SARS-CoV-2 Therapeutics. International Journal of Molecular Sciences. October 2024. doi:10.3390/ijms251910820 · PMID 39409149 · PMC11477007
13. Other Actinoplanes teichomyceticus Parenti et al
14. Journal / agency Parenti F, Beretta G, Berti M, Arioli V. Teichomycins, new antibiotics from Actinoplanes teichomyceticus Nov. Sp. I. Description of the producer strain, fermentation studies and biological properties. The Journal of Antibiotics. April 1978. doi:10.7164/antibiotics.31.276 · PMID 659325
15. Journal / agency Trautmann M, Wiedeck H, Ruhnke M, Oethinger M, Marre R. Teicoplanin: 10 years of clinical experience. Infection. 1994. doi:10.1007/BF01715507 · PMID 7698846
16. Journal / agency Glupczynski Y, Lagast H, Van der Auwera P, Thys JP, Crokaert F, Yourassowsky E, Meunier-Carpentier F, Klastersky J, Kains JP, Serruys-Schoutens E. Clinical evaluation of teicoplanin for therapy of severe infections caused by gram-positive bacteria. Antimicrobial Agents and Chemotherapy. January 1986. doi:10.1128/AAC.29.1.52 · PMID 2942100 · PMC180363
17. Journal / agency Yushchuk O, Ostash B, Truman AW, Marinelli F, Fedorenko V. Teicoplanin biosynthesis: unraveling the interplay of structural, regulatory, and resistance genes. Applied Microbiology and Biotechnology. April 2020. doi:10.1007/s00253-020-10436-y · PMID 32076781

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