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Teicoplanin information


Teicoplanin
Clinical data
Pronunciation/ˌtkˈplnɪn/
TY-koh-PLAY-nin
Trade namesTargocid
AHFS/Drugs.comInternational Drug Names
Pregnancy
category
  • AU: B3
Routes of
administration
Intravenous, intramuscular
ATC code
  • J01XA02 (WHO)
Legal status
Legal status
  • AU: S4 (Prescription only)[1]
  • UK: POM (Prescription only)
  • EU: Rx-only[2]
Pharmacokinetic data
Bioavailability90% (given IM)
Protein binding90% to 95%
MetabolismNil
Elimination half-life70 to 100 hours
ExcretionKidney (97% unchanged)
Identifiers
IUPAC name
  • Ristomycin A 34-O-[2-(acetylamino)-2-deoxy-.beta.-D-glucopyranosyl]-22,31-dichloro-7-demethyl-64-O-demethyl-19-deoxy-56-O-[2-deoxy-2-[(8-methyl-1-oxononyl)amino]-.beta.-D-glucopyranosyl]-42-O-.alpha.-D-mannopyranosyl-
CAS Number
  • 61036-62-2 checkY
PubChem CID
  • 16129712
DrugBank
  • DB06149 checkY
ChemSpider
  • 16736197 checkY
UNII
  • 4U3D3YY81M
KEGG
  • D02142 checkY
ChEMBL
  • ChEMBL415428 ☒N
NIAID ChemDB
  • 007693
CompTox Dashboard (EPA)
  • DTXSID4048642 Edit this at Wikidata
Chemical and physical data
FormulaVariable
Molar mass1564.3 to 1907.7 g/mol
Melting point260 °C (500 °F) (dec.)
InChI
  • InChI=1S/C89H99Cl2N9O33/c1-34(2)9-7-5-4-6-8-10-61(109)95-69-75(114)72(111)59(32-102)130-88(69)133-79-56-26-41-27-57(79)127-53-18-14-39(24-48(53)91)78(132-87-68(93-35(3)104)74(113)71(110)58(31-101)129-87)70-85(122)99-67(86(123)124)46-29-43(106)30-55(128-89-77(116)76(115)73(112)60(33-103)131-89)62(46)45-23-38(13-15-50(45)107)64(82(119)100-70)97-84(121)66(41)98-83(120)65-40-21-42(105)28-44(22-40)125-54-25-37(12-16-51(54)108)63(92)81(118)94-49(80(117)96-65)20-36-11-17-52(126-56)47(90)19-36/h11-19,21-30,34,49,58-60,63-78,87-89,101-103,105-108,110-116H,4-10,20,31-33,92H2,1-3H3,(H,93,104)(H,94,118)(H,95,109)(H,96,117)(H,97,121)(H,98,120)(H,99,122)(H,100,119)(H,123,124)/t49-,58-,59-,60-,63+,64-,65+,66-,67-,68-,69-,70+,71-,72-,73-,74-,75-,76+,77+,78-,87+,88+,89+/m1/s1 checkY
  • Key:FHBQKTSCJKPYIO-OXIGXJDJSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Teicoplanin is an semisynthetic glycopeptide antibiotic with a spectrum of activity similar to vancomycin. Its mechanism of action is to inhibit bacterial cell wall[3] peptidoglycan[4] 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.[3]

Teicoplanin is marketed by Sanofi-Aventis under the trade name Targocid. Other trade names include Ticocin marketed by Cipla(India).

Oral teicoplanin has been demonstrated to be effective in the treatment of pseudomembranous colitis and Clostridium difficile-associated diarrhoea, with comparable efficacy with vancomycin.[5]

Its strength is considered to be due to the length of the hydrocarbon chain.[6]

Teicoplanin is produced by the so-called "rare" actinobacterium Actinoplanes teichomyceticus ATCC 31121,[7] belonging to the Micromonosporaceae family. Biosynthetic pathway leading to teicoplanin, as well as the regulatory circuit governing the biosynthesis, were studied intensively in recent years allowing to construct an integrated model of the biosynthesis.[8]

  1. ^ "Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 30 March 2024.
  2. ^ Human Medicines Evaluation Division (10 December 2020). "Active substance: teicoplanin" (PDF). List of nationally authorised medicinal products. European Medicines Agency.
  3. ^ a b Reynolds PE (November 1989). "Structure, biochemistry and mechanism of action of glycopeptide antibiotics". European Journal of Clinical Microbiology & Infectious Diseases. 8 (11): 943–950. doi:10.1007/BF01967563. PMID 2532132. S2CID 21551939.
  4. ^ "Teicoplanin Susceptibility and Minimum Inhibitory Concentration (MIC) Data" (PDF). TOKU-E.
  5. ^ de Lalla F, Nicolin R, Rinaldi E, Scarpellini P, Rigoli R, Manfrin V, et al. (October 1992). "Prospective study of oral teicoplanin versus oral vancomycin for therapy of pseudomembranous colitis and Clostridium difficile-associated diarrhea". Antimicrobial Agents and Chemotherapy. 36 (10): 2192–2196. doi:10.1128/AAC.36.10.2192. PMC 245474. PMID 1444298.
  6. ^ Gilpin M, Milner P (1997). "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 ?". Royal Society of Chemistry. Archived from the original on 2002-12-21. Retrieved 2006-10-15. - includes picture of Teicoplanin's structure.
  7. ^ "Actinoplanes teichomyceticus Parenti et al". ATCC (American Type Culture Collection).
  8. ^ Yushchuk O, Ostash B, Truman AW, Marinelli F, Fedorenko V (April 2020). "Teicoplanin biosynthesis: unraveling the interplay of structural, regulatory, and resistance genes". Applied Microbiology and Biotechnology. 104 (8): 3279–3291. doi:10.1007/s00253-020-10436-y. PMID 32076781. S2CID 211170874.

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more effective than glycopeptide antibiotics (such as vancomycin and teicoplanin) and beta-lactam antibiotics in the treatment of skin and soft tissue...

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flomoxef 1988 – isepamycin 1988 – midecamycin 1988 – rifapentine 1988 – teicoplanin 1989 – cefpodoxime 1989 – enrofloxacin 1989 – lomefloxacin 1989 – moxifloxacin...

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Penicillin

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This is in contrast to the glycopeptide antibiotics vancomycin and teicoplanin, which are both much larger than the penicillins. Gram-positive bacteria...

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Staphylococcus xylosus

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xylosus is normally sensitive to fleroxacin, methicillin, penicillin, teicoplanin, erythromycin and tetracycline, and resistant to novobiocin. It is highly...

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Sepsis

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For methicillin-resistant Staphylococcus aureus (MRSA), vancomycin or teicoplanin is recommended. For Legionella infection, addition of macrolide or fluoroquinolone...

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faecalis populations: VanA - enterococcal resistance to vancomycin and teicoplanin; inducible on exposure to these agents VanB - lower-level enterococcal...

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Pseudomonas aeruginosa. The glycopeptide antibiotics (e.g. vancomycin, teicoplanin, telavancin) only work against gram-positive pathogens such as Staphylococcus...

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to influence antibiotic resistance of the bacteria to Vancomycin and Teicoplanin glycopeptides, which are used to treat MRSA infections. In this study...

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infections due to MRSA is currently glycopeptide antibiotics (vancomycin and teicoplanin). A number of problems with these antibiotics occur, such as the need...

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Schedule H

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TAMSULOSIN HYDROCHLORIDE 480. TRAPIDIL 481. TEGASEROD MALEATE 482. TEICOPLANIN 483. TELMISARTAN 484. TEMOZOLAMIDE 485. TERAZOSIN 486. TERBUTALINE SULPHATE...

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Blood culture

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Tallo E, Cordero Carrasco JL (March 2012). "[Activity of vancomycin, teicoplanin and linezolid in methicillin resistant coagulase-negative Staphylococci...

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Erysipelothrix rhusiopathiae

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chloramphenicol, daptomycin, gentamicin, netilmicin, polymyxin B, streptomycin, teicoplanin, tetracycline, and trimethoprim/sulfamethoxazole. Penicillins and cephalosporins...

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Actinoplanes

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to the antidiabetic drug acarbose and to the antibiotic validamycin), teicoplanin, and ramoplanin. Actinoplanes comprises the following species: A. abujensis...

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Lactobacillus jensenii

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In the rare occurrence of infection, L. jensenii can be treated with teicoplanin and meropenem. Nardis, C.; Mastromarino, P.; Mosca, L. (September 2013)...

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Leuconostoc lactis

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intrinsic resistance to traditional antibiotics like vancomycin and teicoplanin. There has been at least one recorded case of a 4 year old patient presenting...

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Secondary metabolite

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VanY protein domain

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ATC code J01

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