Teicoplanin

For research use only. Not for therapeutic Use.

  • CAT Number: A000660
  • CAS Number: 61036-62-2
  • Molecular Formula: C88H97Cl2N9O33
  • Molecular Weight: 1879.67
  • Purity: ≥95%
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Teicoplanin(Cat No.:A000660)is a glycopeptide antibiotic effective primarily against Gram-positive bacteria, including Staphylococcus aureus and Enterococcus species. It works by inhibiting bacterial cell wall synthesis, binding to peptidoglycan precursors, and preventing cell wall cross-linking, which leads to cell death. Often used in treating severe infections like endocarditis, septicemia, and bone infections, teicoplanin is valuable for patients with beta-lactam allergies. It has a long half-life, allowing for once-daily dosing, and a favorable safety profile, making it a critical choice in managing resistant bacterial infections, especially in hospital settings.


Catalog Number A000660
CAS Number 61036-62-2
Synonyms

Teichomycin; TEICOPLANIN; 61036-62-2; Antibiotic 8327A; Tecoplanina; Tecoplanine

Molecular Formula C88H97Cl2N9O33
Purity ≥95%
Storage -20°C
IUPAC Name 2-[3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-22-amino-5,15-dichloro-64-[3-(decanoylamino)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-26,31,44,49-tetrahydroxy-21,35,38,54,56,59-hexaoxo-47-[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
InChI InChI=1S/C88H97Cl2N9O33/c1-3-4-5-6-7-8-9-10-60(108)94-68-74(113)71(110)58(32-101)129-87(68)132-78-55-26-40-27-56(78)126-52-18-14-38(24-47(52)90)77(131-86-67(92-34(2)103)73(112)70(109)57(31-100)128-86)69-84(121)98-66(85(122)123)45-29-42(105)30-54(127-88-76(115)75(114)72(111)59(33-102)130-88)61(45)44-23-37(13-15-49(44)106)63(81(118)99-69)96-83(120)65(40)97-82(119)64-39-21-41(104)28-43(22-39)124-53-25-36(12-16-50(53)107)62(91)80(117)93-48(79(116)95-64)20-35-11-17-51(125-55)46(89)19-35/h11-19,21-30,48,57-59,62-77,86-88,100-102,104-107,109-115H,3-10,20,31-33,91H2,1-2H3,(H,92,103)(H,93,117)(H,94,108)(H,95,116)(H,96,120)(H,97,119)(H,98,121)(H,99,118)(H,122,123)
InChIKey BJNLLBUOHPVGFT-UHFFFAOYSA-N
SMILES CCCCCCCCCC(=O)NC1C(C(C(OC1OC2=C3C=C4C=C2OC5=C(C=C(C=C5)C(C6C(=O)NC(C7=C(C(=CC(=C7)O)OC8C(C(C(C(O8)CO)O)O)O)C9=C(C=CC(=C9)C(C(=O)N6)NC(=O)C4NC(=O)C1C2=CC(=CC(=C2)OC2=C(C=CC(=C2)C(C(=O)NC(CC2=CC(=C(O3)C=C2)Cl)C(=O)N1)N)O)O)O)C(=O)O)OC1C(C(C(C(O1)CO)O)O)NC(=O)C)Cl)CO)O)O
Reference

1: Cazaubon Y, Venisse N, Mimoz O, Maire P, Ducher M, Bourguignon L, Goutelle S.
Population pharmacokinetics of teicoplanin administered by subcutaneous or
intravenous route and simulation of optimal loading dose regimen. J Antimicrob
Chemother. 2017 Oct 1;72(10):2804-2812. doi: 10.1093/jac/dkx242. PubMed PMID:
29091222.
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2: Boast A, Gwee A, Gwee A. Teicoplanin-Should We Be Doing Routine Therapeutic
Drug Monitoring in Children? Pediatr Infect Dis J. 2017 Nov;36(11):1110. doi:
10.1097/INF.0000000000001642. PubMed PMID: 29023347.

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3: Ramos-Martín V, Johnson A, McEntee L, Farrington N, Padmore K, Cojutti P, Pea
F, Neely MN, Hope WW. Pharmacodynamics of teicoplanin against MRSA. J Antimicrob
Chemother. 2017 Sep 11. doi: 10.1093/jac/dkx289. [Epub ahead of print] PubMed
PMID: 28962026.
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4: Ismail OH, Antonelli M, Ciogli A, Villani C, Cavazzini A, Catani M, Felletti
S, Bell DS, Gasparrini F. Future perspectives in high efficient and ultrafast
chiral liquid chromatography through zwitterionic teicoplanin-based 2-μm
superficially porous particles. J Chromatogr A. 2017 Oct 20;1520:91-102. doi:
10.1016/j.chroma.2017.09.008. Epub 2017 Sep 6. PubMed PMID: 28911942.
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5: Ramos-Martín V, Neely MN, Padmore K, Peak M, Beresford MW, Turner MA, Paulus
S, López-Herce J, Hope WW. Tools for the Individualized Therapy of Teicoplanin
for Neonates and Children. Antimicrob Agents Chemother. 2017 Sep 22;61(10). pii:
e00707-17. doi: 10.1128/AAC.00707-17. Print 2017 Oct. PubMed PMID: 28760897;
PubMed Central PMCID: PMC5610524.
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6: Knafl D, Thalhammer F, Vossen MG. In-vitro release pharmacokinetics of
amikacin, teicoplanin and polyhexanide in a platelet rich fibrin-layer (PRF)-a
laboratory evaluation of a modern, autologous wound treatment. PLoS One. 2017 Jul
7;12(7):e0181090. doi: 10.1371/journal.pone.0181090. eCollection 2017. PubMed
PMID: 28686663; PubMed Central PMCID: PMC5501641.
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7: Erratum: Intrathecal baclofen pump infection treated by adjunct intrareservoir
teicoplanin instillation. Surg Neurol Int. 2017 Jun 13;8:119. doi:
10.4103/2152-7806.207945. eCollection 2017. PubMed PMID: 28680738; PubMed Central
PMCID: PMC5482158.
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8: Nakano T, Nakamura T, Nakamura Y, Irie K, Sato K, Matsuo K, Imakyure O, Ogata
K, Mishima K, Kamimura H. Effects of Teicoplanin on the PT-INR Controlled by
Warfarin in Infection Patients. Yakugaku Zasshi. 2017;137(7):909-916. doi:
10.1248/yakushi.17-00023. Japanese. PubMed PMID: 28674307.

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9: Wi J, Noh H, Min KL, Yang S, Jin BH, Hahn J, Bae SK, Kim J, Park MS, Choi D,
Chang MJ. Population Pharmacokinetics and Dose Optimization of Teicoplanin during
Venoarterial Extracorporeal Membrane Oxygenation. Antimicrob Agents Chemother.
2017 Aug 24;61(9). pii: e01015-17. doi: 10.1128/AAC.01015-17. Print 2017 Sep.
PubMed PMID: 28674057; PubMed Central PMCID: PMC5571348.

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10: Takechi K, Yanagawa H, Zamami Y, Ishizawa K, Tanaka A, Araki H. Evaluation of
factors associated with the achievement of an optimal teicoplanin trough
concentration&#8233;. Int J Clin Pharmacol Ther. 2017 Aug;55(8):672-677. doi:
10.5414/CP203009. PubMed PMID: 28655381.

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