Teicoplanin
Title: Teicoplanin
CAS Registry Number: 61036-64-4
CAS Name: Teicoplanin A2
Additional Names: teichomycin A2
Manufacturers' Codes: MDL-507
Trademarks: Targocid (Aventis); Targosid (Aventis)
Literature References: Glycopeptide antibiotic complex produced by Actinoplanes teichomyceticus nov. sp.; structurally related to vancomycin, q.v. Comprised of 5 major components differentiated by a specific fatty acid moiety. Inhibits peptidoglycan synthesis in the cell wall of gram-positive bacteria. Isoln: BE 839259; C. Coronelli et al., US 4239751 (1976, 1980 both to Lepetit); F. Parenti et al., J. Antibiot. 31, 276 (1978); M. R. Bardone et al., ibid. 170. Separation of components: A. Borghi et al., DE 3320342; eidem, US 4542018 (1983, 1985 both to Lepetit); eidem, J. Antibiot. 37, 615 (1984). Structural studies: C. Coronelli et al., ibid. 621; J. C. J. Barna et al., J. Am. Chem. Soc. 106, 4895 (1984). Comparative in vitro activity: M. H. Cynamon, P. A. Granato, Antimicrob. Agents Chemother. 21, 504 (1982); H. C. Neu, P. Labthavikul, idem, 24, 425 (1983). Human pharmacokinetics: L. Verbist et al., ibid. 26, 881 (1984); P. L. Carver et al., ibid. 33, 82 (1989). Mechanism of action: S. Somma et al., ibid. 26, 917 (1984). Synergism with rifampin, q.v.: C. Watanakunakorn, J. Antimicrob. Chemother. 19, 439 (1987). HPLC determn in human serum: J. Levy et al., ibid. 533. Clinical trial in gram-positive bacterial infections: Y. Glupczynski et al., Antimicrob. Agents Chemother. 29, 52 (1986). Brief review: A. H. Williams, R. N. Grüneberg, J. Antimicrob. Chemother. 14, 441 (1984). Symposium on chemistry, pharmacology, activity, and clinical trials: J. Hosp. Infect. 7, Suppl. A, 47-112 (1986).
Properties: Amorphous powder, mp 260° (dec). uv max in 0.1N HCl: 278 (E1%1cm 53); in 0.1N NaOH: 297 (E1%1cm 74). Sol in aq soln at pH 7.0; partially sol in methanol, ethanol. Insol in dil mineral acids, in non-polar organic solvents.
Melting point: mp 260° (dec)
Absorption maximum: uv max in 0.1N HCl: 278 (E1%1cm 53); in 0.1N NaOH: 297 (E1%1cm 74)
 
Derivative Type: Teicoplanin A2-1
CAS Registry Number: 91032-34-7
Molecular Formula: C88H95Cl2N9O33
Molecular Weight: 1877.64
Percent Composition: C 56.29%, H 5.10%, Cl 3.78%, N 6.71%, O 28.12%
Properties: White amorphous powder, darkens at 220°, dec 255°.
 
Derivative Type: Teicoplanin A2-2
CAS Registry Number: 91032-26-7
Molecular Formula: C88H97Cl2N9O33
Molecular Weight: 1879.66
Percent Composition: C 56.23%, H 5.20%, Cl 3.77%, N 6.71%, O 28.09%
Properties: White amorphous powder, darkens at 210°, dec 250°.
 
Derivative Type: Teicoplanin A2-3
CAS Registry Number: 91032-36-9
Molecular Formula: C88H97Cl2N9O33
Molecular Weight: 1879.66
Percent Composition: C 56.23%, H 5.20%, Cl 3.77%, N 6.71%, O 28.09%
Properties: White amorphous powder, darkens at 210°, dec 250°.
 
Derivative Type: Teicoplanin A2-4
CAS Registry Number: 91032-37-0
Molecular Formula: C89H99Cl2N9O33
Molecular Weight: 1893.68
Percent Composition: C 56.45%, H 5.27%, Cl 3.74%, N 6.66%, O 27.88%
Properties: White amorphous powder, darkens at 210°, dec 250°.
 
Derivative Type: Teicoplanin A2-5
CAS Registry Number: 91032-38-1
Molecular Formula: C89H99Cl2N9O33
Molecular Weight: 1893.68
Percent Composition: C 56.45%, H 5.27%, Cl 3.74%, N 6.66%, O 27.88%
Properties: White amorphous powder, darkens at 210°, dec 250°.
 
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Antibiotics); Polypeptides.

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