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Merck
CN

T0578

Teicoplanin

Synonym(s):

Targocid, Teichomycin

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About This Item

CAS Number:
61036-62-2
UNSPSC Code:
51282701
NACRES:
NA.76

Key Documents

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SMILES string

Clc1c2ccc(c1)[C@H]([C@@H]4NC(=O)[C@H](NC(=O)[C@@H]8NC(=O)[C@H]9NC(=O)[C@H](NC(=O)[C@@H](c%13cc(c(cc%13)O)Oc%14cc9cc(c%14)O)[N+H3])Cc%10cc(c(cc%10)Oc%11c(c(cc8c%11)O2)O[C@@H]%12O[C@@H]([C@H]([C@@H]([C@H]%12NC(=O)CCCCCCCCC)O)O)CO)Cl)c5cc(c(cc5)O)c6c(cc(cc6O

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)/t48-,57-,58-,59-,62-,63-,64+,65-,66-,67-,68-,69+,70-,71-,72-,73-,74-,75+,76+,77-,86+,87+,88+/m1/s1

InChI key

BJNLLBUOHPVGFT-QRZIFLFXSA-N

assay

≥80% (teicoplanins A2, HPLC)

form

powder

storage condition

(Keep container tightly closed in a dry and well-ventilated place.)

color

white to faint beige
 white to faint yellow
 white to light brown

antibiotic activity spectrum

Gram-positive bacteria

mode of action

cell wall synthesis | interferes

storage temp.

2-8°C

Quality Level

200

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Application

Teicoplanin is a glycopeptide antibiotic produced by Actinoplanes teichomiceticus that is effective against Gram-positive bacteria resistant to β-lactam antibiotics. Teicoplanin and vancomycin have been used clinically for the treatment of methicillin-resistant Staphylococcus aureus (MRSA) infections. Product T0578 is a mixture of six primary teicoplanins; primarily teicoplanins A2 group.

Biochem/physiol Actions

Teicoplanin is a glycopeptide antibiotic produced by Actinoplanes teichomiceticus that is effective against Gram-positive bacteria resistant to β-lactam antibiotics. Its mechanism of action is through inhibition of bacterial cell wall biosynthesis.
Teicoplanin is a glycopeptide antibiotic. It is a mixture of several compounds, five major (named teicoplanin A2-1 through A2-5) and four minor (named teicoplanin RS-1 through RS-4). All teicoplanins share a same glycopeptide core, termed teicoplanin A3-1, a fused ring structure to which two carbohydrates (mannose and N-acetylglucosamine) are attached. The major and minor components also contain a third carbohydrate moiety, β-D-glucosamine, and differ only by the length and conformation of a side chain attached to it. It′s mechanism of action is through inhibition of bacterial cell wall biosynthesis.

Other Notes

Keep container tightly closed in a dry and well-ventilated place.
Mixture of six primary teicoplanins; primarily teicoplanins A2 group.

Packaging

100MG,1G

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000515777
0000515777
0000480613
0000480613
0000430825

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Francis H Y Fung et al.
Annals of clinical biochemistry, 49(Pt 5), 475-481 (2012-08-10)
Teicoplanin is an antibiotic used for the treatment of endocarditis, osteomyelitis, septic arthritis and methicillin-resistant Staphylococcus aureus. Teicoplanin is emerging as a suitable alternative antibiotic to vancomycin, where their trough serum levels are monitored by immunoassay routinely. This is the
Jann-Tay Wang et al.
BMC infectious diseases, 13, 182-182 (2013-04-23)
The present study was designed to investigate whether teicoplanin minimum inhibitory concentrations (MICs) of methicillin-resistant Staphylococcus aureus (MRSA) isolates play a role in the prognosis of patient with teicoplanin-treated MRSA bloodstream infection (BSI). Between 1 January 2006 and 31 December
Giovanni D'Orazio et al.
Journal of chromatography. A, 1285, 118-123 (2013-03-12)
Capillary columns were packed firstly with silica modified-teicoplanin (teico-CSP) particles for a short zone (1-5 cm) and then with a Cogent Bidentate C18 silica phase (25 cm). The first part of the column (inlet) was intended for focusing the sample
Szilvia Tollas et al.
European journal of medicinal chemistry, 54, 943-948 (2012-07-17)
Glycopeptide antibiotic derivative teicoplanin ψ-aglycone has been bound covalently to a fullerenopyrrolidine derivative using azide-alkyne 1,3-dipolar cycloaddition reaction. The aggregation of the antibiotic-fullerene conjugate in aqueous solution has been studied. The conjugate exhibited antibacterial activity against enterococci resistant to teicoplanin.
Hongli Sun et al.
Diagnostic microbiology and infectious disease, 74(4), 399-403 (2012-10-27)
The epidemiology and molecular characteristics of vancomycin-resistant enterococci (VRE) from China deserve further investigation. This study reports on the molecular characterization of 101 unique VRE (96 E. faecium and 5 E. faecalis strains) recovered from diverse samples of 12 hospitals
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