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Merck

T0578

Teicoplanin

Sinónimos:

Targocid, Teichomycin

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Número CAS:
UNSPSC Code:
51282701
NACRES:
NA.76
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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

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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

Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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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.
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
Annamaria Iagnocco et al.
Medical ultrasonography, 14(3), 251-253 (2012-09-08)
Musculoskeletal ultrasound (US) is gaining an increasing role in the assessment of a variegate set of joint and periarticular soft tissues abnormalities in rheumatology. In addition, US represents a useful technique in guiding local procedures such as aspiration of fluid
Jinjian Fu et al.
PloS one, 8(3), e58240-e58240 (2013-03-14)
To assess the effectiveness and safety of linezolid in comparison with glycopeptides (vancomycin and teicoplanin) for the treatment of Staphylococcus aureus infections, we conducted a meta-analysis of relevant randomized controlled trials. A thorough search of Pubmed and other databases was
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

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