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Merck
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Documentos clave

R1781

Sigma-Aldrich

Ramoplanin

Sinónimos:

A 16686, Antibiotic A 16686

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About This Item

Número de CAS:
Número MDL:
Código UNSPSC:
51102829
NACRES:
NA.85

Ensayo

≥75% (as ramoplanin A2)

Nivel de calidad

Formulario

powder

solubilidad

H2O: soluble 10 mg/mL

espectro de actividad antibiótica

Gram-positive bacteria

Modo de acción

cell wall synthesis | interferes

Condiciones de envío

dry ice

temp. de almacenamiento

−20°C

cadena SMILES

ClC1C(CCC(C1)C(NC(=O)[C@H](NC(=O)[C@@H](NC(=O)CNC(=O)C(NC(=O)[C@@H](NC(=O)C(NC(=O)[C@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@H](NC(=O)[C@H](NC(=O)[C@H](NC(=O)[C@H](NC(=O)C(NC(=O)[C@@H](NC(=O)\C=C/C=C\CCC)CC(=O)N)CC(=O)N)C7CCC(CC7)O)CCCN)[C@@H](O

InChI

1S/C106H170ClN21O30/c1-8-9-10-11-15-22-80(140)114-75(50-78(110)138)96(147)118-76(51-79(111)139)97(148)124-86(60-25-36-66(133)37-26-60)102(153)117-72(21-17-46-109)92(143)120-83(56(6)130)100(151)126-89(63-31-42-69(136)43-32-63)105(156)127-88(62-29-40-68(135)41-30-62)104(155)121-82(55(5)129)99(150)119-74(48-58-18-13-12-14-19-58)95(146)116-71(20-16-45-108)93(144)123-87(61-27-38-67(134)39-28-61)103(154)122-84(57(7)131)101(152)125-85(59-23-34-65(132)35-24-59)98(149)112-52-81(141)115-73(47-53(2)3)94(145)113-54(4)91(142)128-90(106(157)158)64-33-44-77(137)70(107)49-64/h10-15,18-19,22,53-57,59-77,82-90,129-137H,8-9,16-17,20-21,23-52,108-109H2,1-7H3,(H2,110,138)(H2,111,139)(H,112,149)(H,113,145)(H,114,140)(H,115,141)(H,116,146)(H,117,153)(H,118,147)(H,119,150)(H,120,143)(H,121,155)(H,122,154)(H,123,144)(H,124,148)(H,125,152)(H,126,151)(H,127,156)(H,128,142)(H,157,158)/b11-10-,22-15-/t54-,55+,56+,57+,59?,60?,61?,62?,63?,64?,65?,66?,67?,68?,69?,70?,71-,72-,73+,74+,75+,76?,77?,82+,83-,84+,85?,86-,87?,88-,89-,90?/m1/s1

Clave InChI

FSBZBQUUCNYWOK-YIOPJBSBSA-N

Descripción general

Chemical structure: glycopeptide
Ramoplanin is a glycolipodepsipeptide antibiotic produced by Actinoplanes sp. It is a complex of structurally related molcules, with ramoplanin A2 as the primary component.
Ramoplanin is a glycolipodepsipeptide antibiotic produced by Actinoplanes sp. It is a complex of structurally related molcules, with ramoplanin A2 as the primary component. It is used for in vitro susceptibility testing and to study antibiotic-resistant enterococci.

Acciones bioquímicas o fisiológicas

Ramoplatin is an antimicrobial which is effective against Gram-positive bacteria, including vancomycin-resistant enterococci. It acts by inhibiting bacterial cell wall synthesis, although its mechanism of action is different from that of glycopeptide-based synthesis inhibitors.

Otras notas

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

Pictogramas

Corrosion

Palabra de señalización

Danger

Frases de peligro

Consejos de prudencia

Clasificaciones de peligro

Eye Dam. 1

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

nwg

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

dust mask type N95 (US), Eyeshields, Gloves


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Letal I Salzberg et al.
Journal of bacteriology, 193(20), 5793-5801 (2011-08-23)
The transglycosylation step of cell wall synthesis is a prime antibiotic target because it is essential and specific to bacteria. Two antibiotics, ramoplanin and moenomycin, target this step by binding to the substrate lipid II and the transglycosylase enzyme, respectively.
Herman Goossens et al.
The Journal of antimicrobial chemotherapy, 51 Suppl 3, iii5-ii12 (2003-06-13)
A survey in eight European countries, including 13 hospitals, of vancomycin-resistant enterococci (VRE) in at-risk hospital wards (such as the ICU and the haematology ward) was performed in 2001, and the in vitro susceptibility of the isolates ramoplanin and other
Chemistry and biology of ramoplanin: a lipoglycodepsipeptide with potent antibiotic activity.
Suzanne Walker et al.
Chemical reviews, 105(2), 449-476 (2005-02-11)
Matthew F Ewles et al.
Biomedical chromatography : BMC, 25(9), 995-1002 (2010-12-15)
A method has been developed and validated for the quantification of ramoplanin, a 2554 Da peptide antibiotic, in human dried blood spots using high-performance liquid chromatography with tandem mass spectrometric detection. The validation data meet FDA acceptance criteria for bioanalytical assays
Romeo Ciabatti et al.
Journal of medicinal chemistry, 50(13), 3077-3085 (2007-06-05)
Ramoplanin is a glycolipodepsipeptide antibiotic active against Gram-positive bacteria including vancomycin-resistant enterococci. Ramoplanin inhibits bacterial cell wall biosynthesis by a mechanism different from that of glycopeptides and hence does not show cross-resistance with these antibiotics. The systemic use of ramoplanin

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