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Merck
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Key Documents

R1781

Sigma-Aldrich

Ramoplanin

Synonyme(s) :

A 16686, Antibiotic A 16686

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About This Item

Numéro CAS:
76168-82-6
Numéro MDL:
MFCD01775776
Code UNSPSC :
51102829
Nomenclature NACRES :
NA.85

Pureté

≥75% (as ramoplanin A2)

Forme

powder

Solubilité

H2O: soluble 10 mg/mL

Spectre d'activité de l'antibiotique

Gram-positive bacteria

Mode d’action

cell wall synthesis | interferes

Conditions d'expédition

dry ice

Température de stockage

−20°C

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

Clé InChI

FSBZBQUUCNYWOK-YIOPJBSBSA-N

Catégories apparentées

Description générale

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. It is used for in vitro susceptibility testing and to study antibiotic-resistant enterococci.

Actions biochimiques/physiologiques

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.

Autres remarques

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

Pictogrammes

Corrosion
GHS05

Mention d'avertissement

Danger

Mentions de danger

H318

Conseils de prudence

P280 - P305 + P351 + P338

Classification des risques

Eye Dam. 1

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

nwg

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

Françoise Van Bambeke
Current opinion in investigational drugs (London, England : 2000), 7(8), 740-749 (2006-09-08)
Hemi-synthetic derivatives of glycopeptides have demonstrated bactericidal activity towards Gram-positive bacteria, including vancomycin-resistant strains (oritavancin and telavancin), and a prolonged half-life, allowing for once-daily (oritavancin and telavancin) or once-weekly (dalbavancin) administration. These compounds have proved effective for the treatment of
Chemistry and biology of ramoplanin: a lipoglycodepsipeptide with potent antibiotic activity.
Suzanne Walker et al.
Chemical reviews, 105(2), 449-476 (2005-02-11)
Xihou Yin et al.
Journal of natural products, 73(4), 583-589 (2010-04-01)
Enduracidins (1, 2) and ramoplanin (3) are structurally and functionally closely related lipodepsipeptide antibiotics. They are active against multi-drug-resistant Gram-positive pathogens, including MRSA. Each peptide contains one chlorinated non-proteinogenic amino acid residue, Cl(2)-Hpg or Cl-Hpg. To investigate the timing of
Mara Brunati et al.
The Journal of antibiotics, 58(7), 473-478 (2005-09-16)
Ramoplanin is a glycolipodepsipeptide antibiotic obtained by fermentation of the Actinoplanes sp. ATCC 33076, isolated as a complex of three closely related components A1, A2 and A3, which differ in their fatty acid moiety. We have investigated the influence of
T Peláez et al.
Antimicrobial agents and chemotherapy, 49(3), 1157-1159 (2005-02-25)
We evaluated the in vitro activity of ramoplanin, an antimicrobial compound that inhibits cell wall synthesis by acting at the level of lipid intermediate formation, against Clostridium difficile. We included strains with reduced susceptibilities to vancomycin (vancomycin-intermediate [Van(i)] strains) or
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