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R1781

Sigma-Aldrich

Ramoplanin

Synonym(s):

A 16686, Antibiotic A 16686

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About This Item

CAS Number:
76168-82-6
MDL number:
MFCD01775776
UNSPSC Code:
51102829
NACRES:
NA.85

Assay

≥75% (as ramoplanin A2)

form

powder

solubility

H2O: soluble 10 mg/mL

antibiotic activity spectrum

Gram-positive bacteria

Mode of action

cell wall synthesis | interferes

shipped in

dry ice

storage temp.

−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

InChI key

FSBZBQUUCNYWOK-YIOPJBSBSA-N

Related Categories

General description

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.

Biochem/physiol Actions

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.

Other Notes

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

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H318

Precautionary Statements

P280 - P305 + P351 + P338

Hazard Classifications

Eye Dam. 1

Storage Class Code

11 - Combustible Solids

WGK

nwg

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
Ashwin Balagopal et al.
Current opinion in pharmacology, 7(5), 455-458 (2007-07-24)
Clostridium difficile disease is the major, known cause of nosocomial diarrhea and is an emerging cause of community-associated diarrhea. Recent outbreaks due to a strain of apparent increased virulence, BI/NAP1, and recognition of increasing metronidazole treatment failures as well as
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
Dongwoo Shin et al.
Proceedings of the National Academy of Sciences of the United States of America, 101(33), 11977-11979 (2004-06-04)
Ramoplanin is a potent antibiotic, first disclosed in 1984, that acts by inhibiting bacterial cell-wall biosynthesis. The original ramoplanin complex was shown to consist of a mixture of three closely related compounds, ramoplanin A1-A3, of which ramoplanin A2 is the
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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