Skip to Content
Merck
All Photos(1)

Key Documents

R1781

Sigma-Aldrich

Ramoplanin

Synonym(s):

A 16686, Antibiotic A 16686

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

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

Assay

≥75% (as ramoplanin A2)

Quality Level

200

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
Lan Chen et al.
Journal of the American Chemical Society, 126(24), 7462-7463 (2004-06-17)
Ramoplanin is a potent cyclic lipoglycodepsipeptide antibiotic that disrupts bacterial cell wall synthesis by binding to the peptidoglycan intermediate Lipid II and blocking its polymerization to form the carbohydrate chains of peptidoglycan. Although ramoplanin is a promising compound for certain
Xiao Fang et al.
Bioorganic & medicinal chemistry letters, 19(21), 6189-6191 (2009-09-29)
Ramoplanin is a potent lipoglycodepsipeptide antibiotic that is active against a wide range of Gram-positive bacteria, including methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant enterococcus (VRE). It acts as an inhibitor of peptidoglycan (PG) biosynthesis that disrupts glycan chain polymerization by
James B Hamburger et al.
Proceedings of the National Academy of Sciences of the United States of America, 106(33), 13759-13764 (2009-08-12)
The glycodepsipeptide antibiotic ramoplanin A2 is in late stage clinical development for the treatment of infections from Gram-positive pathogens, especially those that are resistant to first line antibiotics such as vancomycin. Ramoplanin A2 achieves its antibacterial effects by interfering with
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
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service