Mode of action
ChemicalBook > CAS DataBase List > Ramoplanin

Ramoplanin

Mode of action
Product Name
Ramoplanin
CAS No.
76168-82-6
Chemical Name
Ramoplanin
Synonyms
A 16686;A 16686A;Ramoplanin;Ramoplaninr;Ray mora ning;Antibiotic A 16686;RaMoplanin coMplex;RaMoplanin(A 16686,A 16686A)
CBNumber
CB61074884
Molecular Formula
C106H170ClN21O30
Formula Weight
2254.0597
MOL File
76168-82-6.mol
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Ramoplanin Property

Melting point:
210-230°
alpha 
D20 +78.3° (c = 1.04 in H2O)
storage temp. 
-20°C
solubility 
H2O: soluble10mg/mL
form 
powder
color 
White to Off-White
InChIKey
FSBZBQUUCNYWOK-KFTDLNJOSA-N
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Safety

Hazard Codes 
Xi
Risk Statements 
41
Safety Statements 
26-39
WGK Germany 
nwg
RTECS 
VE5050000
Toxicity
LD50 in mice (mg/kg): 328 i.p., 122 i.v.; orally in rats: 2000 mg/kg (Pallanza)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H318Causes serious eye damage

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
R1781
Product name
Ramoplanin
Purity
≥75% (as ramoplanin A2)
Packaging
250mg
Price
$385
Updated
2024/03/01
Cayman Chemical
Product number
28189
Product name
Ramoplanin Complex
Packaging
10mg
Price
$44
Updated
2024/03/01
Cayman Chemical
Product number
28189
Product name
Ramoplanin Complex
Packaging
250mg
Price
$321
Updated
2024/03/01
Cayman Chemical
Product number
28189
Product name
Ramoplanin Complex
Packaging
50mg
Price
$130
Updated
2024/03/01
Cayman Chemical
Product number
28189
Product name
Ramoplanin Complex
Packaging
100mg
Price
$172
Updated
2024/03/01
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Ramoplanin Chemical Properties,Usage,Production

Mode of action

The lipid carrier involved in transporting the cell wall building block across the membrane is a C55 isoprenyl phosphate. The lipid acquires an additional phosphate group in the transport process and must be dephosphorylated in order to regenerate the native compound for another round of transfer. Ramoplanin as cyclic peptide antibiotics binds to the C55 lipid carrier. Ramoplanin prevents it from participating in transglycosylation thus disrupting the lipid carrier cycle.

Description

Ramoplanin (A 16686, A16686A, MDL 62198) is a novel oral nonabsorbable 17-amino-acid cyclic lipoglycodepsipeptide antibiotic from Biosearch Italy. Ramoplanin is an antibiotic complex, first identified in 1984, that was isolated from the fermentation broth of Actinoplanes sp. ATCC 33076. It is a mixture of three closely related compounds, ramoplanin A1–A3, which differ only in the acyl group attached to the Asn-1 N-terminus; ramoplanin A2 is the most abundant.

Uses

Ramoplanin is a potent cyclic lipoglycodepsipeptide antibiotic that exhibits wide spectrum of antibiotic properties against gram-positive and gram-negative bacteria.

Uses

Ramoplanin is a complex of three high molecular weight glycolipodepsipeptides, varying in the chain length and shape of the dieneone lipid side-chain. Ramoplanin was isolated in the early 1980s as the major metabolite of a strain of Actinoplanes with antiviral and antibiotic activity against drug resistant Gram positive isolates. Ramoplanin acts by inhibiting cell wall biosynthesis via a different mechanism from the vancomycin-related glycopeptides.

Antimicrobial activity

Ramoplanin displays activity against aerobic and anaerobic Grampositive bacteria by preventing cell wall peptidoglycan formation through binding to a key intermediate moiety, lipid II, and thereby disrupting bacterial cell wall synthesis. The primary use of ramoplanin is in the treatment of Clostridium difficile infections.

Mechanism of action

The mechanism of action of ramoplanin involves sequestration of peptidoglycan biosynthesis lipid intermediates, thus physically occluding these substrates from proper utilization by the latestage peptidoglycan biosynthesis enzymes MurG and the transglycosylases (TGases). Ramoplanin is structurally related to two cell wall-active lipodepsipeptide antibiotics, janiemycin and enduracidin, and is functionally related to members of the lantibiotic class of antimicrobial peptides (mersacidin, actagardine, nisin, and epidermin) and glycopeptide antibiotics. As a consequence of its unique mechanism of action, cross-resistance with existing glycopeptides and beta-lactam antibiotics has not been observed.

Pharmacokinetics

Ramoplanin is not absorbed from the intestinal tract. When ramoplanin (200 and 400 mg) was administered orally to two groups of healthy volunteers over a period of 10 days, no ramoplanin could be detected in plasma and urine. With the 200-mg dose, concentrations in stools varied between 467 and 1043 mg/g, and with the 400-mg dose, concentrations were between 765 and 2032 mg/g. Results from an in vitro gut model and hamster model revealed that ramoplanin may be more effective than vancomycin at killing spores and preventing spore recrudescence.

Toxicology

When administered orally in a double-blind randomized placebocontrolled study, no adverse reactions were observed in patients receiving two daily doses of ramoplanin (100 or 400 mg) in comparison with the placebo. Single and repeated topical application in ten healthy human volunteers revealed very low irritation rates and no sensitization after 21 days.

Ramoplanin Preparation Products And Raw materials

Raw materials

Preparation Products

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Ramoplanin Suppliers

Canada 1 China 78 Germany 1 India 1 United Kingdom 1 United States 10 Global 92
LGM Pharma
Tel
1-(800)-881-8210
Fax
615-250-9817
Email
inquiries@lgmpharma.com
Country
United States
ProdList
2123
Advantage
70
Creative Peptides
Tel
Email
info@creative-peptides.com
Country
United States
ProdList
6083
Advantage
56
BOC Sciences
Tel
16314854226; +16314854226
Email
inquiry@bocsci.com
Country
United States
ProdList
19741
Advantage
58
TargetMol Chemicals Inc.
Tel
Email
support@targetmol.com
Country
United States
ProdList
38631
Advantage
58
Aladdin Scientific
Tel
+1-+1(833)-552-7181
Email
sales@aladdinsci.com
Country
United States
ProdList
57505
Advantage
58
Cayman Chemical Company
Tel
--
Fax
--
Email
cayman@caymanchem.com
Country
United States
ProdList
6213
Advantage
81
United States Biological
Tel
--
Fax
--
Email
chemicals@usbio.net
Country
United States
ProdList
6214
Advantage
80
MedChemExpress
Tel
--
Fax
--
Email
sales@medchemexpress.com
Country
United States
ProdList
6398
Advantage
58
Riedel-de Haen AG
Tel
--
Fax
--
Country
United States
ProdList
6773
Advantage
87
LKT Laboratories, Inc.
Tel
--
Fax
--
Email
info@lktlabs.com
Country
United States
ProdList
2164
Advantage
64

76168-82-6, RamoplaninRelated Search:

METHYL ISOCYANOACETATE PHENYLSELENOL TRIS(2,2,6,6-TETRAMETHYL-3,5-HEPTANEDIONATO)EUROPIUM(III) TRIS(2,2,6,6-TETRAMETHYL-3,5-HEPTANEDIONATO)DYSPROSIUM(III) Ethyl isocyanoacetate Ferric acetylacetonate Benzyl isocyanide DICHLORO(ETHYLENEDIAMINE)PLATINUM(II) 1,1,3,3-TETRAMETHYLBUTYL ISOCYANIDE Tosylmethyl isocyanide 2,4-PENTANEDIONE, SILVER DERIVATIVE TERT-BUTYL ISOCYANIDE Cupric acetylacetonate COBALT(II) ACETYLACETONATE Aluminum acetylacetonate SALCOMINE N-BUTYLISOCYANIDE Tris(2,4-pentanedionato)chroMiuM(III)

  • A 16686
  • A 16686A
  • Antibiotic A 16686
  • RaMoplanin(A 16686,A 16686A)
  • RaMoplanin coMplex
  • Ramoplanin
  • Ramoplaninr
  • Ray mora ning
  • 76168-82-6
  • 6168-82-6
  • C106H170ClN21O30