Ramoplanin

ChemicalBook > CAS DataBase List > 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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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