Ramoplanin

Identification

Generic Name
Ramoplanin
DrugBank Accession Number
DB04952
Background

Ramoplanin is a novel glycolipodepsipeptide antibiotic under development for the treatment of CDAD.

Type
Small Molecule
Groups
Investigational
Structure
Thumb
Weight
Average: 2554.066
Monoisotopic: 2552.03504662
Chemical Formula
C119H154ClN21O40
Synonyms
  • Ramoplanin

Pharmacology

Indication

For the treatment of bacterial infections.

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Ramoplanin represents a new class of antibiotics with a novel mechanism of action that is highly effective against Staphylococci.

Mechanism of action

Ramoplanin is the first in a new class of antimicrobials to reach clinical trials. It is a glycolipodepsipeptide produced by the fermentation of Actinoplanes spp.. Ramoplanin blocks bacterial cell wall biosynthesis by interfering with peptidoglycan production. Ramoplanin inhibits the N-acetylglucosaminyltransferase-catalysed conversion of lipid intermediate I to lipid intermediate II, a step that occurs before the transglycosylation and transpeptidation reactions. Ramoplanin’s mechanism of action is distinct from that of glycopeptides. Unlike glycopeptides, ramoplanin does not complex with the D-Ala–D-Ala sequence of cell wall precursors.

Absorption

No/limited absorption.

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
Medicalerrors
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AcenocoumarolThe risk or severity of bleeding can be increased when Ramoplanin is combined with Acenocoumarol.
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Ramoplanin.
DicoumarolThe risk or severity of bleeding can be increased when Ramoplanin is combined with Dicoumarol.
EstetrolThe therapeutic efficacy of Estetrol can be decreased when used in combination with Ramoplanin.
FluindioneThe risk or severity of bleeding can be increased when Ramoplanin is combined with Fluindione.
LactuloseThe therapeutic efficacy of Lactulose can be decreased when used in combination with Ramoplanin.
PhenindioneThe risk or severity of bleeding can be increased when Ramoplanin is combined with Phenindione.
PhenprocoumonThe risk or severity of bleeding can be increased when Ramoplanin is combined with Phenprocoumon.
Picosulfuric acidThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Ramoplanin.
Typhoid vaccineThe therapeutic efficacy of Typhoid vaccine can be decreased when used in combination with Ramoplanin.
Interactions
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Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as cyclic glycodepsipeptides. These are peptidomimetic containing a glycodepisipeptide backbone that lies in a cyclic moiety.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Peptidomimetics
Sub Class
Depsipeptides
Direct Parent
Cyclic glycodepsipeptides
Alternative Parents
Phenolic glycosides / Asparagine and derivatives / Macrolide lactams / Alpha amino acid esters / Macrolactams / Macrolides and analogues / N-acyl-alpha amino acids and derivatives / Alpha amino acid amides / Disaccharides / O-glycosyl compounds
show 26 more
Substituents
1-hydroxy-2-unsubstituted benzenoid / 2-chlorophenol / 2-halophenol / Acetal / Alcohol / Alpha-amino acid amide / Alpha-amino acid ester / Alpha-amino acid or derivatives / Amine / Amino acid or derivatives
show 51 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
  • Gram-positive Bacteria

Chemical Identifiers

UNII
0WX9996O2G
CAS number
76168-82-6
InChI Key
KGZHFKDNSAEOJX-GVRPVQITSA-N
InChI
InChI=1S/C119H154ClN21O40/c1-54(2)17-11-9-14-22-82(153)127-77(50-81(123)152)107(166)141-93-99(101(124)160)180-117(176)92(66-33-44-78(151)72(120)49-66)140-102(161)56(5)126-105(164)75(47-55(3)4)128-83(154)51-125-108(167)87(61-23-34-67(147)35-24-61)136-111(170)86(59(8)146)134-113(172)89(65-31-42-71(43-32-65)177-119-100(97(158)95(156)80(53-143)179-119)181-118-98(159)96(157)94(155)79(52-142)178-118)135-104(163)73(20-15-45-121)129-106(165)76(48-60-18-12-10-13-19-60)131-109(168)84(57(6)144)133-114(173)90(63-27-38-69(149)39-28-63)138-115(174)91(64-29-40-70(150)41-30-64)137-110(169)85(58(7)145)132-103(162)74(21-16-46-122)130-112(171)88(139-116(93)175)62-25-36-68(148)37-26-62/h9-14,18-19,22-44,49,54-59,73-77,79-80,84-100,118-119,142-151,155-159H,15-17,20-21,45-48,50-53,121-122H2,1-8H3,(H2,123,152)(H2,124,160)(H,125,167)(H,126,164)(H,127,153)(H,128,154)(H,129,165)(H,130,171)(H,131,168)(H,132,162)(H,133,173)(H,134,172)(H,135,163)(H,136,170)(H,137,169)(H,138,174)(H,139,175)(H,140,161)(H,141,166)/b11-9-,22-14-/t56-,57-,58+,59+,73+,74+,75-,76+,77+,79+,80+,84-,85+,86+,87-,88+,89-,90+,91+,92+,93-,94+,95+,96-,97-,98-,99+,100-,118+,119+/m0/s1
IUPAC Name
(2R)-N-[(3R,6S,9S,15S,18R,21S,24R,27R,30S,33R,36R,39R,42R,45R,48S,49R)-24,42-bis(3-aminopropyl)-27-benzyl-49-carbamoyl-3-(3-chloro-4-hydroxyphenyl)-21-(4-{[(2S,3S,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}phenyl)-18,39-bis[(1R)-1-hydroxyethyl]-30-[(1S)-1-hydroxyethyl]-15,33,36,45-tetrakis(4-hydroxyphenyl)-6-methyl-9-(2-methylpropyl)-2,5,8,11,14,17,20,23,26,29,32,35,38,41,44,47-hexadecaoxo-1-oxa-4,7,10,13,16,19,22,25,28,31,34,37,40,43,46-pentadecaazacyclononatetracontan-48-yl]-2-[(2Z,4Z)-7-methylocta-2,4-dienamido]butanediamide
SMILES
NCCC[C@H]1NC(=O)[C@@H](CC2=CC=CC=C2)NC(=O)[C@H]([C@@H](O)C)NC(=O)[C@H](NC(=O)[C@H](NC(=O)[C@@H]([C@@H](C)O)NC(=O)[C@@H](CCCN)NC(=O)[C@H](NC(=O)[C@@H](NC(=O)[C@@H](CC(N)=O)NC(=O)\C=C/C=C\CC(C)C)[C@@H](OC(=O)[C@H](NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)CNC(=O)[C@@H](NC(=O)[C@@H]([C@@H](C)O)NC(=O)[C@@H](NC1=O)C1=CC=C(C=C1)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]1O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]1O)C1=CC=C(O)C=C1)C1=CC(Cl)=C(O)C=C1)C(N)=O)C1=CC=C(O)C=C1)C1=CC=C(O)C=C1)C1=CC=C(O)C=C1

References

General References
  1. Fang X, Tiyanont K, Zhang Y, Wanner J, Boger D, Walker S: The mechanism of action of ramoplanin and enduracidin. Mol Biosyst. 2006 Jan;2(1):69-76. Epub 2005 Nov 29. [Article]
  2. Fulco P, Wenzel RP: Ramoplanin: a topical lipoglycodepsipeptide antibacterial agent. Expert Rev Anti Infect Ther. 2006 Dec;4(6):939-45. [Article]
PubChem Compound
73425378
PubChem Substance
175426916
ChemSpider
32813311
Wikipedia
Ramoplanin

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0503 mg/mLALOGPS
logP1.7ALOGPS
logP-9ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)7.85ChemAxon
pKa (Strongest Basic)10.28ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count41ChemAxon
Hydrogen Donor Count36ChemAxon
Polar Surface Area999.59 Å2ChemAxon
Rotatable Bond Count35ChemAxon
Refractivity632.19 m3·mol-1ChemAxon
Polarizability255.35 Å3ChemAxon
Number of Rings10ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.5625
Blood Brain Barrier-0.985
Caco-2 permeable-0.6849
P-glycoprotein substrateSubstrate0.8136
P-glycoprotein inhibitor INon-inhibitor0.698
P-glycoprotein inhibitor IINon-inhibitor0.865
Renal organic cation transporterNon-inhibitor0.9317
CYP450 2C9 substrateNon-substrate0.8407
CYP450 2D6 substrateNon-substrate0.8261
CYP450 3A4 substrateSubstrate0.6122
CYP450 1A2 substrateNon-inhibitor0.8729
CYP450 2C9 inhibitorNon-inhibitor0.8015
CYP450 2D6 inhibitorNon-inhibitor0.8713
CYP450 2C19 inhibitorNon-inhibitor0.722
CYP450 3A4 inhibitorNon-inhibitor0.5083
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7878
Ames testNon AMES toxic0.6914
CarcinogenicityNon-carcinogens0.8517
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.5615 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9872
hERG inhibition (predictor II)Non-inhibitor0.5913
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Drug created on October 21, 2007 22:23 / Updated on February 21, 2021 18:51