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
- Weight
- Average: 2554.066
Monoisotopic: 2552.03504662 - Chemical Formula
- C119H154ClN21O40
- Synonyms
- Ramoplanin
Pharmacology
- Indication
For the treatment of bacterial infections.
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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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAcenocoumarol The risk or severity of bleeding can be increased when Ramoplanin is combined with Acenocoumarol. Ambroxol The risk or severity of methemoglobinemia can be increased when Ramoplanin is combined with Ambroxol. Articaine The risk or severity of methemoglobinemia can be increased when Ramoplanin is combined with Articaine. BCG vaccine The therapeutic efficacy of BCG vaccine can be decreased when used in combination with Ramoplanin. Benzocaine The risk or severity of methemoglobinemia can be increased when Ramoplanin is combined with Benzocaine. - 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
- 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]
- Fulco P, Wenzel RP: Ramoplanin: a topical lipoglycodepsipeptide antibacterial agent. Expert Rev Anti Infect Ther. 2006 Dec;4(6):939-45. [Article]
- External Links
- PubChem Compound
- 73425378
- PubChem Substance
- 175426916
- ChemSpider
- 32813311
- Wikipedia
- Ramoplanin
Clinical Trials
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
Property Value Source Water Solubility 0.0503 mg/mL ALOGPS logP 1.7 ALOGPS logP -8.9 Chemaxon logS -4.7 ALOGPS pKa (Strongest Acidic) 7.85 Chemaxon pKa (Strongest Basic) 10.29 Chemaxon Physiological Charge 2 Chemaxon Hydrogen Acceptor Count 41 Chemaxon Hydrogen Donor Count 36 Chemaxon Polar Surface Area 999.59 Å2 Chemaxon Rotatable Bond Count 35 Chemaxon Refractivity 632.19 m3·mol-1 Chemaxon Polarizability 255.29 Å3 Chemaxon Number of Rings 10 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.5625 Blood Brain Barrier - 0.985 Caco-2 permeable - 0.6849 P-glycoprotein substrate Substrate 0.8136 P-glycoprotein inhibitor I Non-inhibitor 0.698 P-glycoprotein inhibitor II Non-inhibitor 0.865 Renal organic cation transporter Non-inhibitor 0.9317 CYP450 2C9 substrate Non-substrate 0.8407 CYP450 2D6 substrate Non-substrate 0.8261 CYP450 3A4 substrate Substrate 0.6122 CYP450 1A2 substrate Non-inhibitor 0.8729 CYP450 2C9 inhibitor Non-inhibitor 0.8015 CYP450 2D6 inhibitor Non-inhibitor 0.8713 CYP450 2C19 inhibitor Non-inhibitor 0.722 CYP450 3A4 inhibitor Non-inhibitor 0.5083 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7878 Ames test Non AMES toxic 0.6914 Carcinogenicity Non-carcinogens 0.8517 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.5615 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9872 hERG inhibition (predictor II) Non-inhibitor 0.5913
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Not Available
Drug created at October 21, 2007 22:23 / Updated at February 21, 2021 18:51