This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.
Identification
- Generic Name
- Friulimicin B
- DrugBank Accession Number
- DB06087
- Background
Friulimicin B is a naturally occurring antibiotic produced by a micro-organism, Actinoplanes friuliensis. It shows strong cidal activity against a number of Gram-positive pathogens which commonly cause serious infections in hospital patients and which are becoming more routinely acquired in the community.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Friulimicin B (DB06087)
- Weight
- Average: 1303.48
Monoisotopic: 1302.681966863 - Chemical Formula
- C59H94N14O19
- Synonyms
- Friulimycin B
- External IDs
- A 1437 delta
Pharmacology
- Indication
Investigated for use/treatment in bacterial infection.
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Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Friulimicin B, in the presence of calcium, forms a complex with a lipid carrier that acts in cell wall biosynthesis and which is not targeted by other antibiotics currently in use. Friulimicin B appears to block two essential pathways in the cell envelope and the complexes formed prevent the formation of a functional cell wall.
- Absorption
Not Available
- 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.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Amino acids, peptides, and analogues
- Direct Parent
- Oligopeptides
- Alternative Parents
- Cyclic peptides / Asparagine and derivatives / Macrolactams / N-acyl-alpha amino acids and derivatives / Alpha amino acid amides / Beta amino acids and derivatives / Tricarboxylic acids and derivatives / Piperidines / N-acyl amines / Tertiary carboxylic acid amides show 11 more
- Substituents
- Aliphatic heteropolycyclic compound / Alpha-amino acid amide / Alpha-amino acid or derivatives / Alpha-oligopeptide / Amine / Amino acid / Amino acid or derivatives / Asparagine or derivatives / Azacycle / Beta amino acid or derivatives show 26 more
- Molecular Framework
- Aliphatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- AYO43961I1
- CAS number
- 239802-15-4
- InChI Key
- HVYFVLAUKMGKHL-USKUEUQVSA-N
- InChI
- InChI=1S/C59H94N14O19/c1-30(2)19-14-12-10-8-9-11-13-15-22-41(75)65-35(25-40(61)74)52(84)71-49-34(7)64-53(85)39-21-18-24-73(39)57(89)46(31(3)4)69-56(88)48(33(6)60)68-43(77)29-63-50(82)36(26-44(78)79)66-42(76)28-62-51(83)37(27-45(80)81)67-55(87)47(32(5)59(91)92)70-54(86)38-20-16-17-23-72(38)58(49)90/h13,15,30-39,46-49H,8-12,14,16-29,60H2,1-7H3,(H2,61,74)(H,62,83)(H,63,82)(H,64,85)(H,65,75)(H,66,76)(H,67,87)(H,68,77)(H,69,88)(H,70,86)(H,71,84)(H,78,79)(H,80,81)(H,91,92)/b15-13-/t32-,33+,34-,35-,36-,37-,38+,39-,46-,47-,48+,49-/m0/s1
- IUPAC Name
- (2S)-2-[(3S,4S,7S,13S,16R,22S,28S,31S,34R)-16-[(1R)-1-aminoethyl]-3-[(2S)-3-carbamoyl-2-[(3Z)-12-methyltridec-3-enamido]propanamido]-22,28-bis(carboxymethyl)-4-methyl-2,6,12,15,18,21,24,27,30,33-decaoxo-13-(propan-2-yl)-1,5,11,14,17,20,23,26,29,32-decaazatricyclo[32.4.0.0^{7,11}]octatriacontan-31-yl]propanoic acid
- SMILES
- CC(C)CCCCCCC\C=C/CC(=O)N[C@@H](CC(N)=O)C(=O)N[C@H]1[C@H](C)NC(=O)[C@@H]2CCCN2C(=O)[C@@H](NC(=O)[C@H](NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@H]2CCCCN2C1=O)[C@H](C)C(O)=O)[C@@H](C)N)C(C)C
References
- General References
- Muller C, Nolden S, Gebhardt P, Heinzelmann E, Lange C, Puk O, Welzel K, Wohlleben W, Schwartz D: Sequencing and analysis of the biosynthetic gene cluster of the lipopeptide antibiotic Friulimicin in Actinoplanes friuliensis. Antimicrob Agents Chemother. 2007 Mar;51(3):1028-37. Epub 2007 Jan 12. [Article]
- Heinzelmann E, Berger S, Puk O, Reichenstein B, Wohlleben W, Schwartz D: A glutamate mutase is involved in the biosynthesis of the lipopeptide antibiotic friulimicin in Actinoplanes friuliensis. Antimicrob Agents Chemother. 2003 Feb;47(2):447-57. [Article]
- Vertesy L, Ehlers E, Kogler H, Kurz M, Meiwes J, Seibert G, Vogel M, Hammann P: Friulimicins: novel lipopeptide antibiotics with peptidoglycan synthesis inhibiting activity from Actinoplanes friuliensis sp. nov. II. Isolation and structural characterization. J Antibiot (Tokyo). 2000 Aug;53(8):816-27. [Article]
- External Links
- ChemSpider
- 32699135
- Wikipedia
- Friulimicin
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 1 Terminated Treatment Community Acquired Pneumonia (CAP) / Staphylococcal Skin Infections 1
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 0.0161 mg/mL ALOGPS logP -0.5 ALOGPS logP -7.2 Chemaxon logS -4.9 ALOGPS pKa (Strongest Acidic) 3.08 Chemaxon pKa (Strongest Basic) 8.33 Chemaxon Physiological Charge -2 Chemaxon Hydrogen Acceptor Count 20 Chemaxon Hydrogen Donor Count 15 Chemaxon Polar Surface Area 512.63 Å2 Chemaxon Rotatable Bond Count 23 Chemaxon Refractivity 321.78 m3·mol-1 Chemaxon Polarizability 134.16 Å3 Chemaxon Number of Rings 3 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
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 346.5936 predictedDeepCCS 1.0 (2019) [M+H]+ 348.24673 predictedDeepCCS 1.0 (2019) [M+Na]+ 354.4036 predictedDeepCCS 1.0 (2019)
Drug created at November 18, 2007 18:29 / Updated at June 12, 2020 16:52