Virginiamycin M1
Identification
- Generic Name
- Virginiamycin M1
- DrugBank Accession Number
- DB01669
- Background
Pristinamycin IIA is a macrolide antibiotic, a member of the streptogramin A group of antibiotics, and one component of pristinamycin. It is produced by Streptomyces graminofaciens and other bacteria.
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 525.5934
Monoisotopic: 525.247500489 - Chemical Formula
- C28H35N3O7
- Synonyms
- Mikamycin A
- Ostreogrycin A
- Pristinamycin IIA
- Streptogramin A
- Virginiamycin factor M1
- Virginiamycin M1
- External IDs
- NSC-244426
- NSC-87432
- PA-114A
- RP-12536
- RPR-132552
- RPR132552
Pharmacology
- Indication
For the treatment of bacterial infections.
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- Pharmacodynamics
Not Available
- Mechanism of action
Virginiamycin M1 is a macrocyclic lactone antibiotic that acts syngeristically with the structurally unrelated cyclic depsipeptides more commonly known as the virginiamycins B (ostreogrycin B or streptogramin B) and S to inhibit peptide elongation. This is achieved by blocking formation of a peptide bond between the growing peptide chain (peptidyl-tRNA) linked to the 50S ribosome and aminoacyl-tRNA. Virginiamycin M1 has proven to be highly active against Gram positive bacteria, particularly methicillin-resistant S. aureus.
Target Actions Organism UStreptogramin A acetyltransferase Not Available Enterococcus faecium - 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAcenocoumarol The risk or severity of bleeding can be increased when Virginiamycin M1 is combined with Acenocoumarol. Ambroxol The risk or severity of methemoglobinemia can be increased when Virginiamycin M1 is combined with Ambroxol. Articaine The risk or severity of methemoglobinemia can be increased when Virginiamycin M1 is combined with Articaine. BCG vaccine The therapeutic efficacy of BCG vaccine can be decreased when used in combination with Virginiamycin M1. Benzocaine The risk or severity of methemoglobinemia can be increased when Virginiamycin M1 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 macrolide lactams. These are cyclic polyketides containing both a cyclic amide and a cyclic ester group.
- Kingdom
- Organic compounds
- Super Class
- Phenylpropanoids and polyketides
- Class
- Macrolide lactams
- Sub Class
- Not Available
- Direct Parent
- Macrolide lactams
- Alternative Parents
- Macrolactams / Alpha amino acids and derivatives / 2-heteroaryl carboxamides / Tertiary carboxylic acid amides / Enoate esters / Heteroaromatic compounds / Oxazoles / Pyrrolines / Secondary alcohols / Lactones show 10 more
- Substituents
- 2-heteroaryl carboxamide / Alcohol / Alpha,beta-unsaturated carboxylic ester / Alpha-amino acid or derivatives / Aromatic heteropolycyclic compound / Azacycle / Azole / Carbonyl group / Carboxamide group / Carboxylic acid derivative show 24 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- cyclic ketone, 1,3-oxazoles, secondary alcohol, macrolide antibiotic, enamide, lactam, pyrroline, macrolide (CHEBI:9997)
- Affected organisms
- Bacteria
Chemical Identifiers
- UNII
- 8W4UOL59AZ
- CAS number
- 21411-53-0
- InChI Key
- DAIKHDNSXMZDCU-FQTGFAPKSA-N
- InChI
- InChI=1S/C28H35N3O7/c1-17(2)26-19(4)9-10-24(34)29-11-5-7-18(3)13-20(32)14-21(33)15-25-30-22(16-37-25)27(35)31-12-6-8-23(31)28(36)38-26/h5,7-10,13,16-17,19-20,26,32H,6,11-12,14-15H2,1-4H3,(H,29,34)/b7-5+,10-9+,18-13+/t19-,20-,26-/m1/s1
- IUPAC Name
- (10R,11R,12E,17E,19E,21S)-21-hydroxy-11,19-dimethyl-10-(propan-2-yl)-9,26-dioxa-3,15,28-triazatricyclo[23.2.1.0^{3,7}]octacosa-1(27),6,12,17,19,25(28)-hexaene-2,8,14,23-tetrone
- SMILES
- CC(C)[C@H]1OC(=O)C2=CCCN2C(=O)C2=COC(=N2)CC(=O)C[C@H](O)\C=C(/C)\C=C\CNC(=O)\C=C\[C@H]1C
References
- General References
- US Biological [Link]
- External Links
- KEGG Compound
- C11299
- PubChem Compound
- 5459319
- PubChem Substance
- 46506471
- ChemSpider
- 10222381
- ChEBI
- 9997
- ChEMBL
- CHEMBL1236670
- PDBe Ligand
- VIR
- Wikipedia
- Pristinamycin_IIA
- PDB Entries
- 1khr / 1n8r / 1yit / 4hus / 4u25 / 8e3o
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source water solubility Poorly soluble in water Not Available - Predicted Properties
Property Value Source Water Solubility 0.0601 mg/mL ALOGPS logP 2.6 ALOGPS logP 2.38 Chemaxon logS -3.9 ALOGPS pKa (Strongest Acidic) 13.17 Chemaxon pKa (Strongest Basic) -0.16 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 139.04 Å2 Chemaxon Rotatable Bond Count 1 Chemaxon Refractivity 144.17 m3·mol-1 Chemaxon Polarizability 55.74 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.7861 Blood Brain Barrier - 0.9659 Caco-2 permeable - 0.6999 P-glycoprotein substrate Substrate 0.7225 P-glycoprotein inhibitor I Non-inhibitor 0.7261 P-glycoprotein inhibitor II Non-inhibitor 0.8885 Renal organic cation transporter Non-inhibitor 0.8822 CYP450 2C9 substrate Non-substrate 0.85 CYP450 2D6 substrate Non-substrate 0.8337 CYP450 3A4 substrate Substrate 0.6184 CYP450 1A2 substrate Non-inhibitor 0.7669 CYP450 2C9 inhibitor Non-inhibitor 0.843 CYP450 2D6 inhibitor Non-inhibitor 0.9163 CYP450 2C19 inhibitor Non-inhibitor 0.7838 CYP450 3A4 inhibitor Non-inhibitor 0.9423 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9459 Ames test Non AMES toxic 0.6864 Carcinogenicity Non-carcinogens 0.8613 Biodegradation Not ready biodegradable 0.786 Rat acute toxicity 2.6179 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9482 hERG inhibition (predictor II) Non-inhibitor 0.8977
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 233.796705 predictedDarkChem Lite v0.1.0 [M-H]- 220.98746 predictedDeepCCS 1.0 (2019) [M+H]+ 232.939705 predictedDarkChem Lite v0.1.0 [M+H]+ 223.12138 predictedDeepCCS 1.0 (2019) [M+Na]+ 233.274705 predictedDarkChem Lite v0.1.0 [M+Na]+ 228.9101 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Enterococcus faecium
- Pharmacological action
- Unknown
- General Function
- Transferase activity, transferring acyl groups
- Specific Function
- Inactivates the A compounds of streptogramin antibiotics by acetylation, thus providing resistance to these antibiotics.
- Gene Name
- vatD
- Uniprot ID
- P50870
- Uniprot Name
- Streptogramin A acetyltransferase
- Molecular Weight
- 23649.22 Da
References
Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:51