This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Virginiamycin
DrugBank Accession Number
DB11476
Background

Virginiamycin is a streptogramin antibiotic similar to pristinamycin and quinupristin/dalfopristin. It is a combination of pristinamycin IIA and virginiamycin S1. Virginiamycin is used in the fuel ethanol industry to prevent microbial contamination and in livestock to prevent and treat infections. According to a USDA study, antibiotics can save as much as 30% in feed costs among young swine.

Type
Small Molecule
Groups
Vet approved
Structure
Weight
Average: 1349.506
Monoisotopic: 1348.601591285
Chemical Formula
C71H84N10O17
Synonyms
  • Virginiamicina
  • Virginiamycin
  • Virginiamycine
  • Virginiamycinum
External IDs
  • SK&F 7988
  • SKF 7988

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
Not Available
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
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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.
Not Available
Food Interactions
Not Available

Products

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Categories

ATC Codes
D06AX10 — Virginiamycin
Drug Categories
Classification
Not classified
Affected organisms
Not Available

Chemical Identifiers

UNII
C49WS9N75L
CAS number
11006-76-1
InChI Key
MVTQIFVKRXBCHS-SMMNFGSLSA-N
InChI
InChI=1S/C43H49N7O10.C28H35N3O7/c1-4-29-40(56)49-21-12-17-30(49)41(57)48(3)32(23-26-13-7-5-8-14-26)42(58)50-22-19-28(51)24-31(50)37(53)47-35(27-15-9-6-10-16-27)43(59)60-25(2)34(38(54)45-29)46-39(55)36-33(52)18-11-20-44-36;1-17(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/h5-11,13-16,18,20,25,29-32,34-35,52H,4,12,17,19,21-24H2,1-3H3,(H,45,54)(H,46,55)(H,47,53);5,7-10,13,16-17,19-20,26,32H,6,11-12,14-15H2,1-4H3,(H,29,34)/b;7-5+,10-9+,18-13+/t25-,29-,30+,31+,32+,34+,35+;19-,20-,26-/m11/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; N-[(3S,6S,12R,15S,16R,19S,22S)-3-benzyl-12-ethyl-4,16-dimethyl-2,5,11,14,18,21,24-heptaoxo-19-phenyl-17-oxa-1,4,10,13,20-pentaazatricyclo[20.4.0.0^{6,10}]hexacosan-15-yl]-3-hydroxypyridine-2-carboxamide
SMILES
CC(C)[C@H]1OC(=O)C2=CCCN2C(=O)C2=COC(CC(=O)C[C@H](O)\C=C(/C)\C=C\CNC(=O)\C=C\[C@H]1C)=N2.[H][C@@]12CCCN1C(=O)[C@@H](CC)NC(=O)[C@@H](NC(=O)C1=C(O)C=CC=N1)[C@@H](C)OC(=O)[C@@H](NC(=O)[C@]1([H])CC(=O)CCN1C(=O)[C@H](CC1=CC=CC=C1)N(C)C2=O)C1=CC=CC=C1

References

General References
  1. Crooy P, De Neys R: Virginiamycin: nomenclature. J Antibiot (Tokyo). 1972 Jun;25(6):371-2. [Article]
  2. Menzies-Gow N: Virginiamycin and laminitis research. Vet Rec. 2007 Jun 16;160(24):852. [Article]
  3. Miles RD, Janky DM, Harms RH: Virginiamycin and broiler performance. Poult Sci. 1984 Jun;63(6):1218-21. [Article]
  4. Miles RD, Janky DM, Harms RH: Virginiamycin and laying hen performance. Poult Sci. 1985 Jan;64(1):139-43. [Article]
  5. Bleumink E, Nater JP: Allergic contact dermatitis to virginiamycin. Dermatologica. 1972;144(4):253-6. [Article]
  6. Wu J, Panek JS: Total synthesis of (-)-virginiamycin M2. Angew Chem Int Ed Engl. 2010 Aug 16;49(35):6165-8. doi: 10.1002/anie.201002220. [Article]
  7. Van Dijck PJ: Further bacteriological evaluation of virginiamycin. Chemotherapy. 1969;14(5):322-32. [Article]
  8. de Meester C, Rondelet J: [Virginiamycin resistance in staphylococci (author's transl)]. Pathol Biol (Paris). 1977 Dec;25(10):685-9. [Article]
  9. Fraselle G, Cocito C: [Properties of mutants resistant to virginiamycin]. Arch Int Physiol Biochim. 1973 May;81(2):371. [Article]
  10. Ragheb HS, Black LJ, Waisner DL: Determination of virginiamycin in feeds. J Assoc Off Anal Chem. 1979 May;62(3):671-5. [Article]
ChemSpider
58929121
RxNav
11232
ChEMBL
CHEMBL3833352
Wikipedia
Virginiamycin

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
PowderNot applicable100 kg/100kg
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.139 mg/mLALOGPS
logP2.25ALOGPS
logP1.85ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)7.53ChemAxon
pKa (Strongest Basic)2.57ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area224.72 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity213.24 m3·mol-1ChemAxon
Polarizability83.46 Å3ChemAxon
Number of Rings9ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Drug created at February 25, 2016 19:05 / Updated at September 28, 2021 21:54