Virginiamycin

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

Identification

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Name
Virginiamycin
Accession Number
DB11476
Type
Small Molecule
Groups
Vet approved
Description

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.

Structure
Thumb
Synonyms
  • Virginiamycin
Categories
UNII
C49WS9N75L
CAS number
Not Available
Weight
Average: 1349.506
Monoisotopic: 1348.601591285
Chemical Formula
C71H84N10O17
InChI Key
MVTQIFVKRXBCHS-FHWPYUEJSA-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-
IUPAC Name
(12Z,17Z,19Z)-14,21-dihydroxy-11,19-dimethyl-10-(propan-2-yl)-9,26-dioxa-3,15,28-triazatricyclo[23.2.1.0³,⁷]octacosa-1(27),6,12,14,17,19,25(28)-heptaene-2,8,23-trione; N-{3-benzyl-12-ethyl-14,21-dihydroxy-4,16-dimethyl-2,5,11,18,24-pentaoxo-19-phenyl-17-oxa-1,4,10,13,20-pentaazatricyclo[20.4.0.0⁶,¹⁰]hexacosa-13,20-dien-15-yl}-3-hydroxypyridine-2-carboximidic acid
SMILES
[H]\C1=C(/[H])\C(\C)=C([H])/C(O)CC(=O)CC2=NC(=CO2)C(=O)N2CCC=C2C(=O)OC(C(C)C)C(C)\C([H])=C([H])/C(O)=NC1.CCC1N=C(O)C(N=C(O)C2=C(O)C=CC=N2)C(C)OC(=O)C(N=C(O)C2CC(=O)CCN2C(=O)C(CC2=CC=CC=C2)N(C)C(=O)C2CCCN2C1=O)C1=CC=CC=C1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
  1. Crooy P, De Neys R: Virginiamycin: nomenclature. J Antibiot (Tokyo). 1972 Jun;25(6):371-2. [PubMed:4568014]
  2. Menzies-Gow N: Virginiamycin and laminitis research. Vet Rec. 2007 Jun 16;160(24):852. [PubMed:17575256]
  3. Miles RD, Janky DM, Harms RH: Virginiamycin and broiler performance. Poult Sci. 1984 Jun;63(6):1218-21. [PubMed:6429658]
  4. Miles RD, Janky DM, Harms RH: Virginiamycin and laying hen performance. Poult Sci. 1985 Jan;64(1):139-43. [PubMed:3919378]
  5. Bleumink E, Nater JP: Allergic contact dermatitis to virginiamycin. Dermatologica. 1972;144(4):253-6. [PubMed:4561932]
  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. [PubMed:20648503]
  7. Van Dijck PJ: Further bacteriological evaluation of virginiamycin. Chemotherapy. 1969;14(5):322-32. [PubMed:4902789]
  8. de Meester C, Rondelet J: [Virginiamycin resistance in staphylococci (author's transl)]. Pathol Biol (Paris). 1977 Dec;25(10):685-9. [PubMed:418374]
  9. Fraselle G, Cocito C: [Properties of mutants resistant to virginiamycin]. Arch Int Physiol Biochim. 1973 May;81(2):371. [PubMed:4126225]
  10. Ragheb HS, Black LJ, Waisner DL: Determination of virginiamycin in feeds. J Assoc Off Anal Chem. 1979 May;62(3):671-5. [PubMed:39060]
External Links
ChemSpider
10152812
Wikipedia
Virginiamycin
ATC Codes
D06AX10 — Virginiamycin

Clinical Trials

Clinical Trials
Not Available

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 Solubility0.0436 mg/mLALOGPS
logP2.68ALOGPS
logP3.92ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)3.16ChemAxon
pKa (Strongest Basic)2.21ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area235.19 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity214.8 m3·mol-1ChemAxon
Polarizability83.53 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
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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
Macrolide lactam / Macrolactam / Alpha-amino acid or derivatives / 2-heteroaryl carboxamide / Azole / Oxazole / Heteroaromatic compound / Pyrroline / Tertiary carboxylic acid amide / Enoate ester
show 24 more
Molecular Framework
Not Available
External Descriptors
Not Available

Drug created on February 25, 2016 12:05 / Updated on June 04, 2019 07:22