Virginiamycin

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

Download

MOLSDFPDBSMILESInChI

Similar Structures

Structure for Virginiamycin (DB11476)

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Weight

Average: 1349.506
Monoisotopic: 1348.601591285

Chemical Formula

C₇₁H₈₄N₁₀O₁₇

Synonyms

• Virginiamicina
• Virginiamycin
• Virginiamycine
• Virginiamycinum

External IDs

• SK&F 7988
• SKF 7988

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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

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Categories

ATC Codes

D06AX10 — Virginiamycin

• D06AX — Other antibiotics for topical use
• D06A — ANTIBIOTICS FOR TOPICAL USE
• D06 — ANTIBIOTICS AND CHEMOTHERAPEUTICS FOR DERMATOLOGICAL USE
• D — DERMATOLOGICALS

Drug Categories

• Amino Acids, Peptides, and Proteins
• Anti-Bacterial Agents
• Anti-Infective Agents
• Antibiotics for Topical Use
• Dermatologicals
• Enzyme Inhibitors
• Peptides
• Peptides, Cyclic
• Protein Synthesis Inhibitors
• Streptogramins

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]

External Links

ChemSpider

58929121

RxNav

11232

ChEMBL

CHEMBL3833352

Wikipedia

Virginiamycin

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Form	Route	Strength
Powder	Not applicable	100 kg/100kg

Prices

Not Available

Patents

Not Available

Properties

State

Not Available

Experimental Properties

Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.139 mg/mL	ALOGPS
logP	2.25	ALOGPS
logP	1.85	Chemaxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	7.53	Chemaxon
pKa (Strongest Basic)	2.57	Chemaxon
Physiological Charge	0	Chemaxon
Hydrogen Acceptor Count	10	Chemaxon
Hydrogen Donor Count	4	Chemaxon
Polar Surface Area	224.72 Å2	Chemaxon
Rotatable Bond Count	7	Chemaxon
Refractivity	213.24 m3·mol-1	Chemaxon
Polarizability	83.46 Å3	Chemaxon
Number of Rings	9	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

Not Available

Chromatographic Properties

Collision Cross Sections (CCS)

Not Available

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