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Substance Name: Virginiamycin [USAN:INN:BAN]
RN: 11006-76-1
UNII: C49WS9N75L
InChIKey: MVTQIFVKRXBCHS-SMMNFGSLSA-N

Note

  • A cyclic polypeptide antibiotic complex from Streptomyces virginiae, S. loidensis, S. mitakaensis, S. pristina-spiralis, S. ostreogriseus, and others. It consists of 2 major components, VIRGINIAMYCIN FACTOR M1 and virginiamycin Factor S1. It is used to treat infections with gram-positive organisms and as a growth promoter in cattle, swine, and poultry.

Molecular Formula

  • Unspecified

Molecular Weight

  • 1349.4976
 

Classification Codes

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antibacterial
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Food Additive (Veterinary)
  • Natural Product
  • Protein Synthesis Inhibitors
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Names and Synonyms

Name of Substance

  • Virginiamycin
  • Virginiamycin [USAN:INN:BAN]

MeSH Heading

  • Virginiamycin

Synonyms

  • A mixture of two principal antibiotic components, virginiamycin M1 (Factor M1) and virginiamycin S1 (Factor S). Virginiamycin
  • Antibiotic No. 899
  • Antibiotic produced by Streptomyces virginiae; a mixture of two principal antibiotic components, virginiamycin M1 (Factor M1) and virginiamycin S1 (Factor S)
  • EINECS 234-244-6
  • Eskalin
  • Eskalin 500
  • Eskalin V
  • HSDB 7033
  • Micamicina
  • Micamicina [INN-Spanish]
  • Mikamycin
  • Mikamycin [INN:BAN:DCF]
  • Mikamycine
  • Mikamycine [INN-French]
  • Mikamycinum
  • Mikamycinum [INN-Latin]
  • Ostreogricina
  • Ostreogricina [INN-Spanish]
  • Ostreogrycin
  • Ostreogrycin [INN:BAN]
  • Ostreogrycine
  • Ostreogrycine [INN-French]
  • Ostreogrycinum
  • Ostreogrycinum [INN-Latin]
  • Patricin
  • Pristinamicina
  • Pristinamicina [INN-Spanish]
  • Pristinamycin
  • Pristinamycin [INN:BAN:DCF]
  • Pristinamycine
  • Pristinamycine [INN-French]
  • Pristinamycinum
  • Pristinamycinum [INN-Latin]
  • Pyostacine
  • RP 7293
  • RP7293
  • SK&F 7988
  • SKF 7988
  • Stafac
  • Stafac 20
  • Stafac 50
  • Stafac 500
  • Staphylomycin
  • Stapyocine
  • Streptogramin
  • UNII-C49WS9N75L
  • V-MAX 50
  • Vernamycin
  • Virgimycin
  • Virginiamicina
  • Virginiamicina [INN-Spanish]
  • Virginiamycin
  • Virginiamycina
  • Virginiamycina [INN-Spanish]
  • Virginiamycine
  • Virginiamycine [INN-French]
  • Virginiamycinum
  • Virginiamycinum [INN-Latin]

Systematic Names

  • Antibiotic produced by Streptomyces mitakaensis, or the same substance produced by any other means
  • Antibiotic produced by Streptomyces pristina spiralis, or the same substance produced by any other means
  • Antibiotic produced by Streptomyces virginiae
  • Antibiotic substances derived from cultures of Streptomyces osteogriseus, or the same substance produced by any other means
  • Virginiamycin

Registry Numbers

CAS Registry Number

  • 11006-76-1

FDA UNII

  • C49WS9N75L

Other Registry Numbers

  • 11006-28-3
  • 11006-49-8
  • 11100-46-2
  • 11113-94-3
  • 11132-90-4
  • 12620-11-0
  • 1401-44-1
  • 1407-07-4
  • 63496-49-1
  • 63496-50-4
  • 8065-94-9

System Generated Number

  • 0011006761

Structure Descriptors

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

InChIKey

MVTQIFVKRXBCHS-SMMNFGSLSA-N

Smiles

CC[C@H]1NC(=O)[C@@H](NC(=O)c2ncccc2O)[C@@H](C)OC(=O)[C@@H](NC(=O)[C@@H]3CC(=O)CCN3C(=O)[C@H](Cc4ccccc4)N(C)C(=O)[C@@H]5CCCN5C1=O)c6ccccc6.CC(C)[C@H]7OC(=O)C8=CCCN8C(=O)c9coc(CC(=O)C[C@H](O)\C=C(/C)\C=C\CNC(=O)\C=C\[C@H]7C)n9

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 450mg/kg (450mg/kg)   Antibiotics Annual. Vol. 1, Pg. 171, 1953/1954.
mouse LD50 oral 2100mg/kg (2100mg/kg)   "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 1, Pg. 383, 1978.
mouse LD50 subcutaneous 2500mg/kg (2500mg/kg)   "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 1, Pg. 383, 1978.