Enramycin

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Enramycin
Enramycins.png
Clinical data
ATCvet code
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
Formula C107H138Cl2N26O31
Molar mass 2355.33 g·mol−1
3D model (JSmol)
  • CCC(C)CCCC/C=C/C=C/C(=O)NC(CC(=O)O)C(=O)NC1C(OC(=O)C(NC(=O)C(NC(=O)C(NC(=O)NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)N(C(=O)C(NC1=O)C2=CC=C(C=C2)O)CCCCN)C(C)O)C3=CC=C(C=C3)O)C4=CC=C(C=C4)O)C(C)O)CCCNC(=O)N)CC5CNC(=N5)N)C6=CC=C(C=C6)O)CO)C7=CC(=C(C(=C7)Cl)O)Cl)CC8CNC(=N8)N)C)C9=CC=C(C=C9)O)C.O
  • InChI=1S/C107H138Cl2N26O31.H2O/c1-7-51(2)17-12-10-8-9-11-13-19-76(144)120-74(47-77(145)146)92(152)126-80-55(6)166-102(162)86(60-28-38-68(143)39-29-60)132-88(148)52(3)117-90(150)73(46-63-49-116-104(112)119-63)124-106(164)134-100(160)84(61-43-69(108)87(147)70(109)44-61)128-93(153)75(50-136)123-97(157)81(56-20-30-64(139)31-21-56)127-91(151)72(45-62-48-115-103(111)118-62)122-89(149)71(18-16-41-114-105(113)163)121-94(154)78(53(4)137)125-98(158)82(57-22-32-65(140)33-23-57)130-99(159)83(58-24-34-66(141)35-25-58)129-95(155)79(54(5)138)133-107(165)135(42-15-14-40-110)101(161)85(131-96(80)156)59-26-36-67(142)37-27-59;/h9,11,13,19-39,43-44,51-55,62-63,71-75,78-86,136-143,147H,7-8,10,12,14-18,40-42,45-50,110H2,1-6H3,(H,117,150)(H,120,144)(H,121,154)(H,122,149)(H,123,157)(H,125,158)(H,126,152)(H,127,151)(H,128,153)(H,129,155)(H,130,159)(H,131,156)(H,132,148)(H,133,165)(H,145,146)(H3,111,115,118)(H3,112,116,119)(H3,113,114,163)(H2,124,134,160,164);1H2/b11-9+,19-13+;
  • Key:NJCUSQKMYNTYOW-MWUYRYRWSA-N

Enramycin (also known as enduracidin) is a polypeptide antibiotic produced by Streptomyces fungicidus . Enramycin is widely used as a feed additive for pigs and chickens to prevent necrotic enteritis induced by Gram-positive gut pathogens. [1]

Contents

Mechanism of action

Enramycin acts as an inhibitor of the enzyme MurG, which is essential for cell wall biosynthesis in Gram-positive bacteria. MurG catalyzes the transglycosylation reaction in the last step of peptidoglycan biosynthesis. Inhibiting this step greatly compromises cell wall integrity leading to cell lysis. [2]

Spectrum of susceptibility

Enramycin has been found to be very effective against Gram-positive gut pathogens, most notably, Clostridium perfringens ; a leading cause of necrotic enteritis.[ citation needed ] The following represents MIC data for a couple of veterinary pathogens. [3]

Composition

Standard grade enramycin is composed of two main components called enramycin A and enramycin B. These two components are routinely used as analytical reference standards; however, their activity as individual compounds does not appear to be widely studied or characterized. [4]

References

  1. ↑ Schering-Plough. "Enramycin." Darou Gostar Group. N.p., n.d. Web. 13 Mar. 2014.
  2. ↑ Fang X, Tiyanont K, Zhang Y, Wanner J, Boger D, Walker S (January 2006). "The mechanism of action of ramoplanin and enduracidin". Molecular BioSystems. 2 (1): 69–76. doi:10.1039/b515328j. PMID   16880924.
  3. ↑ "Enramycin Susceptibility and Resistance Data" (PDF).
  4. ↑ Inoue K, Hattori Y, Hino T, Oka H (April 2010). "An approach to on-line electrospray mass spectrometric detection of polypeptide antibiotics of enramycin for high-speed counter-current chromatographic separation". Journal of Pharmaceutical and Biomedical Analysis. 51 (5): 1154–60. doi:10.1016/j.jpba.2009.11.010. PMID   20004073.
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