EVERNIMICIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C70H97Cl2NO38
Molecular Weight	1631.409
Optical Activity	UNSPECIFIED
Defined Stereocenters	35 / 35
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]12CO[C@@H](O[C@]3([H])O[C@H](COC)[C@@H](O[C@]4([H])O[C@H](C)[C@H](OC)[C@H](O[C@]5([H])O[C@H](C)[C@@]6([H])O[C@]7(C[C@@H](O)[C@H](O[C@@]8([H])C[C@@H](O[C@@]9([H])C[C@@](C)([C@@H](OC)[C@H](C)O9)[N+]([O-])=O)[C@H](OC(=O)C%10=C(OC)C(Cl)=C(O)C(Cl)=C%10C)[C@@H](C)O8)[C@@H](C)O7)O[C@]6(C)[C@@H]5O)[C@H]4O)[C@H](O)[C@@H]3OC)[C@H](O)[C@]1([H])O[C@@]%11(O2)OC[C@@H](OC(=O)C%12=C(O)C=C(O)C=C%12C)[C@]%13([H])OCO[C@@]%11%13[H]

InChI

InChIKey=UPADRKHAIMTUCC-OWALTSPQSA-N

InChI=1S/C70H97Cl2NO38/c1-24-15-31(74)16-32(75)40(24)61(82)100-36-22-94-70(60-53(36)92-23-93-60)108-37-21-91-63(46(79)52(37)109-70)106-65-56(89-13)45(78)51(35(101-65)20-86-10)104-64-47(80)55(50(87-11)27(4)97-64)105-66-57(81)68(9)59(30(7)98-66)110-69(111-68)18-33(76)48(28(5)107-69)102-38-17-34(99-39-19-67(8,73(84)85)58(90-14)29(6)96-39)49(26(3)95-38)103-62(83)41-25(2)42(71)44(77)43(72)54(41)88-12/h15-16,26-30,33-39,45-53,55-60,63-66,74-81H,17-23H2,1-14H3/t26-,27-,28-,29+,30-,33-,34-,35-,36-,37+,38+,39+,45+,46-,47-,48-,49-,50+,51-,52-,53+,55-,56+,57-,58+,59-,60-,63+,64+,65+,66+,67+,68-,69-,70-/m1/s1

HIDE SMILES / InChI

Description
Sources: https://adisinsight.springer.com/drugs/800002696 | https://www.ncbi.nlm.nih.gov/pubmed/11259679 | https://www.ncbi.nlm.nih.gov/pubmed/10770739

Evernimicin (SCH 27899) is an oligosaccharide antibiotic. It nteracts with the large ribosomal subunit (50S) and inhibits bacterial protein synthesis. Evernimicin exerts activity against a wide spectrum of gram-positive bacteria and activity against some gram-negative bacteria. Evernimicin was being studied for the treatment of susceptible bacterial infections however its development has been discontinued.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
ribosomal large subunit assembly 1 Target ID: GO:0000027 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11259679 \| https://www.ncbi.nlm.nih.gov/pubmed/11259679 \| https://www.ncbi.nlm.nih.gov/pubmed/10770739	Inhibitor 8297

PubMed

Title	Date	PubMed
Evernimicin binds exclusively to the 50S ribosomal subunit and inhibits translation in cell-free systems derived from both gram-positive and gram-negative bacteria.	2000 May	10770739
A novel site of antibiotic action in the ribosome: interaction of evernimicin with the large ribosomal subunit.	2001 Mar 27	11259679

Sample Use Guides

In Vitro Use Guide

Evernimicin exhibited excellent activity (MIC, <0.016 to 1.5 ug/ml) against the gram-positive cocci tested. The antimicrobial activity of evernimicin against S. aureus and S. epidermidis was stronger than that of vancomycin, teicoplanin, and minocycline, in particular against MRSA, with an MIC50 of 0.38 ug/ml and an MIC90 of 0.5 ug/ml.

Name

Type

Language

EVERNIMICIN

Official Name

English

SCH27899

Code

English

EVERNIMICIN [USAN]

Common Name

English

SCH-27899

Code

English

EVERNIMICIN [MART.]

Common Name

English

ZIRACIN

Brand Name

English

EVERNINOMICIN

Common Name

English

evernimicin [INN]

Common Name

English

Code System Code Type Description

EPA CompTox

DTXSID60883194