Compound ID | 987

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Ziracin

Synonym(s): Evernimicin  |  SCH 27899

Class: Aminoglycoside

Spectrum of activity: Gram-positive
Details of activity: Inhibits protein synthesis by binding to 50S subunit; active against a number of Gram positives including MRSS and MRSA, this was more potent than vancomcyin and teicoplanin
Propensity to select resistant mutants: Yes
Description: Boucher HW, Thauvin-eliopoulos C, Loebenberg D, Eliopoulos GM. In vivo activity of evernimicin (SCH 27899) against methicillin-resistant Staphylococcus aureus in experimental infective endocarditis. Antimicrob Agents Chemother. 2001;45(1):208-11.
Institute where first reported: Schering-Plough (Merck & Co., US)
Year first mentioned: 1965
Highest development stage: Phase 3
Development status: Inactive
Reason dropped: Pharmacokinetic complications
Chemical structure(s):
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Molecular weight: 1631.41
Iso. SMILES: C[C@@H]1[C@H]([C@@H](C[C@@H](O1)O[C@@H]2[C@H](O[C@]3(C[C@H]2O)O[C@@H]4[C@H](O[C@H]([C@H]([C@]4(O3)C)O)O[C@@H]5[C@H]([C@@H](O[C@@H]([C@@H]5OC)C)O[C@@H]6[C@H](O[C@H]([C@H]([C@H]6O)OC)O[C@H]7[C@@H]([C@H]8[C@H](CO7)O[C@@]9(O8)[C@H]%10[C@H]([C@@H](CO9)OC(=O)C%11=C(C=C(C=C%11C)O)O)OCO%10)O)COC)O)C)C)O[C@H]%12C[C@]([C@H]([C@@H](O%12)C)OC)(C)[N+](=O)[O-])OC(=O)C%13=C(C(=C(C(=C%13OC)Cl)O)Cl)C
InChI Key: UPADRKHAIMTUCC-OWALTSPQSA-N
Can. SMILES: CC1=C(C(=CC(=C1)O)O)C(=O)O[C@@H]2CO[C@]3([C@H]4[C@H]2OCO4)O[C@H]5CO[C@H]([C@@H]([C@@H]5O3)O)O[C@H]6[C@H]([C@H]([C@@H]([C@@H](COC)O6)O[C@H]7[C@@H]([C@H]([C@H]([C@@H](C)O7)OC)O[C@H]8[C@H]([C@]9(C)[C@@H]([C@@H](C)O8)O[C@]%10(C[C@H]([C@@H]([C@@H](C)O%10)O[C@H]%11C[C@H]([C@@H]([C@@H](C)O%11)OC(=O)C%12=C(C(=C(C(=C%12C)Cl)O)Cl)OC)O[C@H]%13C[C@@](C)([C@H]([C@H](C)O%13)OC)[N+](=O)[O-])O)O9)O)O)O)OC
InChI: 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
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/6917933
Guide to Pharmacology: evernimicin
Citations:
  • https://journals.asm.org/doi/10.1128/aac.44.10.2733-2739.2000?url_ver=Z39.88-2003&rfr_id=ori%3Arid%3Acrossref.org&rfr_dat=cr_pub++0pubmed
  • https://www.ncbi.nlm.nih.gov/pubmed/11132948

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