Compound ID | 378

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Eremomycin

Synonym(s): A82846A

Class: Glycopeptide

Agent Type: Natural product; Direct acting;
Spectrum of activity: Gram-positive
Mechanism of action: Cell wall synthesis inhibitor
Target Pathogen: Active against Clostridium difficile
Description: Natural product from an actinomycete
Institute where first reported: Russian Academy of Medical Sciences
Year first mentioned: 1988
Highest development stage: Phase 2
Development status: Inactive
Reason dropped: In a trial where animals were administered the body surface area extrapolated dosage equivalent to the human dosage, there were some undesired side effects such as a significant increase in blood serum urea and also prolonged use at a high dosage revealed damaging side effects to kidneys and epithelium of the gastrointestinal tract which were reversible; but a derivative of chloroeremomycin was eventually developed as oritavancin
Chemical structure(s):
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Molecular weight: 1557.99
Iso. SMILES: C[C@H]1[C@@H]([C@@](C[C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2OC3=C4C=C5C=C3OC6=C(C=C(C=C6)[C@H]([C@H](C(=O)N[C@H](C(=O)N[C@H]5C(=O)N[C@@H]7C8=CC(=C(C=C8)O)C9=C(C=C(C=C9O)O)[C@H](NC(=O)[C@H]([C@@H](C%10=CC=C(O4)C=C%10)O[C@H]%11C[C@]([C@H]([C@@H](O%11)C)O)(C)N)NC7=O)C(=O)O)CC(=O)N)NC(=O)[C@@H](CC(C)C)NC)O)Cl)CO)O)O)(C)N)O
InChI Key: UECIPBUIMXSXEI-BNSVOVDNSA-N
Can. SMILES: CC(C)C[C@H](C(=O)N[C@@H]1[C@@H](C2=CC=C(C(=C2)Cl)OC3=C(C4=CC(=C3)[C@H](C(=O)N[C@@H]5C6=CC=C(C(=C6)C7=C(C=C(C=C7[C@@H](C(=O)O)NC(=O)[C@H]([C@@H](C8=CC=C(C=C8)O4)O[C@H]9C[C@@](C)([C@H]([C@H](C)O9)O)N)NC5=O)O)O)O)NC(=O)[C@H](CC(=O)N)NC1=O)O[C@H]%10[C@@H]([C@H]([C@@H]([C@@H](CO)O%10)O)O)O[C@H]%11C[C@@](C)([C@H]([C@H](C)O%11)O)N)O)NC
InChI: InChI=1S/C73H89ClN10O26/c1-27(2)16-39(78-7)64(95)83-54-56(90)32-11-15-43(38(74)18-32)106-45-20-33-19-44(60(45)110-71-61(58(92)57(91)46(26-85)107-71)109-49-25-73(6,77)63(94)29(4)104-49)105-35-12-8-30(9-13-35)59(108-48-24-72(5,76)62(93)28(3)103-48)55-69(100)82-53(70(101)102)37-21-34(86)22-42(88)50(37)36-17-31(10-14-41(36)87)51(66(97)84-55)81-67(98)52(33)80-65(96)40(23-47(75)89)79-68(54)99/h8-15,17-22,27-29,39-40,46,48-49,51-59,61-63,71,78,85-88,90-94H,16,23-26,76-77H2,1-7H3,(H2,75,89)(H,79,99)(H,80,96)(H,81,98)(H,82,100)(H,83,95)(H,84,97)(H,101,102)/t28-,29-,39+,40-,46+,48-,49-,51+,52+,53-,54+,55-,56+,57+,58-,59+,61+,62-,63-,71-,72-,73-/m0/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/122131
Guide to Pharmacology: eremomycin
Citations:
  • http://adisinsight.springer.com/drugs/800002322
  • http://www.ncbi.nlm.nih.gov/pubmed/3389957
  • https://doi.org/10.2147/DDDT.S173923
  • https://doi.org/10.7164/antibiotics.42.1790

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