Compound ID | 146

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Solithromycin

Synonym(s): CEM-101  |  CEM101  |  CEM 101  |  OP-1068  |  OP1068  |  OP 1068

Class: Macrolide

Agent Type: Semisynthetic; Small molecule; Direct acting;
Spectrum of activity: Gram-positive & Gram-negative
Mechanism of action: Protein synthesis inhibitor
Target Pathogen: Active against community-acquired bacterial pneumonia, uncomplicated urogenital gonorrhoea, and urethritis
Description: A 16-membered macrolide, fluoroketolide; derivative of telithromycin
Institute where first reported: Toyama Chemical Co. Ltd./Melinta Therapeutics Inc.; Cempra
Year first mentioned: 2008
Highest development stage: Phase 3 (NCT02605122)
Development status: Inactive
Reason dropped: Terminated clinical trials but not related to safety concerns; development not proceeding
Chemical structure(s):
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Molecular weight: 845.01
Iso. SMILES: CC[C@@H]1[C@@]2([C@@H]([C@H](C(=O)[C@@H](C[C@@]([C@@H]([C@H](C(=O)[C@](C(=O)O1)(C)F)C)O[C@H]3[C@@H]([C@H](C[C@H](O3)C)N(C)C)O)(C)OC)C)C)N(C(=O)O2)CCCCN4C=C(N=N4)C5=CC(=CC=C5)N)C
InChI Key: IXXFZUPTQVDPPK-ZAWHAJPISA-N
Can. SMILES: CC[C@@H]1[C@]2(C)[C@@H]([C@@H](C)C(=O)[C@H](C)C[C@](C)([C@@H]([C@@H](C)C(=O)[C@@](C)(C(=O)O1)F)O[C@H]3[C@@H]([C@H](C[C@@H](C)O3)N(C)C)O)OC)N(CCCCN4C=C(C5=CC(=CC=C5)N)N=N4)C(=O)O2
InChI: InChI=1S/C43H65FN6O10/c1-12-32-43(8)35(50(40(55)60-43)19-14-13-18-49-23-30(46-47-49)28-16-15-17-29(45)21-28)26(4)33(51)24(2)22-41(6,56-11)37(27(5)36(53)42(7,44)39(54)58-32)59-38-34(52)31(48(9)10)20-25(3)57-38/h15-17,21,23-27,31-32,34-35,37-38,52H,12-14,18-20,22,45H2,1-11H3/t24-,25-,26+,27+,31+,32-,34-,35-,37-,38+,41-,42+,43-/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/25242512
Guide to Pharmacology: solithromycin
Citations:
  • http://aac.asm.org/content/57/9/4322.full
  • http://aac.asm.org/content/58/1/447.full
  • https://www.sciencedirect.com/science/article/pii/S0924857910004310
  • https://journals.asm.org/doi/10.1128/aac.00860-10

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