Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C43H64N6O11 |
Molecular Weight | 841.0019 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 13 / 13 |
E/Z Centers | 2 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]2(O[C@@H]1O[C@H](C)C[C@@H]([C@H]1O)N(C)C)[C@@H](C)C(=O)[C@@H](C)C(=O)O[C@H](CC)[C@@](C)(O)[C@@H]3OC\C(CO[C@]2(C)C[C@@H](C)\C(=N/C(C)=O)[C@@H]3C)=N/OCC4=CN=C(C=C4)N5C=CC=N5
InChI
InChIKey=WLGSYOKBEDVHQB-XSKCQLPHSA-N
InChI=1S/C43H64N6O11/c1-12-33-43(9,54)39-26(4)35(46-29(7)50)24(2)19-42(8,56-23-31(22-55-39)47-57-21-30-14-15-34(44-20-30)49-17-13-16-45-49)38(27(5)36(51)28(6)40(53)59-33)60-41-37(52)32(48(10)11)18-25(3)58-41/h13-17,20,24-28,32-33,37-39,41,52,54H,12,18-19,21-23H2,1-11H3/b46-35+,47-31+/t24-,25-,26+,27+,28-,32+,33-,37-,38-,39-,41+,42-,43-/m1/s1
Modithromycin (EDP-420, EP-013420, S-013420) is 6-11-bicyclic erythromycin derivative patented by Enanta Pharmaceuticals, Inc as an antibacterial agent. In preclinical studies, Modithromycin exhibited high levels of in vitro activities against N. gonorrhea, including isolates resistant to azithromycin, cefixime, ceftriaxone, spectinomycin, ampicillin, tetracycline, and ciprofloxacin. Modithromycin also has the good in vivo efficacy against S. pneumoniae and H. influenzae, which might be due to its lasting intracellular activity. In healthy adults, clinical trials Modithromycin shows long half-life and its high systemic exposure. Modithromycin was well tolerated, with no serious or severe adverse events reported, and no subject was discontinued from the study due to an adverse event. In 2005 Modithromycin was studied in phase II clinical trials but no further development reports were published.
Approval Year
PubMed
Title | Date | PubMed |
---|---|---|
EDP-420, a bicyclolide (bridged bicyclic macrolide), is active against Mycobacterium avium. | 2007 May |
|
In vitro activities of the novel bicyclolides modithromycin (EDP-420, EP-013420, S-013420) and EDP-322 against MDR clinical Neisseria gonorrhoeae isolates and international reference strains. | 2015 Jan |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19451282
400 mg/day, followed by 2 days of 200 mg/day.
Route of Administration:
Oral
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C174586
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9171
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9875927
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736992-12-4
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9MAY4E090U
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300000034298
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WW-108
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CHEMBL263886
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ACTIVE MOIETY