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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
Structure of MODITHROMYCIN

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

HIDE SMILES / InChI

Molecular Formula C43H64N6O11
Molecular Weight 841.0019
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 13 / 13
E/Z Centers 2
Optical Activity UNSPECIFIED

Description

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.

Originator

Approval Year

PubMed

Sample Use Guides

In Vivo Use Guide
400 mg/day, followed by 2 days of 200 mg/day.
Route of Administration: Oral
Substance Class Chemical
Record UNII
9MAY4E090U
Record Status Validated (UNII)
Record Version