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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
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 13 / 13
E/Z Centers 2
Optical Activity UNSPECIFIED

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

PubMed

TitleDatePubMed
Patents

Sample Use Guides

400 mg/day, followed by 2 days of 200 mg/day.
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Sat Dec 16 17:21:43 GMT 2023
Edited
by admin
on Sat Dec 16 17:21:43 GMT 2023
Record UNII
9MAY4E090U
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MODITHROMYCIN
INN   USAN   WHO-DD  
INN   USAN  
Official Name English
EDP-013420
Code English
EDP-420
Code English
Modithromycin [WHO-DD]
Common Name English
ERYTHROMYCIN, 9-(ACETYLIMINO)-3-DE((2,6-DIDEOXY-3-C-METHYL-3-O-METHYL-.ALPHA.-L-RIBO-HEXOPYRANOSYL)OXY)-9-DEOXO-3-OXO-6,11-O-((2E)-2-(((6-(1H-PYRAZOL-1-YL)-3-PYRIDINYL)METHOXY)IMINO)-1,3-PROPANEDIYL)-, (9E)-
Common Name English
modithromycin [INN]
Common Name English
EP-13420
Code English
MODITHROMYCIN [USAN]
Common Name English
Code System Code Type Description
NCI_THESAURUS
C174586
Created by admin on Sat Dec 16 17:21:43 GMT 2023 , Edited by admin on Sat Dec 16 17:21:43 GMT 2023
PRIMARY
INN
9171
Created by admin on Sat Dec 16 17:21:43 GMT 2023 , Edited by admin on Sat Dec 16 17:21:43 GMT 2023
PRIMARY
PUBCHEM
9875927
Created by admin on Sat Dec 16 17:21:43 GMT 2023 , Edited by admin on Sat Dec 16 17:21:43 GMT 2023
PRIMARY
CAS
736992-12-4
Created by admin on Sat Dec 16 17:21:43 GMT 2023 , Edited by admin on Sat Dec 16 17:21:43 GMT 2023
PRIMARY
FDA UNII
9MAY4E090U
Created by admin on Sat Dec 16 17:21:43 GMT 2023 , Edited by admin on Sat Dec 16 17:21:43 GMT 2023
PRIMARY
SMS_ID
300000034298
Created by admin on Sat Dec 16 17:21:43 GMT 2023 , Edited by admin on Sat Dec 16 17:21:43 GMT 2023
PRIMARY
USAN
WW-108
Created by admin on Sat Dec 16 17:21:43 GMT 2023 , Edited by admin on Sat Dec 16 17:21:43 GMT 2023
PRIMARY
ChEMBL
CHEMBL263886
Created by admin on Sat Dec 16 17:21:43 GMT 2023 , Edited by admin on Sat Dec 16 17:21:43 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY