U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C38H70N2O13
Molecular Weight 762.968
Optical Activity UNSPECIFIED
Defined Stereocenters 18 / 18
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of LEXITHROMYCIN

SMILES

[H][C@@]2(O[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1)[C@@H](C)C(=O)O[C@H](CC)[C@@](C)(O)[C@H](O)[C@@H](C)\C(=N\OC)[C@H](C)C[C@@](C)(O)[C@]([H])(O[C@@H]3O[C@H](C)C[C@@H]([C@H]3O)N(C)C)[C@H]2C

InChI

InChIKey=HPZGUSZNXKOMCQ-SQYJNGITSA-N
InChI=1S/C38H70N2O13/c1-15-26-38(10,46)31(42)21(4)28(39-48-14)19(2)17-36(8,45)33(53-35-29(41)25(40(11)12)16-20(3)49-35)22(5)30(23(6)34(44)51-26)52-27-18-37(9,47-13)32(43)24(7)50-27/h19-27,29-33,35,41-43,45-46H,15-18H2,1-14H3/b39-28+/t19-,20-,21+,22+,23-,24+,25+,26-,27+,29-,30+,31-,32+,33-,35+,36-,37-,38-/m1/s1

HIDE SMILES / InChI

Molecular Formula C38H70N2O13
Molecular Weight 762.968
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 18 / 18
E/Z Centers 1
Optical Activity UNSPECIFIED

Lexithromycin is an early semi-synthetic erythromycin, prepared by reaction of the 9-keto moiety to methyl oxime. Lexithromycin has improved absorption in vivo over erythromycin due to increased hydrophopicity and pH stability. Like all erythromycins, lexithromycin shows broad spectrum antibacterial activity and acts by binding to the 30S and 50S ribosomal sub-units, blocking protein synthesis. Formulations containing lexithromycin were tested in clinical trials as treatment for HIV but were discontinued.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
PubMed

PubMed

TitleDatePubMed
Substance Class Chemical
Created
by admin
on Sat Dec 16 05:09:07 GMT 2023
Edited
by admin
on Sat Dec 16 05:09:07 GMT 2023
Record UNII
7QKO29734U
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LEXITHROMYCIN
INN   USAN  
INN   USAN  
Official Name English
Erythromycin 9-(O-methyloxime)
Common Name English
ERYTHROMYCIN, 9-(O-METHYLOXIME)
Common Name English
WY-48314
Code English
ERYTHROMYCIN METHYLOXIME
Common Name English
lexithromycin [INN]
Common Name English
LEXITHROMYCIN [USAN]
Common Name English
ERTHROMYCIN A 9-(O-METHYLOXIME)
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C261
Created by admin on Sat Dec 16 05:09:07 GMT 2023 , Edited by admin on Sat Dec 16 05:09:07 GMT 2023
Code System Code Type Description
PUBCHEM
6532846
Created by admin on Sat Dec 16 05:09:07 GMT 2023 , Edited by admin on Sat Dec 16 05:09:07 GMT 2023
PRIMARY
CAS
118244-59-0
Created by admin on Sat Dec 16 05:09:07 GMT 2023 , Edited by admin on Sat Dec 16 05:09:07 GMT 2023
ALTERNATIVE
CAS
53066-26-5
Created by admin on Sat Dec 16 05:09:07 GMT 2023 , Edited by admin on Sat Dec 16 05:09:07 GMT 2023
PRIMARY
FDA UNII
7QKO29734U
Created by admin on Sat Dec 16 05:09:07 GMT 2023 , Edited by admin on Sat Dec 16 05:09:07 GMT 2023
PRIMARY
INN
6785
Created by admin on Sat Dec 16 05:09:07 GMT 2023 , Edited by admin on Sat Dec 16 05:09:07 GMT 2023
PRIMARY
NCI_THESAURUS
C87760
Created by admin on Sat Dec 16 05:09:07 GMT 2023 , Edited by admin on Sat Dec 16 05:09:07 GMT 2023
PRIMARY
ChEMBL
CHEMBL2106397
Created by admin on Sat Dec 16 05:09:07 GMT 2023 , Edited by admin on Sat Dec 16 05:09:07 GMT 2023
PRIMARY
SMS_ID
100000082287
Created by admin on Sat Dec 16 05:09:07 GMT 2023 , Edited by admin on Sat Dec 16 05:09:07 GMT 2023
PRIMARY
EVMPD
SUB08499MIG
Created by admin on Sat Dec 16 05:09:07 GMT 2023 , Edited by admin on Sat Dec 16 05:09:07 GMT 2023
PRIMARY
USAN
CC-11
Created by admin on Sat Dec 16 05:09:07 GMT 2023 , Edited by admin on Sat Dec 16 05:09:07 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY