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

Details

Stereochemistry EPIMERIC
Molecular Formula C20H31N3O6S
Molecular Weight 441.542
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 4
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of BACMECILLINAM

SMILES

[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2\N=C\N3CCCCCC3)C(=O)OC(C)OC(=O)OCC

InChI

InChIKey=XHKFBADIZIDYBU-MLFVOLAISA-N
InChI=1S/C20H31N3O6S/c1-5-27-19(26)29-13(2)28-18(25)15-20(3,4)30-17-14(16(24)23(15)17)21-12-22-10-8-6-7-9-11-22/h12-15,17H,5-11H2,1-4H3/b21-12+/t13?,14-,15+,17-/m1/s1

HIDE SMILES / InChI

Molecular Formula C20H31N3O6S
Molecular Weight 441.542
Charge 0
Count
Stereochemistry EPIMERIC
Additional Stereochemistry No
Defined Stereocenters 3 / 4
E/Z Centers 1
Optical Activity UNSPECIFIED

Bacmecillinam is the orally active 1’-ethoxycarbonyloxyethyl ester of macillinam. It is rapidly absorbed and hydrolyzed, liberating the antibacterially active drug mecillinam. Protective effects of bacmecillinam was tested in experimental mouse intraperitoneal infection model. Drug demonstrated the potent protective effects against E. coli GN 2411-5, E. coli 2848, K. pneumoniae 8045, E. cloacae F-1510 and P. mirabilis F-783 infection.

Approval Year

Patents
Substance Class Chemical
Created
by admin
on Sat Dec 16 17:37:44 GMT 2023
Edited
by admin
on Sat Dec 16 17:37:44 GMT 2023
Record UNII
942B99D5UK
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BACMECILLINAM
INN  
INN  
Official Name English
bacmecillinam [INN]
Common Name English
(2S,5R,6R)-6-(((HEXAHYDRO-1H-AZEPIN-1-YL)METHYLENE)AMINO)-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID ESTER WITH ETHYL 1-HYDROXYETHYL CARBONATE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1500
Created by admin on Sat Dec 16 17:37:44 GMT 2023 , Edited by admin on Sat Dec 16 17:37:44 GMT 2023
Code System Code Type Description
EVMPD
SUB05668MIG
Created by admin on Sat Dec 16 17:37:44 GMT 2023 , Edited by admin on Sat Dec 16 17:37:44 GMT 2023
PRIMARY
SMS_ID
100000086088
Created by admin on Sat Dec 16 17:37:44 GMT 2023 , Edited by admin on Sat Dec 16 17:37:44 GMT 2023
PRIMARY
MESH
C021145
Created by admin on Sat Dec 16 17:37:44 GMT 2023 , Edited by admin on Sat Dec 16 17:37:44 GMT 2023
PRIMARY
FDA UNII
942B99D5UK
Created by admin on Sat Dec 16 17:37:44 GMT 2023 , Edited by admin on Sat Dec 16 17:37:44 GMT 2023
PRIMARY
EPA CompTox
DTXSID801023645
Created by admin on Sat Dec 16 17:37:44 GMT 2023 , Edited by admin on Sat Dec 16 17:37:44 GMT 2023
PRIMARY
CAS
50846-45-2
Created by admin on Sat Dec 16 17:37:44 GMT 2023 , Edited by admin on Sat Dec 16 17:37:44 GMT 2023
PRIMARY
NCI_THESAURUS
C72619
Created by admin on Sat Dec 16 17:37:44 GMT 2023 , Edited by admin on Sat Dec 16 17:37:44 GMT 2023
PRIMARY
ChEMBL
CHEMBL2106658
Created by admin on Sat Dec 16 17:37:44 GMT 2023 , Edited by admin on Sat Dec 16 17:37:44 GMT 2023
PRIMARY
INN
4245
Created by admin on Sat Dec 16 17:37:44 GMT 2023 , Edited by admin on Sat Dec 16 17:37:44 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY