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

Details

Stereochemistry ABSOLUTE
Molecular Formula C25H26N6O8S
Molecular Weight 570.574
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of FUZLOCILLIN

SMILES

[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](NC(=O)N3CCN(\N=C\C4=CC=CO4)C3=O)C5=CC=C(O)C=C5)C(O)=O

InChI

InChIKey=YSUBQYRZZFVMTL-YNDGFOBUSA-N
InChI=1S/C25H26N6O8S/c1-25(2)18(22(35)36)31-20(34)17(21(31)40-25)27-19(33)16(13-5-7-14(32)8-6-13)28-23(37)29-9-10-30(24(29)38)26-12-15-4-3-11-39-15/h3-8,11-12,16-18,21,32H,9-10H2,1-2H3,(H,27,33)(H,28,37)(H,35,36)/b26-12+/t16-,17-,18+,21-/m1/s1

HIDE SMILES / InChI
Fuzlocillin is a penicillin antibiotic. This semisynthetic acylureidopenicillin with antibacterial activity binds to and inactivates penicillin-binding proteins (PBPs) located on the inner membrane of the bacterial cell wall. Fuzlocillin (furazlocillin), has been shown to be highly specific for the FtsI gene. Inactivation of PBPs interferes with the cross-linkage of peptidoglycan chains necessary for bacterial cell wall strength and rigidity. This interrupts bacterial cell wall synthesis and results in the weakening of the bacterial cell wall, eventually causing the cell to break down (cell lysis). Among the acylureidopenicillins, furaclocillin exerts increased activity against Escherischia coli, Klebsiella, Proteus and Pseudomonas aeruginosa.

Approval Year

Name Type Language
FUZLOCILLIN
INN  
INN  
Official Name English
(2S,5R,6R)-6-((2R)-2-(3-((E)-FURFURYLIDENEAMINO)-2-OXO-1-IMIDAZOLIDINECARBOXAMIDO)-2-(P-HYDROXYPHENYL)ACETAMIDO)-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID
Common Name English
BAY-VK-4999
Code English
BAY VK 4999
Code English
fuzlocillin [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1500
Created by admin on Fri Dec 15 16:30:12 GMT 2023 , Edited by admin on Fri Dec 15 16:30:12 GMT 2023
Code System Code Type Description
PUBCHEM
9571079
Created by admin on Fri Dec 15 16:30:12 GMT 2023 , Edited by admin on Fri Dec 15 16:30:12 GMT 2023
PRIMARY
ChEMBL
CHEMBL2304036
Created by admin on Fri Dec 15 16:30:12 GMT 2023 , Edited by admin on Fri Dec 15 16:30:12 GMT 2023
PRIMARY
MESH
C017976
Created by admin on Fri Dec 15 16:30:12 GMT 2023 , Edited by admin on Fri Dec 15 16:30:12 GMT 2023
PRIMARY
EPA CompTox
DTXSID301024381
Created by admin on Fri Dec 15 16:30:12 GMT 2023 , Edited by admin on Fri Dec 15 16:30:12 GMT 2023
PRIMARY
CAS
66327-51-3
Created by admin on Fri Dec 15 16:30:12 GMT 2023 , Edited by admin on Fri Dec 15 16:30:12 GMT 2023
PRIMARY
FDA UNII
J6UQP7JHOT
Created by admin on Fri Dec 15 16:30:12 GMT 2023 , Edited by admin on Fri Dec 15 16:30:12 GMT 2023
PRIMARY
INN
4537
Created by admin on Fri Dec 15 16:30:12 GMT 2023 , Edited by admin on Fri Dec 15 16:30:12 GMT 2023
PRIMARY
EVMPD
SUB07855MIG
Created by admin on Fri Dec 15 16:30:12 GMT 2023 , Edited by admin on Fri Dec 15 16:30:12 GMT 2023
PRIMARY
NCI_THESAURUS
C65794
Created by admin on Fri Dec 15 16:30:12 GMT 2023 , Edited by admin on Fri Dec 15 16:30:12 GMT 2023
PRIMARY
SMS_ID
100000084506
Created by admin on Fri Dec 15 16:30:12 GMT 2023 , Edited by admin on Fri Dec 15 16:30:12 GMT 2023
PRIMARY