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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

CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](NC(=O)N3CCN(\N=C\C4=CC=CO4)C3=O)C5=CC=C(O)C=C5)C(=O)N2[C@H]1C(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

Molecular Formula C25H26N6O8S
Molecular Weight 570.574
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 1
Optical Activity UNSPECIFIED

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

Substance Class Chemical
Created
by admin
on Mon Mar 31 18:29:41 GMT 2025
Edited
by admin
on Mon Mar 31 18:29:41 GMT 2025
Record UNII
J6UQP7JHOT
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BAY VK 4999
Preferred Name English
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
fuzlocillin [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1500
Created by admin on Mon Mar 31 18:29:41 GMT 2025 , Edited by admin on Mon Mar 31 18:29:41 GMT 2025
Code System Code Type Description
PUBCHEM
9571079
Created by admin on Mon Mar 31 18:29:41 GMT 2025 , Edited by admin on Mon Mar 31 18:29:41 GMT 2025
PRIMARY
ChEMBL
CHEMBL2304036
Created by admin on Mon Mar 31 18:29:41 GMT 2025 , Edited by admin on Mon Mar 31 18:29:41 GMT 2025
PRIMARY
MESH
C017976
Created by admin on Mon Mar 31 18:29:41 GMT 2025 , Edited by admin on Mon Mar 31 18:29:41 GMT 2025
PRIMARY
EPA CompTox
DTXSID301024381
Created by admin on Mon Mar 31 18:29:41 GMT 2025 , Edited by admin on Mon Mar 31 18:29:41 GMT 2025
PRIMARY
CAS
66327-51-3
Created by admin on Mon Mar 31 18:29:41 GMT 2025 , Edited by admin on Mon Mar 31 18:29:41 GMT 2025
PRIMARY
FDA UNII
J6UQP7JHOT
Created by admin on Mon Mar 31 18:29:41 GMT 2025 , Edited by admin on Mon Mar 31 18:29:41 GMT 2025
PRIMARY
INN
4537
Created by admin on Mon Mar 31 18:29:41 GMT 2025 , Edited by admin on Mon Mar 31 18:29:41 GMT 2025
PRIMARY
EVMPD
SUB07855MIG
Created by admin on Mon Mar 31 18:29:41 GMT 2025 , Edited by admin on Mon Mar 31 18:29:41 GMT 2025
PRIMARY
NCI_THESAURUS
C65794
Created by admin on Mon Mar 31 18:29:41 GMT 2025 , Edited by admin on Mon Mar 31 18:29:41 GMT 2025
PRIMARY
SMS_ID
100000084506
Created by admin on Mon Mar 31 18:29:41 GMT 2025 , Edited by admin on Mon Mar 31 18:29:41 GMT 2025
PRIMARY
Related Record Type Details
ACTIVE MOIETY