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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H17N9O5S2
Molecular Weight 515.526
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of CEFOZOPRAN

SMILES

[H][C@]12SCC(C[N+]3=C4C=CC=NN4C=C3)=C(N1C(=O)[C@H]2NC(=O)C(=N/OC)\C5=NSC(N)=N5)C([O-])=O

InChI

InChIKey=QDUIJCOKQCCXQY-WHJQOFBOSA-N
InChI=1S/C19H17N9O5S2/c1-33-24-11(14-23-19(20)35-25-14)15(29)22-12-16(30)28-13(18(31)32)9(8-34-17(12)28)7-26-5-6-27-10(26)3-2-4-21-27/h2-6,12,17H,7-8H2,1H3,(H3-,20,22,23,25,29,31,32)/b24-11-/t12-,17-/m1/s1

HIDE SMILES / InChI

Molecular Formula C19H17N9O5S2
Molecular Weight 515.526
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 1
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/1624391 http://www.ncbi.nlm.nih.gov/pubmed/1624391

Cefozopran hydrochloride is a third-generation cephalosporin that was launched for the treatment of severe infections in immunocompromised patients caused by staphylococci and enterococci. While it shows a very broad antibacterial spectrum against Gram-positive and Gram-negative organisms, it is particularly potent against S. aureus, Enterococcus faecalis, P. aeruginosa, and Citrobacter freundii. It is resistant to hydrolysis by most chromosomal and plasmid mediated β-lactamases and is reported to be active against respiratory, urinary tract, obstetrical, gynecological, soft tissue, and surgical infections. Similar to β-lactams, cephalosporins interfere with PBP (penicillin binding protein) activity involved in the final phase of peptidoglycan synthesis. PBP’s are enzymes which catalyze a pentaglycine crosslink between alanine and lysine residues providing additional strength to the cell wall. Without a pentaglycine crosslink, the integrity of the cell wall is severely compromised and ultimately leads to cell lysis and death. Resistance to cephalosporins is commonly due to cells containing plasmid encoded β-lactamases.

CNS Activity

Curator's Comment: Known to be CNS penetrant in mouse. Human data not available

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Unknown

Approved Use

Unknown
Curative
Unknown

Approved Use

Unknown
Curative
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
[Pharmacokinetic, bacteriological and clinical studies on cefozopran in the pediatric field].
1994 Nov
Patents

Sample Use Guides

In the single-dose phase: 0.5, 1.0 and 2.0 g of cefozopran hydrochloride In the multiple-dose phase: 2.0 g every 12 h for 4 days
Route of Administration: Intravenous
In Vitro Use Guide
Antibacterial activity MICs of Cefozopran (CZOP) was determined against a total of 19 strains. For Gram-positive cocci, MICs of CZOP ranged from 0.39 to 0.78 ug/ml against Staphylococcus aureus (3 strains), from 0.05 to 6.25 ug/ml against Streptococcus pneumoniae (5 strains), and 12.5 ug/ml against Enterococcus faecalis (1 strain).
Substance Class Chemical
Created
by admin
on Sat Dec 16 17:18:29 GMT 2023
Edited
by admin
on Sat Dec 16 17:18:29 GMT 2023
Record UNII
1LG87K28LW
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CEFOZOPRAN
INN   MI   WHO-DD  
INN  
Official Name English
Cefozopran [WHO-DD]
Common Name English
CEFOZOPRAN HYDROCHLORIDE [JAN]
Common Name English
(-)-1-(((6R,7R)-7-(2-(5-AMINO-1,2,4-THIADIAZOL-3-YL)GLYOXYLAMIDO)-2-CARBOXY-8-OXO-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-EN-3-YL)METHYL)-1H-IMIDAZO(1,2-B)PYRIDAZIN-4-IUM HYDROXIDE INNER SALT, 7^2-(Z)-(O-METHYLOXIME)
Common Name English
CEFOZOPRAN [MI]
Common Name English
cefozopran [INN]
Common Name English
Classification Tree Code System Code
WHO-VATC QJ01DE03
Created by admin on Sat Dec 16 17:18:30 GMT 2023 , Edited by admin on Sat Dec 16 17:18:30 GMT 2023
WHO-ATC J01DE03
Created by admin on Sat Dec 16 17:18:30 GMT 2023 , Edited by admin on Sat Dec 16 17:18:30 GMT 2023
NCI_THESAURUS C357
Created by admin on Sat Dec 16 17:18:30 GMT 2023 , Edited by admin on Sat Dec 16 17:18:30 GMT 2023
Code System Code Type Description
DRUG CENTRAL
551
Created by admin on Sat Dec 16 17:18:30 GMT 2023 , Edited by admin on Sat Dec 16 17:18:30 GMT 2023
PRIMARY
MERCK INDEX
m3209
Created by admin on Sat Dec 16 17:18:30 GMT 2023 , Edited by admin on Sat Dec 16 17:18:30 GMT 2023
PRIMARY Merck Index
EPA CompTox
DTXSID701025943
Created by admin on Sat Dec 16 17:18:30 GMT 2023 , Edited by admin on Sat Dec 16 17:18:30 GMT 2023
PRIMARY
ChEMBL
CHEMBL1276663
Created by admin on Sat Dec 16 17:18:30 GMT 2023 , Edited by admin on Sat Dec 16 17:18:30 GMT 2023
PRIMARY
SMS_ID
100000081827
Created by admin on Sat Dec 16 17:18:30 GMT 2023 , Edited by admin on Sat Dec 16 17:18:30 GMT 2023
PRIMARY
PUBCHEM
9571080
Created by admin on Sat Dec 16 17:18:30 GMT 2023 , Edited by admin on Sat Dec 16 17:18:30 GMT 2023
PRIMARY
WIKIPEDIA
CEFOZOPRAN
Created by admin on Sat Dec 16 17:18:30 GMT 2023 , Edited by admin on Sat Dec 16 17:18:30 GMT 2023
PRIMARY
CHEBI
3502
Created by admin on Sat Dec 16 17:18:30 GMT 2023 , Edited by admin on Sat Dec 16 17:18:30 GMT 2023
PRIMARY
MESH
C070918
Created by admin on Sat Dec 16 17:18:30 GMT 2023 , Edited by admin on Sat Dec 16 17:18:30 GMT 2023
PRIMARY
CAS
113359-04-9
Created by admin on Sat Dec 16 17:18:30 GMT 2023 , Edited by admin on Sat Dec 16 17:18:30 GMT 2023
PRIMARY
NCI_THESAURUS
C76172
Created by admin on Sat Dec 16 17:18:30 GMT 2023 , Edited by admin on Sat Dec 16 17:18:30 GMT 2023
PRIMARY
FDA UNII
1LG87K28LW
Created by admin on Sat Dec 16 17:18:30 GMT 2023 , Edited by admin on Sat Dec 16 17:18:30 GMT 2023
PRIMARY
EVMPD
SUB07410MIG
Created by admin on Sat Dec 16 17:18:30 GMT 2023 , Edited by admin on Sat Dec 16 17:18:30 GMT 2023
PRIMARY
INN
6918
Created by admin on Sat Dec 16 17:18:30 GMT 2023 , Edited by admin on Sat Dec 16 17:18:30 GMT 2023
PRIMARY
DRUG BANK
DB13667
Created by admin on Sat Dec 16 17:18:30 GMT 2023 , Edited by admin on Sat Dec 16 17:18:30 GMT 2023
PRIMARY
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SALT/SOLVATE -> PARENT
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