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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H17N9O5S2.ClH
Molecular Weight 551.987
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of CEFOZOPRAN HYDROCHLORIDE

SMILES

Cl.[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=NTJHUKMPVIFDNY-XFDPNJHTSA-N
InChI=1S/C19H17N9O5S2.ClH/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);1H/b24-11-;/t12-,17-;/m1./s1

HIDE SMILES / InChI

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).
Name Type Language
CEFOZOPRAN HYDROCHLORIDE
MART.   WHO-DD  
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(SUP 2)-(Z)-(O-METHYLOXIME), HYDROCHLORIDE
Common Name English
SCE-2787
Code English
Cefozopran hydrochloride [WHO-DD]
Common Name English
CEFOZOPRAN HYDROCHLORIDE [MART.]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C357
Created by admin on Fri Dec 15 19:02:42 GMT 2023 , Edited by admin on Fri Dec 15 19:02:42 GMT 2023
Code System Code Type Description
DRUG BANK
DBSALT002706
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PRIMARY
EVMPD
SUB13278MIG
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NCI_THESAURUS
C92168
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FDA UNII
060I5C0GRC
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SMS_ID
100000076315
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CAS
113981-44-5
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EPA CompTox
DTXSID1048592
Created by admin on Fri Dec 15 19:02:42 GMT 2023 , Edited by admin on Fri Dec 15 19:02:42 GMT 2023
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PUBCHEM
5491954
Created by admin on Fri Dec 15 19:02:42 GMT 2023 , Edited by admin on Fri Dec 15 19:02:42 GMT 2023
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