INTRODUCTION

 Cefoperazone is a semisynthetic, broad-spectrum, third-generation

cephalosporin with antibacterial activity. Cefoperazone binds to and
inactivates penicillin-binding proteins (PBPs) located on the inner
membrane of the bacterial cell wall. PBPs are enzymes involved in the
terminal stages of assembling the bacterial cell wall and in reshaping
the cell wall during growth and division. Inactivation of PBPs
interferes with the cross-linkage of peptidoglycan chains necessary
for bacterial cell wall strength and rigidity. This results in the
weakening of the bacterial cell wall and causes cell lysis.

 Cefoperazone is a semi-synthetic parenteral cephalosporin with a

tetrazolyl moiety that confers beta-lactamase resistance. It has a role
as an antibacterial drug.

 Cefoperazone is a Cephalosporin Antibacterial. The chemical

classification of cefoperazone is Cephalosporins.

 It is a third-generation antiobiotic agent and it is used in the

treatment of various bacterial infections caused by susceptible
organisms in the body, including respiratory tract infections,
peritonitis, skin infections, endometritis, and bacterial septicemia.

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 Cefoperazone is a semisynthetic broad-spectrum cephalosporin
proposed to be effective against Pseudomonas infections. It is a third-
generation antiobiotic agent and it is used in the treatment of various
bacterial infections caused by susceptible organisms in the body,
including respiratory tract infections, peritonitis, skin infections,
endometritis, and bacterial septicemia. While its clinical use has been
discontinued in the U.S., cefoperazone is available in several
European countries most commonly under the product name,
Sulperazon.

 Cefoperazone is a third-generation cephalosporin antibiotic used in

the treatment of infections of skin and skin structures, respiratory
tract, urinary tract, gynecological infections including gonorrhea,
intraabdominal infections, and septicemia caused by susceptible
microorganisms. It is not recommended for use in patients who are
allergic to cephalosporins or penicillins.

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3
WHAT ARE SOME THINGS I NEED TO KNOW
OR DO WHILE I TAKE CEFOPERAZONE?
Tell all of your health care providers that you take cefoperazone. This
includes your doctors, nurses, pharmacists, and dentists.
Have blood work checked as you have been told by the doctor. Talk
with the doctor.
Avoid alcohol and products that have alcohol in them while taking
cefoperazone and for at least 72 hours after your last dose. Drinking
alcohol or taking products that have alcohol in them, like some cough
syrups, may cause flushing, sweating, headaches, and fast heartbeat.
Very bad and sometimes deadly allergic reactions have rarely
happened. Talk with your doctor.
This medicine may raise the chance of bleeding. Sometimes, bleeding
can be life-threatening. Talk with the doctor.
Do not use longer than you have been told. A second infection may
happen.
This medicine may affect certain lab tests. Tell all of your health care
providers and lab workers that you take cefoperazone.
If you have high blood sugar (diabetes), talk with your doctor about
which glucose tests are best to use.
If you are 65 or older, use cefoperazone with care. You could have
more side effects.
Tell your doctor if you are pregnant, plan on getting pregnant, or are
breast-feeding. You will need to talk about the benefits and risks to
you and the baby.

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 CHEMICAL STRUCTURES

Figure :

 The above chemical structure is for Cefoperazone.

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 2D - STRUCTURE

Figure:

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 3D - STURUCTURE

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 CHEMICAL FORMULA

 Molecular Formula: C25H26N9NaO8S2

 Molecular Weight : 667.7 g/mol

 IUPAC Name : (6R,7R)-7-[[(2R)-2-[(4-ethyl-2,3-dioxopiperazine-1-

carbonyl)amino]-2-(4-hydroxyphenyl)acetyl]amino]-3-[(1-
methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-
azabicyclo[4.2.0]oct-2-ene-2-carboxylate

SPECTRUM OF BACTERIAL SUSCEPTIBILITY

 Cefoperazone has a broad spectrum of activity and has been used to

target bacteria responsible for causing infections of the respiratory
and urinary tract, skin, and the female genital tract. The following
represents MIC susceptibility data for a few medically significant
microorganisms.
 Haemophilus influenzae: 0.12 - 0.25 µg/ml
 Staphylococcus aureus: 0.125 - 32 µg/ml
 Streptococcus pneumoniae: ≤0.007 - 1 µg/ml

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 USES OF CEFOPERAZONE
C
Ceeffo
oppeerraazzo
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off ffo
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ngg

Bone Diseases, Infectious

Escherichia coli Infections

Genital Diseases, Female

Haemophilus Infections

Klebsiella Infections

Pneumonia, Bacterial

Proteus Infections

Pseudomonas Infections

Salmonella Infections

Serratia Infections

Skin Diseases, Bacterial

Soft Tissue Infections

Staphylococcal Infections

Streptococcal Infections

Urinary Tract Infections

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 SIDE EFFECT OF CEFOPERAZONE

HYPERSENSITIVITY

A case of occupational contact dermatitis due to cephalosporin

allergy has been reported in a nurse who prepared cephalosporin
solutions for administration to patients. The dermatitis resolved after
the nurse stopped preparing the solutions.

Hypersensitivity reactions, often manifested as skin rashes, are

common with cefoperazone and may require drug discontinuation.
Drug fever and changes in Coombs' tests have also been reported.
Allergic cross-reactivity may occur in patients allergic to penicillin.
Cephalosporin class antibiotics have been associated with
anaphylaxis, stevens – Johnson syndrome, erothema multiforme, and
toxic epidermal necrolysis.

GASTROINTESTINAL
The frequent occurrence of diarrhea is thought to be due to the
disturbance of intestinal flora from high biliary concentrations of
cefoperazone. In a study evaluating the intestinal side effects of
cefoperazone, Clostridium difficulty was found in the stool of several
patients with diarrhea. In at least three of these cases no treatment
was necessary and symptoms resolved.

Gastrointestinal side effects have included nausea, vomiting and

diarrhea, the latter being the most frequent. Clostridium difficile has
been documented in some patients receiving cefoperazone.

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 HEPATIC
Hepatic side effects have included alterations in serum transaminases
and alkaline phosphatase in 5% to 10% of patients, but drug
discontinuation was usually not necessary. These changes are usually
mild and transient and return to normal following completion of
therapy. Cephalosporins as a class have been associated with hepatic
dysfunction including cholestasis.

HEMATOLOGIC
The effect of cefoperazone on hemostasis has been evaluated in at
least one study and reported in several cases. In most of these cases,
the patient had normal coagulation parameters, prothrombin time
and partial thromboplastin time prior to starting cefoperazone
therapy. Within several days to weeks, prolongation of prothrombin
time and partial thromboplastin time developed. Bleeding occurred
in some cases. Administration of vitamin K or fresh frozen plasma
corrected the changes in most of these patients. Cefoperazone was
continued in several patients.

Hematologic abnormalities have included eosinophilia, neutropenia,

decreases in hemoglobin and hematocrit, thrombocytopenia,
hypoprothrombinemia, and leukopenia. In most cases, these
alterations do not require drug discontinuation or dosage
reduction. Cephalosporins as a class have been associated
with aplastic anemia, hemolytic anemia, prolonged prothrombin
time, hemorrhage, neutropenia, pancytopenia, and agranulocytosis.

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 RENAL
Renal side effects have included transient elevations of BUN and
creatinine, and acute interstitial nephritis with renal failure.
Cephalosporins as a class have been associated with renal
dysfunction and toxic nephropathy.

LOCAL
Local side effects have included pain after intramuscular injection
and phlebitis after intravenous infusion.

DERMATOLOGIC
Dermatologic side effects associated with cephalosporin class
antibiotics have included rash, Stevens-Johnson syndrome, erythema
multiforme, and toxic epidermal necrolysis.

NERVOUS SYSTEM
Nervous system side effects associated with some cephalosporins
have included seizures in renally impaired patients.

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 IDENTIFIERS

CAS REGISTRY NUMBER

62893-19-0
LINK : https://www.commonchemistry.org/ChemicalDetail.aspx?ref=62893-19-0

PubChem REGISTRY NUMBER

44185
LINK : https://pubchem.ncbi.nlm.nih.gov/compound/44185

Drug Bank REGISTRY NUMBER

DB01329
LINK : https://www.drugbank.ca/drugs/DB01329

ChemSpider REGISTRY NUMBER

40206
LINK : http://www.chemspider.com/Chemical-Structure.40206.html

UNII REGISTRY NUMBER

7U75I1278D
LINK : https://fdasis.nlm.nih.gov/srs/unii/7U75I1278D

KEGG REGISTRY NUMBER

D07645
LINK : https://www.kegg.jp/entry/D07645

ChEMBL REGISTRY NUMBER

CHEMBL507674
LINK : https://www.ebi.ac.uk/chembl/compound_report_card/CHEMBL507674/

CompTox Dashboard ( EPA ) REGISTRY NUMBER

DTXSID2022759
LINK : https://comptox.epa.gov/dashboard/dsstoxdb/results?search=DTXSID2022759

ECHA Info Card – REGISTRY NUMBER

100.057.936
LINK : https://echa.europa.eu/substance-information/-/substanceinfo/100.057.936

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 CHEMICAL AND PHYSICAL PROPERTIES

PROPERTY NAME PROPERTY VALUE

Molecular Weight 667.7 g/mol

Hydrogen Bond Donor Count 3

Hydrogen Bond Acceptor Count 13

Rotatable Bond Count 9

Exact Mass 667.124345 g/mol

Monoisotopic Mass 667.124345 g/mol

Topological Polar Surface Area 274 Ų

Heavy Atom Count 45

Formal Charge 0

Complexity 1250

Isotope Atom Count 0

Defined Atom Stereocenter Count 3

Undefined Atom Stereocenter Count 0

Defined Bond Stereocenter Count 0

Undefined Bond Stereocenter Count 0

Covalently-Bonded Unit Count 2

Compound Is Canonicalized Yes

TABLE NO :

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 SAFETY AND HAZARDS

Pictogram(s)

Irritant Health Hazard

Signal Danger

Aggregated GHS information provided by 50 companies

from 3 notifications to the ECHA C&L Inventory. Each
notification may be associated with multiple
companies.
H317 (98%): May cause an allergic skin reaction
[Warning Sensitization, Skin]
H334 (96%): May cause allergy or asthma symptoms or
GHS Hazard
breathing difficulties if inhaled [Danger Sensitization,
Statements
respiratory]
Information may vary between notifications depending
on impurities, additives, and other factors. The
percentage value in parenthesis indicates the notified
classification ratio from companies that provide hazard
codes. Only hazard codes with percentage values above
10% are shown.

Precautionary P261, P272, P280, P285, P302+P352, P304+P341,

Statement P321, P333+P313, P342+P311, P363, and P501
Codes

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