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

Details

Stereochemistry ABSOLUTE
Molecular Formula C14H14N8O4S3
Molecular Weight 454.507
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CEFAZOLIN

SMILES

CC1=NN=C(SCC2=C(N3[C@H](SC2)[C@H](NC(=O)CN4C=NN=N4)C3=O)C(O)=O)S1

InChI

InChIKey=MLYYVTUWGNIJIB-BXKDBHETSA-N
InChI=1S/C14H14N8O4S3/c1-6-17-18-14(29-6)28-4-7-3-27-12-9(11(24)22(12)10(7)13(25)26)16-8(23)2-21-5-15-19-20-21/h5,9,12H,2-4H2,1H3,(H,16,23)(H,25,26)/t9-,12-/m1/s1

HIDE SMILES / InChI

Molecular Formula C14H14N8O4S3
Molecular Weight 454.507
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Cefazolin is a semisynthetic cephalosporin analog with broad-spectrum antibiotic action due to inhibition of bacterial cell wall synthesis. By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, cefazolin inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins. Cefazolin is used to treat bacterial infections of the skin, moderately severe bacterial infections involving the lung, bone, joint, stomach, blood, and urinary tract. It is clinically effective against infections caused by staphylococci and streptococci species of Gram positive bacteria. This drug also can be used for perioperative prophylaxis.

CNS Activity

Approval Year

PubMed

PubMed

TitleDatePubMed
Relationship between the transport and toxicity of cephalosporins in the kidney.
1975 Aug
Double-blind comparison of phlebitis associated with cefazolin and cephalothin.
1976 Jul
Hemolysis induced by cefazolin and cephalothin in a patient with penicillin sensitivity.
1978 May-Jun
IgE antibodies for penicillins and cephalosporins in rats. III. Antigenic specificity of rat anti-cephalosporin-OvA IgE sera.
1981 Jan
Combination of amikacin and carbenicillin with or without cefazolin as empirical treatment of febrile neutropenic patients. The International Antimicrobial Therapy Project Group of the European Organization for Research and Treatment of Cancer.
1983 Oct
[Nephrotoxicity of cefodizime sodium in rats--single and 14-day repeated intravenous administration].
1988 Jun
Drugs as allergens: an immunoassay for detecting IgE antibodies to cephalosporins.
1990
Low convulsive activity of a new carbapenem antibiotic, DK-35C, as compared with existing congeners.
1999 Nov 5
Amykacin-related apneic episode in an infant on peritoneal dialysis.
2000 Apr
Antibacterials for the prophylaxis and treatment of bacterial endocarditis in children.
2001
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.
2001 Nov
beta-Lactam allergenic determinants: fine structural recognition of a cross-reacting determinant on benzylpenicillin and cephalothin.
2002 Nov
The vitro efficacy of beta-lactam and beta-lactamase inhibitors against multidrug resistant clinical strains of Mycobacterium tuberculosis.
2004 Apr
Antitumor activity of common antibiotics against superficial bladder cancer.
2004 Mar
In situ investigation of drug diffusion in hydrogels by the refractive index method.
2004 May 15
Efficacy of a non-vancomycin-based peritoneal dialysis peritonitis protocol.
2005 Apr
Effect of isoniazid on the pharmacodynamics of cefazolin-induced seizures in rats.
2005 Apr
Human organic anion transporter hOAT3 is a potent transporter of cephalosporin antibiotics, in comparison with hOAT1.
2005 Oct 1
Attenuation of ischemia-reperfusion injury by ascorbic acid in the canine renal transplantation.
2006 Dec
Chemiluminescence flow-injection analysis of beta-lactam antibiotics using the luminol-permanganate reaction.
2006 Jul-Aug
Infective endocarditis with an aortic periannular abscess extending along the right coronary artery.
2006 Jun
Novel purification strategy for human PON1 and inhibition of the activity by cephalosporin and aminoglikozide derived antibiotics.
2006 May
Epileptogenic activity of methicillin-resistant Staphylococcus aureus (MRSA) antibiotics in rats.
2006 Oct
Stability of cefazolin sodium in four heparinized and non-heparinized dialysate solutions at 38 degrees C.
2006 Sep-Oct
[Simultaneous spectrophotometric determination of certain beta-lactam antibiotics in rabbit serum using multivariate calibration methods].
2007 Feb
Interaction of beta-lactam antibiotics with the mitochondrial carnitine/acylcarnitine transporter.
2008 Jun 17
An intractable case of Pseudomonas aeruginosa infection after scleral buckling for rhegmatogenous retinal detachment.
2008 Mar
Cefazolin-induced hypoprothrombinemia.
2008 May 1
Kinetic spectrophotometric determination of certain cephalosporins in pharmaceutical formulations.
2009
[Antibiotic susceptibility of pathogenic bacteria isolated from 893 children with lower respiratory infection in Guiyang].
2009 Dec
Kinetic spectrofluorimetric determination of certain cephalosporins in human plasma.
2009 Feb 15
Laser-induced silver nanoparticles on titanium oxide for photocatalytic degradation of methylene blue.
2009 Oct 29
Ectopic intrauterine device in the bladder of a pregnant woman.
2010
Histological characteristics of newly formed cementum in surgically created one-wall intrabony defects in a canine model.
2010 Feb
Sensitive chemiluminescence determination of thirteen cephalosporin antibiotics with luminol-copper(II) reaction.
2010 Oct
Stability of fortified cefazolin ophthalmic solutions prepared in artificial tears containing surfactant-based versus oxidant-based preservatives.
2010 Oct
Investigation of the effects of some drugs and phenolic compounds on human dihydrofolate reductase activity.
2015 Mar
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis.
2015 May 18
Patents

Sample Use Guides

In Vivo Use Guide
Moderate to severe infections: 500 mg to 1 gram, every 6 to 8 hours; mild infections caused by susceptible gram-positive cocci: 250 mg to 500 mg, every 8 hours; acute, uncomplicated urinary tract infections: 1 gram, every 12 hours; Pneumococcal pneumonia: 500 mg, every 12 hours; Severe, life threatening infections (e.g., endocarditis, septicemia): 1 gram to 1.5 grams, every 6 hours
Route of Administration: intramuscular; intravenous
In Vitro Use Guide
Susceptibilities of 259 isolates of pathogenic bacteria to cefazolin were measured by broth and agar dilution procedures. Beta-hemolytic streptococci were inhibited by 0.25 mug/ml, whereas Staphylococcus aureus and alphahemolytic streptococci were inhibited by 2.0 mug/ml. Enterococci were resistant to less than 32 mug/ml. Wide variation was seen with gram-negative species. Most isolates of Klebsiella species and Proteus mirabilis were inhibited by 4.0 or 8.0 mug/ml. Escherichia coli were less susceptible, and most isolates of Pseudomonas aeruginosa, Serratia species, and Enterobacter species were resistant to 128 mug/ml.
Substance Class Chemical
Created
by admin
on Mon Oct 21 19:50:42 UTC 2019
Edited
by admin
on Mon Oct 21 19:50:42 UTC 2019
Record UNII
IHS69L0Y4T
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CEFAZOLIN
HSDB   INN   MART.   MI   USP   USP-RS   VANDF   WHO-DD  
INN  
Official Name English
CEFAZOLIN [MI]
Common Name English
CEFAZOLIN [INN]
Common Name English
CEFAZOLIN [WHO-DD]
Common Name English
(6R,7R)-3-(((5-METHYL-1,3,4-THIADIAZOL-2-YL)THIO)METHYL)-8-OXO-7-(2-(1H-TETRAZOL-1-YL)ACETAMIDO)5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID
Systematic Name English
5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 3-(((5-METHYL-1,3,4-THIADIAZOL-2-YL)THIO)METHYL)-8-OXO-7-(((1H-TETRAZOL-1-YL)ACETYL)AMINO)-(6R-TRANS)
Common Name English
J01DB04
Code English
CEFAZOLIN [VANDF]
Common Name English
CEFAZOLIN [HSDB]
Common Name English
CEFAZOLIN [MART.]
Common Name English
CEFAZOLIN [USP-RS]
Common Name English
CEFAZOLIN [USP]
Common Name English
Classification Tree Code System Code
NDF-RT N0000011161
Created by admin on Mon Oct 21 19:50:42 UTC 2019 , Edited by admin on Mon Oct 21 19:50:42 UTC 2019
NDF-RT N0000011161
Created by admin on Mon Oct 21 19:50:42 UTC 2019 , Edited by admin on Mon Oct 21 19:50:42 UTC 2019
NDF-RT N0000011161
Created by admin on Mon Oct 21 19:50:42 UTC 2019 , Edited by admin on Mon Oct 21 19:50:42 UTC 2019
NDF-RT N0000011161
Created by admin on Mon Oct 21 19:50:42 UTC 2019 , Edited by admin on Mon Oct 21 19:50:42 UTC 2019
NDF-RT N0000011161
Created by admin on Mon Oct 21 19:50:42 UTC 2019 , Edited by admin on Mon Oct 21 19:50:42 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 6.2.1
Created by admin on Mon Oct 21 19:50:42 UTC 2019 , Edited by admin on Mon Oct 21 19:50:42 UTC 2019
NDF-RT N0000011161
Created by admin on Mon Oct 21 19:50:42 UTC 2019 , Edited by admin on Mon Oct 21 19:50:42 UTC 2019
WHO-ATC J01DB04
Created by admin on Mon Oct 21 19:50:42 UTC 2019 , Edited by admin on Mon Oct 21 19:50:42 UTC 2019
NDF-RT N0000011161
Created by admin on Mon Oct 21 19:50:42 UTC 2019 , Edited by admin on Mon Oct 21 19:50:42 UTC 2019
NCI_THESAURUS C357
Created by admin on Mon Oct 21 19:50:42 UTC 2019 , Edited by admin on Mon Oct 21 19:50:42 UTC 2019
NDF-RT N0000175488
Created by admin on Mon Oct 21 19:50:42 UTC 2019 , Edited by admin on Mon Oct 21 19:50:42 UTC 2019
NDF-RT N0000011161
Created by admin on Mon Oct 21 19:50:42 UTC 2019 , Edited by admin on Mon Oct 21 19:50:42 UTC 2019
NDF-RT N0000011161
Created by admin on Mon Oct 21 19:50:42 UTC 2019 , Edited by admin on Mon Oct 21 19:50:42 UTC 2019
LIVERTOX 160
Created by admin on Mon Oct 21 19:50:42 UTC 2019 , Edited by admin on Mon Oct 21 19:50:42 UTC 2019
WHO-VATC QJ51DB04
Created by admin on Mon Oct 21 19:50:42 UTC 2019 , Edited by admin on Mon Oct 21 19:50:42 UTC 2019
NDF-RT N0000011161
Created by admin on Mon Oct 21 19:50:42 UTC 2019 , Edited by admin on Mon Oct 21 19:50:42 UTC 2019
NDF-RT N0000011161
Created by admin on Mon Oct 21 19:50:42 UTC 2019 , Edited by admin on Mon Oct 21 19:50:42 UTC 2019
NDF-RT N0000011161
Created by admin on Mon Oct 21 19:50:42 UTC 2019 , Edited by admin on Mon Oct 21 19:50:42 UTC 2019
WHO-VATC QJ01DB04
Created by admin on Mon Oct 21 19:50:42 UTC 2019 , Edited by admin on Mon Oct 21 19:50:42 UTC 2019
Code System Code Type Description
ChEMBL
CHEMBL1435
Created by admin on Mon Oct 21 19:50:42 UTC 2019 , Edited by admin on Mon Oct 21 19:50:42 UTC 2019
PRIMARY
NCI_THESAURUS
C28913
Created by admin on Mon Oct 21 19:50:42 UTC 2019 , Edited by admin on Mon Oct 21 19:50:42 UTC 2019
PRIMARY
WIKIPEDIA
CEFAZOLIN
Created by admin on Mon Oct 21 19:50:42 UTC 2019 , Edited by admin on Mon Oct 21 19:50:42 UTC 2019
PRIMARY
PUBCHEM
33255
Created by admin on Mon Oct 21 19:50:42 UTC 2019 , Edited by admin on Mon Oct 21 19:50:42 UTC 2019
PRIMARY
RXCUI
2180
Created by admin on Mon Oct 21 19:50:42 UTC 2019 , Edited by admin on Mon Oct 21 19:50:42 UTC 2019
PRIMARY RxNorm
MESH
D002437
Created by admin on Mon Oct 21 19:50:42 UTC 2019 , Edited by admin on Mon Oct 21 19:50:42 UTC 2019
PRIMARY
ECHA (EC/EINECS)
247-362-8
Created by admin on Mon Oct 21 19:50:42 UTC 2019 , Edited by admin on Mon Oct 21 19:50:42 UTC 2019
PRIMARY
EPA CompTox
25953-19-9
Created by admin on Mon Oct 21 19:50:42 UTC 2019 , Edited by admin on Mon Oct 21 19:50:42 UTC 2019
PRIMARY
CAS
25953-19-9
Created by admin on Mon Oct 21 19:50:42 UTC 2019 , Edited by admin on Mon Oct 21 19:50:42 UTC 2019
PRIMARY
EVMPD
SUB07379MIG
Created by admin on Mon Oct 21 19:50:42 UTC 2019 , Edited by admin on Mon Oct 21 19:50:42 UTC 2019
PRIMARY
DRUG BANK
DB01327
Created by admin on Mon Oct 21 19:50:42 UTC 2019 , Edited by admin on Mon Oct 21 19:50:42 UTC 2019
PRIMARY
INN
2991
Created by admin on Mon Oct 21 19:50:42 UTC 2019 , Edited by admin on Mon Oct 21 19:50:42 UTC 2019
PRIMARY
MERCK INDEX
M3188
Created by admin on Mon Oct 21 19:50:42 UTC 2019 , Edited by admin on Mon Oct 21 19:50:42 UTC 2019
PRIMARY Merck Index
HSDB
25953-19-9
Created by admin on Mon Oct 21 19:50:42 UTC 2019 , Edited by admin on Mon Oct 21 19:50:42 UTC 2019
PRIMARY
LactMed
25953-19-9
Created by admin on Mon Oct 21 19:50:42 UTC 2019 , Edited by admin on Mon Oct 21 19:50:42 UTC 2019
PRIMARY
Related Record Type Details
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
SALT/SOLVATE -> PARENT
TRANSPORTER -> INHIBITOR
BINDER->LIGAND
BINDING
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC