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

Details

Stereochemistry ABSOLUTE
Molecular Formula C18H18N6O5S2
Molecular Weight 462.503
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CEFAMANDOLE

SMILES

CN1N=NN=C1SCC2=C(N3[C@H](SC2)[C@H](NC(=O)[C@H](O)C4=CC=CC=C4)C3=O)C(O)=O

InChI

InChIKey=OLVCFLKTBJRLHI-AXAPSJFSSA-N
InChI=1S/C18H18N6O5S2/c1-23-18(20-21-22-23)31-8-10-7-30-16-11(15(27)24(16)12(10)17(28)29)19-14(26)13(25)9-5-3-2-4-6-9/h2-6,11,13,16,25H,7-8H2,1H3,(H,19,26)(H,28,29)/t11-,13-,16-/m1/s1

HIDE SMILES / InChI

Molecular Formula C18H18N6O5S2
Molecular Weight 462.503
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Cefamandole (also known as cephamandole) is a broad-spectrum cephalosporin antibiotic. The clinically used form of cefamandole is an ester form, cefamandole nafate, a prodrug. Cefamandole is no longer available in USA, but it has prescription in UK. Cefamandole under brand name mandol is indicated for the treatment of serious infections caused by susceptible strains of the designated microorganisms such as: lower respiratory infections, including pneumonia, caused by S. pneumoniae. So as urinary tract infections caused by E. coli, Proteus spp.; peritonitis caused by E. coli and Enterobacter spp. Septicemia caused by E. coli; skin and skin structure infections caused by S. aureus; bone and joint infections caused by S. aureus (penicillinase- and non-penicillinase-producing). Like all beta-lactam antibiotics, cefamandole binds to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, causing the inhibition of the third and last stage of bacterial cell wall synthesis. Bacterial cell wall autolytic enzymes such as autolysins then mediate cell lysis; it is possible that cefamandole interferes with an autolysin inhibitor.

Approval Year

PubMed

PubMed

TitleDatePubMed
Comparative incidence of phlebitis due to buffered cephalothin, cephapirin, and cefamandole.
1976 Apr
Comparison of thrombophlebitis associated with three cephalosporin antibiotics.
1976 Sep
[Experimental studies in animals on the nephrotoxicity of some new cephalosporin antibiotics: cefamandole, EMD 29 645, and 29 946 (author's transl)].
1980
Cefamandole for treatment of obstetrical and gynecological infections.
1980
Acute tubular necrosis following high-dose cefamandole therapy for Hemophilus parainfluenzae endocarditis.
1981 May-Jun
Empiric therapy for infections in patients with granulocytopenia. Continuous v interrupted infusion of tobramycin plus cefamandole.
1984 May
Extravascular hemolysis following the administration of cefamandole.
1985 Feb
Determination of in vitro susceptibility of Mycobacterium tuberculosis to cephalosporins by radiometric and conventional methods.
1985 Jan
Determination of MICs of conventional and experimental drugs in liquid medium by the radiometric method against Mycobacterium avium complex.
1987
In-vitro activity of seventeen antimicrobial compounds against seven species of mycobacteria.
1988 Dec
Acute renal failure due to cephamandole.
1988 Feb 6
The in vitro activity of beta-lactamase inhibitors in combination with cephalosporins against M. tuberculosis.
1995 Apr
Review of the use of cephalosporins in children with anaphylactic reactions from penicillins.
2002 Jul
Antimicrobial therapy for acute cholangitis: Tokyo Guidelines.
2007
[Primary peritonitis in Sub-Saharian Africa: a 15 case series].
2007 Apr
Enzymatic synthesis of cephalosporins. The immobilized acylase from Arthrobacter viscosus: a new useful biocatalyst.
2007 Dec
Use of selected cephalosporins in penicillin-allergic patients: a paradigm shift.
2007 Mar
Safe use of selected cephalosporins in penicillin-allergic patients: a meta-analysis.
2007 Mar
Inhaled tobramycin solution-associated recurrent eosinophilia and severe persistent bronchospasm in a patient with cystic fibrosis: a case report.
2007 Mar 2
Estimation of the two sample preparation techniques for infrared spectroscopic identification of Cefamandole nafate in solid state.
2007 Sep
New active site oriented glyoxyl-agarose derivatives of Escherichia coli penicillin G acylase.
2007 Sep 10
Superficial and deep sternal wound infection after more than 9000 coronary artery bypass graft (CABG): incidence, risk factors and mortality.
2007 Sep 23
Pharmacodynamic optimization of beta-lactams in the patient care setting.
2008
[Regional lymphotropic antibiotic therapy as a part of comprehensive treatment of children with purulent-inflammatory diseases of maxillofacial region].
2008
Semiparametric mixed-effects analysis of PK/PD models using differential equations.
2008 Aug
Should we change antibiotic prophylaxis for lung surgery? Postoperative pneumonia is the critical issue.
2008 Dec
Involvement of multidrug resistance-associated protein 2 (Abcc2) in molecular weight-dependent biliary excretion of beta-lactam antibiotics.
2008 Jun
The occurrence of osteoarthritis at a minimum of ten years after reconstruction of the anterior cruciate ligament.
2008 Jun 10
Spectrophotometeric Determination of Cefuroxime Axetil from bulk and in its tablet dosage form.
2008 Mar-Apr
Efficacy of collagen silver-coated polyester and rifampin-soaked vascular grafts to resist infection from MRSA and Escherichia coli in a dog model.
2008 Nov
Determination of cephalosporins in solid binary mixtures by polarized IR- and Raman spectroscopy.
2008 Sep 10
Rapid nanoparticle-mediated monitoring of bacterial metabolic activity and assessment of antimicrobial susceptibility in blood with magnetic relaxation.
2008 Sep 23
Translocation of bacterial NOD2 agonist and its link with inflammation.
2009
Suspected anaphylactic reactions associated with anaesthesia.
2009 Feb
A case of multidrug-resistant Salmonella enterica serovar Typhi treated with a bench to bedside approach.
2009 Feb 28
Detection of Extended Spectrum β-lactamase Production Among Uropathogens.
2009 Jan
Prevalence and molecular characterization of extended-spectrum beta-lactamase-producing Klebsiella pneumoniae in Riyadh, Saudi Arabia.
2009 Jul-Aug
Data correction pre-processing for electronically stored blood culture results: implications on microbial spectrum and empiric antibiotic therapy.
2009 Jun 7
Antibiotic delivery polyurethanes containing albumin and polyallylamine nanoparticles.
2009 Mar 2
Antibiotic prophylaxis for lung surgery: bronchial colonization is the critical issue?
2009 Sep
Differential down-regulation of HLA-DR on monocyte subpopulations during systemic inflammation.
2010
Synergy of fosfomycin with other antibiotics for Gram-positive and Gram-negative bacteria.
2010 Apr
Single-dose versus multiple-dose antibiotic prophylaxis for the surgical treatment of closed fractures.
2010 Apr
Sequencing and genetic variation of multidrug resistance plasmids in Klebsiella pneumoniae.
2010 Apr 12
Selective decontamination of the gastrointestinal tract in patients undergoing esophageal resection.
2010 Dec 16
Prevalence and risk factors for extended spectrum Beta-lactamase-producing uropathogens in patients with urinary tract infection.
2010 Jul
Impact of the RNA chaperone Hfq on multidrug resistance in Escherichia coli.
2010 May
Differentiation between probiotic and wild-type Bacillus cereus isolates by antibiotic susceptibility test and Fourier transform infrared spectroscopy (FT-IR).
2010 May 30
Structures of the Michaelis complex (1.2 Å) and the covalent acyl intermediate (2.0 Å) of cefamandole bound in the active sites of the Mycobacterium tuberculosis β-lactamase K73A and E166A mutants.
2010 Nov 16
Molecular and evolutionary bases of within-patient genotypic and phenotypic diversity in Escherichia coli extraintestinal infections.
2010 Sep 30
Patents

Sample Use Guides

In Vivo Use Guide
The usual dosage range for cefamandol (cefamandole) is 500 mg to 1 g every 4 to 8 hours. In infections of skin structures and in uncomplicated pneumonia, a dosage of 500 mg every 6 hours is adequate. In uncomplicated urinary tract infections, a dosage of 500 mg every 8 hours is sufficient. In more serious urinary tract infections, a dosage of 1 g every 8 hours may be needed. In severe infections, 1-g doses may be given at 4 to 6-hour intervals. In life-threatening infections or infections due to less susceptible organisms, doses up to 2 g every 4 hours (ie, 12 g/day) may be needed. Infants and Children: administration of 50 to 100 mg/kg/ day in equally divided doses every 4 to 8 hours has been effective for most infections susceptible to Mandol (cefamandole). This may be increased to a total daily dose of 150 mg/kg (not to exceed the maximum adult dose) for severe infections.
Route of Administration: intravenous; intramuscular
In Vitro Use Guide
The intracellular activity of cefamandole against phagocytosed Staphylococcus aureus was studied using a sensitive and standardized method of murine peritoneal macrophages. Cefamandole exerted an intracellular antibacterial activity against E. coli which was greater than their extracellular one. With concentrations of antibiotic up to 16 x MBC a dose-dependent decrease of the initial number of intracellular E. coli which ranged from 32% to 90% was observed. However, similar antibiotic concentrations above the MBC affected the viability of extracellular E. coli by only 20% to 30%. The intracellular antibacterial activity of antibiotic against E. coli was further enhanced by immune serum. Cefamandole at 4 x the MBC did not affect the survival of intracellular S. aureus, but killed 41% of extracellular bacteria by 1 h and 99% after 3 h. The data suggest that cefamandole possesses an intracellular antibacterial activity against E. coli that seems at least in part due to a positive cooperation of antibiotic with the O2-independent microbicidal system of macrophages.
Substance Class Chemical
Created
by admin
on Mon Oct 21 19:50:46 UTC 2019
Edited
by admin
on Mon Oct 21 19:50:46 UTC 2019
Record UNII
5CKP8C2LLI
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CEFAMANDOLE
INN   MART.   MI   USAN   VANDF   WHO-DD  
USAN   INN  
Official Name English
CEFAMANDOLE [WHO-DD]
Common Name English
CEFAMANDOLE [INN]
Common Name English
COMPOUND-83405
Code English
7-D-MANDELAMIDO-3-(((1-METHYL-1H-TETRAZOL-5-YL)THIO)METHYL)-3-CEPHEM-4-CARBOXYLIC ACID
Common Name English
CEFAMANDOLE [MI]
Common Name English
5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 7-((HYDROXYPHENYLACETYL)AMINO)-3-(((1-METHYL-1H-TETRAZOL-5-YL)THIO)METHYL)-8-OXO-, (6R-(6.ALPHA.,7.BETA.(R*)))-
Common Name English
CEFAMANDOLE [VANDF]
Common Name English
CEFAMANDOLE [USAN]
Common Name English
(6R,7R)-7-(R)-MANDELAMIDO-3-(((1-METHYL-1H-TETRAZOL-5-YL)THIO)METHYL)-8-OXO-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-CARBOXYLIC ACID
Common Name English
CEFAMANDOLE [MART.]
Common Name English
J01DC03
Code English
COMPOUND 83405
Code English
Classification Tree Code System Code
WHO-ATC J01DC03
Created by admin on Mon Oct 21 19:50:46 UTC 2019 , Edited by admin on Mon Oct 21 19:50:46 UTC 2019
NCI_THESAURUS C357
Created by admin on Mon Oct 21 19:50:46 UTC 2019 , Edited by admin on Mon Oct 21 19:50:46 UTC 2019
WHO-VATC QJ01DC03
Created by admin on Mon Oct 21 19:50:46 UTC 2019 , Edited by admin on Mon Oct 21 19:50:46 UTC 2019
Code System Code Type Description
NCI_THESAURUS
C353
Created by admin on Mon Oct 21 19:50:46 UTC 2019 , Edited by admin on Mon Oct 21 19:50:46 UTC 2019
PRIMARY
INN
3329
Created by admin on Mon Oct 21 19:50:46 UTC 2019 , Edited by admin on Mon Oct 21 19:50:46 UTC 2019
PRIMARY
WIKIPEDIA
CEFAMANDOLE
Created by admin on Mon Oct 21 19:50:46 UTC 2019 , Edited by admin on Mon Oct 21 19:50:46 UTC 2019
PRIMARY
CAS
34444-01-4
Created by admin on Mon Oct 21 19:50:46 UTC 2019 , Edited by admin on Mon Oct 21 19:50:46 UTC 2019
PRIMARY
MESH
D002435
Created by admin on Mon Oct 21 19:50:46 UTC 2019 , Edited by admin on Mon Oct 21 19:50:46 UTC 2019
PRIMARY
RXCUI
2178
Created by admin on Mon Oct 21 19:50:46 UTC 2019 , Edited by admin on Mon Oct 21 19:50:46 UTC 2019
PRIMARY RxNorm
MERCK INDEX
M3186
Created by admin on Mon Oct 21 19:50:46 UTC 2019 , Edited by admin on Mon Oct 21 19:50:46 UTC 2019
PRIMARY Merck Index
ChEMBL
CHEMBL1146
Created by admin on Mon Oct 21 19:50:46 UTC 2019 , Edited by admin on Mon Oct 21 19:50:46 UTC 2019
PRIMARY
EPA CompTox
34444-01-4
Created by admin on Mon Oct 21 19:50:46 UTC 2019 , Edited by admin on Mon Oct 21 19:50:46 UTC 2019
PRIMARY
DRUG BANK
DB01326
Created by admin on Mon Oct 21 19:50:46 UTC 2019 , Edited by admin on Mon Oct 21 19:50:46 UTC 2019
PRIMARY
ECHA (EC/EINECS)
252-030-0
Created by admin on Mon Oct 21 19:50:46 UTC 2019 , Edited by admin on Mon Oct 21 19:50:46 UTC 2019
PRIMARY
EVMPD
SUB07373MIG
Created by admin on Mon Oct 21 19:50:46 UTC 2019 , Edited by admin on Mon Oct 21 19:50:46 UTC 2019
PRIMARY
PUBCHEM
456255
Created by admin on Mon Oct 21 19:50:46 UTC 2019 , Edited by admin on Mon Oct 21 19:50:46 UTC 2019
PRIMARY
Related Record Type Details
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
SALT/SOLVATE -> PARENT
TRANSPORTER -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY