Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C18H17N6O5S2.Na |
Molecular Weight | 484.485 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].[H][C@]12SCC(CSC3=NN=NN3C)=C(N1C(=O)[C@H]2NC(=O)[C@H](O)C4=CC=CC=C4)C([O-])=O
InChI
InChIKey=OJMNTWPPFNMOCJ-CFOLLTDRSA-M
InChI=1S/C18H18N6O5S2.Na/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);/q;+1/p-1/t11-,13-,16-;/m1./s1
Molecular Formula | Na |
Molecular Weight | 22.9898 |
Charge | 1 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | C18H17N6O5S2 |
Molecular Weight | 461.495 |
Charge | -1 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
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
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2354204 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3266730 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | MANDOL Approved UseUnknown Launch Date2.75702415E11 |
|||
Curative | MANDOL Approved UseUnknown Launch Date2.75702415E11 |
|||
Curative | MANDOL Approved UseUnknown Launch Date2.75702415E11 |
|||
Curative | MANDOL Approved UseUnknown Launch Date2.75702415E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
113 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/671221/ |
15 mg single, intravenous dose: 15 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
CEFAMANDOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
5934 μg × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/671221/ |
15 mg single, intravenous dose: 15 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
CEFAMANDOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
23.64 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/671221/ |
15 mg single, intravenous dose: 15 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
CEFAMANDOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
5.1 g 1 times / day multiple, intravenous Dose: 5.1 g, 1 times / day Route: intravenous Route: multiple Dose: 5.1 g, 1 times / day Sources: |
unhealthy, 43 - 58 years n = 2 Health Status: unhealthy Age Group: 43 - 58 years Sex: F Population Size: 2 Sources: |
Disc. AE: Hypoprothrombinemia... AEs leading to discontinuation/dose reduction: Hypoprothrombinemia (2 patients) Sources: |
2 g 6 times / day multiple, intravenous Highest studied dose Dose: 2 g, 6 times / day Route: intravenous Route: multiple Dose: 2 g, 6 times / day Sources: |
unhealthy n = 20 |
Other AEs: Glutamic-oxaloacetic transaminase increased, Lactic dehydrogenase increased... Other AEs: Glutamic-oxaloacetic transaminase increased (20%) Sources: Lactic dehydrogenase increased (20%) Alkaline phosphatase increased (20%) |
1 g single, intramuscular |
unhealthy n = 24 Health Status: unhealthy Condition: renal impairment Sex: M Population Size: 24 Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Hypoprothrombinemia | 2 patients Disc. AE |
5.1 g 1 times / day multiple, intravenous Dose: 5.1 g, 1 times / day Route: intravenous Route: multiple Dose: 5.1 g, 1 times / day Sources: |
unhealthy, 43 - 58 years n = 2 Health Status: unhealthy Age Group: 43 - 58 years Sex: F Population Size: 2 Sources: |
Alkaline phosphatase increased | 20% | 2 g 6 times / day multiple, intravenous Highest studied dose Dose: 2 g, 6 times / day Route: intravenous Route: multiple Dose: 2 g, 6 times / day Sources: |
unhealthy n = 20 |
Glutamic-oxaloacetic transaminase increased | 20% | 2 g 6 times / day multiple, intravenous Highest studied dose Dose: 2 g, 6 times / day Route: intravenous Route: multiple Dose: 2 g, 6 times / day Sources: |
unhealthy n = 20 |
Lactic dehydrogenase increased | 20% | 2 g 6 times / day multiple, intravenous Highest studied dose Dose: 2 g, 6 times / day Route: intravenous Route: multiple Dose: 2 g, 6 times / day Sources: |
unhealthy n = 20 |
PubMed
Title | Date | PubMed |
---|---|---|
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 |
|
Occurrence and antibiotic resistance of mesophilic Aeromonas in three riverine freshwaters of Marrakech, Morocco. | 2001 Dec 1 |
|
[Characterization of cefoperazone resistance gene on plasmid pFC in E. coli HX88108]. | 2001 Mar |
|
Antibiotic prophylaxis in orthopedic prosthetic surgery. | 2001 Nov |
|
Serotypes, virulence factors, antibiotic sensitivity, beta-lactamase activity and plasmid analysis of Salmonella from children with diarrhea in Tripoli (Libya). | 2002 |
|
Cross-reactivity of cefotetan and ceftriaxone antibodies, associated with hemolytic anemia, with other: cephalosporins and penicillin. | 2002 Aug |
|
Surgical prophylaxis in practice. | 2002 Jan |
|
Review of the use of cephalosporins in children with anaphylactic reactions from penicillins. | 2002 Jul |
|
Penetration of linezolid into bone, fat, muscle and haematoma of patients undergoing routine hip replacement. | 2002 Jul |
|
Practical aspects of choosing an antibiotic for patients with a reported allergy to an antibiotic. | 2002 Jul 1 |
|
Modified antimicrobial disc susceptibility testing for nutritionally-variant streptococci. | 2002 Mar |
|
Comparison of screening methods for TEM- and SHV-derived extended-spectrum beta-lactamase detection. | 2002 Nov |
|
Kinetics of cefamandole nafate degradation in solid phase. | 2003 Apr |
|
Formation of Propionibacterium acnes biofilms on orthopaedic biomaterials and their susceptibility to antimicrobials. | 2003 Aug |
|
Vibrio vulnificus in Taiwan. | 2004 Aug |
|
Polyurethanes loaded with antibiotics: influence of polymer-antibiotic interactions on in vitro activity against Staphylococcus epidermidis. | 2004 Oct |
|
Voltammetric analysis of Cu (II), Cd (II) and Zn (II) complexes and their cyclic voltammetry with several cephalosporin antibiotics. | 2005 Feb |
|
Acute ST-segment elevation myocardial infarction after amoxycillin-induced anaphylactic shock in a young adult with normal coronary arteries: a case report. | 2005 Feb 25 |
|
Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. | 2005 Jan |
|
Antibiotic resistance in exopolysaccharide-forming Staphylococcus epidermidis clinical isolates from orthopaedic implant infections. | 2005 Nov |
|
Systemic and local antibiotic prophylaxis in the prevention of Staphylococcus epidermidis graft infection. | 2005 Oct 21 |
|
Nosocomial bloodstream infections caused by Klebsiella pneumoniae: impact of extended-spectrum beta-lactamase (ESBL) production on clinical outcome in a hospital with high ESBL prevalence. | 2006 Feb 14 |
|
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 |
|
Safe use of selected cephalosporins in penicillin-allergic patients: a meta-analysis. | 2007 Mar |
|
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 |
|
[Regional lymphotropic antibiotic therapy as a part of comprehensive treatment of children with purulent-inflammatory diseases of maxillofacial region]. | 2008 |
|
Involvement of multidrug resistance-associated protein 2 (Abcc2) in molecular weight-dependent biliary excretion of beta-lactam antibiotics. | 2008 Jun |
|
Translocation of bacterial NOD2 agonist and its link with inflammation. | 2009 |
|
Detection of Extended Spectrum β-lactamase Production Among Uropathogens. | 2009 Jan |
|
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 |
|
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 |
|
Impact of the RNA chaperone Hfq on multidrug resistance in Escherichia coli. | 2010 May |
|
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 |
Sample Use Guides
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:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2695512
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
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Record UNII |
IY6234ODVR
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Record Version |
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C357
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