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
SMILES
[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=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
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 |
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Target ID: CHEMBL2354204 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3266730 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Curative | MANDOL Approved UseUnknown Launch Date1978 |
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Curative | MANDOL Approved UseUnknown Launch Date1978 |
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Curative | MANDOL Approved UseUnknown Launch Date1978 |
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Curative | MANDOL Approved UseUnknown Launch Date1978 |
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 |
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Comparison of thrombophlebitis associated with three cephalosporin antibiotics. | 1976 Sep |
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Extravascular hemolysis following the administration of cefamandole. | 1985 Feb |
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Determination of in vitro susceptibility of Mycobacterium tuberculosis to cephalosporins by radiometric and conventional methods. | 1985 Jan |
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Determination of MICs of conventional and experimental drugs in liquid medium by the radiometric method against Mycobacterium avium complex. | 1987 |
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In-vitro activity of seventeen antimicrobial compounds against seven species of mycobacteria. | 1988 Dec |
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Acute renal failure due to cephamandole. | 1988 Feb 6 |
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The in vitro activity of beta-lactamase inhibitors in combination with cephalosporins against M. tuberculosis. | 1995 Apr |
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The penetration of ceftriaxone and cefamandole into bone, fat and haematoma and relevance of serum protein binding to their penetration into bone. | 2001 Apr |
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[Infectious complications of mandibular osteotomy]. | 2001 Feb |
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Incidence and risk factors of bacteriuria after transurethral resection of the prostate. | 2001 Mar |
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Antibiotic prophylaxis in orthopedic prosthetic surgery. | 2001 Nov |
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Cephalosporins in surgical prophylaxis. | 2001 Nov |
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Serotypes, virulence factors, antibiotic sensitivity, beta-lactamase activity and plasmid analysis of Salmonella from children with diarrhea in Tripoli (Libya). | 2002 |
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Surgical prophylaxis in practice. | 2002 Jan |
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Modified antimicrobial disc susceptibility testing for nutritionally-variant streptococci. | 2002 Mar |
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Interaction of human and rat organic anion transporter 2 with various cephalosporin antibiotics. | 2003 Mar 28 |
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Polyurethanes loaded with antibiotics: influence of polymer-antibiotic interactions on in vitro activity against Staphylococcus epidermidis. | 2004 Oct |
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Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. | 2005 Jan |
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IgA pemphigus--occurrence of anti-desmocollin 1 and anti-desmoglein 1 antibody reactivity in an individual patient. | 2006 Dec |
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Ameba-associated microorganisms and diagnosis of nosocomial pneumonia. | 2006 Feb |
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Semiparametric mixed-effects analysis of PK/PD models using differential equations. | 2008 Aug |
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Spectrophotometeric Determination of Cefuroxime Axetil from bulk and in its tablet dosage form. | 2008 Mar-Apr |
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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 |
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Rapid nanoparticle-mediated monitoring of bacterial metabolic activity and assessment of antimicrobial susceptibility in blood with magnetic relaxation. | 2008 Sep 23 |
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Suspected anaphylactic reactions associated with anaesthesia. | 2009 Feb |
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A case of multidrug-resistant Salmonella enterica serovar Typhi treated with a bench to bedside approach. | 2009 Feb 28 |
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Detection of Extended Spectrum β-lactamase Production Among Uropathogens. | 2009 Jan |
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Prevalence and molecular characterization of extended-spectrum beta-lactamase-producing Klebsiella pneumoniae in Riyadh, Saudi Arabia. | 2009 Jul-Aug |
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Data correction pre-processing for electronically stored blood culture results: implications on microbial spectrum and empiric antibiotic therapy. | 2009 Jun 7 |
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Differential down-regulation of HLA-DR on monocyte subpopulations during systemic inflammation. | 2010 |
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Sequencing and genetic variation of multidrug resistance plasmids in Klebsiella pneumoniae. | 2010 Apr 12 |
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Prevalence and risk factors for extended spectrum Beta-lactamase-producing uropathogens in patients with urinary tract infection. | 2010 Jul |
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.
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WHO-VATC |
QJ01DC03
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CEFAMANDOLE
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m3186
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)