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
Molecular Formula | C18H18N6O5S2 |
Molecular Weight | 462.503 |
Charge | 0 |
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 |
---|---|---|
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 |
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Cefamandole for treatment of obstetrical and gynecological infections. | 1980 |
|
Acute tubular necrosis following high-dose cefamandole therapy for Hemophilus parainfluenzae endocarditis. | 1981 May-Jun |
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In-vitro activity of seventeen antimicrobial compounds against seven species of mycobacteria. | 1988 Dec |
|
The in vitro activity of beta-lactamase inhibitors in combination with cephalosporins against M. tuberculosis. | 1995 Apr |
|
[Monitoring of uropathogens and their susceptibility to antibiotics]. | 2001 |
|
Occurrence and antibiotic resistance of mesophilic Aeromonas in three riverine freshwaters of Marrakech, Morocco. | 2001 Dec 1 |
|
Antibiotic prophylaxis in orthopedic prosthetic surgery. | 2001 Nov |
|
Cephalosporins in surgical prophylaxis. | 2001 Nov |
|
Systemic and local antibiotic prophylaxis in the prevention of prosthetic vascular graft infection: an experimental study. | 2002 Feb |
|
Surgical prophylaxis in practice. | 2002 Jan |
|
Effects on antibiotic resistance of Staphylococcus epidermidis following adhesion to polymethylmethacrylate and to silicone surfaces. | 2002 Mar |
|
Interaction of human organic anion transporters with various cephalosporin antibiotics. | 2002 Mar 8 |
|
beta-Lactam allergenic determinants: fine structural recognition of a cross-reacting determinant on benzylpenicillin and cephalothin. | 2002 Nov |
|
The synergistic effect of EDTA/antimicrobial combinations on Pseudomonas aeruginosa. | 2004 |
|
Effects of bovine lactoferrin hydrolysate on the in vitro antimicrobial susceptibility of Escherichia coli strains isolated from baby pigs. | 2004 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 |
|
Antibiotic resistance in exopolysaccharide-forming Staphylococcus epidermidis clinical isolates from orthopaedic implant infections. | 2005 Nov |
|
IgA pemphigus--occurrence of anti-desmocollin 1 and anti-desmoglein 1 antibody reactivity in an individual patient. | 2006 Dec |
|
Ameba-associated microorganisms and diagnosis of nosocomial pneumonia. | 2006 Feb |
|
Coupling between chemical reactivity and structural relaxation in pharmaceutical glasses. | 2006 Oct |
|
Antimicrobial therapy for acute cholangitis: Tokyo Guidelines. | 2007 |
|
Safe use of selected cephalosporins in penicillin-allergic patients: a meta-analysis. | 2007 Mar |
|
Superficial and deep sternal wound infection after more than 9000 coronary artery bypass graft (CABG): incidence, risk factors and mortality. | 2007 Sep 23 |
|
Involvement of multidrug resistance-associated protein 2 (Abcc2) in molecular weight-dependent biliary excretion of beta-lactam antibiotics. | 2008 Jun |
|
Spectrophotometeric Determination of Cefuroxime Axetil from bulk and in its tablet dosage form. | 2008 Mar-Apr |
|
Determination of cephalosporins in solid binary mixtures by polarized IR- and Raman spectroscopy. | 2008 Sep 10 |
|
A case of multidrug-resistant Salmonella enterica serovar Typhi treated with a bench to bedside approach. | 2009 Feb 28 |
|
Antibiotic delivery polyurethanes containing albumin and polyallylamine nanoparticles. | 2009 Mar 2 |
|
Synergy of fosfomycin with other antibiotics for Gram-positive and Gram-negative bacteria. | 2010 Apr |
|
Prevalence and risk factors for extended spectrum Beta-lactamase-producing uropathogens in patients with urinary tract infection. | 2010 Jul |
|
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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Sun Dec 18 17:37:15 UTC 2022
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Record UNII |
5CKP8C2LLI
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Validated (UNII)
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WHO-ATC |
J01DC03
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NCI_THESAURUS |
C357
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WHO-VATC |
QJ01DC03
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C353
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3329
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CEFAMANDOLE
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M3186
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CHEMBL1146
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