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 |
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Curative | MANDOL Approved UseUnknown Launch Date2.75702415E11 |
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Curative | MANDOL Approved UseUnknown Launch Date2.75702415E11 |
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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 |
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[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 |
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Acute tubular necrosis following high-dose cefamandole therapy for Hemophilus parainfluenzae endocarditis. | 1981 May-Jun |
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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 |
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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 |
|
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 |
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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 |
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 |
5CKP8C2LLI
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C357
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