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 |
---|---|---|---|
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 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 |
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Comparative incidence of phlebitis due to buffered cephalothin, cephapirin, and cefamandole. | 1976 Apr |
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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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Determination of MICs of conventional and experimental drugs in liquid medium by the radiometric method against Mycobacterium avium complex. | 1987 |
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[Infectious complications of mandibular osteotomy]. | 2001 Feb |
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Difficulties in the assay of cefamandole highlight the importance of specific methodologies in pharmacokinetic studies. | 2001 Jul |
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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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Cross-reactivity of cefotetan and ceftriaxone antibodies, associated with hemolytic anemia, with other: cephalosporins and penicillin. | 2002 Aug |
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Surgical prophylaxis in practice. | 2002 Jan |
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Review of the use of cephalosporins in children with anaphylactic reactions from penicillins. | 2002 Jul |
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Practical aspects of choosing an antibiotic for patients with a reported allergy to an antibiotic. | 2002 Jul 1 |
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[Beta-lactam resistance in aquatic Enterobacter cloacae strains using phenotypic and genotypic criteria]. | 2002 Jul-Dec |
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beta-Lactam allergenic determinants: fine structural recognition of a cross-reacting determinant on benzylpenicillin and cephalothin. | 2002 Nov |
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Interaction of human and rat organic anion transporter 2 with various cephalosporin antibiotics. | 2003 Mar 28 |
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The synergistic effect of EDTA/antimicrobial combinations on Pseudomonas aeruginosa. | 2004 |
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Effects of bovine lactoferrin hydrolysate on the in vitro antimicrobial susceptibility of Escherichia coli strains isolated from baby pigs. | 2004 Feb |
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Escherichia coli producing CTX-M-2 beta-lactamase in cattle, Japan. | 2004 Jan |
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Incorporation of different antibiotics into carbonated hydroxyapatite coatings on titanium implants, release and antibiotic efficacy. | 2004 Sep 14 |
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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 |
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Systemic and local antibiotic prophylaxis in the prevention of Staphylococcus epidermidis graft infection. | 2005 Oct 21 |
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Enzymatic synthesis of cephalosporins. The immobilized acylase from Arthrobacter viscosus: a new useful biocatalyst. | 2007 Dec |
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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 |
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Estimation of the two sample preparation techniques for infrared spectroscopic identification of Cefamandole nafate in solid state. | 2007 Sep |
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Superficial and deep sternal wound infection after more than 9000 coronary artery bypass graft (CABG): incidence, risk factors and mortality. | 2007 Sep 23 |
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[Regional lymphotropic antibiotic therapy as a part of comprehensive treatment of children with purulent-inflammatory diseases of maxillofacial region]. | 2008 |
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Semiparametric mixed-effects analysis of PK/PD models using differential equations. | 2008 Aug |
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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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Translocation of bacterial NOD2 agonist and its link with inflammation. | 2009 |
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Suspected anaphylactic reactions associated with anaesthesia. | 2009 Feb |
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Antibiotic prophylaxis for lung surgery: bronchial colonization is the critical issue? | 2009 Sep |
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Differential down-regulation of HLA-DR on monocyte subpopulations during systemic inflammation. | 2010 |
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Single-dose versus multiple-dose antibiotic prophylaxis for the surgical treatment of closed fractures. | 2010 Apr |
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Differentiation between probiotic and wild-type Bacillus cereus isolates by antibiotic susceptibility test and Fourier transform infrared spectroscopy (FT-IR). | 2010 May 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.
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WHO-VATC |
QJ01DC03
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C353
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CEFAMANDOLE
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M3186
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SUB07373MIG
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)