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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
Structure of CEFAMANDOLE

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

HIDE SMILES / InChI

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

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
MANDOL

Approved Use

Unknown

Launch Date

2.75702415E11
Curative
MANDOL

Approved Use

Unknown

Launch Date

2.75702415E11
Curative
MANDOL

Approved Use

Unknown

Launch Date

2.75702415E11
Curative
MANDOL

Approved Use

Unknown

Launch Date

2.75702415E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
113 μg/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
5934 μg × min/mL
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

T1/2

ValueDoseCo-administeredAnalytePopulation
23.64 min
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

Doses

DosePopulationAdverse 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
Health Status: unhealthy
Sex: F
Population Size: 20
Sources:
Other AEs: Glutamic-oxaloacetic transaminase increased, Lactic dehydrogenase increased...
Other AEs:
Glutamic-oxaloacetic transaminase increased (20%)
Lactic dehydrogenase increased (20%)
Alkaline phosphatase increased (20%)
Sources:
1 g single, intramuscular
Dose: 1 g
Route: intramuscular
Route: single
Dose: 1 g
Sources:
unhealthy
n = 24
Health Status: unhealthy
Condition: renal impairment
Sex: M
Population Size: 24
Sources:
AEs

AEs

AESignificanceDosePopulation
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
Health Status: unhealthy
Sex: F
Population Size: 20
Sources:
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
Health Status: unhealthy
Sex: F
Population Size: 20
Sources:
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
Health Status: unhealthy
Sex: F
Population Size: 20
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer




Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes [IC50 1570 uM]
yes [Ki 1140 uM]
yes [Ki 30 uM]
yes [Ki 50 uM]
PubMed

PubMed

TitleDatePubMed
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
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
Patents

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
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
by admin
on Sun Dec 18 17:37:15 UTC 2022
Edited
by admin
on Sun Dec 18 17:37:15 UTC 2022
Record UNII
5CKP8C2LLI
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CEFAMANDOLE
INN   MART.   MI   USAN   VANDF   WHO-DD  
USAN   INN  
Official Name English
cefamandole [INN]
Common Name English
COMPOUND-83405
Code English
7-D-MANDELAMIDO-3-(((1-METHYL-1H-TETRAZOL-5-YL)THIO)METHYL)-3-CEPHEM-4-CARBOXYLIC ACID
Common Name English
CEFAMANDOLE [MI]
Common Name English
5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 7-((HYDROXYPHENYLACETYL)AMINO)-3-(((1-METHYL-1H-TETRAZOL-5-YL)THIO)METHYL)-8-OXO-, (6R-(6.ALPHA.,7.BETA.(R*)))-
Common Name English
CEFAMANDOLE [VANDF]
Common Name English
CEFAMANDOLE [USAN]
Common Name English
(6R,7R)-7-(R)-Mandelamido-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-carboxylic acid
Common Name English
CEFAMANDOLE [MART.]
Common Name English
J01DC03
Code English
COMPOUND 83405
Code English
Cefamandole [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-ATC J01DC03
Created by admin on Sun Dec 18 17:37:17 UTC 2022 , Edited by admin on Sun Dec 18 17:37:17 UTC 2022
NCI_THESAURUS C357
Created by admin on Sun Dec 18 17:37:17 UTC 2022 , Edited by admin on Sun Dec 18 17:37:17 UTC 2022
WHO-VATC QJ01DC03
Created by admin on Sun Dec 18 17:37:17 UTC 2022 , Edited by admin on Sun Dec 18 17:37:17 UTC 2022
Code System Code Type Description
NCI_THESAURUS
C353
Created by admin on Sun Dec 18 17:37:17 UTC 2022 , Edited by admin on Sun Dec 18 17:37:17 UTC 2022
PRIMARY
INN
3329
Created by admin on Sun Dec 18 17:37:17 UTC 2022 , Edited by admin on Sun Dec 18 17:37:17 UTC 2022
PRIMARY
WIKIPEDIA
CEFAMANDOLE
Created by admin on Sun Dec 18 17:37:17 UTC 2022 , Edited by admin on Sun Dec 18 17:37:17 UTC 2022
PRIMARY
DAILYMED
5CKP8C2LLI
Created by admin on Sun Dec 18 17:37:17 UTC 2022 , Edited by admin on Sun Dec 18 17:37:17 UTC 2022
PRIMARY
CAS
34444-01-4
Created by admin on Sun Dec 18 17:37:17 UTC 2022 , Edited by admin on Sun Dec 18 17:37:17 UTC 2022
PRIMARY
MESH
D002435
Created by admin on Sun Dec 18 17:37:17 UTC 2022 , Edited by admin on Sun Dec 18 17:37:17 UTC 2022
PRIMARY
FDA UNII
5CKP8C2LLI
Created by admin on Sun Dec 18 17:37:17 UTC 2022 , Edited by admin on Sun Dec 18 17:37:17 UTC 2022
PRIMARY
RXCUI
2178
Created by admin on Sun Dec 18 17:37:17 UTC 2022 , Edited by admin on Sun Dec 18 17:37:17 UTC 2022
PRIMARY RxNorm
MERCK INDEX
M3186
Created by admin on Sun Dec 18 17:37:17 UTC 2022 , Edited by admin on Sun Dec 18 17:37:17 UTC 2022
PRIMARY Merck Index
ChEMBL
CHEMBL1146
Created by admin on Sun Dec 18 17:37:17 UTC 2022 , Edited by admin on Sun Dec 18 17:37:17 UTC 2022
PRIMARY
DRUG CENTRAL
527
Created by admin on Sun Dec 18 17:37:17 UTC 2022 , Edited by admin on Sun Dec 18 17:37:17 UTC 2022
PRIMARY
EPA CompTox
DTXSID7022750
Created by admin on Sun Dec 18 17:37:17 UTC 2022 , Edited by admin on Sun Dec 18 17:37:17 UTC 2022
PRIMARY
CHEBI
3480
Created by admin on Sun Dec 18 17:37:17 UTC 2022 , Edited by admin on Sun Dec 18 17:37:17 UTC 2022
PRIMARY
DRUG BANK
DB01326
Created by admin on Sun Dec 18 17:37:17 UTC 2022 , Edited by admin on Sun Dec 18 17:37:17 UTC 2022
PRIMARY
ECHA (EC/EINECS)
252-030-0
Created by admin on Sun Dec 18 17:37:17 UTC 2022 , Edited by admin on Sun Dec 18 17:37:17 UTC 2022
PRIMARY
EVMPD
SUB07373MIG
Created by admin on Sun Dec 18 17:37:17 UTC 2022 , Edited by admin on Sun Dec 18 17:37:17 UTC 2022
PRIMARY
PUBCHEM
456255
Created by admin on Sun Dec 18 17:37:17 UTC 2022 , Edited by admin on Sun Dec 18 17:37:17 UTC 2022
PRIMARY
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