U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
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

1978
Curative
MANDOL

Approved Use

Unknown

Launch Date

1978
Curative
MANDOL

Approved Use

Unknown

Launch Date

1978
Curative
MANDOL

Approved Use

Unknown

Launch Date

1978
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
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
In-vitro activity of seventeen antimicrobial compounds against seven species of mycobacteria.
1988 Dec
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
The penetration of ceftriaxone and cefamandole into bone, fat and haematoma and relevance of serum protein binding to their penetration into bone.
2001 Apr
[Infectious complications of mandibular osteotomy].
2001 Feb
Incidence and risk factors of bacteriuria after transurethral resection of the prostate.
2001 Mar
Antibiotic prophylaxis in orthopedic prosthetic surgery.
2001 Nov
Cephalosporins in surgical prophylaxis.
2001 Nov
Serotypes, virulence factors, antibiotic sensitivity, beta-lactamase activity and plasmid analysis of Salmonella from children with diarrhea in Tripoli (Libya).
2002
Surgical prophylaxis in practice.
2002 Jan
Modified antimicrobial disc susceptibility testing for nutritionally-variant streptococci.
2002 Mar
Interaction of human and rat organic anion transporter 2 with various cephalosporin antibiotics.
2003 Mar 28
Polyurethanes loaded with antibiotics: influence of polymer-antibiotic interactions on in vitro activity against Staphylococcus epidermidis.
2004 Oct
Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1.
2005 Jan
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
Semiparametric mixed-effects analysis of PK/PD models using differential equations.
2008 Aug
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
Rapid nanoparticle-mediated monitoring of bacterial metabolic activity and assessment of antimicrobial susceptibility in blood with magnetic relaxation.
2008 Sep 23
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
Differential down-regulation of HLA-DR on monocyte subpopulations during systemic inflammation.
2010
Sequencing and genetic variation of multidrug resistance plasmids in Klebsiella pneumoniae.
2010 Apr 12
Prevalence and risk factors for extended spectrum Beta-lactamase-producing uropathogens in patients with urinary tract infection.
2010 Jul
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.
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
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NCI_THESAURUS C357
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WHO-VATC QJ01DC03
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Code System Code Type Description
NCI_THESAURUS
C353
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INN
3329
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WIKIPEDIA
CEFAMANDOLE
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CAS
34444-01-4
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MESH
D002435
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FDA UNII
5CKP8C2LLI
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RXCUI
2178
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PRIMARY RxNorm
MERCK INDEX
m3186
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PRIMARY Merck Index
ChEMBL
CHEMBL1146
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PRIMARY
DRUG CENTRAL
527
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EPA CompTox
DTXSID7022750
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CHEBI
3480
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DRUG BANK
DB01326
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ECHA (EC/EINECS)
252-030-0
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EVMPD
SUB07373MIG
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SMS_ID
100000081790
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PUBCHEM
456255
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