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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H17N6O5S2.Na
Molecular Weight 484.485
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CEFAMANDOLE SODIUM

SMILES

[Na+].[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=OJMNTWPPFNMOCJ-CFOLLTDRSA-M
InChI=1S/C18H18N6O5S2.Na/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);/q;+1/p-1/t11-,13-,16-;/m1./s1

HIDE SMILES / InChI

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C18H17N6O5S2
Molecular Weight 461.495
Charge -1
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

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
In-vitro activity of seventeen antimicrobial compounds against seven species of mycobacteria.
1988 Dec
Acute renal failure due to cephamandole.
1988 Feb 6
Antibiotic prophylaxis in orthopedic prosthetic surgery.
2001 Nov
Modified antimicrobial disc susceptibility testing for nutritionally-variant streptococci.
2002 Mar
Interaction of human organic anion transporters with various cephalosporin antibiotics.
2002 Mar 8
Escherichia coli producing CTX-M-2 beta-lactamase in cattle, Japan.
2004 Jan
Cross-reactivity and tolerability of cephalosporins in patients with immediate hypersensitivity to penicillins.
2004 Jul 6
Cardiac actinomycosis in a patient presenting with acute cardiac tamponade and a mass mimicking pericardial tumour.
2004 May
Incorporation of different antibiotics into carbonated hydroxyapatite coatings on titanium implants, release and antibiotic efficacy.
2004 Sep 14
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
Case report: infective endocarditis caused by Brevundimonas vesicularis.
2006 Dec 29
Pharmacodynamic optimization of beta-lactams in the patient care setting.
2008
Involvement of multidrug resistance-associated protein 2 (Abcc2) in molecular weight-dependent biliary excretion of beta-lactam antibiotics.
2008 Jun
A case of multidrug-resistant Salmonella enterica serovar Typhi treated with a bench to bedside approach.
2009 Feb 28
Prevalence and molecular characterization of extended-spectrum beta-lactamase-producing Klebsiella pneumoniae in Riyadh, Saudi Arabia.
2009 Jul-Aug
Sequencing and genetic variation of multidrug resistance plasmids in Klebsiella pneumoniae.
2010 Apr 12
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 Fri Dec 15 15:49:52 GMT 2023
Edited
by admin
on Fri Dec 15 15:49:52 GMT 2023
Record UNII
IY6234ODVR
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CEFAMANDOLE SODIUM
JAN   MART.   WHO-DD  
Common Name English
Monosodium (6R,7R)-7-(R)-mandelamido-3-[[(1-methyl-1-H-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
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-(6A,7B(R*)))-, MONOSODIUM SALT
Common Name English
NSC-758169
Code English
Cefamandole sodium [WHO-DD]
Common Name English
CEFAMANDOLE SODIUM [MART.]
Common Name English
CEFAMANDOLE SODIUM [JAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C357
Created by admin on Fri Dec 15 15:49:52 GMT 2023 , Edited by admin on Fri Dec 15 15:49:52 GMT 2023
Code System Code Type Description
PUBCHEM
23672568
Created by admin on Fri Dec 15 15:49:52 GMT 2023 , Edited by admin on Fri Dec 15 15:49:52 GMT 2023
PRIMARY
EVMPD
SUB35548
Created by admin on Fri Dec 15 15:49:52 GMT 2023 , Edited by admin on Fri Dec 15 15:49:52 GMT 2023
PRIMARY
ECHA (EC/EINECS)
250-009-0
Created by admin on Fri Dec 15 15:49:52 GMT 2023 , Edited by admin on Fri Dec 15 15:49:52 GMT 2023
PRIMARY
ChEMBL
CHEMBL1146
Created by admin on Fri Dec 15 15:49:52 GMT 2023 , Edited by admin on Fri Dec 15 15:49:52 GMT 2023
PRIMARY
FDA UNII
IY6234ODVR
Created by admin on Fri Dec 15 15:49:52 GMT 2023 , Edited by admin on Fri Dec 15 15:49:52 GMT 2023
PRIMARY
EPA CompTox
DTXSID2045579
Created by admin on Fri Dec 15 15:49:52 GMT 2023 , Edited by admin on Fri Dec 15 15:49:52 GMT 2023
PRIMARY
CAS
30034-03-8
Created by admin on Fri Dec 15 15:49:52 GMT 2023 , Edited by admin on Fri Dec 15 15:49:52 GMT 2023
PRIMARY
NSC
758169
Created by admin on Fri Dec 15 15:49:52 GMT 2023 , Edited by admin on Fri Dec 15 15:49:52 GMT 2023
PRIMARY
NCI_THESAURUS
C47967
Created by admin on Fri Dec 15 15:49:52 GMT 2023 , Edited by admin on Fri Dec 15 15:49:52 GMT 2023
PRIMARY
SMS_ID
100000128479
Created by admin on Fri Dec 15 15:49:52 GMT 2023 , Edited by admin on Fri Dec 15 15:49:52 GMT 2023
PRIMARY
CHEBI
34614
Created by admin on Fri Dec 15 15:49:52 GMT 2023 , Edited by admin on Fri Dec 15 15:49:52 GMT 2023
PRIMARY
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PARENT -> SALT/SOLVATE
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ACTIVE MOIETY