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

Details

Stereochemistry ABSOLUTE
Molecular Formula C18H18N6O5S2
Molecular Weight 462.5056
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CEFAMANDOLE

SMILES

Cn1c(nnn1)SCC2=C(C(=O)O)N3C(=O)[C@]([H])([C@@]3([H])SC2)N=C([C@@]([H])(c4ccccc4)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

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
The in vitro activity of beta-lactamase inhibitors in combination with cephalosporins against M. tuberculosis.
1995 Apr
Occurrence and antibiotic resistance of mesophilic Aeromonas in three riverine freshwaters of Marrakech, Morocco.
2001 Dec 1
Determination of unbound cefamandole in rat blood by microdialysis and microbore liquid chromatography.
2001 Feb
Difficulties in the assay of cefamandole highlight the importance of specific methodologies in pharmacokinetic studies.
2001 Jul
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
Systemic and local antibiotic prophylaxis in the prevention of prosthetic vascular graft infection: an experimental study.
2002 Feb
Penetration of linezolid into bone, fat, muscle and haematoma of patients undergoing routine hip replacement.
2002 Jul
Practical aspects of choosing an antibiotic for patients with a reported allergy to an antibiotic.
2002 Jul 1
Modified antimicrobial disc susceptibility testing for nutritionally-variant streptococci.
2002 Mar
beta-Lactam allergenic determinants: fine structural recognition of a cross-reacting determinant on benzylpenicillin and cephalothin.
2002 Nov
Comparison of screening methods for TEM- and SHV-derived extended-spectrum beta-lactamase detection.
2002 Nov
Vibrio vulnificus in Taiwan.
2004 Aug
Cross-reactivity and tolerability of cephalosporins in patients with immediate hypersensitivity to penicillins.
2004 Jul 6
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
Ameba-associated microorganisms and diagnosis of nosocomial pneumonia.
2006 Feb
Nosocomial bloodstream infections caused by Klebsiella pneumoniae: impact of extended-spectrum beta-lactamase (ESBL) production on clinical outcome in a hospital with high ESBL prevalence.
2006 Feb 14
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
New active site oriented glyoxyl-agarose derivatives of Escherichia coli penicillin G acylase.
2007 Sep 10
Pharmacodynamic optimization of beta-lactams in the patient care setting.
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
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
Suspected anaphylactic reactions associated with anaesthesia.
2009 Feb
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 prophylaxis for lung surgery: bronchial colonization is the critical issue?
2009 Sep
Synergy of fosfomycin with other antibiotics for Gram-positive and Gram-negative bacteria.
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
Differentiation between probiotic and wild-type Bacillus cereus isolates by antibiotic susceptibility test and Fourier transform infrared spectroscopy (FT-IR).
2010 May 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.
Name Type Language
CEFAMANDOLE
INN   MART.   MI   USAN   VANDF   WHO-DD  
USAN   INN  
Official Name English
CEFAMANDOLE [WHO-DD]
Common 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
Classification Tree Code System Code
WHO-ATC J01DC03
Created by admin on Sat Jun 26 06:34:54 UTC 2021 , Edited by admin on Sat Jun 26 06:34:54 UTC 2021
NCI_THESAURUS C357
Created by admin on Sat Jun 26 06:34:54 UTC 2021 , Edited by admin on Sat Jun 26 06:34:54 UTC 2021
WHO-VATC QJ01DC03
Created by admin on Sat Jun 26 06:34:54 UTC 2021 , Edited by admin on Sat Jun 26 06:34:54 UTC 2021
Code System Code Type Description
NCI_THESAURUS
C353
Created by admin on Sat Jun 26 06:34:54 UTC 2021 , Edited by admin on Sat Jun 26 06:34:54 UTC 2021
PRIMARY
INN
3329
Created by admin on Sat Jun 26 06:34:54 UTC 2021 , Edited by admin on Sat Jun 26 06:34:54 UTC 2021
PRIMARY
WIKIPEDIA
CEFAMANDOLE
Created by admin on Sat Jun 26 06:34:54 UTC 2021 , Edited by admin on Sat Jun 26 06:34:54 UTC 2021
PRIMARY
CAS
34444-01-4
Created by admin on Sat Jun 26 06:34:54 UTC 2021 , Edited by admin on Sat Jun 26 06:34:54 UTC 2021
PRIMARY
MESH
D002435
Created by admin on Sat Jun 26 06:34:54 UTC 2021 , Edited by admin on Sat Jun 26 06:34:54 UTC 2021
PRIMARY
FDA UNII
5CKP8C2LLI
Created by admin on Sat Jun 26 06:34:54 UTC 2021 , Edited by admin on Sat Jun 26 06:34:54 UTC 2021
PRIMARY
RXCUI
2178
Created by admin on Sat Jun 26 06:34:54 UTC 2021 , Edited by admin on Sat Jun 26 06:34:54 UTC 2021
PRIMARY RxNorm
MERCK INDEX
M3186
Created by admin on Sat Jun 26 06:34:54 UTC 2021 , Edited by admin on Sat Jun 26 06:34:54 UTC 2021
PRIMARY Merck Index
ChEMBL
CHEMBL1146
Created by admin on Sat Jun 26 06:34:54 UTC 2021 , Edited by admin on Sat Jun 26 06:34:54 UTC 2021
PRIMARY
DRUG CENTRAL
527
Created by admin on Sat Jun 26 06:34:54 UTC 2021 , Edited by admin on Sat Jun 26 06:34:54 UTC 2021
PRIMARY
EPA CompTox
34444-01-4
Created by admin on Sat Jun 26 06:34:54 UTC 2021 , Edited by admin on Sat Jun 26 06:34:54 UTC 2021
PRIMARY
DRUG BANK
DB01326
Created by admin on Sat Jun 26 06:34:54 UTC 2021 , Edited by admin on Sat Jun 26 06:34:54 UTC 2021
PRIMARY
ECHA (EC/EINECS)
252-030-0
Created by admin on Sat Jun 26 06:34:54 UTC 2021 , Edited by admin on Sat Jun 26 06:34:54 UTC 2021
PRIMARY
EVMPD
SUB07373MIG
Created by admin on Sat Jun 26 06:34:54 UTC 2021 , Edited by admin on Sat Jun 26 06:34:54 UTC 2021
PRIMARY
PUBCHEM
456255
Created by admin on Sat Jun 26 06:34:54 UTC 2021 , Edited by admin on Sat Jun 26 06:34:54 UTC 2021
PRIMARY