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

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
Comparative incidence of phlebitis due to buffered cephalothin, cephapirin, and cefamandole.
1976 Apr
Cefamandole for treatment of obstetrical and gynecological infections.
1980
Acute tubular necrosis following high-dose cefamandole therapy for Hemophilus parainfluenzae endocarditis.
1981 May-Jun
Determination of MICs of conventional and experimental drugs in liquid medium by the radiometric method against Mycobacterium avium complex.
1987
[Infectious complications of mandibular osteotomy].
2001 Feb
Difficulties in the assay of cefamandole highlight the importance of specific methodologies in pharmacokinetic studies.
2001 Jul
Antibiotic prophylaxis in orthopedic prosthetic surgery.
2001 Nov
Cephalosporins in surgical prophylaxis.
2001 Nov
Cross-reactivity of cefotetan and ceftriaxone antibodies, associated with hemolytic anemia, with other: cephalosporins and penicillin.
2002 Aug
Surgical prophylaxis in practice.
2002 Jan
Review of the use of cephalosporins in children with anaphylactic reactions from penicillins.
2002 Jul
Practical aspects of choosing an antibiotic for patients with a reported allergy to an antibiotic.
2002 Jul 1
[Beta-lactam resistance in aquatic Enterobacter cloacae strains using phenotypic and genotypic criteria].
2002 Jul-Dec
beta-Lactam allergenic determinants: fine structural recognition of a cross-reacting determinant on benzylpenicillin and cephalothin.
2002 Nov
Interaction of human and rat organic anion transporter 2 with various cephalosporin antibiotics.
2003 Mar 28
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
Escherichia coli producing CTX-M-2 beta-lactamase in cattle, Japan.
2004 Jan
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
Systemic and local antibiotic prophylaxis in the prevention of Staphylococcus epidermidis graft infection.
2005 Oct 21
Enzymatic synthesis of cephalosporins. The immobilized acylase from Arthrobacter viscosus: a new useful biocatalyst.
2007 Dec
Inhaled tobramycin solution-associated recurrent eosinophilia and severe persistent bronchospasm in a patient with cystic fibrosis: a case report.
2007 Mar 2
Estimation of the two sample preparation techniques for infrared spectroscopic identification of Cefamandole nafate in solid state.
2007 Sep
Superficial and deep sternal wound infection after more than 9000 coronary artery bypass graft (CABG): incidence, risk factors and mortality.
2007 Sep 23
[Regional lymphotropic antibiotic therapy as a part of comprehensive treatment of children with purulent-inflammatory diseases of maxillofacial region].
2008
Semiparametric mixed-effects analysis of PK/PD models using differential equations.
2008 Aug
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
Translocation of bacterial NOD2 agonist and its link with inflammation.
2009
Suspected anaphylactic reactions associated with anaesthesia.
2009 Feb
Antibiotic prophylaxis for lung surgery: bronchial colonization is the critical issue?
2009 Sep
Differential down-regulation of HLA-DR on monocyte subpopulations during systemic inflammation.
2010
Single-dose versus multiple-dose antibiotic prophylaxis for the surgical treatment of closed fractures.
2010 Apr
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 [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 Thu Jul 06 21:23:34 UTC 2023 , Edited by admin on Thu Jul 06 21:23:34 UTC 2023
NCI_THESAURUS C357
Created by admin on Thu Jul 06 21:23:34 UTC 2023 , Edited by admin on Thu Jul 06 21:23:34 UTC 2023
WHO-VATC QJ01DC03
Created by admin on Thu Jul 06 21:23:34 UTC 2023 , Edited by admin on Thu Jul 06 21:23:34 UTC 2023
Code System Code Type Description
NCI_THESAURUS
C353
Created by admin on Thu Jul 06 21:23:34 UTC 2023 , Edited by admin on Thu Jul 06 21:23:34 UTC 2023
PRIMARY
INN
3329
Created by admin on Thu Jul 06 21:23:34 UTC 2023 , Edited by admin on Thu Jul 06 21:23:34 UTC 2023
PRIMARY
WIKIPEDIA
CEFAMANDOLE
Created by admin on Thu Jul 06 21:23:34 UTC 2023 , Edited by admin on Thu Jul 06 21:23:34 UTC 2023
PRIMARY
CAS
34444-01-4
Created by admin on Thu Jul 06 21:23:34 UTC 2023 , Edited by admin on Thu Jul 06 21:23:34 UTC 2023
PRIMARY
MESH
D002435
Created by admin on Thu Jul 06 21:23:34 UTC 2023 , Edited by admin on Thu Jul 06 21:23:34 UTC 2023
PRIMARY
FDA UNII
5CKP8C2LLI
Created by admin on Thu Jul 06 21:23:34 UTC 2023 , Edited by admin on Thu Jul 06 21:23:34 UTC 2023
PRIMARY
RXCUI
2178
Created by admin on Thu Jul 06 21:23:34 UTC 2023 , Edited by admin on Thu Jul 06 21:23:34 UTC 2023
PRIMARY RxNorm
MERCK INDEX
M3186
Created by admin on Thu Jul 06 21:23:34 UTC 2023 , Edited by admin on Thu Jul 06 21:23:34 UTC 2023
PRIMARY Merck Index
ChEMBL
CHEMBL1146
Created by admin on Thu Jul 06 21:23:34 UTC 2023 , Edited by admin on Thu Jul 06 21:23:34 UTC 2023
PRIMARY
DRUG CENTRAL
527
Created by admin on Thu Jul 06 21:23:34 UTC 2023 , Edited by admin on Thu Jul 06 21:23:34 UTC 2023
PRIMARY
EPA CompTox
DTXSID7022750
Created by admin on Thu Jul 06 21:23:34 UTC 2023 , Edited by admin on Thu Jul 06 21:23:34 UTC 2023
PRIMARY
CHEBI
3480
Created by admin on Thu Jul 06 21:23:34 UTC 2023 , Edited by admin on Thu Jul 06 21:23:34 UTC 2023
PRIMARY
DRUG BANK
DB01326
Created by admin on Thu Jul 06 21:23:34 UTC 2023 , Edited by admin on Thu Jul 06 21:23:34 UTC 2023
PRIMARY
ECHA (EC/EINECS)
252-030-0
Created by admin on Thu Jul 06 21:23:34 UTC 2023 , Edited by admin on Thu Jul 06 21:23:34 UTC 2023
PRIMARY
EVMPD
SUB07373MIG
Created by admin on Thu Jul 06 21:23:34 UTC 2023 , Edited by admin on Thu Jul 06 21:23:34 UTC 2023
PRIMARY
SMS_ID
100000081790
Created by admin on Thu Jul 06 21:23:34 UTC 2023 , Edited by admin on Thu Jul 06 21:23:34 UTC 2023
PRIMARY
PUBCHEM
456255
Created by admin on Thu Jul 06 21:23:34 UTC 2023 , Edited by admin on Thu Jul 06 21:23:34 UTC 2023
PRIMARY