Cefamandole

Identification

Summary

Cefamandole is a beta-lactam antibiotic used in the treatment of various infections caused by susceptible strains of bacteria, such as lower respiratory infections, urinary tract infections, skin infections, and bone and joint infections.

Generic Name
Cefamandole
DrugBank Accession Number
DB01326
Background

Cefamandole is also known as cephamandole. It is a parenterally administered broad-spectrum cephalosporin antibiotic. It is generally formulated as a formate ester, cefamandole nafate. It is no longer marketed in the United States.

Type
Small Molecule
Groups
Approved, Experimental
Structure
Weight
Average: 462.503
Monoisotopic: 462.078009096
Chemical Formula
C18H18N6O5S2
Synonyms
  • (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
  • (6R,7R)-7-{[(2R)-2-hydroxy-2-phenylacetyl]amino}-3-{[(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  • Cefadole
  • Cefamandol
  • Céfamandole
  • Cefamandole
  • Cefamandolum
  • Cephadole
  • Cephamandole
  • L-Cefamandole

Pharmacology

Indication

For the treatment of serious infections caused by susceptible strains of microorganisms.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofGram-negative infections bacterial infections••••••••••••••••••• ••• ••••••••
Treatment ofGram-negative infections bacterial infections••••••••••••••••••• ••• ••••••••
Used in combination to treatSepsis••••••••••••••••••• ••• ••••••••
Used in combination to treatSevere bacterial infections••••••••••••••••••• ••• ••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

The parenteral prodrug formate ester cefamandole nafate is a broad-spectrum cephalosporin antibiotic. The bactericidal action of cefamandole results from inhibition of cell-wall synthesis. Cephalosporins have in vitro activity against a wide range of gram-positive and gram-negative organisms.

Mechanism of action

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. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that cefamandole interferes with an autolysin inhibitor.

TargetActionsOrganism
APenicillin-binding protein 2
inhibitor
Bacteroides fragilis
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

75%

Metabolism
Not Available
Route of elimination

Not Available

Half-life

The half-life after an intravenous dose is 32 minutes; after intramuscular administration, the half-life is 60 minutes.

Clearance

Not Available

Adverse Effects
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Toxicity

Symptoms of overdose include blood in the urine, diarrhea, nausea, upper abdominal pain, and vomiting.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbacavirCefamandole may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbciximabThe therapeutic efficacy of Abciximab can be decreased when used in combination with Cefamandole.
AcamprosateThe excretion of Acamprosate can be decreased when combined with Cefamandole.
AceclofenacThe risk or severity of nephrotoxicity can be increased when Cefamandole is combined with Aceclofenac.
AcemetacinThe risk or severity of nephrotoxicity can be increased when Cefamandole is combined with Acemetacin.
Food Interactions
  • Avoid alcohol. Ingesting alcohol with cefamandole may precipitate a disulfiram like reaction due to elevated levels of acetaldehyde in the blood.

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Categories

ATC Codes
J01DC03 — Cefamandole
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as cephalosporins. These are compounds containing a 1,2-thiazine fused to a 2-azetidinone to for a oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid moiety or a derivative thereof.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Lactams
Sub Class
Beta lactams
Direct Parent
Cephalosporins
Alternative Parents
N-acyl-alpha amino acids and derivatives / Phenylacetamides / Alkylarylthioethers / 1,3-thiazines / Tetrazoles / Tertiary carboxylic acid amides / Heteroaromatic compounds / Azetidines / Secondary carboxylic acid amides / Secondary alcohols
show 12 more
Substituents
Alcohol / Alkylarylthioether / Alpha-amino acid or derivatives / Aromatic alcohol / Aromatic heteropolycyclic compound / Aryl thioether / Azacycle / Azetidine / Azole / Benzenoid
show 27 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
cephalosporin, semisynthetic derivative (CHEBI:3480)
Affected organisms
  • Enteric bacteria and other eubacteria

Chemical Identifiers

UNII
5CKP8C2LLI
CAS number
34444-01-4
InChI Key
OLVCFLKTBJRLHI-AXAPSJFSSA-N
InChI
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
IUPAC Name
(6R,7R)-7-[(2R)-2-hydroxy-2-phenylacetamido]-3-{[(1-methyl-1H-1,2,3,4-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
SMILES
[H][C@]12SCC(CSC3=NN=NN3C)=C(N1C(=O)[C@H]2NC(=O)[C@H](O)C1=CC=CC=C1)C(O)=O

References

Synthesis Reference

Ta Sen Chou, Gary D. Zintgraff, "Process for preparing pure cefamandole from alkali metal and ammonium salts thereof." U.S. Patent US4115644, issued June, 1977.

US4115644
General References
Not Available
Human Metabolome Database
HMDB0015421
KEGG Drug
D02344
KEGG Compound
C06879
PubChem Compound
456255
PubChem Substance
46508882
ChemSpider
401748
BindingDB
50350468
RxNav
2178
ChEBI
3480
ChEMBL
CHEMBL1146
ZINC
ZINC000003830394
Therapeutic Targets Database
DAP000448
PharmGKB
PA448837
PDBe Ligand
SMX
RxList
RxList Drug Page
Wikipedia
Cefamandole
PDB Entries
3ny4

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0TerminatedTreatmentOsteomyelitis1
Not AvailableUnknown StatusNot AvailableCommunity Acquired Pneumonia (CAP)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Injection, powder, for solutionIntramuscular1 G
Injection, powder, for solutionIntramuscular500 MG
Injection, powder, for solutionIntramuscular
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)182-184Greene, J.M. and Indelicato, J.M.; US. Patent 3,928,592; December 23,1975; assigned to Eli Lilly & Co.
logP0.50SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility0.581 mg/mLALOGPS
logP-0.05ALOGPS
logP0.027Chemaxon
logS-2.9ALOGPS
pKa (Strongest Acidic)3.13Chemaxon
pKa (Strongest Basic)-1.7Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count8Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area150.54 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity126.65 m3·mol-1Chemaxon
Polarizability42.45 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.8573
Blood Brain Barrier-0.9918
Caco-2 permeable-0.795
P-glycoprotein substrateSubstrate0.769
P-glycoprotein inhibitor INon-inhibitor0.8401
P-glycoprotein inhibitor IINon-inhibitor0.8066
Renal organic cation transporterNon-inhibitor0.8467
CYP450 2C9 substrateNon-substrate0.7367
CYP450 2D6 substrateNon-substrate0.822
CYP450 3A4 substrateSubstrate0.5185
CYP450 1A2 substrateNon-inhibitor0.8336
CYP450 2C9 inhibitorNon-inhibitor0.7509
CYP450 2D6 inhibitorNon-inhibitor0.8653
CYP450 2C19 inhibitorNon-inhibitor0.7454
CYP450 3A4 inhibitorNon-inhibitor0.7111
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5818
Ames testNon AMES toxic0.7075
CarcinogenicityNon-carcinogens0.9222
BiodegradationNot ready biodegradable0.8565
Rat acute toxicity2.2075 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9594
hERG inhibition (predictor II)Non-inhibitor0.5988
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0a4i-1900000000-171ae249ec803b8d5abd
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-01ot-0114900000-49d060c733d6d85edfee
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0900300000-f492f5dda1573a533078
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-05di-3597200000-b52942140155120c2983
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00dr-9110000000-c65a72de13c5cfb46bf4
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0bt9-1932400000-1c8ecea72aa63bb1eedd
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4l-9410000000-b159f643e6a8ab6bdf37
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-211.5095634
predicted
DarkChem Lite v0.1.0
[M-H]-195.93224
predicted
DeepCCS 1.0 (2019)
[M+H]+211.6263634
predicted
DarkChem Lite v0.1.0
[M+H]+198.32779
predicted
DeepCCS 1.0 (2019)
[M+Na]+211.7773634
predicted
DarkChem Lite v0.1.0
[M+Na]+205.23787
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Kind
Protein
Organism
Bacteroides fragilis
Pharmacological action
Yes
Actions
Inhibitor
General Function
Penicillin binding
Specific Function
Not Available
Gene Name
pbpA
Uniprot ID
Q70KI2
Uniprot Name
Penicillin-binding protein 2
Molecular Weight
69434.305 Da
References
  1. Yotsuji A, Mitsuyama J, Hori R, Yasuda T, Saikawa I, Inoue M, Mitsuhashi S: Mechanism of action of cephalosporins and resistance caused by decreased affinity for penicillin-binding proteins in Bacteroides fragilis. Antimicrob Agents Chemother. 1988 Dec;32(12):1848-53. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
Gene Name
SLC22A6
Uniprot ID
Q4U2R8
Uniprot Name
Solute carrier family 22 member 6
Molecular Weight
61815.78 Da
References
  1. Takeda M, Babu E, Narikawa S, Endou H: Interaction of human organic anion transporters with various cephalosporin antibiotics. Eur J Pharmacol. 2002 Mar 8;438(3):137-42. [Article]
  2. Jung KY, Takeda M, Shimoda M, Narikawa S, Tojo A, Kim DK, Chairoungdua A, Choi BK, Kusuhara H, Sugiyama Y, Sekine T, Endou H: Involvement of rat organic anion transporter 3 (rOAT3) in cephaloridine-induced nephrotoxicity: in comparison with rOAT1. Life Sci. 2002 Mar 8;70(16):1861-74. [Article]
  3. Jariyawat S, Sekine T, Takeda M, Apiwattanakul N, Kanai Y, Sophasan S, Endou H: The interaction and transport of beta-lactam antibiotics with the cloned rat renal organic anion transporter 1. J Pharmacol Exp Ther. 1999 Aug;290(2):672-7. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
Gene Name
SLC22A8
Uniprot ID
Q8TCC7
Uniprot Name
Solute carrier family 22 member 8
Molecular Weight
59855.585 Da
References
  1. Takeda M, Babu E, Narikawa S, Endou H: Interaction of human organic anion transporters with various cephalosporin antibiotics. Eur J Pharmacol. 2002 Mar 8;438(3):137-42. [Article]
  2. Jung KY, Takeda M, Shimoda M, Narikawa S, Tojo A, Kim DK, Chairoungdua A, Choi BK, Kusuhara H, Sugiyama Y, Sekine T, Endou H: Involvement of rat organic anion transporter 3 (rOAT3) in cephaloridine-induced nephrotoxicity: in comparison with rOAT1. Life Sci. 2002 Mar 8;70(16):1861-74. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates saturable uptake of estrone sulfate, dehydroepiandrosterone sulfate and related compounds.
Gene Name
SLC22A11
Uniprot ID
Q9NSA0
Uniprot Name
Solute carrier family 22 member 11
Molecular Weight
59970.945 Da
References
  1. Takeda M, Babu E, Narikawa S, Endou H: Interaction of human organic anion transporters with various cephalosporin antibiotics. Eur J Pharmacol. 2002 Mar 8;438(3):137-42. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates sodium-independent multispecific organic anion transport. Transport of prostaglandin E2, prostaglandin F2, tetracycline, bumetanide, estrone sulfate, glutarate, dehydroepiandrosterone sulf...
Gene Name
SLC22A7
Uniprot ID
Q9Y694
Uniprot Name
Solute carrier family 22 member 7
Molecular Weight
60025.025 Da
References
  1. Khamdang S, Takeda M, Babu E, Noshiro R, Onozato ML, Tojo A, Enomoto A, Huang XL, Narikawa S, Anzai N, Piyachaturawat P, Endou H: Interaction of human and rat organic anion transporter 2 with various cephalosporin antibiotics. Eur J Pharmacol. 2003 Mar 28;465(1-2):1-7. [Article]

Drug created at June 30, 2007 17:22 / Updated at February 12, 2022 17:15