Cefamandole
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Basic information
- CAS
34444-01-4- Standard SMILES
Cn1nnnc1SCC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)[C@H](O)c3ccccc3)[C@H]2SC1- InChIKey
OLVCFLKTBJRLHI-AXAPSJFSSA-N- Molecular formula
- C18H18N6O5S2
- Average molar mass
- 462.5 g/mol
- Monoisotopic mass
- 462.07801004
Overview
Cefamandole is a cephalosporin compound having (R)-mandelamido and N-methylthiotetrazole side-groups. It has a role as an antibacterial drug. It is a cephalosporin and a semisynthetic derivative. It is a conjugate acid of a cefamandole(1-).
Names & identifiers
- Preferred name
- Cefamandole
- IUPAC
- (6R,7R)-7-[[(2R)-2-hydroxy-2-phenylacetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- English name
- Cefamandole
- Molecular formula
- C18H18N6O5S2
- Molecular weight
- 462.5
Names & synonyms
cefamandole34444-01-4CefadoleCEPHAMANDOLECefamandolCephadoleCefamandolumL-CefamandoleCompound 83405COMPOUND-83405cefamandolo5CKP8C2LLI
Show more names
Florfenicol-d3 AMine(r*)))-CefoxinolideR hidalgoense
(6R,7R)-7-[[(2R)-2-hydroxy-2-phenylacetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidCHEBI:3480(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 acidDTXSID7022750J01DC03(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(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 acid5-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-(6alpha,7beta(R*)))-
Database identifiers
- CAS
34444-01-4- PubChem CID
- 456255
- DTXSID
Properties
Computed structural propertiesFilling in
- XLogP
- -0.9
- Topological polar surface area
- 201 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 10
- Rotatable bonds
- 7
- Heavy atoms
- 31
- Formal charge
- 0
- Complexity
- 777
Experimental & physicochemical properties
Drugs
Pharmaceuticals -> Antibiotics
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Antibiotics
LogP
0.50
0.25
Solubility5.81e-01 g/L
Melting Point182-184
Physical DescriptionSolid
Dissociation Constants3.4
Collision Cross Section
195.97 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
197.9 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with Waters Major Mix]
Physicochemical properties
- Melting point
- 107 · 107-109oC
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Hazard information
Other Safety InformationIMAP assessments - 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*)]]-: Human health tier I assessment
Toxicology
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
cefamandole
DILI Positive
Intramuscular; Intravenous
DOI:10.1016/j.drudis.2019.09.022
Chemistry & industry
Pharmacology
ATC Code
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
Protein Binding75%
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.
Biological Half-LifeThe half-life after an intravenous dose is 32 minutes; after intramuscular administration, the half-life is 60 minutes.
MeSH Pharmacological ClassificationSubstances that inhibit the growth or reproduction of BACTERIA.
Cellular LocationsMembrane
Applications
DescriptionCefamandole is also known as cephamandole. It is a parenterally administered broad-spectrum cephalosporin antibiotic. The pharmacological action and indications for use of cefamandole is analogous to that of cefuroxime and cefamandole. Synonyms of this drug are mandoxef, kefandol, kefadol, and many others.
UsesIntermediate for the oreparation of Phenylephrine Glucuronide.
Related reactions
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Compound notes
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