Basic information
- CAS
859-07-4- Standard SMILES
CC(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)Cc3ccccc3)[C@H]2SC1- InChIKey
GOFCPYKUMJBHBH-RHSMWYFYSA-N- Molecular formula
- C18H18N2O6S
- Average molar mass
- 390.4 g/mol
- Monoisotopic mass
- 390.08855747
Overview
Cefaloram is a cephalosporin derivative with potent antibacterial activity which binds to and inactivates penicillin-binding proteins (PBPs) located on the inner membrane of the bacterial cell wall. PBPs are enzymes involved in the terminal stages of assembling the bacterial cell wall and in reshaping the cell wall during growth and division, inactivation of which interferes with the cross-linkage of peptidoglycan chains necessary for bacterial cell wall strength and rigidity, resulting in the weakening of the bacterial cell wall and causing cell lysis. It has a role as an antibacterial drug.
Names & identifiers
- Preferred name
- Cephalosporin G
- IUPAC
- (6R,7R)-3-(acetyloxymethyl)-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- English name
- cefaloram
- Molecular formula
- C18H18N2O6S
- Molecular weight
- 390.41
Names & synonyms
Cefaloram859-07-4CephaloramDTXSID9046106K3086GQJ9ZDTXCID7026106Cephalosporin GRefChem:9182337-phenylacetylcephalosporanic acid(6R,7R)-3-(Acetoxymethyl)-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo(4.2.0)oct-2-en-2-carbonsaeure 3-(Acetoxymethyl)-8-oxo-7-(phenylacetamido)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid212-725-1Cefaloramum
Show more names
(7R)-7-(Phenylacetylamino)-3-(acetoxymethyl)cepham-3-ene-4-carboxylic acid(7R)-3-(Acetoxymethyl)-7β-[(α-oxophenethyl)amino]cepham-3-ene-4-carboxylic acid(6R,7R)-3-(Acetoxymethyl)-8-oxo-7-[(phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid(6R,7R)-3-(acetoxymethyl)-8-keto-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid(6R,7R)-3-(acetyloxymethyl)-8-oxo-7-(2-phenylethanoylamino)-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, 3-[(acetyloxy)methyl]-8-oxo-7-[(2-phenylacetyl)amino]-, (6R,7R)-
Cefaloramo(6R,7R)-3-(acetoxymethyl)-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid(6R,7R)-3-(acetyloxymethyl)-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidCHEBI:192380(6R,7R)-3-[(ACETYLOXY)METHYL]-8-OXO-7-(2-PHENYLACETAMIDO)-5-THIA-1-AZABICYCLO[4.2.0]OCT-2-ENE-2-CARBOXYLIC ACIDCefaloram [INN]3-(Acetoxymethyl)-8-oxo-7-(phenylacetamido)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acidCefaloram [INN:BAN]
Database identifiers
- CAS
859-07-4- PubChem CID
- 68940
- DTXSID
DTXSID9046106- ChEMBL
CHEMBL1700858- ChEBI
CHEBI:192380- UNII
- K3086GQJ9Z
- EC Number
- 212-725-1
- Nikkaji
- J7.146C
Properties
Computed structural properties
- XLogP
- 0.2
- Topological polar surface area
- 138 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 7
- Heavy atoms
- 27
- Formal charge
- 0
- Complexity
- 685
Experimental & physicochemical properties
DrugsPharmaceuticals -> Antibiotics
Physicochemical properties
- Melting point
- 160 · 160-162 °C (decomp)
- Boiling point
- 742.8 · 742.8±60.0 °C(Predicted)
- Density
- 1.48 · 1.48±0.1 g/cm3(Predicted)
- pka
- 2.68 · 2.68±0.50(Predicted)
- FDA UNII
- 3086 GQJ9Z · K3086GQJ9Z
Chemistry & industry
Suppliers5 total
深圳市创鑫生物科技有限公司13417589054 · [email protected]
深圳市创鑫生物科技有限公司13417589054 · [email protected]
陕西缔都医药化工有限公司029-029-029-81148696 18161915376 · [email protected]
长沙福臻生物科技有限公司15111215862 18229892877 · [email protected]
资川生化科技(苏州)有限公司0512-66317708 13372112871 · [email protected]
Additional notes
DefinitionChEBI: Cefaloram is a cephalosporin derivative with potent antibacterial activity which binds to and inactivates penicillin-binding proteins (PBPs) located on the inner membrane of the bacterial cell wall. PBPs are enzymes involved in the terminal stages of assembling the bacterial cell wall and in reshaping the cell wall during growth and division, inactivation of which interferes with the cross-linkage of peptidoglycan chains necessary for bacterial cell wall strength and rigidity, resulting in the weakening of the bacterial cell wall and causing cell lysis. It has a role as an antibacterial drug.
Related reactions
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Compound notes
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