Basic information
- CAS
51762-05-1- Standard SMILES
COC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)[C@H](N)C3=CCC=CC3)[C@H]2SC1- InChIKey
RDMOROXKXONCAL-UEKVPHQBSA-N- Molecular formula
- C16H19N3O5S
- Average molar mass
- 365.4 g/mol
- Monoisotopic mass
- 365.10454189
Overview
Cefroxadine is a first-generation cephalosporin antibiotic having methoxy and [(2R)-2-amino-2-(cyclohexa-1,4-dien-1-yl)acetyl]amino side groups located at positions 3 and 7 respectively.
Names & identifiers
- Preferred name
- Cefroxadine
- IUPAC
- (6R,7R)-7-[[(2R)-2-amino-2-cyclohexa-1,4-dien-1-ylacetyl]amino]-3-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- English name
- Cefroxadine
- Molecular formula
- C16H19N3O5S
- Molecular weight
- 365.4
Names & synonyms
cefroxadine51762-05-1OrasporCefroxadinCgp 9000CefroxadinumCefroxadinoCefthan-DSCGP-9000cefroxadinaDTXSID1022768B908C4MV2R
Show more names
(6R,7R)-7-[[(R)-Amino(1,4-cyclohexadien-1-yl)acetyl]amino]-3-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidcxdC12979cgp9000BRN 0587499antibioticcgp9000Cefroxadine. Oraspor
DTXCID602768CHEBI:313797-(D-2-amino-2-(1,4-cyclohexadienyl)acetamido)-3-methoxy-3-cephem-4-carboxylic acid(6R,7R)-7-(((2R)-2-amino-2-cyclohexa-1,4-dien-1-yl-acetyl)amino)-3-methoxy-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid(6R,7R)-7-[[(2R)-2-amino-2-cyclohexa-1,4-dien-1-yl-acetyl]amino]-3-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidRefChem:124252J01DA35257-391-8
Database identifiers
- CAS
51762-05-1- PubChem CID
- 5284529
- DTXSID
DTXSID1022768- ChEMBL
Properties
Computed structural properties
- XLogP
- -2.3
- Topological polar surface area
- 147 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 5
- Heavy atoms
- 25
- Formal charge
- 0
- Complexity
- 715
Experimental & physicochemical properties
Drugs
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Antibiotics
Physicochemical properties
- Melting point
- 170 ° · 170° (dec)
- alpha
- 20 · D20 +87° (c = 1.093 in 0.1N HCl)
- Boiling point
- 251 °C · 251°C (rough estimate)
- Density
- 1.3163 · 1.3163 (rough estimate)
- refractive index
- 1.639 · 1.6390 (estimate)
- pka
- 3.3 · pKa 3.30±0.02(H2O t=35.0 I=0.00)(Approximate)
- FDA UNII
- 908 C4MV2R · B908C4MV2R
- ATC code
- 1 DB11 · J01DB11
- Symbol(GHS)
- 8 · GHS08
- Signal word
- Danger
- Hazard statements
- 334 · H334-H317
- Precautionary statements
- 261 · P261-P285-P304+P341-P342+P311-P501-P261-P272-P280-P302+P352-P333+P313-P321-P363-P501
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]
P233, P260, P261, P271, P272, P280, P284, P302+P352, P304+P340, P321, P333+P317, P342+P316, P362+P364, P403, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesSkin Sens. 1 (100%)
Safety data
- Toxicity
- LD50 in mice (mg/kg): >6000 orally; 7090 i.p. (Scartazzini, Bickel, 1978)
- Signal word
- Danger
- Symbol(GHS)
- GHS08
- Hazard statements
- H334-H317
- Precautionary statements
- P261-P285-P304+P341-P342+P311-P501-P261-P272-P280-P302+P352-P333+P313-P321-P363-P501
Chemistry & industry
Pharmacology
ATC Code
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
Protein BindingCefrixadine is 10% bound to human plasma proteins.
PharmacodynamicsCefroxadine is a cephalosporin antibiotic which produces a bactericidal effect on susceptible bacteria.
Mechanism of Action
Cefrixadine is a cephalosporin antibiotic, a class of β-lactam antibiotics similar to penicillins, which binds to and inhibits penicillin binding proteins (PBPs). PBPs are responsible for catalyzing the transpeptidase reaction which cross-links the peptide side chains on the sugar residues of a peptidoglycan unit, adding the unit to the peptidoglycan layer. This disrupts the balance between the hydrolysis of peptidoglycan, in order to insert new peptidoglycan units, by murein hydrolase and the attachment of the new units which leads to overall destruction of the peptidoglycan layer. With the loss of its peptidoglycan layer the cell also loses its resistance to the high osmotic pressure inside its membrane and lyses.
Biological Half-LifeThe serum half life is 0.9-1.1 h.
Absorption, Distribution and Excretion
Oral bioavailability of 90%.
Primarily eliminated in the urine (80-96%).
Volume of distrubution of 15 L.
The total body clearance is 340 mL/min and the renal clearance is 250 mL/min.
Applications
DescriptionCefroxadine was synthesized by Ciba-Geigy in 1972. A methoxyl group replaced the methyl group of cephradine at the 3 position of the cephem nucleus. Cefroxadine shows stronger activities than cephalexin, especially bactericidal and bacteriolytic activities, and it has better oral absorption that is less affected by a recent meal. Cefroxadine shows less renal toxicity than cephalexin in toxicological studies using animals.
Related reactions
0 records
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Compound notes
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