Basic information
- CAS
50370-12-2- Standard SMILES
CC1=C(C(=O)[O-])N2C(=O)[C@@H](NC(=O)[C@H]([NH3+])c3ccc(O)cc3)[C@H]2SC1- InChIKey
BOEGTKLJZSQCCD-UEKVPHQBSA-N- Molecular formula
- C16H17N3O5S
- Average molar mass
- 363.4 g/mol
- Monoisotopic mass
- 363.08889182
Overview
Long-acting, broad-spectrum, water-soluble, cephalexin derivative.
Names & identifiers
- Preferred name
- CID 6560167
- IUPAC
- (6R,7R)-7-[[(2R)-2-azaniumyl-2-(4-hydroxyphenyl)acetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
- English name
- CEFADROXIL
- Molecular formula
- C16H17N3O5S
- Molecular weight
- 363.39
Names & synonyms
cdxduricefUltracefcephadroxil(6R,7R)-7-[[(R)-Amino(p-hydroxyphenyl)acetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acids-578RoxilEvacefNeucefNSC438
Database identifiers
- CAS
50370-12-2、66592-87-8- PubChem CID
- 6560167
Properties
Computed structural properties
- XLogP
- -1.4
- Topological polar surface area
- 163 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 3
- Heavy atoms
- 25
- Formal charge
- 0
- Complexity
- 624
Experimental & physicochemical properties
LogP-0.4
Solubility3.99e-01 g/L
Melting Point197 °C
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 197 °C · 197°C (rough estimate)
- Boiling point
- 238 °C · 238°C (rough estimate)
- Density
- 1.59 · 1.59
- refractive index
- 1.639 · 1.6390 (estimate)
- storage temp.
- 2 · under inert gas (nitrogen or Argon) at 2–8 °C
- solubility
- 9.17 · Water:9.17(Max Conc. mg/mL);25.23(Max Conc. mM)
- pka
- 3.12 · 3.12±0.50(Predicted)
- form
- powder or crystals
- color
- White to off-white
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- wgk
- 2
- rtecs
- XI0337000
- risk_code
- 36/37/38-42/43
- Signal word
- Danger
- Symbol(GHS)
- GHS07,GHS08
- hazard_code
- Xn
- safety_code
- 26-36
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H315-H317-H319-H334-H335
- Hazard Classifications
- Eye Irrit. 2Resp. Sens. 1Skin Irrit. 2Skin Sens. 1STOT SE 3
- Precautionary statements
- P280-P302+P352-P305+P351+P338
Chemistry & industry
Pharmacology
Protein BindingBinding rates of cefadroxil were 28.1% by U.F. method
PharmacodynamicsCefadroxil, a first-generation cephalosporin antibiotic, is used to treat urinary tract infections, skin and skin structure infections, pharyngitis, and tonsillitis.
Mechanism of Action
Like all beta-lactam antibiotics, cefadroxil 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 cefadroxil interferes with an autolysin inhibitor.
Biological Half-Life1.5 hours
Absorption, Distribution and Excretion
Cefadroxil is well absorbed on oral administration; food does not interfere with its absorption.
Over 90% of the drug is excreted unchanged in the urine within 24 hours. Cefadroxil was detected in the placenta and breast milk.
Cellular LocationsMembrane
Applications
DescriptionCephadroxil is an orally administered antibiotic, which is very similar to cephalexin. After oral administration, its peak serum level is slightly lower than that of cephalexin, but it is excreted more slowly. Therefore, it can be used for oral administration at 8- or 12-hourly intervals (Buck and Price, 1977; Pfeffer et al., 1977). Cephadroxil is still available in a number of European countries (for example, Spain, Belgium, Luxembourg, Portugal, and Finland, among others).
UsesAntibacterial;Bacterial transpeptidase inhibitor
Upstream & downstream products
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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