Cefadroxil
🧬 Cross-allergy: Cephalosporins
JFDA label: Biodroxil 125mg suspension
Mechanism of Action
Inhibitor of Bacterial penicillin-binding protein — Bacterial penicillin-binding protein inhibitor
| Target | Action | Gene / class |
|---|---|---|
| Bacterial penicillin-binding protein efficacy | INHIBITOR |
Indications
Approved
- Pharyngitis and/or tonsillitis
- Skin and skin structure infections
- Urinary tract infection
Off-label
- Prosthetic joint infection with Staphylococci (oxacillin-susceptible)
Antimicrobial Spectrum
Expected / intrinsic spectrum (EUCAST breakpoints & labels) — not local resistance. Source: EUCAST v16 · openfda-label.
Bacteria
| Organism | Activity | MIC |
|---|---|---|
| Acinetobacter calcoaceticus | Active | — |
| Enterobacterales | Susceptible | 16.0 mg/L |
| Enterococcus faecalis | Active | — |
| Enterococcus faecium | Active | — |
| Escherichia coli | Active | — |
| Morganella morganii | Active | — |
| Proteus mirabilis | Active | — |
| Proteus morganii | Active | — |
| Staphylococcus aureus | Active | — |
| Streptococcus faecalis | Active | — |
| Streptococcus faecium | Active | — |
| Streptococcus pyogenes | Active | — |
Class profile
| gramStatus | Both |
|---|---|
| spectrumBreadth | Moderate |
| atypicalCoverage | No |
| isBactericidal | 1 |
| moaCategory | Cell wall synthesis inhibitor (beta-lactam, 1st generation cephalosporin) |
| pdIndex | Time-dependent |
| postAntibioticEffect | None |
| mrsaCoverage | 0 |
| resistanceMechanisms | Beta-lactamase production,PBP mutations |
Contraindications
Source: Lexicomp
- Hypersensitivity to cefadroxil, any component of the formulation, or other cephalosporins Absolute
Adverse Reactions
Other (1)
Common Gastrointestinal: Diarrhea
Dosing
Source: Lexicomp
Warnings & Precautions
Source: Lexicomp
Hypersensitivity reactions
Hypersensitivity reactions, including anaphylaxis, may occur. If an allergic reaction occurs, discontinue treatment and institute appropriate supportive measures.
Penicillin allergy
Use with caution in patients with a history of penicillin allergy.
Superinfection
Prolonged use may result in fungal or bacterial superinfection, including C. difficile-associated diarrhea (CDAD) and pseudomembranous colitis; CDAD has been observed >2 months postantibiotic treatment. Disease-related concerns:
Colitis
Use with caution in patients with a history of gastrointestinal disease, particularly colitis.
Renal impairment
Use with caution in patients with renal impairment (CrCl 2); dosage adjustment may be needed. Concurrent drug therapy issues:
Drug-drug interactions
Potentially significant interactions may exist, requiring dose or frequency adjustment, additional monitoring, and/or selection of alternative therapy. Consult drug interactions database for more detailed information. Dosage form specific issues:
Benzyl alcohol and derivatives
Some dosage forms may contain sodium benzoate/benzoic acid; benzoic acid (benzoate) is a metabolite of benzyl alcohol; large amounts of benzyl alcohol (≥99 mg/kg/day) have been associated with a potentially fatal toxicity (“gasping syndrome”) in neonates; the “gasping syndrome” consists of metabolic acidosis, respiratory distress, gasping respirations, CNS dysfunction (including convulsions, intracranial hemorrhage), hypotension, and cardiovascular collapse (AAP ["Inactive" 1997]; CDC 1982); some data suggest that benzoate displaces bilirubin from protein binding sites (Ahlfors 2001); avoid or use dosage forms containing benzyl alcohol derivative with caution in neonates. See manufacturer’s labeling.
Propylene glycol
Some dosage forms may contain propylene glycol; large amounts are potentially toxic and have been associated with hyperosmolality, lactic acidosis, seizures and respiratory depression; use caution (AAP 1997; Zar 2007). See manufacturer’s labeling
Suspension
May contain sulfur dioxide (sulfite); hypersensitivity reactions, including anaphylaxis and/or asthmatic exacerbations, may occur (may be life threatening). Other warnings/precautions:
Appropriate use
Only IM penicillin has been shown to be effective in the prophylaxis of rheumatic fever. Cefadroxil is generally effective in the eradication of streptococci from the oropharynx; efficacy data for cefadroxil in the prophylaxis of subsequent rheumatic fever episodes are not available.
Pregnancy & Lactation
Pregnancy
Adverse events have not been observed in animal reproduction studies. Cefadroxil crosses the placenta. Limited data is available concerning the use of cefadroxil in pregnancy; however, adverse fetal effects were not noted in a small clinical trial.
Lactation
Very small amounts of cefadroxil are excreted in breast milk. The manufacturer recommends that caution be exercised when administering cefadroxil to nursing women. Nondose-related effects could include modification of bowel flora.
Monitoring
| Efficacy | Culture and susceptibility testing; clinical resolution (temperature, WBC, CRP, procalcitonin) |
|---|---|
| Toxicity | Renal function (dose adjustment in renal impairment); hepatic function for hepatically cleared agents; signs of C. difficile infection (diarrhoea) |
| Clinical pearl | Culture results guide de-escalation to narrower-spectrum therapy. Review antibiotic appropriateness at 48–72 h (antimicrobial stewardship). |
| Counseling | Complete the full course. Report persistent diarrhoea, rash, or lack of improvement after 48–72 h. |
Chemistry & Properties
| Formula | C16H17N3O5S |
|---|---|
| Molecular weight | 363.39 g/mol |
| IUPAC name | (6R,7R)-7-[[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid |
| CAS | 50370-12-2 |
| PubChem CID | 47965 |
| InChIKey | BOEGTKLJZSQCCD-UEKVPHQBSA-N |
| logP | 0.15 (XLogP -2.1) |
| Polar surface area | 132.96 Ų |
| H-bond acceptors / donors | 6 / 4 |
| Drug-likeness (QED) | 0.56 |
| Lipinski violations | 0 |
SMILES
CC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)[C@H](N)c3ccc(O)cc3)[C@H]2SC1Biology & Pharmacokinetics
Pharmacokinetics
| BBB penetrant | No |
|---|
Enzyme interactions
| Enzyme | Role | Detail |
|---|---|---|
| CYP2D6 | Substrate | — |
Transporters
BCRP (Inhibitor)BSEP (Inhibitor)BSEP (Inhibitor)MCT1 (Inhibitor)MRP1 (Inhibitor)MRP2 (Inhibitor)MRP3 (Inhibitor)MRP4 (Inhibitor)OAT1 (Inhibitor)OAT2 (Inhibitor)OAT3 (Inhibitor)OAT4 (Inhibitor)OATP1B1 (Inhibitor)OATP1B1 (Inhibitor)OATP1B3 (Inhibitor)OATP1B3 (Inhibitor)OATP2B1 (Inhibitor)OCTN2 (Inhibitor)P-gp (Inhibitor)PEPT1 (Inhibitor)PEPT2 (Inhibitor)BCRP (Substrate)MRP1 (Substrate)MRP2 (Substrate)MRP3 (Substrate)MRP4 (Substrate)OATP1B3 (Substrate)P-gp (Substrate)PEPT1 (Substrate)PEPT2 (Substrate)
Drug–drug interactions (8, DDInter)
| Interacting drug | Severity | Management |
|---|---|---|
| Balsalazide | moderate | |
| Chloramphenicol | moderate | |
| Dicoumarol | moderate | |
| Ethinylestradiol | moderate | |
| Mycophenolic acid | moderate | |
| Pemetrexed | moderate | |
| Picosulfuric acid | moderate | |
| Warfarin | moderate |
Registered Products (23)
| Brand | Form / strength | Pack | Agent | Citizen (JOD) |
|---|---|---|---|---|
| Biodroxil | Suspension 125 mg/5 ml | 60 ml pack varies | Nabulsi Drug Store | 1.570 |
| Droxil | Suspension 250 mg/5 ml | 60 ml | UNITED PHARM.MFG.CO.LTD(UPM)/JORDAN | 1.920 |
| Midroxil Dry Suspension | Suspension 250 mg/5 ml | 60 ml pack varies | MIDDLE EAST PHARMA&CHEMICAL IND/JORDAN | 2.060 |
| Biodroxil | Suspension 125 mg/5 ml | 100 ml pack varies | Nabulsi Drug Store | 2.610 |
| Cefadril-250 suspension. | Suspension 250 mg/5 ml | 60 ml | AL-RAM PHARMA.INDUS.CO.LTD/JORDAN | 2.750 |
| Droxicef sus | Suspension 250 mg/5 ml | 60 ml | Pharma International Company/ Jordan | 2.750 |
| Midroxil Capsules | Capsule 500 mg | 12 cap pack varies | MIDDLE EAST PHARMA&CHEMICAL IND/JORDAN | 2.880 |
| Midroxil Dry Suspension | Suspension 250 mg/5 ml | 100 ml pack varies | MIDDLE EAST PHARMA&CHEMICAL IND/JORDAN | 3.430 |
| Cedrox 500 Capsules | Capsule 500 mg | 12 cap | Hikma Pharmaceuticals Co.Ltd/Jordan | 4.600 |
| Cefadril-500mg cap. | Capsule 500 mg | 12 cap pack varies | AL-RAM PHARMA.INDUS.CO.LTD/JORDAN | 4.600 |
| Droxicef cap | Capsule 500 mg | 12 cap | Pharma International Company/ Jordan | 4.600 |
| Droxil Capsules | Capsule 500 mg | 12 cap pack varies | UNITED PHARM.MFG.CO.LTD(UPM)/JORDAN | 4.600 |
| Midroxil Capsules | Capsule 500 mg | 20 cap pack varies | MIDDLE EAST PHARMA&CHEMICAL IND/JORDAN | 4.800 |
| Cedrox 500 Suspension | Suspension 500 mg/5 ml | 60 ml | Hikma Pharmaceuticals Co.Ltd/Jordan | 5.210 |
| Midroxil Dry Suspension | Suspension 500 mg/5 ml | 60 ml pack varies | MIDDLE EAST PHARMA&CHEMICAL IND/JORDAN | 5.210 |
| Droxicef tab | Tablet 1 g | 10 tab | Pharma International Company/ Jordan | 6.150 |
| Cedrox | Tablet 1 g | 12 tab | Hikma Pharmaceuticals Co.Ltd/Jordan | 8.070 |
| Midroxil Dry Suspension | Suspension 500 mg/5 ml | 100 ml pack varies | MIDDLE EAST PHARMA&CHEMICAL IND/JORDAN | 8.680 |
| Droxil Capsules | Capsule 500 mg | 300 cap pack varies | UNITED PHARM.MFG.CO.LTD(UPM)/JORDAN | 94.300 |
| Midroxil Capsules | Capsule 500 mg | 500's pack varies | MIDDLE EAST PHARMA&CHEMICAL IND/JORDAN | 102.000 |
| Cefadril-500mg cap. | Capsule 500 mg | 600 cap pack varies | AL-RAM PHARMA.INDUS.CO.LTD/JORDAN | 174.800 |
| Cefadril-500mg cap. | Capsule 500 mg | 700 cap pack varies | AL-RAM PHARMA.INDUS.CO.LTD/JORDAN | 183.670 |
| Cefadril-500mg cap. | Capsule 500 mg | 1200 cap pack varies | AL-RAM PHARMA.INDUS.CO.LTD/JORDAN | 349.600 |