Cefaclor

Short description: Chemical compound

Cefaclor

Clinical data
Trade names| Biocef, Ceclor, Medacef, Distaclor, Keflor, Raniclor
AHFS/Drugs.com| Monograph
MedlinePlus| a682729
Pregnancy
category|

* AU: B1
* US: B (No risk in non-human studies)

Routes of
administration| Oral
ATC code|

* J01DC04 (WHO)

Legal status
Legal status|

* In general: ℞ (Prescription only)

Pharmacokinetic data
Bioavailability| Well absorbed, independent of food intake
Metabolism| 15% to 40%
Elimination half-life| 0.6 to 0.9 hours
Excretion| Renal
Identifiers

IUPAC name

* (6R,7R)-7-{[(2R)-2-amino-2-phenylacetyl]amino}- 3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene- 2-carboxylic acid

CAS Number|

* 53994-73-3 Y

PubChem CID|

* 51038

DrugBank|

* DB00833 Y

ChemSpider|

* 46260 N

UNII|

* 3Z6FS3IK0K

KEGG|

* D00256 Y

ChEMBL|

* ChEMBL8867 N

Chemical and physical data
Formula| C15H14ClN3O4S
Molar mass| 367.80 g·mol−1
3D model (JSmol)|

* Interactive image

SMILES

* O=C2N1/C(=C(/Cl)CS[C@@H]1[C@@H]2NC(=O)[C@@H](c3ccccc3)N)C(=O)O.O

InChI

* InChI=1S/C15H14ClN3O4S.H2O/c16-8-6-24-14-10(13(21)19(14)11(8)15(22)23)18-12(20)9(17)7-4-2-1-3-5-7;/h1-5,9-10,14H,6,17H2,(H,18,20)(H,22,23);1H2/t9-,10-,14-;/m1./s1 Y

* Key:WKJGTOYAEQDNIA-IOOZKYRYSA-N Y

NY (what is this?) (verify)

Cefaclor, sold under the trade name Ceclor among others, is a second-generation cephalosporin antibiotic used to treat certain bacterial infections such as pneumonia and infections of the ear, lung, skin, throat, and urinary tract. It is also available from other manufacturers as a generic.[1]

It was patented in 1973 and approved for medical use in 1979.[2]

## Contents

* 1 Medical uses
* 1.1 Spectrum of activity
* 2 Cautions and contraindications
* 3 Side effects
* 3.1 Pregnancy and breastfeeding
* 4 Interactions
* 4.1 Coumarins
* 4.2 Probenecid
* 4.3 Antacids
* 5 References

## Medical uses

Cefaclor belongs to the family of antibiotics known as the cephalosporins (cefalosporins). The cephalosporins are broad-spectrum antibiotics that are used for the treatment of septicaemia, pneumonia, meningitis, biliary tract infections, peritonitis, and urinary tract infections. The pharmacology of the cephalosporins is similar to that of the penicillins, excretion being principally renal. Cephalosporins penetrate the cerebrospinal fluid poorly unless the meninges are inflamed; cefotaxime is a more suitable cephalosporin than cefaclor for infections of the central nervous system, e.g. meningitis. Cefaclor is active against many bacteria, including both Gram-negative and Gram-positive organisms.[citation needed]

### Spectrum of activity

Cefaclor is frequently used against bacteria responsible for causing skin infections, otitis media, urinary tract infections, and others. Cefaclor has been shown to be active against most strains of the following microorganisms, both in vitro and in clinical infections: Gram positive aerobes - Staphylococci (including coagulase-positive, coagulase-negative, and penicillinase-producing strains), Streptococcus pneumoniae, and Streptococcus pyogenes (group A β-hemolytic streptococci). [3] The following represents MIC susceptibility data for a few medically significant microorganisms.

* Haemophilus influenzae: 0.03 μg/mL - 128 μg/mL
* Staphylcoccus aureus: 0.6 μg/mL - 128 μg/mL
* Streptococcus pyogenes: 0.06 μg/mL - 4 μg/mL

[4]

## Cautions and contraindications

Cautions include known sensitivity to beta-lactam antibacterials, such as penicillins (Cefaclor should be avoided if there is a history of immediate hypersensitivity reaction); renal impairment (no dose adjustment required, although manufacturer advises caution); pregnancy and breast-feeding (but appropriate to use); false positive urinary glucose (if tested for reducing substances) and false positive Coombs test. Cefaclor has also been reported to cause a serum sickness-like reaction in children.[5][6]

Cefaclor is contraindicated in case of hypersensitivity (i.e. allergy) to cephalosporins.[citation needed]

## Side effects

Skin allergy to cefaclor

The principal side effect of the cephalosporins is hypersensitivity. Penicillin-sensitive patients may also be allergic to the cephalosporins, depending on the side chain and it's relation to the penicillin allergy. Most patients with penicillin allergy can tolerate the majority of cephalosporins without allergic reactions. The previous percentage of 10% cross reactivity rates are a gross overestimation.[7] Allergic reactions may present as, for example, rashes, pruritus (itching), urticaria, serum sickness-like reactions with rashes, fever and arthralgia, and anaphylaxis. The frequency and severity of serum sickness-like reactions in children has led researchers to question its role in pediatric illness.[8] Other side effects include gastrointestinal disturbances (e.g. diarrhea, nausea and vomiting, abdominal discomfort, disturbances in liver enzymes, transient hepatitis and cholestatic jaundice), headache, and Stevens–Johnson syndrome. Rare side effects include eosinophilia and blood disorders (including thrombocytopenia, leucopenia, agranulocytosis, aplastic anaemia and haemolytic anaemia); reversible interstitial nephritis; hyperactivity, nervousness, sleep disturbances, hallucinations, confusion, hypertonia, and dizziness. Toxic epidermal necrolysis has been reported. In the UK, The Committee on the Safety of Medicines (CSM) has warned that the risk of diarrhea and rarely antibiotic-associated colitis are more likely with higher doses.[citation needed]

### Pregnancy and breastfeeding

Cefaclor is passed into the breast milk in small quantities, but is generally accepted to be safe to take during breastfeeding.[9] Cefaclor is not known to be harmful in pregnancy.[10]

## Interactions

### Coumarins

Cephalosporins possibly enhance the anticoagulant effect of coumarins (e.g. Warfarin) - change in patient's clinical condition, particularly associated with liver disease, intercurrent illness, or drug administration, necessitates more frequent testing of INR, and dose adjustment as necessary.[citation needed]

### Probenecid

Excretion of cephalosporins is reduced by probenecid (resulting in increased concentrations of drug in the blood plasma).[citation needed]

### Antacids

Absorption of cefaclor is reduced by antacids. Therefore antacids should not be taken right before or at the same time as cefaclor.[11][12]

## References

1. ↑ "Drugs@FDA: FDA-Approved Drugs". https://www.accessdata.fda.gov/scripts/cder/drugsatfda/index.cfm.
2. ↑ (in en) Analogue-based Drug Discovery. John Wiley & Sons. 2006. p. 493. ISBN 9783527607495. https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA493.
3. ↑ "Cefaclor drugs and health products". sdrugs.com. http://www.medicatione.com/?c=ing&s=cefaclor.
4. ↑ "Cefaclor Susceptibilty and Resistance Data". TOKU-E. 18 August 2014. http://www.toku-e.com/Assets/MIC/Cefaclor.pdf.
5. ↑ "Serum sickness-like reactions from cefaclor in children". Journal of the American Academy of Dermatology 25 (5 Pt 1): 805–808. November 1991. doi:10.1016/S0190-9622(08)80973-5. PMID 1802903.
6. ↑ "Serum sickness-like syndrome associated with cefaclor therapy". Allergy 47 (4 Pt 2): 439–440. August 1992. doi:10.1111/j.1398-9995.1992.tb02086.x. PMID 1456417.
7. ↑ Zagursky RJ, Pichichero ME. Cross-reactivity in β-Lactam Allergy [published correction appears in J Allergy Clin Immunol Pract. 2022 Feb;10(2):651]
8. ↑ "Adverse skin and joint reactions associated with oral antibiotics in children: the role of cefaclor in serum sickness-like reactions". Journal of Paediatrics and Child Health 39 (9): 677–681. December 2003. doi:10.1046/j.1440-1754.2003.00267.x. PMID 14629499.
9. ↑ "Summary of Cefaclor's use during lactation". LactMED. U.S. National Library of Medicine. http://toxnet.nlm.nih.gov/cgi-bin/sis/search/f?./temp/~gthK7d:1.
10. ↑ "Prospective follow-up of adverse reactions in breast-fed infants exposed to maternal medication". American Journal of Obstetrics and Gynecology 168 (5): 1393–1399. May 1993. doi:10.1016/s0002-9378(11)90771-6. PMID 8498418.
11. ↑ "Ceclor Uses, Side Effects & Warnings". Drugs.com. https://www.drugs.com/mtm/ceclor.html.
12. ↑ "Pharmacokinetics of cefaclor AF: effects of age, antacids and H2-receptor antagonists". Postgraduate Medical Journal 68 (Suppl 3): S3–S9. 1992. PMID 1287615.

* v
* t
* e

Antibiotics active on the cell wall and envelope (J01C-J01D)

Intracellular|

* Inhibit peptidoglycan subunit synthesis and transport: NAM synthesis inhibition (Fosfomycin)
* DADAL/AR inhibitors (Cycloserine)
* bactoprenol inhibitors (Bacitracin)

Glycopeptide|

* Inhibit PG chain elongation: Vancomycin# (Oritavancin
* Telavancin)
* Teicoplanin (Dalbavancin)
* Ramoplanin§

β-lactams/
(inhibit PBP
cross-links)|

| Penicillins
(Penams)|

| Narrow
spectrum|

| β-lactamase sensitive
(1st generation)|

* Benzylpenicillin (G)#
* Benzathine benzylpenicillin#
* Procaine benzylpenicillin#
* Phenoxymethylpenicillin (V)#
* Propicillin‡
* Pheneticillin‡
* Azidocillin‡
* Clometocillin‡
* Penamecillin‡

|

β-lactamase resistant
(2nd generation)|

* Cloxacillin# (Dicloxacillin
* Flucloxacillin)
* Oxacillin
* Nafcillin
* Methicillin‡

Extended
spectrum|

| Aminopenicillins (3rd generation)|

* Amoxicillin#
* Ampicillin# (Pivampicillin
* Hetacillin‡
* Bacampicillin‡
* Metampicillin‡
* Talampicillin‡)
* Epicillin‡

|

Carboxypenicillins (4th generation)|

* Ticarcillin
* Carbenicillin‡ / Carindacillin‡
* Temocillin‡

Ureidopenicillins (4th generation)|

* Piperacillin
* Azlocillin‡
* Mezlocillin‡

Other|

* Mecillinam‡ (Pivmecillinam‡)
* Sulbenicillin‡

Penems|

* Faropenem‡
* Ritipenem§

Carbapenems|

* Ertapenem
* Antipseudomonal (Doripenem
* Imipenem
* Meropenem)
* Biapenem‡
* Panipenem‡

Cephalosporins
/ Cephamycins
(Cephems)|

| 1st generation|

* Cefazolin#
* Cefalexin #
* Cefadroxil
* Cefapirin
* Cefazedone‡
* Cefazaflur‡
* Cefradine‡
* Cefroxadine‡
* Ceftezole‡
* Cefaloglycin‡
* Cefacetrile‡
* Cefalonium‡
* Cefaloridine‡
* Cefalotin‡
* Cefatrizine‡

|

2nd generation|

* Cefaclor
* Cefotetan
* Cephamycin (Cefoxitin
* Cefprozil
* Cefuroxime
* Cefuroxime axetil
* Cefamandole‡
* Cefminox‡
* Cefonicid‡
* Ceforanide‡
* Cefbuperazone‡
* Cefuzonam‡
* Cefmetazole‡)
* Carbacephem‡ (Loracarbef‡)

3rd generation|

* Cefixime#
* Ceftriaxone#
* Cefotaxime#
* Antipseudomonal (Ceftazidime#
* Cefoperazone‡)
* Cefdinir
* Cefcapene
* Cefdaloxime
* Ceftizoxime
* Cefmenoxime
* Cefpiramide
* Cefpodoxime
* Ceftibuten
* Cefditoren
* Cefotiam‡
* Cefetamet‡
* Cefodizime‡
* Cefpimizole‡
* Cefsulodin‡
* Cefteram‡
* Ceftiolene‡
* Oxacephem (Flomoxef‡
* Latamoxef‡)

4th generation|

* Cefepime
* Cefozopran‡
* Cefpirome‡
* Cefquinome‡

5th generation|

* Ceftaroline fosamil
* Ceftolozane
* Ceftobiprole

Veterinary|

* Ceftiofur
* Cefquinome
* Cefovecin

Monobactams|

* Aztreonam#
* Tigemonam‡
* Carumonam‡
* Nocardicin A‡

β-lactamase inhibitors|

* Penam (Sulbactam
* Tazobactam)
* Clavam (Clavulanic acid]])
* Sulbactam
* non-β-lactam (Relebactam
* Avibactam
* Vaborbactam)

Combinations|

* Amoxicillin/clavulanic acid#
* Imipenem/cilastatin#
* Imipenem/cilastatin/relebactam
* Ampicillin/flucloxacillin
* Ampicillin/sulbactam (Sultamicillin)
* Ceftazidime/avibactam
* Piperacillin/tazobactam
* Ceftolozane/tazobactam
* Cefoperazone/sulbactam
* Meropenem/vaborbactam

Other|

* polymyxins/detergent
* Colistin
* Polymyxin B
* depolarizing
* Daptomycin
* Hydrolyze NAM-NAG
* lysozyme
* Tyrothricin
* Gramicidin
* Tyrocidine
* Isoniazid#
* Teixobactin

* #WHO-EM
* ‡Withdrawn from market
* Clinical trials:
* †Phase III
* §Never to phase III

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