Cefaclor

Last updated
Cefaclor
Cefaclor.svg
Clinical data
Trade names Biocef, Ceclor, Medacef, Distaclor, Keflor, Raniclor
AHFS/Drugs.com Monograph
MedlinePlus a682729
Pregnancy
category
  • AU:B1
Routes of
administration 		Oral
ATC code
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
  • (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
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.053.536 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C15H14ClN3O4S
Molar mass 367.80 g·mol−1
3D model (JSmol)
  • O=C2N1/C(=C(/Cl)CS[C@@H]1[C@@H]2NC(=O)[C@@H](c3ccccc3)N)C(=O)O.O
  • 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 Yes check.svgY
  • Key:WKJGTOYAEQDNIA-IOOZKYRYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (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]

Contents

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

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.

[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 Allergy to Antibiotic Cefaclor.JPG
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]

Related Research Articles

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The side effects of penicillin are bodily responses to penicillin and closely related antibiotics that do not relate directly to its effect on bacteria. A side effect is an effect that is not intended with normal dosing. Some of these reactions are visible and some occur in the body's organs or blood. Penicillins are a widely used group of medications that are effective for the treatment of a wide variety of bacterial infections in human adults and children as well as other species. Some side effects are predictable, of which some are common but not serious, some are uncommon and serious and others are rare. The route of administration of penicillin can have an effect on the development of side effects. An example of this is irritation and inflammation that develops at a peripheral infusion site when penicillin is administered intravenously. In addition, penicillin is available in different forms. There are different penicillin medications as well as a number of β-lactam antibiotics derived from penicillin.

References

  1. ↑ "Drugs@FDA: FDA-Approved Drugs".
  2. ↑ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 493. ISBN   9783527607495.
  3. ↑ Salvi R. "Cefaclor drugs and health products". sdrugs.com.
  4. ↑ "Cefaclor Susceptibilty and Resistance Data" (PDF). TOKU-E. 18 August 2014. Archived from the original (PDF) on 2016-03-03. Retrieved 2013-08-13.
  5. ↑ Hebert AA, Sigman ES, Levy ML (November 1991). "Serum sickness-like reactions from cefaclor in children". Journal of the American Academy of Dermatology. 25 (5 Pt 1): 805–808. doi:10.1016/S0190-9622(08)80973-5. PMID   1802903.
  6. ↑ Parra FM, Igea JM, Martín JA, Alonso MD, Lezaun A, Sainz T (August 1992). "Serum sickness-like syndrome associated with cefaclor therapy". Allergy. 47 (4 Pt 2): 439–440. doi:10.1111/j.1398-9995.1992.tb02086.x. PMID   1456417. S2CID   46029579.
  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. ↑ King BA, Geelhoed GC (December 2003). "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. doi:10.1046/j.1440-1754.2003.00267.x. PMID   14629499. S2CID   25762196.
  9. ↑ "Summary of Cefaclor's use during lactation". LactMED. U.S. National Library of Medicine. Retrieved 22 May 2011.
  10. ↑ Ito S, Blajchman A, Stephenson M, Eliopoulos C, Koren G (May 1993). "Prospective follow-up of adverse reactions in breast-fed infants exposed to maternal medication". American Journal of Obstetrics and Gynecology. 168 (5): 1393–1399. doi:10.1016/s0002-9378(11)90771-6. PMID   8498418.
  11. ↑ "Ceclor Uses, Side Effects & Warnings". Drugs.com.
  12. ↑ Satterwhite JH, Cerimele BJ, Coleman DL, Hatcher BL, Kisicki J, DeSante KA (1992). "Pharmacokinetics of cefaclor AF: effects of age, antacids and H2-receptor antagonists". Postgraduate Medical Journal. 68 (Suppl 3): S3–S9. PMID   1287615.
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