Content
• Introduction and Definition
A

• Advantage and Disadvantage

• SAR

• Classification
B

C

• Mechanism of action...
 Wide-spectrumβ-lactumbactericidal, chemical properties
being similar to the penicillins

 Cephamycins

: Streptomyces s...
Advantages
1. Non-toxic
2. ↓ risk of allergy.
3. More stable in
acidic medium
[less ring strain]
4. Higher
penicillinase
r...
Mechanism of action:
Cephalosporins are bactericidal and have the
same mode of action as other beta-lactam
antibiotics (s...
These has been conventionally classified into four
generations. Based on Generation system
• This is based on chronologica...
First generation:
Developed in 1960, active against Gm+ weaker on Gm- orgnisms.
• Cephalothin: 1st cephalosporin used. (Pa...
Second generation:
• Cefuroxime: Resistant to Gm- beta lactamase (Parenteral)
Important use: meningitis caused by H. influ...
Third generation
•
Broad-spectrum.
•
Active against Gm- enterobacteriacae.
•
Some are anti-pseudomal
•
Resistant to beta-l...
Ceftriaxone:
• Longer duration of action. (MONOCEF/CEFERA)
• Good CSF penetration.
USES: Bacterial meningitis
Multi-Resist...
Cefoperazone:
(CEFOMYCIN/NOVACIP)
• Strong anti-pseudomonal property.
• Cidal against S.typhi, B.fragilis.
• More suscepti...
Fourth generation:
Cefepime:
(CEPIME/MEGAPIME)
• Highly resistant to beta-lactamase.
• Active against pseudomonas and Stap...
Cephalosporins are given parenterally and orally.
Extent of binding to plasma protein vary from one to another.
e.g. Cefaz...
1. Alternative to penicillin in allergic
patients
2. Upper respiratory tract infections
and otitis media
cefaclor
cefuroxi...
1. Hypersensitivity reactions- most common
Anaphylaxis, bronchspasm, urticaria
Maculopapular rash- more common
2. Nephroto...
^ "cephalosporin" at Dorland's Medical Dictionary

^ "Cephalosporin spectrum of
resistance". Retrieved 1 July 2012.
^ Stor...
M. Zaharna Clin. Chem. 2009
Cephalosporins antibiotics
Cephalosporins antibiotics
Cephalosporins antibiotics
Cephalosporins antibiotics
Cephalosporins antibiotics
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Cephalosporins antibiotics

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by student in o6u pharmacy(ahmed abo elkhair)

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Cephalosporins antibiotics

  1. 1. Content • Introduction and Definition A • Advantage and Disadvantage • SAR • Classification B C • Mechanism of action • Therapeutic uses • Pharmacokinetics • Side effect
  2. 2.  Wide-spectrumβ-lactumbactericidal, chemical properties being similar to the penicillins  Cephamycins : Streptomyces species or are synthetic derivatives produced by substituting oxygen for sulfur (methoxy group) in cephalosporin nucleus.  Cephalosporium acremonium, containing common 7-aminocephalosporanic acid nucleus the
  3. 3. Advantages 1. Non-toxic 2. ↓ risk of allergy. 3. More stable in acidic medium [less ring strain] 4. Higher penicillinase resistance. 5. Good activity ≠ Gve & G+ve Disadvantage 1. Difficult to isolate & purify [with highly polar side chain] 2. Lower potency [less strained ring] 3. ↓ absorbed orally.
  4. 4. Mechanism of action: Cephalosporins are bactericidal and have the same mode of action as other beta-lactam antibiotics (such as penicillin). Cephalosporins disrupt the synthesis of the peptidoglycan layer of bacterial cell walls.  The peptidoglycan layer is important for cell wall structural integrity.
  5. 5. These has been conventionally classified into four generations. Based on Generation system • This is based on chronological sequence of development, but more importantly ,takes into consideration the overall antibacterial spectrum as well as potency. • First-generation cephalosporins are predominantly active against Gram-positive bacteria, and successive generations have increased activity against Gram-negative bacteria (albeit often with reduced activity against Gram-positive organisms).
  6. 6. First generation: Developed in 1960, active against Gm+ weaker on Gm- orgnisms. • Cephalothin: 1st cephalosporin used. (Parenteral) active against: Streptococci, Staphylococci, gonococci, meningococci, C.diptheriae and clostridia. • Cephalexin: Orally active. commonly used. (SPORIDEX) • Cefadroxil: Excellent tissue penetration (cefadrox) Excreted unchanged in urine. Dose adjustment in renal impaired patients. • Cephazolin: Active against klebsiella and E.coli. (Parenteral) Preferred parenteral 1st gen cephalosporin for surgical prophylaxis , (ALCIZONE/ORIZOLIN)
  7. 7. Second generation: • Cefuroxime: Resistant to Gm- beta lactamase (Parenteral) Important use: meningitis caused by H. influenzae, • Cefuroxime axetil: Ester of cefuroxime, effective oral Uses: URTI, LRTI, UTI, skin and soft tissue infection group B streptococci,salmonella, E.coli (CEFTUM,ZOCEF)
  8. 8. Third generation • Broad-spectrum. • Active against Gm- enterobacteriacae. • Some are anti-pseudomal • Resistant to beta-lactamase. Cefotaxim: (TAXIM/OMNATAX)  Prototype of third generation cephalosporin.  Widely distributed in body tissues and fluids, penetrates CSF best when meninges are inflamed. Uses: Aerobic Gm- bacteria infection, poor on anaerobes (B. fragilis), Staphylococci and pseudomonas. prominent indications: meningitis 11
  9. 9. Ceftriaxone: • Longer duration of action. (MONOCEF/CEFERA) • Good CSF penetration. USES: Bacterial meningitis Multi-Resistant typhoid fever Complicated Uniary tract infection Ceftazidime: • Active against pseudomonas. • Burn. 12 (CEFZID/TAZID)
  10. 10. Cefoperazone: (CEFOMYCIN/NOVACIP) • Strong anti-pseudomonal property. • Cidal against S.typhi, B.fragilis. • More susceptible to beta-lactamase. USES: severe urinary, biliary, respiratory, skin-soft tissue infection, meningitis and septicaemia. Cefixime: • • (ORIFIX/TAXIM-O/OMNATAX) Orally active 3rd generation Broad spectrum of action- enterobacteriaceae, H. influenzae, Strep pyogenes. Not active against Staph and Pseudomonas . Cefpodoxim proxetil. (CEPODEM) • Orally active 3rd generation • Active against enterobacteriaceae and streptococci. • Excellent outcome in RTI, UTI and soft-tissue infection. Cefdinir: (SEFDIN/ADCEF) • Orally active • 13 Excellent results in pneumonia,COPD,ENT & skin infections.
  11. 11. Fourth generation: Cefepime: (CEPIME/MEGAPIME) • Highly resistant to beta-lactamase. • Active against pseudomonas and Staph besides host of organisms Uses: Serious life-threatening hospital acquired pneumonia Febrile neutropenia. Bacterremia and septicaemia. Cefpirome: (CEFROM/CEFORTH) • Treatment of serious and resistant hospital acquired infections including septicaemia ,pneumonia. • Covers some Gm+ organisms as well.
  12. 12. Cephalosporins are given parenterally and orally. Extent of binding to plasma protein vary from one to another. e.g. Cefazolin is 80% protein bound ( hence, long t1/2 ) Cephalexin is 10-15% protein bound Relatively lipid insoluble ( like penicillins ) Hence,do not penetrate cells or the CNS, except for third generations. Mostly excreted unchanged by the kidney (glomerular & tubular secretion ), except, ceftazidime & cefoperazone( glomerular) Probenecid slows their elimination and prolong their half-live ( except Ceftazidime & cefoperazone) Half-life 30-90 min; ceftriaxone 4-7 hr
  13. 13. 1. Alternative to penicillin in allergic patients 2. Upper respiratory tract infections and otitis media cefaclor cefuroxime axetil cefixime cefprozil 3. Septicaemia caused by G- bacteria ( P.aeruginosae) A penicillin(eg.Piperacillin/ Ticarcillin) +aminoglycoside OR A cephalosporin(eg. ceftazidime ) + AG 4. Urinary tract infections Cefuroxime, Cefixime . 5. Prophlaxis in surgery Appendectomy ( bowel anaerobes ) eg. Cefoxitin Obstetrical &gynecological, urological, orthopedic procedures, etc ( S. aureus & S. epidermidis ) eg. Cefazoline 6. Meningitis- N. Meningitidis Ceftriaxone Cefotaxime( pref. in neonate)
  14. 14. 1. Hypersensitivity reactions- most common Anaphylaxis, bronchspasm, urticaria Maculopapular rash- more common 2. Nephrotoxicity ; esp. cephradine 3. Thrombophlebitis ( i.v admin. ) 4. Superinfections 5. Diarrhea-oral cephalosporins, cefoperazone, ceftriaxone & moxalactam. 6. cefamandole, moxalactam & cefoperazone may cause: a) bleeding disorders b) Flushing, tachycardia, vomiting with alcohol intake
  15. 15. ^ "cephalosporin" at Dorland's Medical Dictionary ^ "Cephalosporin spectrum of resistance". Retrieved 1 July 2012. ^ Stork CM (2006). "Antibiotics, antifungals, and antivirals". In Nelson LH,
  16. 16. M. Zaharna Clin. Chem. 2009
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