Ceftazidime

Ceftazidime
Ceftazidime
Systematic (IUPAC) name
(6R,7R,Z)-7-(2-(2-aminothiazol-4-yl)-
2-(2-carboxypropan-2-yloxyimino)acetamido)-8-oxo-
3-(pyridinium-1-ylmethyl)-5-thia-1-aza-bicyclo[4.2.0]
oct-2-ene-2-carboxylate
Clinical data
Trade names Fortaz, Tazicef
AHFS/Drugs.com monograph
MedlinePlus a686007
Pregnancy cat. B1(AU) B(US)
Legal status Prescription Only (S4) (AU)
Routes Intravenous, intramuscular
Pharmacokinetic data
Bioavailability 91% (IM)
Metabolism negligible
Half-life 1.6–2 hours
Excretion 90–96% renal
Identifiers
CAS number 72558-82-8
ATC code J01DD02
PubChem CID 5481173
DrugBank APRD00857
ChemSpider 4587145 YesY
UNII DZR1ENT301 YesY
ChEBI CHEBI:3508 YesY
ChEMBL CHEMBL201 YesY
Chemical data
Formula C22H22N6O7S2 
Mol. mass 546.58 g/mol
SMILES eMolecules & PubChem
 YesY(what is this?)  (verify)

Ceftazidime (INN) (play /sɛfˈtæzɨdiːm/) is a third-generation cephalosporin antibiotic. Like other third-generation cephalosporins, it has broad spectrum activity against Gram-positive and Gram-negative bacteria. Unlike most third-generation agents, it is active against Pseudomonas aeruginosa, however it has weaker activity against Gram-positive microorganisms and is not used for such infections. Ceftazidime pentahydrate is marketed under various trade names including Cefzim (Pharco B International), Fortum (GSK), and Fortaz.

Clinical use

Main article: Cephalosporin

Ceftazidime is usually reserved for the treatment of infections caused by Pseudomonas aeruginosa. It is also used in the empirical therapy of febrile neutropenia, in combination with other antibiotics. It is usually given IV or IM every 8–12 hours (2 - 3 times a day), with dosage varying by the indication, infection severity, and/or renal function of the recipient.

Ceftazidine is first line treatment for the rare tropical infection, melioidosis.[1]

Chemistry

In addition to the syn-configuration of the imino side chain, compared to other third-generation cephalosporins, the more complex moiety (containing two methyl and a carboxylic acid group) confers extra stability to β-lactamase enzymes produced by many Gram-negative bacteria. The extra stability to β-lactamases increases the activity of ceftazidime against otherwise resistant Gram-negative organisms including Pseudomonas aeruginosa. The charged pyridinum moiety increases water-solubility.

References

  1. ^ White NJ (2003). "Melioidosis". Lancet 361 (9370): 1715–722. doi:10.1016/S0140-6736(03)13374-0. PMID 12767750. 
v · d · eAntibacterials: cell envelope antibiotics (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)

Benzylpenicillin (G)#: Clometocillin • Benzathine benzylpenicillin#  • Procaine benzylpenicillin# • Azidocillin • Penamecillin

Phenoxymethylpenicillin (V)#: Propicillin • Benzathine phenoxymethylpenicillin • Pheneticillin
Penems
Biapenem • Ertapenem • antipseudomonal (Doripenem • Imipenem • Meropenem) • Panipenem
Cefixime# • Ceftriaxone# • antipseudomonal (Ceftazidime# • Cefoperazone) • Cefcapene • Cefdaloxime • Cefdinir • Cefditoren • Cefetamet • Cefmenoxime • Cefodizime • Cefotaxime • Cefpimizole • Cefpiramide • Cefpodoxime • Cefsulodin • Cefteram • Ceftibuten • Ceftiolene • Ceftizoxime • oxacephem (Flomoxef, Latamoxef ‡)
4th (antips-)
Ceftobiprole • Ceftaroline fosamil
Aztreonam • Tigemonam • Carumonam • Tabtoxin
Combinations
Other
polymyxins/detergent (Colistin, Polymyxin B) • depolarizing (Daptomycin) • hydrolyze NAM-NAG (Lysozyme) • Gramicidin

M: BAC

bact (clas)

gr+f/gr+a(t)/gr-p(c)/gr-o

drug(J1p, w, n, m, vacc)

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  • Ceftazidime — Ceftazidine anhydre Général Nom IUPAC acide (6R,7R,Z) 7 (2 (2 aminothiazol 4 yl) 2 (2 carboxypropan 2 yloxyimino)acétamido) 8 oxo 3 (pyridinium 1 ylméthyl) 5 thia 1 aza bicyclo[4.2.0] oct 2 ène 2 car …   Wikipédia en Français

  • Ceftazidime — ЦЕФТАЗИДИМ ( Сеftаzidimе )*. Цефалоспориновый антибиотик третьего поколения для парентерального применения. По химической структуре близок к другим препаратам этой группы (см. Цефтриаксон). Синонимы: Кефадим, Мироцеф, Фортум, Сefоrtаn, Сеftim,… …   Словарь медицинских препаратов

  • ceftazidime — noun A third generation cephalosporin antibiotic, usually reserved for the treatment of infections caused by Pseudomonas aeruginosa …   Wiktionary

  • ceftazidime — cef·taz·i·dime sef taz ə .dēm n a semisynthetic cephalosporin antibiotic that is administered parenterally in the form of its hydrate C22H22N6O7S2·5H2O * * * cef·ta·zi·dime (sef tazґĭ dēm″) [USP] a semisynthetic, broad spectrum,… …   Medical dictionary

  • ceftazidime — n. a third generation cephalosporin antibiotic that has good activity against Gram negative bacteria (including Pseudomonas). It is administered by intravenous or intramuscular injection for the treatment of urinary and respiratory tract… …   The new mediacal dictionary

  • ceftazidime — noun a parenteral cephalosporin (trade names Fortaz and Tazicef) used to treat moderate infections • Syn: ↑Fortaz, ↑Tazicef • Usage Domain: ↑trade name (for: ↑Tazicef), ↑trade name ( …   Useful english dictionary

  • ceftazidime sodium — A cephalosporin antibiotic especially effective against enterobacteria and species of Pseudomonas …   Medical dictionary

  • 72558-82-8 — Ceftazidime Ceftazidine anhydre Général Nom IUPAC acide (6R,7R,Z) 7 (2 (2 aminothiazol 4 yl) 2 (2 carboxypropan 2 yloxyimino)acétamido) 8 oxo 3 (pyridinium 1 ylméthyl) 5 thia 1 aza bicyclo[4.2 …   Wikipédia en Français

  • 78439-06-2 — Ceftazidime Ceftazidine anhydre Général Nom IUPAC acide (6R,7R,Z) 7 (2 (2 aminothiazol 4 yl) 2 (2 carboxypropan 2 yloxyimino)acétamido) 8 oxo 3 (pyridinium 1 ylméthyl) 5 thia 1 aza bicyclo[4.2 …   Wikipédia en Français

  • C22H22N6O7S2 — Ceftazidime Ceftazidine anhydre Général Nom IUPAC acide (6R,7R,Z) 7 (2 (2 aminothiazol 4 yl) 2 (2 carboxypropan 2 yloxyimino)acétamido) 8 oxo 3 (pyridinium 1 ylméthyl) 5 thia 1 aza bicyclo[4.2 …   Wikipédia en Français

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