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    Synopsis

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    Chemistry

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    Also known as: 72558-82-8, Tazidime, Fortaz, Ceftazidime anhydrous, Pentacef, Tazicef
    Molecular Formula
    C22H22N6O7S2
    Molecular Weight
    546.6  g/mol
    InChI Key
    ORFOPKXBNMVMKC-DWVKKRMSSA-N
    Ceftazidime
    Semisynthetic, broad-spectrum antibacterial derived from CEPHALORIDINE and used especially for Pseudomonas and other gram-negative infections in debilitated patients.
    1 2D Structure

    Ceftazidime

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(2-carboxypropan-2-yloxyimino)acetyl]amino]-8-oxo-3-(pyridin-1-ium-1-ylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
    2.1.2 InChI
    InChI=1S/C22H22N6O7S2/c1-22(2,20(33)34)35-26-13(12-10-37-21(23)24-12)16(29)25-14-17(30)28-15(19(31)32)11(9-36-18(14)28)8-27-6-4-3-5-7-27/h3-7,10,14,18H,8-9H2,1-2H3,(H4-,23,24,25,29,31,32,33,34)/b26-13-/t14-,18-/m1/s1
    2.1.3 InChI Key
    ORFOPKXBNMVMKC-DWVKKRMSSA-N
    2.1.4 Canonical SMILES
    CC(C)(C(=O)O)ON=C(C1=CSC(=N1)N)C(=O)NC2C3N(C2=O)C(=C(CS3)C[N+]4=CC=CC=C4)C(=O)[O-]
    2.1.5 Isomeric SMILES
    CC(C)(C(=O)O)O/N=C(/C1=CSC(=N1)N)\C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C[N+]4=CC=CC=C4)C(=O)[O-]
    2.2 Synonyms
    2.2.1 MeSH Synonyms

    1. Ceftazidime Anhydrous

    2. Ceftazidime Pentahydrate

    3. Fortaz

    4. Fortum

    5. Gr 20263

    6. Gr-20263

    7. Gr20263

    8. Ly 139381

    9. Ly-139381

    10. Ly139381

    11. Pyridinium, 1-((7-(((2-amino-4-thiazolyl)((1-carboxy-1-methylethoxy)imino)acetyl)amino)-2-carboxy-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-3-yl)methyl)-, Inner Salt, Pentahydrate, (6r-(6alpha,7beta(z)))-

    12. Tazidime

    2.2.2 Depositor-Supplied Synonyms

    1. 72558-82-8

    2. Tazidime

    3. Fortaz

    4. Ceftazidime Anhydrous

    5. Pentacef

    6. Tazicef

    7. Ceptaz

    8. Ceftazidima

    9. Ceftazidimum

    10. Ceftazidime Pentahydrate

    11. Gr 20263

    12. Chebi:3508

    13. (6r,7r)-7-[[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-(2-carboxypropan-2-yloxyimino)acetyl]amino]-8-oxo-3-(pyridin-1-ium-1-ylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

    14. Fortaz (tn)

    15. (6r,7r)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-(2-carboxypropan-2-yloxyimino)acetyl]amino]-8-oxo-3-(pyridin-1-ium-1-ylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

    16. 7-[[(2e)-2-(2-amino-1,3-thiazol-4-yl)-2-(2-carboxypropan-2-yloxyimino)acetyl]amino]-8-oxo-3-(pyridin-1-ium-1-ylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

    17. Gr-20263

    18. Ly-139381

    19. 78439-06-2

    20. Caz

    21. J01dd07

    22. Nsc-759260

    23. Ceftazidime (tn)

    24. Ceptaz (tn)

    25. Schembl36849

    26. Bidd:gt0734

    27. Chembl44354

    28. Dtxsid5022770

    29. Hms2090m13

    30. (6r,7r)-7-{[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-{[(2-carboxypropan-2-yl)oxy]imino}acetyl]amino}-8-oxo-3-(pyridinium-1-ylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

    31. Hy-b0593

    32. Bdbm50420259

    33. Akos015951273

    34. Ccg-269983

    35. Db00438

    36. Ncgc00179584-05

    37. Ceftazidime (arginine Formulation)

    38. Ab00513848

    39. C06889

    40. D07654

    41. Ab00513848-02

    42. Cefprozil, Antibiotic For Culture Media Use Only

    43. A839420

    44. Q-200811

    45. (6r,7r)-7-((z)-2-(2-aminothiazol-4-yl)-2-(((2-carboxypropan-2-yl)oxy)imino)acetamido)-8-oxo-3-(pyridin-1-ium-1-ylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate (contains Ca. 10% Na2co3)

    46. (6r,7r)-7-((z)-2-(2-aminothiazol-4-yl)-2-(((2-carboxypropan-2-yl)oxy)imino)acetamido)-8-oxo-3-(pyridin-1-ium-1-ylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate(containsca.10%na2co3)

    47. (6r,7r)-7-({(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(1-carboxy-1-methylethoxy)imino]acetyl}amino)-8-oxo-3-(pyridinium-1-ylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

    48. 1-{[(6r,7r)-7-[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(1-carboxy-1-methylethoxy)imino]acetamido]-2-carboxylato-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}pyridin-1-ium

    49. 7beta-{[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-{[(2-carboxypropan-2-yl)oxy]imino}acetyl]amino}-3-(pyridinium-1-ylmethyl)-3,4-didehydrocepham-4-carboxylate

    2.3 Create Date
    2005-08-01
    3 Chemical and Physical Properties
    Molecular Weight 546.6 g/mol
    Molecular Formula C22H22N6O7S2
    XLogP30.4
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count12
    Rotatable Bond Count8
    Exact Mass546.09913941 g/mol
    Monoisotopic Mass546.09913941 g/mol
    Topological Polar Surface Area245 Ų
    Heavy Atom Count37
    Formal Charge0
    Complexity1020
    Isotope Atom Count0
    Defined Atom Stereocenter Count2
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count1
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 8  
    Drug NameCeftazidime
    PubMed HealthCeftazidime (Injection)
    Drug ClassesAntibiotic
    Drug LabelCeftazidime is a semisynthetic, broad-spectrum, beta-lactam antibiotic for parenteral administration. It isthe pentahydrate of pyridinium, 1-[[7-[[(2-amino-4-thiazolyl)[(1-carboxy-1-methylethoxy) imino] acetyl]amino]-2-carboxy-8-oxo-5-thia-1-azabic...
    Active IngredientCeftazidime
    Dosage FormInjectable
    RouteInjection
    Strength500mg/vial; 2gm/vial; 1gm/vial; 6gm/vial
    Market StatusPrescription
    CompanyWockhardt; Acs Dobfar

    2 of 8  
    Drug NameFortaz
    PubMed HealthCeftazidime (Injection)
    Drug ClassesAntibiotic
    Drug LabelCeftazidime is a semisynthetic, broad-spectrum, beta-lactam antibiotic for parenteral administration. It is the pentahydrate of pyridinium, 1-[[7-[[(2-amino-4-thiazolyl)[(1-carboxy-1-methylethoxy)imino]acetyl]amino]-2-carboxy-8-oxo-5-thia-1-azabicycl...
    Active IngredientCeftazidime
    Dosage FormInjectable
    RouteInjection
    Strength500mg/vial; 2gm/vial; 1gm/vial; 6gm/vial
    Market StatusPrescription
    CompanyCovis Injectables

    3 of 8  
    Drug NameFortaz in plastic container
    PubMed HealthCeftazidime (Injection)
    Drug ClassesAntibiotic
    Drug LabelCeftazidime is a semisynthetic, broad-spectrum, beta-lactam antibiotic for parenteral administration. It is the pentahydrate of pyridinium, 1-[[7-[[(2-amino-4-thiazolyl)[(1-carboxy-1-methylethoxy)imino]acetyl]amino]-2-carboxy-8-oxo-5-thia-1-azabicycl...
    Active IngredientCeftazidime sodium
    Dosage FormInjectable
    RouteInjection
    Strengtheq 40mg base/ml; eq 20mg base/ml
    Market StatusPrescription
    CompanyCovis Injectables

    4 of 8  
    Drug NameTazicef
    Active IngredientCeftazidime
    Dosage FormInjectable
    RouteInjection
    Strength500mg/vial; 2gm/vial; 1gm/vial; 6gm/vial
    Market StatusPrescription
    CompanyHospira

    5 of 8  
    Drug NameCeftazidime
    PubMed HealthCeftazidime (Injection)
    Drug ClassesAntibiotic
    Drug LabelCeftazidime is a semisynthetic, broad-spectrum, beta-lactam antibiotic for parenteral administration. It isthe pentahydrate of pyridinium, 1-[[7-[[(2-amino-4-thiazolyl)[(1-carboxy-1-methylethoxy) imino] acetyl]amino]-2-carboxy-8-oxo-5-thia-1-azabic...
    Active IngredientCeftazidime
    Dosage FormInjectable
    RouteInjection
    Strength500mg/vial; 2gm/vial; 1gm/vial; 6gm/vial
    Market StatusPrescription
    CompanyWockhardt; Acs Dobfar

    6 of 8  
    Drug NameFortaz
    PubMed HealthCeftazidime (Injection)
    Drug ClassesAntibiotic
    Drug LabelCeftazidime is a semisynthetic, broad-spectrum, beta-lactam antibiotic for parenteral administration. It is the pentahydrate of pyridinium, 1-[[7-[[(2-amino-4-thiazolyl)[(1-carboxy-1-methylethoxy)imino]acetyl]amino]-2-carboxy-8-oxo-5-thia-1-azabicycl...
    Active IngredientCeftazidime
    Dosage FormInjectable
    RouteInjection
    Strength500mg/vial; 2gm/vial; 1gm/vial; 6gm/vial
    Market StatusPrescription
    CompanyCovis Injectables

    7 of 8  
    Drug NameFortaz in plastic container
    PubMed HealthCeftazidime (Injection)
    Drug ClassesAntibiotic
    Drug LabelCeftazidime is a semisynthetic, broad-spectrum, beta-lactam antibiotic for parenteral administration. It is the pentahydrate of pyridinium, 1-[[7-[[(2-amino-4-thiazolyl)[(1-carboxy-1-methylethoxy)imino]acetyl]amino]-2-carboxy-8-oxo-5-thia-1-azabicycl...
    Active IngredientCeftazidime sodium
    Dosage FormInjectable
    RouteInjection
    Strengtheq 40mg base/ml; eq 20mg base/ml
    Market StatusPrescription
    CompanyCovis Injectables

    8 of 8  
    Drug NameTazicef
    Active IngredientCeftazidime
    Dosage FormInjectable
    RouteInjection
    Strength500mg/vial; 2gm/vial; 1gm/vial; 6gm/vial
    Market StatusPrescription
    CompanyHospira

    4.2 Drug Indication

    Ceftazidime is indicated for the treatment of lower respiratory tract infections, skin and skin structure infections, urinary tract infections, bacterial septicemia, bone and joint infections, gynecologic infections, intra-abdominal infections (including peritonitis), and central nervous system infections (including meningitis) caused by susceptible bacteria. Ceftazidime is indicated in combination with [avibactam] to treat infections caused by susceptible Gram-negative organisms, including complicated intra-abdominal infections (cIAI), in conjunction with [metronidazole], and complicated urinary tract infections (cUTI), including pyelonephritis, in patients aged three months and older. This combination is also indicated to treat hospital-acquired and ventilator-associated bacterial pneumonia (HABP/VABP) in patients aged 18 years and older. In all cases, to mitigate the risk of bacterial resistance and preserve clinical efficacy, ceftazidime should only be used for infections that are confirmed or strongly suspected to be caused by susceptible bacterial strains.

    FDA Label

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Ceftazidime is a semisynthetic, broad-spectrum, third-generation cephalosporin antibiotic that is bactericidal through inhibition of enzymes responsible for cell-wall synthesis, primarily penicillin-binding protein 3 (PBP3). Among cephalosporins, ceftazidime is notable for its resistance to numerous -lactamases and its broad spectrum of activity against Gram-negative bacteria, including _Pseudomonas aeruginosa_. However, it is less active than first- and second-generation cephalosporins against _Staphylococcus aureus_ and other Gram-positive bacteria and also has low activity against anaerobes. Ceftazidime has confirmed activity against clinically relevant Gram-negative bacteria including _Citrobacter_ spp., _Enterobacter_ spp., _Klebsiella_ spp., _Proteus_ spp., _Serratia spp., _Escherichia coli_, _Haemophilus influenzae_, _Neisseria meningitidis_, _Pseudomonas aeruginosa_, and some Gram-positive bacteria including _Staphylococcus_ spp. and _Streptococcus_ spp. There are also _in vitro_ data for ceftazidime efficacy against a wide variety of other bacteria, such as _Acinetobacter baumannii_ and _Neisseria gonorrhoeae_, but no clear clinical studies to support the use of ceftazidime for infections caused by these bacteria. Although -lactam antibiotics like ceftazidime are generally well tolerated, there remains a risk of serious acute hypersensitivity reactions, which is higher in patients with a known allergy to ceftazidime or any other -lactam antibiotic. As with all antibiotics, ceftazidime may result in the overgrowth of non-susceptible organisms and potentially serious effects including _Clostridium difficile_-associated diarrhea (CDAD); CDAD should be considered in patients who develop diarrhea and, in confirmed cases, supportive care initiated immediately. Ceftazidime is primarily renally excreted such that high and prolonged serum concentrations can occur in patients with renal insufficiency, leading to seizures, nonconvulsive status epilepticus (NCSE), encephalopathy, coma, asterixis, neuromuscular excitability, and myoclonia. Treatment may lead to the development or induction of resistance with a risk of treatment failure. Periodic susceptibility testing should be considered, and monotherapy failure may necessitate the addition of another antibiotic such as an aminoglycoside. Cephalosporin use may decrease prothrombin activity, which may be improved by exogenous vitamin K. Inadvertent intra-arterial administration of ceftazidime may result in distal necrosis.

    5.2 MeSH Pharmacological Classification

    Anti-Bacterial Agents

    Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

    5.3 FDA Pharmacological Classification
    5.3.1 Pharmacological Classes
    Cephalosporins [CS]; Cephalosporin Antibacterial [EPC]
    5.4 ATC Code

    J - Antiinfectives for systemic use

    J01 - Antibacterials for systemic use

    J01D - Other beta-lactam antibacterials

    J01DD - Third-generation cephalosporins

    J01DD02 - Ceftazidime

    5.5 Absorption, Distribution and Excretion

    Absorption

    Ceftazidime administered intravenously in healthy males produced mean Cmax values of between 42 and 170 g/mL for doses between 500 mg and 2 g, and are reached immediately following the end of the infusion period. The Cmax for 1 g of ceftazidime administered intramuscularly is attained approximately one hour following injection and is between 37 and 43 mg/L. Following intramuscular administration of 500 mg and 1 g of ceftazidime, the serum concentration remained above 4 g/mL for six and eight hours, respectively. Ceftazidime Cmax and AUC show linear proportionality to the dose over the therapeutic range. In individuals with normal renal function, ceftazidime given intravenously every eight hours for 10 days as either 1 or 2 g doses showed no accumulation.

    Route of Elimination

    Approximately 80% to 90% of an intramuscular or intravenous dose of ceftazidime is excreted unchanged by the kidneys over a 24-hour period. When administered intravenously, 50% of the dose appears in the urine within two hours, with another 32% of the dose appearing by eight hours post-administration.

    Volume of Distribution

    Ceftazidime has a volume of distribution of 15-20 L.

    Clearance

    The mean renal clearance of ceftazidime in healthy subjects ranges from 72 to 141 mL/min while the calculated plasma clearance is approximately 115 mL/min.

    5.6 Metabolism/Metabolites

    Ceftazidime is not appreciably metabolized.

    5.7 Biological Half-Life

    Ceftazidime has an elimination half-life of 1.5-2.8 hours in healthy subjects. As ceftazidime is primarily renally excreted, its half-life is significantly prolonged in patients with renal impairment. In patients with creatinine clearance < 12 mL/min, the half-life is prolonged to between 14 and 30 hours.

    5.8 Mechanism of Action

    The bacterial cell wall, which is located at the periphery of Gram-positive bacteria and within the periplasm of Gram-negative bacteria, comprises a glycopeptide polymer synthesized through cross-linking of glycans to peptide stems on alternating saccharides, which is known commonly as peptidoglycan. Cell wall formation, recycling, and remodelling require numerous enzymes, including a family of enzymes with similar active site character despite distinct and sometimes overlapping roles as carboxypeptidases, endopeptidases, transpeptidases, and transglycosylases, known as "penicillin-binding proteins" (PBPs). The number of PBPs differs between bacteria, in which some are considered essential and others redundant. In general, inhibition of one or more essential PBPs results in impaired cell wall homeostasis, loss of cell integrity, and is ultimately bactericidal. Ceftazidime is a semisynthetic third-generation cephalosporin with broad activity against numerous Gram-negative and some Gram-positive bacteria. Like other -lactam antibiotics, ceftazidime exhibits its bactericidal effect primarily through direct inhibition of specific PBPs in susceptible bacteria. _In vitro_ experiments in Gram-negative bacteria such as _Escherichia coli_, _Pseudomonas aeruginosa_, _Acinetobacter baumannii_, and _Klebsiella pneumoniae_ suggest that ceftazidime primarily binds to PBP3, with weaker binding to PBP1a/1b and PBP2 as well; although binding to other PBPs, such as PBP4, is detectable, the concentrations required are much greater than those achieved clinically. Similarly, ceftazidime showed binding to _Staphylococcus aureus_ PBP 1, 2, and 3 with a much lower affinity for PBP4. Recent data for _Mycobacterium abcessus_ suggest that ceftazidime can inhibit PonA1, PonA2, and PbpA at intermediate concentrations.

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    DOSAGE - POWDER;INTRAVENOUS - EQ 0.5GM BASE;2...DOSAGE - POWDER;INTRAVENOUS - EQ 0.5GM BASE;2GM/VIAL

    USFDA APPLICATION NUMBER - 206494

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    DOSAGE - INJECTABLE;INJECTION - 1GM/VIAL **Fe...DOSAGE - INJECTABLE;INJECTION - 1GM/VIAL **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

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    DOSAGE - INJECTABLE;INJECTION - 500MG/VIAL **...DOSAGE - INJECTABLE;INJECTION - 500MG/VIAL **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

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