Cefazolin
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Systematic (IUPAC) name |
(6R,7R)-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl}-8-oxo-7-[(1H-tetrazol-1-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid |
Clinical data |
Trade names |
Ancef, Kefzol |
AHFS/Drugs.com |
monograph |
Pregnancy cat. |
B1 (AU) B (US) |
Legal status |
℞ Prescription only |
Routes |
Intravenous, intramuscular |
Pharmacokinetic data |
Bioavailability |
NA |
Metabolism |
? |
Half-life |
1.8 hours (given IV)
2 hours (given IM) |
Excretion |
Renal, unchanged |
Identifiers |
CAS number |
25953-19-9 Y |
ATC code |
J01DB04 QJ51DB04 |
PubChem |
CID 33255 |
DrugBank |
DB01327 |
ChemSpider |
30723 Y |
UNII |
IHS69L0Y4T Y |
KEGG |
D02299 Y |
ChEBI |
CHEBI:474053 Y |
ChEMBL |
CHEMBL1435 Y |
Chemical data |
Formula |
C14H14N8O4S3 |
Mol. mass |
454.51 g/mol |
SMILES
- O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)Cn3nnnc3)CSc4nnc(s4)C)C(=O)O
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InChI
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InChI=1S/C14H14N8O4S3/c1-6-17-18-14(29-6)28-4-7-3-27-12-9(11(24)22(12)10(7)13(25)26)16-8(23)2-21-5-15-19-20-21/h5,9,12H,2-4H2,1H3,(H,16,23)(H,25,26)/t9-,12-/m1/s1 Y
Key:MLYYVTUWGNIJIB-BXKDBHETSA-N Y
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Y (what is this?) (verify)
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Cefazolin (INN), also known as cefazoline or cephazolin, is a first-generation cephalosporin antibiotic.
The drug is usually administered by either intramuscular injection (injection into a large muscle) or intravenous infusion (intravenous fluid into a vein).
Contents
- 1 Indications
- 2 Spectrum of bacterial susceptibility and resistance
- 3 Adverse effects
- 4 Brands
- 5 References
- 6 External links
Indications[edit]
Cefazolin is mainly used to treat bacterial infections of the skin. It can also be used to treat moderately severe bacterial infections involving the lung, bone, joint, stomach, blood, heart valve, and urinary tract. It is clinically effective against infections caused by staphylococci and streptococci of Gram-positive bacteria. These organisms are common on normal human skin. Resistance to cefazolin is seen in several species of bacteria. Cefazolin is extensively used as prophylaxis antibiotic before wide range of surgical operations.
Spectrum of bacterial susceptibility and resistance[edit]
Neisseria meningitidis, Streptococcus pneumoniae and Streptococcus pyogenes are generally susceptible to cefazolin, while Bacteroides fragilis, Citrobacter freundii, Enterobacter and Proteus mirabilis are resistant to it. Escherichia coli, Fusobacterium and Peptostreptococcus have developed resistance to cefazolin to varying degrees. For detailed information of minimum inhibition concentration of cefazolin, please refer to Cefazolin Susceptibilty and Resistance Data sheet. [1]
Adverse effects[edit]
Adverse drug reactions from cefazolin are not common. Possible side effects include diarrhea, stomach pain or upset stomach, vomiting, and rash.
Like those of several other cephalosporins, the chemical structure of cefazolin contains an N-methylthiodiazole (NMTD or 1-MTD) side-chain. As the antibiotic is broken down in the body, it releases free NMTD, which can cause hypoprothrombinemia (likely due to inhibition of the enzyme vitamin K epoxide reductase) and a reaction with ethanol similar to that produced by disulfiram (Antabuse), due to inhibition of aldehyde dehydrogenase.[2]
Brands[edit]
Cefazolin is marketed under the following brand names: Ancef, Cefacidal, Cefamezin, Cefrina, Elzogram, Faxilen, Gramaxin, Kefazol, Kefol, Kefzolan, Kezolin, Novaporin, Reflin, Zinol and Zolicef.
References[edit]
- ^ "Cefazolin Susceptibilty and Resistance Data". Retrieved 15 August 2013.
- ^ Stork CM (2006). "Antibiotics, antifungals, and antivirals". In Nelson LH, Flomenbaum N, Goldfrank LR, Hoffman RL, Howland MD, Lewin NA (eds.). Goldfrank's toxicologic emergencies. New York: McGraw-Hill. p. 847. ISBN 0-07-143763-0. Retrieved 2009-07-03.
External links[edit]
- MedlinePlus Drug Information: Cefazolin Sodium Injection.
Antibacterials: cell envelope antibiotics (J01C-J01D)
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Intracellular |
- inhibit peptidoglycan subunit synthesis and transport: NAM synthesis inhibition (Fosfomycin)
- DADAL/AR inhibitors (Cycloserine)
- bactoprenol inhibitors (Bacitracin)
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Glycopeptide |
- inhibit PG chain elongation: Vancomycin# (Oritavancin
- Telavancin)
- Teicoplanin (Dalbavancin)
- Ramoplanin
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β-lactams/
(inhibit PBP
cross-links) |
Penicillins
(penams)
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Extended sp.
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- aminopenicillins: Amoxicillin#
- Ampicillin# (Pivampicillin
- Hetacillin
- Bacampicillin
- Metampicillin
- Talampicillin)
- Epicillin
- carboxypenicillins: Carbenicillin (Carindacillin)
- Ticarcillin
- Temocillin
- ureidopenicillins: Azlocillin
- Piperacillin
- Mezlocillin
- other: Mecillinam (Pivmecillinam)
- Sulbenicillin
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Narrow sp.
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β-lactamase sensitive
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- Benzylpenicillin (G)#: Clometocillin
- Benzathine benzylpenicillin#
- Procaine benzylpenicillin#
- Azidocillin
- Penamecillin
- Phenoxymethylpenicillin (V)#: Propicillin
- Benzathine phenoxymethylpenicillin
- Pheneticillin
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β-lactamase resistant
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- Cloxacillin# (Dicloxacillin
- Flucloxacillin)
- Oxacillin
- Meticillin
- Nafcillin
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Penems
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Carbapenems
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- Biapenem
- Ertapenem
- antipseudomonal (Doripenem
- Imipenem
- Meropenem)
- Panipenem
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Cephalosporins/Cephamycins
(cephems)
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1st (PEcK)
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- Cefazolin#
- Cefacetrile
- Cefadroxil
- Cefalexin
- Cefaloglycin
- Cefalonium
- Cefaloridine
- Cefalotin
- Cefapirin
- Cefatrizine
- Cefazedone
- Cefazaflur
- Cefradine
- Cefroxadine
- Ceftezole
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2nd (HEN)
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- Cefaclor
- Cefamandole
- Cefminox
- Cefonicid
- Ceforanide
- Cefotiam
- Cefprozil
- Cefbuperazone
- Cefuroxime
- Cefuzonam
- cephamycin (Cefoxitin
- Cefotetan
- Cefmetazole)
- carbacephem (Loracarbef)
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3rd
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- Cefixime#
- Ceftriaxone#
- antipseudomonal (Ceftazidime#
- Cefoperazone)
- Cefcapene
- Cefdaloxime
- Cefdinir
- Cefditoren
- Cefetamet
- Cefmenoxime
- Cefodizime
- Cefotaxime
- Cefpimizole
- Cefpiramide
- Cefpodoxime
- Cefsulodin
- Cefteram
- Ceftibuten
- Ceftiolene
- Ceftizoxime
- oxacephem (Flomoxef
- Latamoxef ‡)
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4th (antips-)
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- Cefepime
- Cefozopran
- Cefpirome
- Cefquinome
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5th
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- Ceftobiprole
- Ceftaroline fosamil
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Veterinary
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- Ceftiofur
- Cefquinome
- Cefovecin
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Monobactams
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- Aztreonam
- Tigemonam
- Carumonam
- Nocardicin A
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β-lactamase inh.
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- penam (Sulbactam
- Tazobactam)
- clavam (Clavulanic acid)
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Combinations
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- Amoxicillin/clavulanic acid#
- Imipenem/cilastatin#
- Ampicillin/flucloxacillin
- Ampicillin/sulbactam (Sultamicillin)
- Piperacillin/tazobactam
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Other |
- polymyxins/detergent (Colistin
- Polymyxin B)
- depolarizing (Daptomycin)
- hydrolyze NAM-NAG (Lysozyme)
- Gramicidin
- Isoniazid
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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gr+f/gr+a (t)/gr-p (c)/gr-o
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drug (J1p, w, n, m, vacc)
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