Cefazolin

Cefazolin

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
ATC code	J01DB04 QJ51DA04
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	eMolecules & PubChem
InChI 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
Y(what is this?)  (verify)

Cefazolin (INN), also known as cefazoline or cephazolin, is a first-generation cephalosporin antibiotic.

The drug is usually administrated by either intramuscular injection (injection into a large muscle) or intravenous infusion (intravenous fluid into a vein).

Indications

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.

Adverse effects

Adverse drug reactions from cefazolin are not common. Possible side effects include diarrhea, stomach pain or upset stomach, vomiting, and rash.

Like that of several other cephalosporins, the chemical structure of cefazolin contains an N-methylthiotetrazole (NMTT or 1-MTT) side-chain. As the antibiotic is broken down in the body, it releases free NMTT, 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.^[1]

Brands

Cefazolin is marketed under the following brand names: Ancef, Cefacidal, Cefamezin, Cefrina, Elzogram, Faxilen, Gramaxin, Kefazol, Kefol, Kefzol, Kefzolan, Kezolin, Novaporin, Reflin,Zinol and Zolicef.

References

1. ^ 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. pp. 847. ISBN 0-07-143763-0. http://books.google.com/books?id=cvJuLqBxGUcC&pg=PA847. Retrieved 2009-07-03. 

External links

• MedlinePlus Drug Information: Cefazolin Sodium Injection.