Cefazolin: Difference between revisions

Cefazolin
Clinical data
Pregnancy; category	AU: B1; ;
Routes of; administration	Intravenous, intramuscular
ATC code	J01DB04 (WHO) QJ51DA04 (WHO);
Legal status
Legal status	In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	NA
Metabolism	?
Elimination half-life	1.8 hours (given IV); 2 hours (given IM)
Excretion	Renal, unchanged
Identifiers
	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;
CAS Number	25953-19-9;
PubChem CID	33255;
DrugBank	DB01327 ;
ChemSpider	30723 ;
UNII	IHS69L0Y4T;
KEGG	D02299 ;
ChEBI	CHEBI:474053 ;
ChEMBL	ChEMBL1435 ;
CompTox Dashboard (EPA)	DTXSID2022753 ;
ECHA InfoCard	100.043.042
Chemical and physical data
Formula	C14H14N8O4S3
Molar mass	454.51 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)Cn3nnnc3)CSc4nnc(s4)C)C(=O)O;
	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 ; Key:MLYYVTUWGNIJIB-BXKDBHETSA-N ;
	(verify)

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Revision as of 14:03, 7 August 2011

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

^ Stork CM (2006). "Antibiotics, antifungals, and antivirals". In Nelson LH, Flomenbaum N, Goldfrank LR, Hoffman RL, Howland MD, Lewin NA (eds.) (ed.). Goldfrank's toxicologic emergencies. New York: McGraw-Hill. p. 847. ISBN 0-07-143763-0. {{cite book}}: |access-date= requires |url= (help); |editor= has generic name (help); External link in |chapterurl= (help); Unknown parameter |chapterurl= ignored (|chapter-url= suggested) (help)CS1 maint: multiple names: editors list (link)

External links

MedlinePlus Drug Information: Cefazolin Sodium Injection.

This systemic antibiotic-related article is a stub. You can help Wikipedia by expanding it.

[Goldfrank-1] Stork CM (2006). "Antibiotics, antifungals, and antivirals". In Nelson LH, Flomenbaum N, Goldfrank LR, Hoffman RL, Howland MD, Lewin NA (eds.) (ed.). Goldfrank's toxicologic emergencies. New York: McGraw-Hill. p. 847. ISBN 0-07-143763-0. {{cite book}}: |access-date= requires |url= (help); |editor= has generic name (help); External link in |chapterurl= (help); Unknown parameter |chapterurl= ignored (|chapter-url= suggested) (help)CS1 maint: multiple names: editors list (link)

[1]

@@ Line 1: / Line 1: @@
-{{Drugbox| verifiedrevid = 401029558
+{{Drugbox| verifiedrevid = 443508421
 |
 |IUPAC_name = (6''R'',7''R'')-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl}-8-oxo-7-[(1''H''-tetrazol-1-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
@@ Line 21: / Line 21: @@
 | ATC_suffix=DB04
 | ATC_supplemental={{ATCvet|J51|DA04}}
+| ChEBI_Ref = {{ebicite|correct|EBI}}
 | ChEBI = 474053
 | PubChem=33255
+| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
 | DrugBank=DB01327
+| KEGG_Ref = {{keggcite|correct|kegg}}
 | KEGG = D02299
 | smiles = O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)Cn3nnnc3)CSc4nnc(s4)C)C(=O)O