Download Martindale: The Complete Drug Reference

Martindale: The Complete Drug Reference
Cefuroxime
Date of monograph revision: 07-Apr-1997; 20-Jul-1998; 06-Oct-1999; 02-Oct-2001;
12-Nov-2003; 25-Jul-2006; 10-Sep-2008; 20-Nov-2009; 20-Aug-2010; (latest
modification: 26-Feb-2011)
Drug Nomenclature (Latest modification: 07-Feb-2011)
Synonyms: 640/359; Cefuroxim; Cefuroxima; Cefuroximum; Kefuroksiimi; Sefuroksim
BAN: Cefuroxime
USAN: Cefuroxime
INN: Cefuroxime [rINN (en)]
INN: Cefuroxima [rINN (es)]
INN: Céfuroxime [rINN (fr)]
INN: Cefuroximum [rINN (la)]
INN: Цефуроксим [rINN (ru)]
INN: ‫[ س ي فوروك س يم‬rINN (ar)]
INN: 头孢呋辛 [rINN (cn)]
Chemical name: (Z)-3-Carbamoyloxymethyl-7-[2-(2-furyl)-2methoxyiminoacetamido]-3-cephem-4-carboxylic acid
Molecular formula: C16H16N4O8S =424.4
CAS: 55268-75-2
ATC code: J01DC02
ATC code (veterinary): QJ01DC02; QJ51DA06
UNII code: O1R9FJ93ED
Martindale code: 15872-m
Martindale: The Complete Drug Reference
Chemical Structure of Cefuroxime
Cefuroxime Axetil
Date of monograph revision: 07-Apr-1997; 20-Jul-1998; 06-Oct-1999; 02-Oct-2001;
12-Nov-2003; 25-Jul-2006; 10-Sep-2008; 20-Nov-2009; 20-Aug-2010; (latest
modification: 26-Feb-2011)
Drug Nomenclature (Latest modification: 07-Feb-2011)
Synonyms: CCI-15641; Cefuroksimas aksetilas; Cefuroksymu aksetyl; Cefuroximaxetil; Cefuroxima axetilo; Cefuroximaxetil; Céfuroxime axétil; Cefuroximum Axetili;
Cefuroximum Axetilum; Kefuroksiimiaksetiili; Sefuroksim Aksetil
BAN: Cefuroxime Axetil [BANM]
USAN: Cefuroxime Axetil
INN: Cefuroxime Axetil [rINNM (en)]
INN: Cefuroxima axetilo [rINNM (es)]
INN: Céfuroxime, Axétil de [rINNM (fr)]
INN: Cefuroximi Axetilum [rINNM (la)]
INN: Цефуроксима Аксетил [rINNM (ru)]
Molecular formula: C20H22N4O10S =510.5
CAS: 64544-07-6
ATC code: J01DC02
ATC code (veterinary): QJ01DC02
UNII code: Z49QDT0J8Z
Martindale code: 16570-x
Pharmacopoeias:
In Chin., Eur. (see
), Jpn, and US.
Ph. Eur. 7.1 (Cefuroxime Axetil). A white or almost white powder. Slightly soluble in
water and in alcohol; soluble in acetone, in ethyl acetate, and in methyl alcohol. Store in
airtight containers. Protect from light.
Martindale: The Complete Drug Reference
USP 33 (Cefuroxime Axetil). A mixture of the diastereoisomers of cefuroxime axetil. A
white or almost white powder. The amorphous form is insoluble in water and in ether;
slightly soluble in dehydrated alcohol; freely soluble in acetone; soluble in chloroform, in
ethyl acetate, and in methyl alcohol. The crystalline form is insoluble in water and in
ether; slightly soluble in dehydrated alcohol; freely soluble in acetone; sparingly soluble
in chloroform, in ethyl acetate, and in methyl alcohol. Store in airtight containers.
Cefuroxime Sodium
Date of monograph revision: 07-Apr-1997; 20-Jul-1998; 06-Oct-1999; 02-Oct-2001;
12-Nov-2003; 25-Jul-2006; 10-Sep-2008; 20-Nov-2009; 20-Aug-2010; (latest
modification: 26-Feb-2011)
Drug Nomenclature (Latest modification: 07-Feb-2011)
Synonyms: Cefuroksimo natrio druska; Cefuroksym sodowy; Cefuroxim sodná sůl;
Cefuroxim-nátrium; Cefuroxima sódica; Céfuroxime sodique; Cefuroximnatrium;
Cefuroximum Natricum; Kefuroksiiminatrium; Sefuroksim Sodyum
BAN: Cefuroxime Sodium [BANM]
INN: Cefuroxime Sodium [rINNM (en)]
INN: Cefuroxima sódica [rINNM (es)]
INN: Céfuroxime Sodique [rINNM (fr)]
INN: Natrii Cefuroximum [rINNM (la)]
INN: Натрий Цефуроксим [rINNM (ru)]
Molecular formula: C16H15N4NaO8S =446.4
CAS: 56238-63-2
ATC code: J01DC02
ATC code (veterinary): QJ01DC02
UNII code: R8A7M9MY61
Martindale code: 35-h
Pharmacopoeias:
Martindale: The Complete Drug Reference
In Chin., Eur. (see
), Jpn, and US.
Ph. Eur. 7.1 (Cefuroxime Sodium). A white or almost white slightly hygroscopic powder.
Freely soluble in water; very slightly soluble in alcohol. A 1% solution in water has a pH
of 5.5 to 8.5. Store in airtight containers.
USP 33 (Cefuroxime Sodium). A white or faintly yellow powder. Freely soluble in water;
very slightly soluble in alcohol, in chloroform, in ether, and in ethyl acetate; soluble in
methyl alcohol. pH of a 10% solution in water is between 6.0 and 8.5. Store in airtight
containers.
Physicochemical Characteristics (Latest modification: 15-Apr-2004)
Incompatibility and stability
Cefuroxime sodium may be incompatible with aminoglycosides.
References.
1. 1. Barnes AR. Chemical stabilities of cefuroxime sodium and metronidazole in an
admixture for intravenous infusion. J Clin Pharm Ther 1990; 15: 187–96. PubMed
2. 2. Stiles ML, et al. Stability of ceftazidime (with arginine) and of cefuroxime sodium in
infusion-pump reservoirs. Am J Hosp Pharm 1992; 49: 2761–4. PubMed
3. 3. Hebron B, Scott H. Shelf life of cefuroxime eye-drops when dispensed in artificial tear
preparations. Int J Pharm Pract 1993; 2: 163–7.
Adverse Effects and Precautions (Latest modification: 25-Mar-2004)
As for Cefalotin Sodium,
.
Gastrointestinal disturbances, including diarrhoea, nausea, and vomiting, have occurred
in some patients receiving cefuroxime axetil. There have been rare reports of erythema
multiforme, Stevens-Johnson syndrome, and toxic epidermal necrolysis. Mild to
Martindale: The Complete Drug Reference
moderate hearing loss has been reported in some children given cefuroxime for the
treatment of meningitis.
Antibiotic-associated colitis
For reports of pseudomembranous colitis associated with cefuroxime axetil, see
Cefalotin,
.
Hypersensitivity
A report1 of a serum sickness-like reaction to cefuroxime. Similar reactions have
occurred with cefaclor (
), although it is unclear whether they represent a class effect.
A patient who developed a type-1 hypersensitivity reaction to cefuroxime, characterised
by itchy maculopapular rash, exhibited cross-sensitivity to cefotaxime and ceftriaxone on
patch testing, possibly because of similarities in the side-chain;2 no cross-sensitivity to
cefazolin, cefepime, cefoxitin, or ceftazidime, or to various penicillins, was seen on
testing and the patient subsequently tolerated doses of amoxicillin and ceftazidime. The
authors noted that cefuroxime had been found in another study to be the most frequent
cause of immediate-type hypersensitivity reactions to cephalosporins.
1. 1. Katta R, Anusuri V. Serum sickness-like reaction to cefuroxime: a case report and
review of the literature. J Drugs Dermatol 2007; 6: 747–8. PubMed
2. 2. Varela Losada S, et al. Immediate-type allergic reaction to cefuroxime: crossreactivity with other cephalosporins, and good tolerance to ceftazidime. J Investig
Allergol Clin Immunol 2009; 19: 164–5. PubMed
Porphyria
Cefuroxime has been used safely in a few patients with porphyria although there is
conflicting experimental evidence of porphyrinogenicity.
Sodium content
Martindale: The Complete Drug Reference
Each g of cefuroxime sodium contains about 2.2 mmol of sodium.
Interactions (Latest modification: 25-Mar-2004)
Probenecid reduces the renal clearance of cefuroxime.
Antimicrobial Action (Latest modification: 25-Mar-2004)
Cefuroxime is bactericidal and has a similar spectrum of antimicrobial action and pattern
of resistance to those of cefamandole (
). It is more resistant to hydrolysis by beta-
lactamases than cefamandole, and therefore may be more active against betalactamase-producing strains of, for example, Haemophilus influenzae and Neisseria
gonorrhoeae. However, treatment failures have occurred in patients with H. influenzae
meningitis given cefuroxime and might be associated with a relatively high minimum
bactericidal concentration when compared with the minimum inhibitory concentration or
with a significant inoculum effect. Reduced affinity of penicillin-binding proteins for
cefuroxime has also been reported to be responsible for resistance in a beta-lactamasenegative strain of H. influenzae.
References.
1. 1. Arditi M, et al. Cefuroxime treatment failure and Haemophilus influenzae meningitis:
case report and review of literature. Pediatrics 1989; 84: 132–5. PubMed
2. 2. Mendelman PM, et al. Cefuroxime treatment failure of nontypable Haemophilus
influenzae meningitis associated with alteration of penicillin-binding proteins. J Infect
Dis 1990; 162: 1118–23. PubMed
3. 3. Brown NM, et al. Cefuroxime resistance in Haemophilus influenzae. Lancet 1992;
340: 552. PubMed
Pharmacokinetics (Latest modification: 27-Jul-2010)
Cefuroxime axetil is absorbed from the gastrointestinal tract and is rapidly hydrolysed in
the intestinal mucosa and blood to cefuroxime; absorption is enhanced in the presence
Martindale: The Complete Drug Reference
of food. Peak plasma concentrations occur about 2 to 3 hours after an oral dose. The
sodium salt is given by intramuscular or intravenous injection. Peak plasma
concentrations of about 27 micrograms/mL have been achieved 45 minutes after an
intramuscular dose of 750 mg with measurable amounts present 8 hours after a dose.
Up to 50% of cefuroxime in the circulation is bound to plasma proteins. The plasma halflife is about 70 minutes and is prolonged in patients with renal impairment and in
neonates.
Cefuroxime is widely distributed in the body including pleural fluid, sputum, bone,
synovial fluid, and aqueous humour, but only achieves therapeutic concentrations in the
CSF when the meninges are inflamed. It crosses the placenta and has been detected in
breast milk.
Cefuroxime is excreted unchanged, by glomerular filtration and renal tubular secretion,
and high concentrations occur in the urine. On injection, most of a dose of cefuroxime is
excreted within 24 hours, the majority within 6 hours. Probenecid competes for renal
tubular secretion with cefuroxime resulting in higher and more prolonged plasma
concentrations of cefuroxime. Small amounts of cefuroxime are excreted in bile.
Plasma concentrations are reduced by dialysis.
Uses and Administration (Latest modification: 05-Sep-2009)
Cefuroxime is a second-generation cephalosporin antibacterial used in the treatment of
infections caused by susceptible Gram-positive and Gram-negative bacteria, including
infections of the bones and joints, CNS, skin and skin structures, respiratory tract,
genito-urinary tract (including gonorrhoea), and Lyme disease. It is also used for
surgical infection prophylaxis. For details of these infections and their treatment, see
under Choice of Antibacterial,
.
Cefuroxime is given orally as the acetoxyethyl ester, cefuroxime axetil, in the form of
tablets or suspension with or after food, or by injection as the sodium salt. Cefuroxime
sodium may be given by deep intramuscular injection, by slow intravenous injection over
Martindale: The Complete Drug Reference
3 to 5 minutes, or by intermittent or continuous intravenous infusion. Doses of
cefuroxime axetil and cefuroxime sodium are expressed in terms of the equivalent
amount of cefuroxime; 1.20 g of cefuroxime axetil and 1.05 g of cefuroxime sodium are
each equivalent to about 1 g of cefuroxime.
The usual oral dose is 250 mg twice daily; for uncomplicated urinary-tract infections
125 mg twice daily may be adequate and for respiratory-tract infections 250 to 500 mg
twice daily is recommended. For Lyme disease an oral dose of 500 mg is given twice
daily for 20 days.
By injection the usual dose is 750 mg of cefuroxime every 8 hours but in more severe
infections 1.5 g may be given intravenously every 8, or in some cases every 6 hours.
Those with pneumonia or with acute exacerbations of chronic bronchitis may respond to
sequential therapy with parenteral cefuroxime 1.5 g twice daily or 750 mg twice daily
respectively, followed by oral cefuroxime 500 mg twice daily in each case.
For the treatment of meningitis due to sensitive strains of bacteria, cefuroxime is given
intravenously in doses of 3 g every 8 hours.
In the treatment of gonorrhoea, a single dose of 1.5 g by intramuscular injection,
divided between 2 injection sites, has been used. A single 1-g oral dose of cefuroxime
has been given for uncomplicated gonorrhoea. In each case an oral dose of probenecid
1 g may be given with cefuroxime.
For surgical infection prophylaxis, the usual dose is 1.5 g of cefuroxime intravenously
before the procedure; this may be supplemented by 750 mg intramuscularly every 8
hours for up to 24 to 48 hours depending upon the procedure. For total joint
replacement, 1.5 g of cefuroxime powder may be mixed with the methylmethacrylate
cement.
The dose of ceftriaxone may need to be reduced in patients with renal impairment, see
. For details of doses in children, see also
.
Martindale: The Complete Drug Reference
Reviews.
1. 1. Perry CM, Brogden RN. Cefuroxime axetil: a review of its antibacterial activity,
pharmacokinetic properties and therapeutic efficacy. Drugs 1996; 52: 125–58. PubMed
2. 2. Scott LJ, et al. Cefuroxime axetil: an updated review of its use in the management of
bacterial infections. Drugs 2001; 61: 1455–1500. PubMed
Administration in children
Cefuroxime may be given to neonates and children for the treatment of infections
caused by susceptible Gram-positive and Gram-negative bacteria and for surgical
prophylaxis. It is given orally (as cefuroxime axetil), or (as the sodium salt) by injection,
either intramuscularly or intravenously (by slow injection over 3 to 5 minutes, or
intermittent or continuous infusion).
The BNFC 2010/11 suggests the following treatment doses for cefuroxime:
given orally
children 3 months to 2 years of age: 10 mg/kg (to a maximum dose of 125 mg)
twice daily
those over 2 years of age: 15 mg/kg (to a maximum dose of 250 mg) twice daily, or
given parenterally
neonates under 7 days of age: 25 mg/kg every 12 hours
neonates 7 to 21 days of age: 25 mg/kg every 8 hours
neonate 21 to 28 days of age: 25 mg/kg every 6 hours
these doses may be doubled in neonates with severe infections, but should be given
intravenously
Martindale: The Complete Drug Reference
children from 1 month of age: 20 mg/kg (to a maximum dose of 750 mg) every 8
hours; this dose may be increased to 50 to 60 mg/kg (to a maximum dose of 1.5 g)
every 6 or 8 hours in severe infection and cystic fibrosis
For surgical prophylaxis the BNFC 2010/11 suggests that children from the age of 1
month may be given a dose of 50 mg/kg (to a maximum dose of 1.5 g) intravenously
before the procedure; this may be supplemented by up to 3 further doses of 30 mg/kg
(to a maximum dose of 750 mg) intramuscularly or intravenously at 8-hour intervals for
high-risk procedures.
In the USA, the American Academy of Pediatrics1 suggests the following doses:
orally
children 1 month and older: 20 to 30 mg/kg in 2 divided doses (to a maximum daily
dose of 1 to 2 g) for mild to moderate infections
intravenously or intramuscularly
children 1 month and older: 75 to 100 mg/kg in 3 divided doses (to a maximum
daily dose of 2 to 4 g) for mild to moderate infections, or 100 to 150 mg/kg in 3
divided doses (to a maximum daily dose of 4 to 6 g) in severe infections
1. 1. American Academy of Pediatrics. 2009 Red Book: Report of the Committee on
Infectious Diseases, 28th ed. Elk Grove Village, Illinois, USA: American Academy of
Pediatrics, 2009.
Administration in renal impairment
Parenteral doses of cefuroxime may need to be reduced in renal impairment. Licensed
product information suggests the following doses based on creatinine clearance (CC):
CC 10 to 20 mL/minute: 750 mg twice daily
Martindale: The Complete Drug Reference
CC less than 10 mL/minute: 750 mg once daily
Patients undergoing haemodialysis should receive an additional 750-mg dose following
each dialysis; those undergoing continuous peritoneal dialysis may be given 750 mg
twice daily.
Preparations (Latest modification: 07-Feb-2011)
Single-ingredient Preparations
The symbol ¤ denotes a preparation which is discontinued or no longer actively
marketed.
Argentina: Ceflux¤; Cefogram¤; Cefurox; Ligramex¤; Australia: Zinnat; Austria:
Curocef; Furoxim¤; Zinnat; Belgium: Axetine¤; Cefurim; Doccefuro¤; Kefurox; Zinacef;
Zinnat; Brazil: Cefunorth¤; Cefuran¤; Keroxime; Medcef; Zinacef; Zinnat; Canada:
Ceftin; Kefurox¤; Zinacef¤; Chile: Curocef; Zinnat; Czech Republic: Axetine; Lifurox¤;
Medoxin; Xorimax; Zinacef; Zinnat; Zinoxime¤; Denmark: Axacef¤; Lifurox¤; Zinacef;
Zinnat; Finland: Kefurion¤; Lifurox¤; Zinacef; Zinnat; France: Cepazine¤; Zinnat;
Germany: Cefu¤; Cefudura¤; Cefuhexal; Cefurax¤; Cefuro-Puren; Cefurox-Reu¤;
Cefurox-Wolff; Cefurox; Elobact; Zinacef¤; Zinnat; Greece: Anaptivan; Cefoprim;
Cefur; Cefuroprol; Cerofene; Ceruxim; Cupax; Ecoline; Feacef; Foucacillin; Fredyr;
Furaxil; Galemin; Genephoxal; Gonif; Helatocil; Interbion; Lyprovir; Medoxem;
Mevecan; Mosalan; Nelabocin; Nipogalin; Normafenac; Receant; Saxetil; Sedopan;
Vekfazolin; Yokel; Zagorine; Zetagal; Zilisten; Zinacef; Zinadol; Hong Kong: Anikef¤;
Axetine¤; Axim; Sefuxim; Zinacef; Zinnat; Hungary: Cefurin¤; Ceroxim; Cexim¤;
Xorim; Xorimax; Zinacef; Zinnat; India: Altacef; Cefasyn; Cefogen; Cefoxim; Forcef;
Supacef; Indonesia: Anbacim; Cefurox¤; Celocid; Cethixim; Kalcef; Kenacef¤;
Oxtercid; Roxbi¤; Sharox; Soxime; Zinacef¤; Zinnat; Ireland: Ceftal; Zinacef; Zinnat;
Israel: Cefurax; Ceroxim; Kefurim; Zinacef; Zinnat; Italy: Biociclin¤; Biofurex¤;
Bioxima¤; Cefamar¤; Cefoprim¤; Cefumax¤; Cefur¤; Cefurex¤; Cefurin; Colifossim¤;
Curoxim; Deltacef¤; Duxima; Gibicef¤; Ipacef¤; Itorex; Kefox¤; Kesint¤; Lafurex¤;
Martindale: The Complete Drug Reference
Lamposporin¤; Medoxim¤; Oraxim; Polixima¤; Supero; Tilexim; Ultroxim¤; Zinnat;
Zinocep; Zoref; Malaysia: Altacef; Ceflour; Efurox; Furoxime; Xorimax; Xylid; Zinacef;
Zinnat; Zocef; Mexico: Cefabiot; Cefagen; Cefuracet; Cetoxil; Froxal; Fucerox;
Furobioxin; Lemoxin¤; Magnaspor; Novador; Ximaken; Xorufec; Zinnat; Netherlands:
Cefofix¤; Zinacef; Zinnat; Norway: Lifurox¤; Zinacef; New Zealand: Axetine; Zinacef;
Zinnat; Philippines: Aeruginox; Altacef; Ambixime; Axet; Axurocef; C-Tri T; Cefogen;
Ceftil; Cefucil; Cefumax; Cervin; Cidokez; Cimex; Clovixime; Curecef; Darcef; Ecocef;
Elixime; Emixor; Eroxmit; Eurimax; Finax; Fubaxyn¤; Furocef; Furocem; Furomax;
Furoxim; Furoxy; Harox; Ifurax; Infekor; Jectocef; Kefezy; Kefox; Kefstar; Kefsyn;
Keunzef; Lasuzef; Laxinat; Loxatrel¤; Medxil; Medxime; Microzef; Panaxim; Panjecxime;
Pheoronex; Plerozef; Profurex; Rexofen; Rezafil; Rocef; Romicef; Rovix; Roxetil;
Roxicef; Roxime; Roxym; Ruxim; Sharox¤; Shincef; Teikeden; Unoximed; Xorimax;
Zefur; Zefuxim; Zegen; Zinacef; Zinnat; Zoltax; Zurenix; Poland: Biofuroksym;
Bioracef; Ceroxim; Novocef; Oframax; Plixym¤; Tarsime; Xorim; Xorimax; Zamur;
Zinacef; Zinnat; Portugal: Antibioxime; Axacef; Cefaricida¤; Cefofix¤; Cefrix¤;
Condronac; Curoxime; Famicef; Furaxetil¤; Lusocef¤; Pluscef¤; Saracef; Zipos; Zoref;
Russia: Axetine (Аксетин); Cefurabol (Цефурабол); Cefurus (Цефурус); Kefstar
(Кефстар); Ketocef (Кетоцеф); Zinacef (Зинацеф); Zinnat (Зиннат); South Africa:
Betaroxime; Cefasyn; Cefu-Hexal; Ceroxim; Cipofix¤; Curoax; Intracef¤; Lifurom¤;
Medaxime¤; Zefroxe; Zinacef; Zinnat; Singapore: Bearcef; Ceftil; Cefxin; Shincef;
Xorimax; Zinacef; Zinnat; Spain: Curoxima; Lifurox¤; Nivador¤; Selan; Zinnat;
Sweden: Axacef¤; Lifurox¤; Zinacef; Zinnat; Switzerland: Cefurim; Zinacef; Zinat;
Thailand: Axetine¤; Axurocef¤; Cefamar; Cefogen¤; Cefurim; Farmacef; Furoxime;
Magnaspor; Sefuxim; Zinacef; Zinnat; Zonef; Turkey: Aksef; Cefaks; Cefatin; Cefurol;
Enfexia; Multisef; Oraceftin; Sefaktil; Seffur; Sefuroks; Zinnat; United Arab Emirates:
Cefuzime; United Kingdom: Zinacef; Zinnat; Ukraine: Aksef (Аксеф); Biofuroksym
(Биофуроксим); Cefoctam (Цефоктам); Cefutil (Цефутил); Enfexia (Энфексия);
Kimacef (Кимацеф); Spizef (Спизеф); Zinacef (Зинацеф); United States: Ceftin;
Kefurox¤; Zinacef; Venezuela: Xorim; Zencef; Zinacef; Zinnat;
Pharmacopoeial Preparations
Martindale: The Complete Drug Reference
BP 2011: Cefuroxime Axetil Tablets; Cefuroxime Eye Drops; Cefuroxime Injection; USP
33: Cefuroxime Axetil for Oral Suspension; Cefuroxime Axetil Tablets; Cefuroxime for
Injection; Cefuroxime Injection