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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