Cefamandole/Cefatrizine 221
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Cefamandole/Cefatrizine 221 Cefamandole Sodium (BANM, rINNM) hours and high urinary concentrations are achieved. Pharmacopoeias. In Eur. (see p.vii), Jpn, and US. Cefamandol sódico; Céfamandole Sodique; Cephamandole So- Probenecid competes for renal tubular secretion with US also includes Cephapirin Benzathine for veterinary use. Ph. Eur. 6.2 (Cefapirin Sodium). A white or pale yellow powder. dium; Natrii Cefamandolum. cefamandole resulting in higher and prolonged plasma Soluble in water; practically insoluble in dichloromethane. A 1% Натрий Цефамандол concentrations of cefamandole. Therapeutic concen- solution in water has a pH of 6.5 to 8.5. Protect from light. C18H17N6NaO5S2 = 484.5. trations of cefamandole are achieved in bile. USP 31 (Cephapirin Sodium). A white to off-white crystalline CAS — 30034-03-8. Cefamandole is removed by haemodialysis to some powder, odourless or having a slight odour. Very soluble in wa- ATC — J01DC03. extent. ter; insoluble in most organic solvents. pH of a solution in water ATC Vet — QJ01DC03. containing the equivalent of cefapirin 1% is between 6.5 and 8.5. Store in airtight containers. Adverse Effects and Precautions Uses and Administration Cefamandole is a second-generation cephalosporin an- Profile As for Cefalotin Sodium, p.219. Cefapirin is a first-generation cephalosporin antibacterial with As mentioned under Cefalotin, cephalosporins with an tibacterial used in the treatment of infections due to actions and uses very similar to those of cefalotin (p.219). It is N-methylthiotetrazole side-chain such as cefamandole susceptible bacteria and for surgical infection prophy- used as the sodium salt but doses are expressed in terms of cefa- (and possibly those with methylthiadiazolethiol or N- laxis. pirin base; 1.05 g of cefapirin sodium is equivalent to about 1 g It is given principally as cefamandole nafate (the sodi- of cefapirin. The usual dose is the equivalent of 0.5 to 1 g of ce- methylthiotriazine side-chains as well) may produce fapirin every 4 to 6 hours by intramuscular injection or intrave- bleeding disorders associated with hypoprothrombin- um salt of cefamandole formyl ester). Doses are ex- nously. In severe infections up to 12 g daily may be given, pref- aemia and/or platelet disorders. pressed in terms of the equivalent amount of cefaman- erably intravenously. Sodium content. 1.05 g of cefamandole sodium and 1.11g of dole; 1.05 g of cefamandole sodium and 1.11 g of Administration in renal impairment. Reduced doses of ce- cefamandole nafate each contain about 2.2 mmol of sodium. cefamandole nafate are each equivalent to about 1 g of fapirin sodium may be necessary in patients with renal impair- cefamandole. It is given by deep intramuscular injec- ment. One regimen, based on creatinine clearance (CC), that has Interactions tion, by slow intravenous injection over 3 to 5 minutes, been suggested is: A disulfiram-like interaction with alcohol may occur or by intermittent or continuous infusion in doses of 0.5 • CC 5 to 20 mL/minute: 1 g every 12 hours and has been attributed to the N-methylthiotetrazole to 2 g every 4 to 8 hours for adults depending on the • CC less than 5 mL/minute: 1 g every 24 hours side-chain of cefamandole; patients should avoid alco- severity of the infection. Children over 1 month of age Patients undergoing haemodialysis may receive 7.5 to 15 mg/kg hol during, and for at least several days after, cefaman- may be given 50 to 100 mg/kg daily in equally divided after each dialysis. dole treatment. Interactions are also possible with prep- doses; 150 mg/kg daily may be given in severe infec- Sodium content. Each g of cefapirin sodium contains about arations containing significant amounts of alcohol. tions, but this dose should not be exceeded. For details 2.2 mmol of sodium. Cefamandole, and other cephalosporins with an N- of reduced doses in patients with renal impairment, see Preparations methylthiotetrazole side-chain, may enhance the hypo- below. If cefamandole is used with an aminoglycoside, USP 31: Cephapirin for Injection. the drugs should be given separately. prothrombinaemic response to anticoagulants as dis- Proprietary Preparations (details are given in Part 3) cussed under Warfarin (p.1428). For surgical infection prophylaxis, a dose of 1 or 2 g Cz.: Cefatrexyl†; Fr.: Cefaloject; Gr.: Cefatrex†; Spain: Brisfirina. Probenecid reduces the renal clearance of cefamandole intravenously or intramuscularly 30 to 60 minutes be- and many other cephalosporins. fore surgical incision, followed by 1 or 2 g every 6 hours for 24 to 48 hours, is recommended. For patients Cefatrizine (BAN, USAN, pINN) ◊ References. undergoing procedures involving implantation of pros- 1. Portier H, et al. Interaction between cephalosporins and alcohol. BL-S640; Cefatrizina; Céfatrizine; Cefatrizinum; SKF-60771; S- Lancet 1980; ii: 263. thetic devices, cefamandole should be continued for up 640P. (7R)-7-(α-D-4-Hydroxyphenylglycylamino)-3-(1H-1,2,3-tri- 2. Drummer S, et al. Antabuse-like effect of β-lactam antibiotics. N to 72 hours. Children over 3 months of age may be Engl J Med 1980; 303: 1417–18. azol-4-ylthiomethyl)-3-cephem-4-carboxylic acid. treated similarly to adults and given 50 to 100 mg/kg Цефатризин daily in equally divided doses. Antimicrobial Action C18H18N6O5S2 = 462.5. Cefamandole is bactericidal and acts similarly to cefal- Administration in renal impairment. Doses of cefaman- CAS — 51627-14-6. otin, but has a broader spectrum of activity. It generally dole should be reduced for patients with renal impairment. After ATC — J01DB07. has similar or less activity against Gram-positive sta- an initial dose of 1 to 2 g the following maintenance doses have ATC Vet — QJ01DB07. been recommended based on creatinine clearance (CC): phylococci and streptococci, but is resistant to some • CC 50 to 80 mL/minute: 0.75 to 2 g every 6 hours beta-lactamases produced by Gram-negative bacteria. • CC 25 to 50 mL/minute: 0.75 to 2 g every 8 hours HO O It is more active than cefalotin against many of the En- • CC 10 to 25 mL/minute: 0.5 to 1.25 g every 8 hours HH terobacteriaceae including some strains of Entero- S • CC 2 to 10 mL/minute: 0.5 to 1 g every 12 hours N bacter, Escherichia coli, Klebsiella, Salmonella, and • CC less than 2 mL/minute: 0.25 to 0.75 g every 12 hours H some Proteus spp. However, resistance to cefamandole NH2 N SN Preparations O N and other beta lactams has emerged in some species, COOH NH notably Enterobacter, during treatment with cefaman- USP 31: Cefamandole Nafate for Injection. Proprietary Preparations (details are given in Part 3) dole. Cefamandole is very active in vitro against Hae- Austral.: Mandol; Austria: Mandokef; Belg.: Mandol; Cz.: Mandol†; Gr.: mophilus influenzae although an inoculum effect has Acemycin; Cefadin; Mandokef; Hong Kong: Mandol†; Hung.: Cefam; Cefatrizine Propylene Glycol (BANM, pINNM) Mandokef†; Indon.: Dardokef; Dofacef; Irl.: Kefadol†; Ital.: Cefam; Cema- been reported for beta-lactamase-producing strains. do; Lampomandol; Mancef; Mandokef†; Mandolsan†; Septomandolo†; Cefatrizina propilenglicol; Cefatrizinas propilenglikolis; Céfatrizine Like cefalotin, most strains of Bacteroides fragilis are Neth.: Mandol; NZ: Mandol; Pol.: Tarcefandol; Port.: Mandokef†; Rus.: propylèneglycol; Cefatrizin-propilénglikol; Cefatrizinpropyleng- Cefat (Цефат); Mandol (Мандол); S.Afr.: Kefdole†; Mandokef; Switz.: lykol; Cefatrizin-propylenglykol; Cefatrizinum propylen glycolum; resistant to cefamandole, as are Pseudomonas spp. Mandokef; Thai.: Cefadol; Cefmandol; Mandol†. Cefatrizinum Propylenglycolum; Kefatritsiinipropyleeniglykoli. ◊ References. (7R)-7-(α-D-4-Hydroxyphenylglycylamino)-3-(1H-1,2,3-triazol- 1. Sabath LD. Reappraisal of the antistaphylococcal activities of 4-ylthiomethyl)-3-cephem-4-carboxylate propylene glycol. first-generation (narrow-spectrum) and second-generation (ex- Cefapirin Sodium (BANM, pINNM) panded-spectrum) cephalosporins. Antimicrob Agents Chemoth- Цефатризин Пропиленгликол er 1989; 33: 407–11. BL-P-1322; Cefapirin sodná sůl; Cefapirina sódica; Céfapirine sodique; Cefapirinnatrium; Cefapirin-nátrium; Cefapirino natrio C18H18N6O5S2, (C3H8O2)n. CAS — 64217-62-5. Pharmacokinetics druska; Cefapirinum natricum; Cephapirin Sodium (USAN); Kefa- piriininatrium; Natrii Cefapirinum. Sodium (7R)-7-[2-(4-pyri- ATC — J01DB07. Cefamandole is poorly absorbed from the gastrointes- ATC Vet — QJ01DB07. tinal tract. It is given intramuscularly or intravenously, dylthio)acetamido]cephalosporanate; Sodium (7R)-3-ace- usually as the nafate which is rapidly hydrolysed to re- toxymethyl-7-[2-(4-pyridylthio)acetamido]-3-cephem-4-carbox- Pharmacopoeias. In Eur. (see p.vii) and Jpn. ylate. Ph. Eur. 6.2 (Cefatrizine Propylene Glycol). A white or almost lease cefamandole in vivo. Peak plasma concentrations Натрий Цефапирин white powder. Slightly soluble in water; practically insoluble in for cefamandole of about 13 and 25 micrograms/mL alcohol and in dichloromethane. C17H16N3NaO6S2 = 445.4. have been achieved 0.5 to 2 hours after intramuscular CAS — 21593-23-7 (cefapirin); 24356-60-3 (cefapirin so- Profile doses of 0.5 and 1 g respectively; concentrations are dium). Cefatrizine is a cephalosporin antibacterial with actions and uses very low after 6 hours. About 70% is bound to plasma ATC — J01DB08. similar to those of cefalexin (p.218), although it might be more proteins. The plasma half-life varies from about 0.5 to ATC Vet — QJ01DB08. active in vitro. It is given orally as the base or, more often, as a 1.2 hours depending on the route of injection;