Synonym
Cefuroxime Sodium; Cefuroxime sodium salt; Anaptivan; Biociclin; Sodium cefuroxime; Colifossim; Cephuroxime; Ketocef; Zinacef;
IUPAC/Chemical Name
sodium;(6R,7R)-3-(carbamoyloxymethyl)-7-[[(2Z)-2-(furan-2-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
InChi Key
URDOHUPGIOGTKV-JTBFTWTJSA-M
InChi Code
InChI=1S/C16H16N4O8S.Na/c1-26-19-9(8-3-2-4-27-8)12(21)18-10-13(22)20-11(15(23)24)7(5-28-16(17)25)6-29-14(10)20;/h2-4,10,14H,5-6H2,1H3,(H2,17,25)(H,18,21)(H,23,24);/q;+1/p-1/b19-9-;/t10-,14-;/m1./s1
SMILES Code
CO/N=C(/C1=CC=CO1)\C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)COC(=O)N)C(=O)[O-].[Na+]
Appearance
White to light yellow solid powder.
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Cefuroxime sodium is an orally active second-generation cephalosporin antibiotic with increased stability to β-lactamase.
In vitro activity:
The in vitro and in vivo susceptibilities of the Lyme disease pathogen Borrelia burgdorferi to cefuroxime were compared with those of several other antibiotics commonly used to treat this disease. Cefuroxime demonstrated a higher MBC in vitro (1.0 microgram/ml) than ceftriaxone (0.08 microgram/ml) or erythromycin (0.32 microgram/ml), but the MBC was similar to that of amoxicillin (0.8 microgram/ml) and doxycycline (1.6 micrograms/ml). B. burgdorferi was considerably less susceptible to tetracycline (3.2 micrograms/ml) and penicillin G (6.4 micrograms/ml). Of the three other Borrelia species tested, two (Borrelia turicatae and Borrelia anserina) also demonstrated susceptibility to cefuroxime, while the third (Borrelia hermsii) was less susceptible. Results obtained with four antimicrobial agents in the in vivo hamster model parallel the antibiotic susceptibilities in the in vitro study. The three antibiotics with similar MBCs in vitro, i.e., cefuroxime, doxycycline, and amoxicillin, demonstrated comparable activities in preventing borreliosis in B. burgdorferi-challenged hamsters (50% curative doses = 28.6, 36.5 and 45.0 mg/kg, respectively). Penicillin G, which demonstrated the highest MBC in vitro, had very weak protective activity in the hamster model system. These results indicate that the in vitro and in vivo activities of cefuroxime against B. burgdorferi are comparable to those of several oral antibiotics currently being used in the treatment of early Lyme disease and suggest that the oral form of this cephalosporin may be an effective alternative therapy for this disease.
Reference: Antimicrob Agents Chemother. 1990 Nov;34(11):2133-6. https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/2073103/
In vivo activity:
The intravenous LD50 of cefuroxime sodium for mice is 10.4 g/kg. The maximum dosage administered in other acute toxicity tests is well tolerated by mice (10 g/kg, subcutaneous), by rats (4 g/kg, intravenous, 5 g/kg, subcutaneous) and by cats, dogs and monkeys (2 g/kg, intramuscularly). However, when cefuroxime sodium is administered subcutaneously (s.c.) or intramuscularly (i.m.) for 3 months to rats (100, 300 or 900 mg/kg/day) followed by a recovery period, and also for 6 months to rats and dogs (50, 150 or 450 mg/kg/day) and for 1 month to monkeys (150 or 450 mg/kg/day), there are no serious toxic effects in all tests. In rats large doses cause some increase in urine volume and electrolyte excretion, and slightly aggravates an age related nephropathy. Administration to rats intravenously (i.v.) for 1 month of up to 400 mg/kg/day has no toxic effects. In reproduction studies on mice and rabbits there are no adverse effects on fertility, organogenesis or the rearing of young.
Reference: Toxicology. 1979 May;13(1):1-5. https://www.sciencedirect.com/science/article/abs/pii/S0300483X79800037?via%3Dihub
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
89.0 |
199.39 |
| Water |
50.0 |
112.01 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
446.37
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
In vitro protocol:
1. Johnson RC, Kodner CB, Jurkovich PJ, Collins JJ. Comparative in vitro and in vivo susceptibilities of the Lyme disease spirochete Borrelia burgdorferi to cefuroxime and other antimicrobial agents. Antimicrob Agents Chemother. 1990 Nov;34(11):2133-6. doi: 10.1128/AAC.34.11.2133. PMID: 2073103; PMCID: PMC172012.
2. Benson JM, Boudinot FD, Pennell AT, Cunningham FE, DiPiro JT. In vitro protein binding of cefonicid and cefuroxime in adult and neonatal sera. Antimicrob Agents Chemother. 1993 Jun;37(6):1343-7. doi: 10.1128/AAC.37.6.1343. PMID: 8328784; PMCID: PMC187963.
In vivo protocol:
1. Capel-Edwards K, Atkinson RM, Pratt DA. Toxicological studies on cefuroxime sodium. Toxicology. 1979 May;13(1):1-5. doi: 10.1016/s0300-483x(79)80003-7. PMID: 117570.
2. Ryan DM, O'Callaghan C, Muggleton PW. Cefuroxime, a new cephalosporin antibiotic: activity in vivo. Antimicrob Agents Chemother. 1976 Mar;9(3):520-5. doi: 10.1128/AAC.9.3.520. PMID: 1259408; PMCID: PMC429563.
1: Vieira DC, Fiuza TF, Salgado HR. Development and validation of a rapid
turbidimetric assay to determine the potency of cefuroxime sodium in powder for
dissolution for injection. Pathogens. 2014 Jul 30;3(3):656-66. doi:
10.3390/pathogens3030656. PubMed PMID: 25438016; PubMed Central PMCID:
PMC4243433.
2: Elbashir AA, Ahmed SM, Aboul-Enein HY. Optimization and validation of
spectrofluorimetric method for determination of cefadroxile and cefuroxime sodium
in pharmaceutical formulations. Luminescence. 2013 Jul-Aug;28(4):490-5. doi:
10.1002/bio.2481. Epub 2013 Jan 24. PubMed PMID: 23345111.
3: Zhao L, Li Q, Li X, Yin R, Chen X, Geng L, Bi K. Bioequivalence and population
pharmacokinetic modeling of two forms of antibiotic, cefuroxime lysine and
cefuroxime sodium, after intravenous infusion in beagle dogs. J Biomed
Biotechnol. 2012;2012:507294. doi: 10.1155/2012/507294. Epub 2012 Jul 15. PubMed
PMID: 22911056; PubMed Central PMCID: PMC3403372.
4: Vieira DC, Salgado HR. Comparison of HPLC and UV spectrophotometric methods
for the determination of cefuroxime sodium in pharmaceutical products. J
Chromatogr Sci. 2011 Aug;49(7):508-11. PubMed PMID: 21801481.
5: Nagesh C, Shankaraiah MM, Venkatesh JS, Setty SR. Role of liquid membrane
phenomenon in the anti-bacterial activity of Cefuroxime Sodium. J Basic Clin
Pharm. 2010 Mar;1(2):77-80. Epub 2010 May 15. PubMed PMID: 24825969; PubMed
Central PMCID: PMC3979183.
6: Schmidt CA, Agarrayua DA, Laporta LV, Machado JC, Manfio ML, Bittencourt CF.
Development and validation of a microbiological agar assay for determination of
cefuroxime sodium in pharmaceutical preparations. J Microbiol Methods. 2009
Jun;77(3):308-15. doi: 10.1016/j.mimet.2009.03.012. Epub 2009 Apr 1. PubMed PMID:
19344741.
7: Barnes AR. Chemical stabilities of cefuroxime sodium and metronidazole in an
admixture for intravenous infusion. J Clin Pharm Ther. 1990 Jun;15(3):187-96.
PubMed PMID: 2365756.
8: Marble DA, Bosso JA, Townsend RJ. Compatibility of clindamycin phosphate with
aztreonam in polypropylene syringes and with cefoperazone sodium, cefonicid
sodium, and cefuroxime sodium in partial-fill glass bottles. Drug Intell Clin
Pharm. 1988 Jan;22(1):54-7. PubMed PMID: 3349921.
9: Smith RC. No more overfill in cefuroxime sodium vials. Am J Hosp Pharm. 1986
Sep;43(9):2154. PubMed PMID: 3766566.
10: Das Gupta V, Stewart KR. Stability of cefuroxime sodium in some aqueous
buffered solutions and intravenous admixtures. J Clin Hosp Pharm. 1986
Feb;11(1):47-54. PubMed PMID: 3958213.
11: Furniss LD. Overfill in cefuroxime sodium vials. Am J Hosp Pharm. 1985
May;42(5):1045-6. PubMed PMID: 4003410.
12: Havard CW, Fernando A, Bannister B, Brumfitt W, Hamilton-Miller JM. Clinical
and pharmacokinetic comparison of cefuroxime sodium and cefuroxime lysine in the
treatment of lower respiratory tract infections. J Antimicrob Chemother. 1981
Nov;8(5):401-8. PubMed PMID: 7319981.
13: Gupta VD. Chemical stability of cefuroxime sodium after reconstitution in
0.9% sodium chloride injection and storage in polypropylene syringes for
pediatric use. Int J Pharm Compd. 2003 Jul-Aug;7(4):310-2. PubMed PMID: 23979702.
14: ABO EL-SOOUD K, El-Banna HA, Hanafy MS, Goudah A. Pharmacokinetics and
intramuscular bioavailability of cefuroxime sodium in goats. Res Vet Sci. 2000
Dec;69(3):219-24. PubMed PMID: 11124092.
15: Stewart JT, Warren FW, Johnson SM. Stability of cefuroxime sodium and
aminophylline or theophylline. Am J Hosp Pharm. 1994 Mar 15;51(6):809-11. PubMed
PMID: 8010322.
16: Stiles ML, Allen LV Jr, Fox JL. Stability of ceftazidime (with arginine) and
of cefuroxime sodium in infusion-pump reservoirs. Am J Hosp Pharm. 1992
Nov;49(11):2761-4. PubMed PMID: 1471642.
17: Păun L, Ceauşu E. Cefuroxime sodium for injection in the treatment of acute
severe infections in children and adults. Arch Roum Pathol Exp Microbiol. 1989
Apr-Jun;48(2):171-5. PubMed PMID: 2634369.
18: Morelli B. "Zero-crossing" derivative spectrophotometric determination of
mixtures of cephapirin sodium and cefuroxime sodium in pure form and in
injections. Analyst. 1988 Jul;113(7):1077-82. PubMed PMID: 3223581.
19: Eggleton B. Cost savings from overfill in cefuroxime sodium vials
questionable. Am J Hosp Pharm. 1985 Nov;42(11):2436, 2442. PubMed PMID: 4073059.
20: Lee A. Cefuroxime sodium. N C Med J. 1985 Mar;46(3):171-7. PubMed PMID:
3856752.
