Synonym
Cefuroxime pivoxetil; CCI-23628; CCI23628; CCI 23628
IUPAC/Chemical Name
1-((2-methoxy-2-methylpropanoyl)oxy)ethyl (6R,7R)-3-((carbamoyloxy)methyl)-7-((Z)-2-(furan-2-yl)-2-(methoxyimino)acetamido)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
InChi Key
MGYPWVCKENORQX-KMMUMHRISA-N
InChi Code
InChI=1S/C23H28N4O11S/c1-11(38-21(31)23(2,3)33-4)37-20(30)16-12(9-36-22(24)32)10-39-19-15(18(29)27(16)19)25-17(28)14(26-34-5)13-7-6-8-35-13/h6-8,11,15,19H,9-10H2,1-5H3,(H2,24,32)(H,25,28)/b26-14-/t11?,15-,19-/m1/s1
SMILES Code
CO/N=C(c1ccco1)\C(N[C@H]2[C@H]3SCC(COC(N)=O)=C(C(OC(OC(C(C)(OC)C)=O)C)=O)N3C2=O)=O
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
Shelf Life
>3 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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
568.55
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 |
1: Daniel M, Szajewska H, Pańczyk-Tomaszewska M. 7-day compared with 10-day antibiotic treatment for febrile urinary tract infections in children: protocol of a randomised controlled trial. BMJ Open. 2018 Mar 2;8(3):e019479. doi: 10.1136/bmjopen-2017-019479. PMID: 29500209; PMCID: PMC5855174.
2: Rimmler C, Lanckohr C, Akamp C, Horn D, Fobker M, Wiebe K, Redwan B, Ellger B, Koeck R, Hempel G. Physiologically based pharmacokinetic evaluation of cefuroxime in perioperative antibiotic prophylaxis. Br J Clin Pharmacol. 2019 Dec;85(12):2864-2877. doi: 10.1111/bcp.14121. Epub 2019 Dec 15. PMID: 31487057; PMCID: PMC6955413.
3: Marx MA, Fant WK. Cefuroxime axetil. Drug Intell Clin Pharm. 1988 Sep;22(9):651-8. doi: 10.1177/106002808802200901. PMID: 3063476.
4: Emmerson AM. Cefuroxime axetil. J Antimicrob Chemother. 1988 Aug;22(2):101-4. doi: 10.1093/jac/22.2.101. PMID: 3053551.
5: Alrammaal HH, Batchelor HK, Morris RK, Chong HP. Efficacy of perioperative cefuroxime as a prophylactic antibiotic in women requiring caesarean section: A systematic review. Eur J Obstet Gynecol Reprod Biol. 2019 Nov;242:71-78. doi: 10.1016/j.ejogrb.2019.08.022. Epub 2019 Aug 31. PMID: 31569027.
6: Scott LJ, Ormrod D, Goa KL. Cefuroxime axetil: an updated review of its use in the management of bacterial infections. Drugs. 2001;61(10):1455-500. doi: 10.2165/00003495-200161100-00008. PMID: 11558834.
7: Aalbers M, ter Horst PG, Hospes W, Hijmering ML, Spanjersberg AJ. Targeting cefuroxime plasma concentrations during coronary artery bypass graft surgery with cardiopulmonary bypass. Int J Clin Pharm. 2015 Aug;37(4):592-8. doi: 10.1007/s11096-015-0101-8. Epub 2015 Mar 20. PMID: 25791346.
8: Smith BR, LeFrock JL. Cefuroxime: antimicrobial activity, Pharmacology, and clinical efficacy. Ther Drug Monit. 1983 Jun;5(2):149-60. PMID: 6349019.
9: Skhirtladze-Dworschak K, Hutschala D, Reining G, Dittrich P, Bartunek A, Dworschak M, Tschernko EM. Cefuroxime plasma and tissue concentrations in patients undergoing elective cardiac surgery: Continuous vs bolus application. A pilot study. Br J Clin Pharmacol. 2019 Apr;85(4):818-826. doi: 10.1111/bcp.13865. Epub 2019 Feb 13. PMID: 30636060; PMCID: PMC6422641.
10: Pakes GE, Graham JA, Rauch AM, Collins JJ. Cefuroxime axetil in the treatment of sinusitis. A review. Arch Fam Med. 1994 Feb;3(2):165-75. doi: 10.1001/archfami.3.2.165. PMID: 7994439.
