Synonym
Cefazaflur (free base)
IUPAC/Chemical Name
(6R,7R)-3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-8-oxo-7-(2-((trifluoromethyl)thio)acetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
InChi Key
HGXLJRWXCXSEJO-GMSGAONNSA-N
InChi Code
InChI=1S/C13H13F3N6O4S3/c1-21-12(18-19-20-21)28-3-5-2-27-10-7(9(24)22(10)8(5)11(25)26)17-6(23)4-29-13(14,15)16/h7,10H,2-4H2,1H3,(H,17,23)(H,25,26)/t7-,10-/m1/s1
SMILES Code
Cn1c(SCC2=C(C(O)=O)N3[C@@H]([C@@H](C3=O)NC(CSC(F)(F)F)=O)SC2)nnn1
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
470.46
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: Counts GW, Gregory D, Zeleznik D, Turch M. Cefazaflur, a new parenteral cephalosporin: in vitro studies. Antimicrob Agents Chemother. 1977 Apr;11(4):708-11. doi: 10.1128/aac.11.4.708. PMID: 324399; PMCID: PMC352055.
2: Actor P, Guarini JR, Uri J, Bartus HF, Zajac I, Weisbach JA. In vitro studies with cefazaflur and other parenteral cephalosporins. J Antibiot (Tokyo). 1977 Sep;30(9):730-5. doi: 10.7164/antibiotics.30.730. PMID: 924896.
3: Harvengt C, Muenier H, Lamy F. Pharmacokinetic study of cefazaflur compared to cephalothin and cefazolin. J Clin Pharmacol. 1977 Feb-Mar;17(2-3):128-33. doi: 10.1002/j.1552-4604.1977.tb04599.x. PMID: 833342.
4: Aswapokee N, Neu HC. In vitro activity and beta-lactamase stability of cefazaflur compared with those of beta-lactamase-stable cephalosporins. Antimicrob Agents Chemother. 1979 Mar;15(3):444-6. doi: 10.1128/aac.15.3.444. PMID: 313753; PMCID: PMC352680.
5: Bergan T. Pharmacokinetic properties of the cephalosporins. Drugs. 1987;34 Suppl 2:89-104. doi: 10.2165/00003495-198700342-00008. PMID: 3319507.
6: Irwin VP, Timoney RF. Cefazaflur: kinetics of hydrolysis in aqueous solution, acid dissociation constant and alkaline decomposition to fluorescent products. J Pharm Pharmacol. 1989 May;41(5):360. doi: 10.1111/j.2042-7158.1989.tb06477.x. PMID: 2569531.
7: Pitkin DH, Actor P, Baldinus JG, Post A, Weisbach JA. Semiautomated turbidimetric microbiological assay for cefazaflur. J Antibiot (Tokyo). 1978 Apr;31(4):359-62. doi: 10.7164/antibiotics.31.359. PMID: 26651.
8: DeMarinis RM, Uri JV, Weisbach JA. Synthesis and in vitro antibacterial activity of 7-trifluoromethylthioacetamido cephamycins related to SK&F 59962 (cefazaflur). J Antibiot (Tokyo). 1976 Sep;29(9):973-5. doi: 10.7164/antibiotics.29.973. PMID: 993139.
9: Laverdiere M, Welter D, Sabath LD. Use of a heavy inoculum in the in vitro evaluation of the anti-staphylococcal activity of 19 cephalosporins. Antimicrob Agents Chemother. 1978 Apr;13(4):669-75. doi: 10.1128/aac.13.4.669. PMID: 352261; PMCID: PMC352308.
10: Verbist L. Comparison of the antibacterial activity of nine cephalosporins against Enterobacteriaceae and nonfermentative gram-negative bacilli. Antimicrob Agents Chemother. 1976 Oct;10(4):657-63. doi: 10.1128/aac.10.4.657. PMID: 984801; PMCID: PMC429810.
