Synonym
Cloxacillin benzathine; Benzathine cloxacillin; Cloxacillin benzathine salt; UNII-AC79L7PV2G; Cloxacillin Benzathine (2:1)
IUPAC/Chemical Name
4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(((3-(2-chlorophenyl)-5-methyl-4-isoxazolyl)carbonyl)amino)-3,3-dimethyl-7-oxo-, (2S-(2alpha,5alpha,6beta))-, compd. with N,N'-bis(phenylmethyl)-1,2-ethanediamine (2:1)
InChi Key
COCFKSXGORCFOW-VZHMHXRYSA-N
InChi Code
InChI=1S/2C19H18ClN3O5S.C16H20N2/c2*1-8-11(12(22-28-8)9-6-4-5-7-10(9)20)15(24)21-13-16(25)23-14(18(26)27)19(2,3)29-17(13)23;1-3-7-15(8-4-1)13-17-11-12-18-14-16-9-5-2-6-10-16/h2*4-7,13-14,17H,1-3H3,(H,21,24)(H,26,27);1-10,17-18H,11-14H2/t2*13-,14+,17-;/m11./s1
SMILES Code
O=C([C@@H](C(C)(C)S[C@]1([H])[C@@H]2NC(C3=C(C)ON=C3C4=CC=CC=C4Cl)=O)N1C2=O)O.O=C([C@@H](C(C)(C)S[C@]5([H])[C@@H]6NC(C7=C(C)ON=C7C8=CC=CC=C8Cl)=O)N5C6=O)O.C9(CNCCNCC%10=CC=CC=C%10)=CC=CC=C9
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
>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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
1,112.11
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: Araújo RS, Garcia GM, Vilela JMC, Andrade MS, Oliveira LAM, Kano EK, Lange CC, Brito MAVPE, Brandão HM, Mosqueira VCF. Cloxacillin benzathine-loaded polymeric nanocapsules: Physicochemical characterization, cell uptake, and intramammary antimicrobial effect. Mater Sci Eng C Mater Biol Appl. 2019 Nov;104:110006. doi: 10.1016/j.msec.2019.110006. Epub 2019 Jul 19. PMID: 31499941.
2: Guccione J, D'Andrea L, Pesce A, Toni F, Borriello G, Salzano C, Diuccio F, Pascale M, Ciaramella P. Antibiotic dry buffalo therapy: effect of intramammary administration of benzathine cloxacillin against Staphylococcus aureus mastitis in dairy water buffalo. BMC Vet Res. 2020 Jun 12;16(1):191. doi: 10.1186/s12917-020-02410-7. PMID: 32532337; PMCID: PMC7291747.
3: Daigneault J, George LW, Baggot JD. Ocular and serum disposition kinetics of cloxacillin after topical administration of benzathine cloxacillin and intravenous administration of sodium cloxacillin to calves. Am J Vet Res. 1990 Mar;51(3):381-5. PMID: 2316914.
4: Riva G, Keller H. Penicillintherapie [Penicillin therapy]. Schweiz Med Wochenschr. 1968 Apr;98(15):561-8. German. PMID: 4971632.
5: Kietzmann M, Niedorf F, Gossellin J. Tissue distribution of cloxacillin after intramammary administration in the isolated perfused bovine udder. BMC Vet Res. 2010 Oct 6;6:46. doi: 10.1186/1746-6148-6-46. PMID: 20925913; PMCID: PMC2959039.
6: Daigneault J, George LW. Topically applied benzathine cloxacillin for treatment of experimentally induced infectious bovine keratoconjunctivitis. Am J Vet Res. 1990 Mar;51(3):376-80. PMID: 2316913.
7: Ward DA, Clark ES. Ocular pharmacology. Vet Clin North Am Food Anim Pract. 1991 Nov;7(3):779-91. doi: 10.1016/s0749-0720(15)31084-7. PMID: 1760761.
8: Cummins KA, McCaskey TA. Multiple infusions of cloxacillin for treatment of mastitis during the dry period. J Dairy Sci. 1987 Dec;70(12):2658-65. doi: 10.3168/jds.S0022-0302(87)80336-3. PMID: 3448114.
9: George LW, Keefe T, Daigneault J. Effectiveness of two benzathine cloxacillin formulations for treatment of naturally occurring infectious bovine keratoconjunctivitis. Am J Vet Res. 1989 Jul;50(7):1170-4. PMID: 2774340.
10: Davis WT, Maplesden DC, Natzke RP, Philpot WN, Garrett P, Card CS. Benzathine cloxacillin intramammary infusion for treatment of mastitis in dry cows. Vet Med Small Anim Clin. 1975 Mar;70(3):287-9. PMID: 1038883.
