WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 300142
CAS#: 405165-61-9 (HCl)
Description: Besifloxacin is a fourth-generation fluoroquinolone antibiotic. The marketed compound is besifloxacin hydrochloride. It was developed by SSP Co. Ltd., Japan, and designated SS734. SSP licensed U.S. and European rights to SS734 for ophthalmic use to InSite Vision Incorporated (OTCBB: INSV) in 2000. InSite Vision developed an eye drop formulation (ISV-403) and conducted preliminary clinical trials before selling the product and all rights to Bausch & Lomb in 2003.
MedKoo Cat#: 300142
Name: Besifloxacin HCl
CAS#: 405165-61-9 (HCl)
Chemical Formula: C19H22Cl2FN3O3
Exact Mass:
Molecular Weight: 430.3014
Elemental Analysis: C, 53.03; H, 5.15; Cl, 16.48; F, 4.42; N, 9.77; O, 11.15
Synonym: BOL 303224a; BOL-303224a; BOL303224a; BOL-303224-A; SS734; SS-734; SS 734; Besifloxacin HCl; Besivance.
IUPAC/Chemical Name: (+)-7-[(3R)-3-aminohexahydro-1H-azepin-1-yl]-8-chloro-1- cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid hydrochloride.
InChi Key: PMQBICKXAAKXAY-HNCPQSOCSA-N
InChi Code: InChI=1S/C19H21ClFN3O3.ClH/c20-15-16-12(18(25)13(19(26)27)9-24(16)11-4-5-11)7-14(21)17(15)23-6-2-1-3-10(22)8-23;/h7,9-11H,1-6,8,22H2,(H,26,27);1H/t10-;/m1./s1
SMILES Code: O=C(C1=CN(C2CC2)C3=C(C=C(F)C(N4C[C@H](N)CCCC4)=C3Cl)C1=O)O.[H]Cl
Appearance: 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.
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
The following data is based on the product molecular weight 430.3014 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: Proksch JW, Ward KW. Ocular pharmacokinetics/pharmacodynamics of besifloxacin, moxifloxacin, and gatifloxacin following topical administration to pigmented rabbits. J Ocul Pharmacol Ther. 2010 Oct;26(5):449-58. PubMed PMID: 20874668.
2: Sanders ME, Moore QC 3rd, Norcross EW, Sanfilippo CM, Hesje CK, Shafiee A, Marquart ME. Comparison of besifloxacin, gatifloxacin, and moxifloxacin against strains of pseudomonas aeruginosa with different quinolone susceptibility patterns in a rabbit model of keratitis. Cornea. 2011 Jan;30(1):83-90. PubMed PMID: 20847656.
3: Yoshida J, Kim A, Pratzer KA, Stark WJ. Aqueous penetration of moxifloxacin 0.5% ophthalmic solution and besifloxacin 0.6% ophthalmic suspension in cataract surgery patients. J Cataract Refract Surg. 2010 Sep;36(9):1499-502. PubMed PMID: 20692561.
4: Comstock TL, Paterno MR, Decory HH, Usner DW. Safety and tolerability of besifloxacin ophthalmic suspension 0.6% in the treatment of bacterial conjunctivitis: data from six clinical and phase I safety studies. Clin Drug Investig. 2010;30(10):675-85. doi: 10.2165/11536720-000000000-00000. PubMed PMID: 20629472.
5: Norcross EW, Sanders ME, Moore Q 3rd, Sanfilippo CM, Hesje CK, Shafiee A, Marquart ME. Comparative efficacy of besifloxacin and other fluoroquinolones in a prophylaxis model of penicillin-resistant Streptococcus pneumoniae rabbit endophthalmitis. J Ocul Pharmacol Ther. 2010 Jun;26(3):237-43. PubMed PMID: 20565309.
6: Zhang JZ, Krenzer KL, López FJ, Ward KW. Comparative effects of besifloxacin and other fluoroquinolones on corneal reepithelialization in the rabbit. J Cataract Refract Surg. 2010 Jun;36(6):1049-50. PubMed PMID: 20494783.
7: Torkildsen G, Proksch JW, Shapiro A, Lynch SK, Comstock TL. Concentrations of besifloxacin, gatifloxacin, and moxifloxacin in human conjunctiva after topical ocular administration. Clin Ophthalmol. 2010 Apr 26;4:331-41. PubMed PMID: 20463802; PubMed Central PMCID: PMC2861941.
8: Comstock TL, Karpecki PM, Morris TW, Zhang JZ. Besifloxacin: a novel anti-infective for the treatment of bacterial conjunctivitis. Clin Ophthalmol. 2010 Apr 26;4:215-25. PubMed PMID: 20463787; PubMed Central PMCID: PMC2861926.
9: Haas W, Pillar CM, Hesje CK, Sanfilippo CM, Morris TW. Bactericidal activity of besifloxacin against staphylococci, Streptococcus pneumoniae and Haemophilus influenzae. J Antimicrob Chemother. 2010 Jul;65(7):1441-7. Epub 2010 Apr 30. PubMed PMID: 20435780; PubMed Central PMCID: PMC2882870.
10: Chang MH, Fung HB. Besifloxacin: a topical fluoroquinolone for the treatment of bacterial conjunctivitis. Clin Ther. 2010 Mar;32(3):454-71. Review. PubMed PMID: 20399984.
Related:
405165-61-9 (Besifloxacin HCl)
141388-76-3 (Besifloxacin free).
