Balofloxacin
Basic information
- CAS
127294-70-6- Standard SMILES
CNC1CCCN(c2c(F)cc3c(=O)c(C(=O)O)cn(C4CC4)c3c2OC)C1- InChIKey
MGQLHRYJBWGORO-UHFFFAOYSA-N- Molecular formula
- C20H24FN3O4
- Average molar mass
- 389.4 g/mol
- Monoisotopic mass
- 389.17508442
Overview
showed potent bactericidal activity & inhibited the supercoiling activity of DNA gyrase of S. aureus, E. coli, & P aeruginosa; structure given in first source
Names & identifiers
- Preferred name
- Balofloxacin
- IUPAC
- 1-cyclopropyl-6-fluoro-8-methoxy-7-[3-(methylamino)piperidin-1-yl]-4-oxoquinoline-3-carboxylic acid
- English name
- Balofloxacin
- Molecular formula
- C20H24FN3O4
- Molecular weight
- 389.42
Names & synonyms
Balofloxacin127294-70-6Q-RoxinDTXSID5046695balofloxacinebalofloxacinoQ022B63JPM1-cyclopropyl-6-fluoro-8-methoxy-7-[3-(methylamino)piperidin-1-yl]-4-oxoquinoline-3-carboxylic acidDTXCID30266953-Quinolinecarboxylic acid, 1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-(3-(methylamino)-1-piperidinyl)-4-oxo-3-Quinolinecarboxylic acid, 1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-[3-(methylamino)-1-piperidinyl]-4-oxo-1-cyclopropyl-6-fluoro-8-methoxy-7-(3-methylaminopiperidin-1-yl)-4-oxoquinoline-3-carboxylic acid
Show more names
q35Barlow of sandBALOFLOXACIN 98.5%Balofloxacin425.46Balofloxacin, >=99%Balofloxacin hydrateBalofloxacin USP/EP/BPCypermethrin Impurity 4Balofloxacin, 10 mM in DMSO
balofloxacinumBalofoxBazucin1-cyclopropyl-6-fluoro-8-methoxy-7-(3-(methylamino)piperidin-1-yl)-4-oxoquinoline-3-carboxylic acidRefChem:1163831-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-(3-methylaminopiperidine-1-yl)-4-oxoquinoline-3-carboxylic acid1-Cyclopropyl-6-fluoro-8-methoxy-7-(3-(methylamino)piperidin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acidBalofloxacin [INN]
Properties
Computed structural properties
- XLogP
- 0.6
- Topological polar surface area
- 82.1 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 5
- Heavy atoms
- 28
- Formal charge
- 0
- Complexity
- 668
Experimental & physicochemical properties
Drugs
Pharmaceuticals -> Antibiotics
Pharmaceuticals -> Anti infectives for systemic use -> Antibacterials for systemic use
Physicochemical properties
- Melting point
- 137 °C · 137°C
- Boiling point
- 608.3 · 608.3±55.0 °C(Predicted)
- Density
- 1.4 · 1.40±0.1 g/cm3(Predicted)
- storage temp.
- 2 · Keep in dark place,Inert atmosphere,2-8°C
- solubility
- 2 O · H2O : < 0.1 mg/mL (insoluble)DMSO : 0.67 mg/mL (1.72 mM; Need ultrasonic)
- pka
- 6.44 · 6.44±0.50(Predicted)
- form
- Solid
- color
- White to off-white
- BRN
- 8362117 · 8362117
- InChI
- InChI=1S/C20H24FN3O4/c1-22-11-4-3-7-23(9-11)17-15(21)8-13-16(19(17)28-2)24(12-5-6-12)10-14(18(13)25)20(26)27/h8,10-12,22H,3-7,9H2,1-2H3,(H,26,27)
- InChIKey
- MGQLHRYJBWGORO-UHFFFAOYSA-N
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 3
- Signal word
- Warning
- Symbol(GHS)
- GHS02
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H228
- Precautionary statements
- P403-P501c
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Substances that inhibit the growth or reproduction of BACTERIA.
Compounds that inhibit the activity of DNA TOPOISOMERASE II. Included in this category are a variety of ANTINEOPLASTIC AGENTS which target the eukaryotic form of topoisomerase II and ANTIBACTERIAL AGENTS which target the prokaryotic form of topoisomerase II.
Applications
DescriptionBalofloxacin, a novel orally-active fluoroquinolone antibiotic, was introduced in South Korea for the treatment of urinary tract infections (UTI). It can be synthetized by reaction of 3-(methylamino)piperidine with the classical 4-quinolone-3-carboxylic acid template. In vitro antibacterial activity of balofloxacin against gram-positive bacteria (Staphylococcus aureus including methicillin-resistant S. aureus, Staphylococcus epidermis, Streptococcus pneumonia, Streptococcus pyrogenes) was almost equal to that of sparfloxacin or tosufloxacin, in contrast its activity against gram-negative bacteria was 2 times or more lower. In clinical trials, balofloxacin was well tolerated and showed comparable efficacy to ofloxacin in patients with UTls. After oral administration, balofloxacin was well absorbed, and was primarily eliminated unchanged in the urine with an elimination half-life of approximately 8 h. In animal studies, balofloxacin did not exhibit any phototoxicity.
UsesFluorinated quinolone antibacterial.
UsesBalofloxacin is quinolone antibiotic, inhibiting the synthesis of bacterial DNA by interference with the enqyme DNA gyrase.
Upstream & downstream products
Upstream raw materials
Related reactions
2 records
Compound notes
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