Basic information
- CAS
110871-86-8- Standard SMILES
C[C@@H]1CN(c2c(F)c(N)c3c(=O)c(C(=O)[O-])cn(C4CC4)c3c2F)C[C@H](C)[NH2+]1- InChIKey
DZZWHBIBMUVIIW-DTORHVGOSA-N- Molecular formula
- C19H22F2N4O3
- Average molar mass
- 392.4 g/mol
- Monoisotopic mass
- 392.1659969
Overview
Sparfloxacin is a fluoroquinolone antibiotic indicated for bacterial infections. Sparfloxacin exerts its antibacterial activity by inhibiting DNA gyrase, a bacterial topoisomerase. DNA gyrase is an essential enzyme which controls DNA topology and assists in DNA replication, repair, deactivation, and transcription.
Names & identifiers
- Preferred name
- CID 6956367
- IUPAC
- 5-amino-1-cyclopropyl-7-[(3S,5R)-3,5-dimethylpiperazin-4-ium-1-yl]-6,8-difluoro-4-oxoquinoline-3-carboxylate
- English name
- Sparfloxacin
- Molecular formula
- C19H22F2N4O3
- Molecular weight
- 392.4
Names & synonyms
ParoxZagamci978Sparaat4140SparcinRP-64206CP 103826PD 1315-1Sparfloxacin
Database identifiers
- CAS
110871-86-8- PubChem CID
- 6956367
Properties
Computed structural properties
- XLogP
- 0.8
- Topological polar surface area
- 106 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 2
- Heavy atoms
- 28
- Formal charge
- 0
- Complexity
- 685
Experimental & physicochemical properties
LogP2.5
Solubility
Practically insoluble
1.13e-01 g/L
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 265 °C · 265°C
- Boiling point
- 640 ℃ · 640℃
- Density
- 1.436 · 1.436±0.06 g/cm3(Predicted)
- Flash point
- 110 ° · >110°(230°F)
- storage temp.
- 2 · Keep in dark place,Inert atmosphere,2-8°C
- solubility
- 10 mg/ml; · DMF: 10 mg/ml; DMF:PBS(pH 7.2)(1:1): 0.50 mg/ml
- pka
- 1 · pKa1 6.25, pKa2 9.30(at 25℃)
- form
- powder
- color
- white to light yellow
- biological source
- synthetic
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
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 2
- rtecs
- VB1986500
- hs_code
- 29339900
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H335
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P261-P264-P271-P280-P302+P352-P305+P351+P338
Chemistry & industry
Pharmacology
Protein BindingLow plasma protein binding in serum at about 45%.
Pharmacodynamics
Sparfloxacin is a synthetic fluoroquinolone broad-spectrum antimicrobial agent in the same class as ofloxacin and norfloxacin. Sparfloxacin has in vitro activity against a wide range of gram-negative and gram-positive microorganisms. Sparfloxacin exerts its antibacterial activity by inhibiting DNA gyrase, a bacterial topoisomerase. DNA gyrase is an essential enzyme which controls DNA topology and assists in DNA replication, repair, deactivation, and transcription. Quinolones differ in chemical structure and mode of action from (beta)-lactam antibiotics. Quinolones may, therefore, be active against bacteria resistant to (beta)-lactam antibiotics. Although cross-resistance has been observed between sparfloxacin and other fluoroquinolones, some microorganisms resistant to other fluoroquinolones may be susceptible to sparfloxacin. In vitro tests show that the combination of sparfloxacin and rifampin is antagonistic against Staphylococcus aureus.
Mechanism of ActionThe bactericidal action of sparfloxacin results from inhibition of the enzymes topoisomerase II (DNA gyrase) and topoisomerase IV, which are required for bacterial DNA replication, transcription, repair, and recombination.
Biological Half-LifeMean terminal elimination half-life of 20 hours (range 16-30 hours). Prolonged in patients with renal impairment (creatinine clearance <50 mL/min).
Metabolism/MetabolitesHepatic. Metabolized primarily by phase II glucuronidation to form a glucuronide conjugate. Metabolism does not utilize or interfere with the cytochrome P450 enzyme system.
Absorption, Distribution and Excretion
Well absorbed following oral administration with an absolute oral bioavailability of 92%. Unaffected by administration with milk or food, however concurrent administration of antacids containing magnesium hydroxide and aluminum hydroxide reduces the oral bioavailability of sparfloxacin by as much as 50%.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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