Basic information
- Standard SMILES
C[C@@H]1CN(c2c(F)c(N)c3c(=O)c(C(=O)O)cn(C4CC4)c3c2F)C[C@H](C)N1- InChIKey
DZZWHBIBMUVIIW-DTORHVGOSA-N- Molecular formula
- C19H22F2N4O3
- Average molar mass
- 392.4 g/mol
- Monoisotopic mass
- 392.165997
Overview
Sparfloxacin is a quinolone, a quinolinemonocarboxylic acid, a N-arylpiperazine, a quinolone antibiotic and a fluoroquinolone antibiotic.
Names & identifiers
- Preferred name
- Sparfloxacin
- IUPAC
- 5-amino-1-cyclopropyl-7-[(3R,5S)-3,5-dimethylpiperazin-1-yl]-6,8-difluoro-4-oxoquinoline-3-carboxylic acid
Names & synonyms
Show more names
Database identifiers
- CAS
110871-86-8- PubChem CID
- 60464
- DTXSID
DTXSID9023590- ChEMBL
CHEMBL850- ChEBI
CHEBI:9212- UNII
- Q90AGA787L
- EC Number
- 629-019-8
- Nikkaji
- J324.247A
Properties
Computed structural properties
- XLogP
- 0.1
- Topological polar surface area
- 98.9 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 9
- Rotatable bonds
- 3
- Heavy atoms
- 28
- Formal charge
- 0
- Complexity
- 691
Experimental & physicochemical properties
Drugs
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Anti infectives for systemic use -> Antibacterials for systemic use
Pharmaceuticals -> Antibiotics
Solubility
Practically insoluble
1.13e-01 g/L
Human Drugs
Breast Feeding; Lactation; Milk, Human; Anti-Infective Agents; Antibacterial Agents; Quinolones; Fluoroquinolones
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Collision Cross Section
190.2 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID9023590]
216.1 Ų [M+K]+
Safety & regulation
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 40 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Toxicology
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
Sparfloxacin
DILI Positive
DOI:10.1016/j.drudis.2019.09.022
Chemistry & industry
Pharmacology
ATC Code
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
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.
MeSH Pharmacological Classification
Drugs used in the treatment of tuberculosis. They are divided into two main classes: first-line agents, those with the greatest efficacy and acceptable degrees of toxicity used successfully in the great majority of cases; and second-line drugs used in drug-resistant cases or those in which some other patient-related condition has compromised the effectiveness of primary therapy.
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.
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
Linked notes
Loading…