Compound ID | 2041

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Sparfloxacin

Synonym(s): Zagam  |  AT-4140

Class: Fluoroquinolone

Spectrum of activity: Gram-positive  &  Gram-negative
Details of activity: Binds to type II topoisomerases, gyrase and topoisomerase IV and thus, inhibits DNA cleavage and ligation reactions. It kills bacterial cells by increasing the concentration of enzyme–DNA cleavage complexes, thereby inhibiting cell replication.
Description: Synthetic quinoline derivative.
Institute where first reported: Mylan
Year first mentioned: 1985
Highest developmental phase: Approved by FDA in 1996
Development status: Discontinued in most countries
Reason Dropped: Phototoxicity and QTc prolongation
Chemical structure(s):
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Molecular weight: 392.4
Iso. SMILES: C[C@@H]1CN(C[C@@H](N1)C)C2=C(C(=C3C(=C2F)N(C=C(C3=O)C(=O)O)C4CC4)N)F
InChI Key: DZZWHBIBMUVIIW-DTORHVGOSA-N
Can. SMILES: C[C@H]1CN(C[C@@H](C)N1)C2=C(C3=C(C(=C2F)N)C(=O)C(=CN3C4CC4)C(=O)O)F
InChI: InChI=1S/C19H22F2N4O3/c1-8-5-24(6-9(2)23-8)17-13(20)15(22)12-16(14(17)21)25(10-3-4-10)7-11(18(12)26)19(27)28/h7-10,23H,3-6,22H2,1-2H3,(H,27,28)/t8-,9+
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/60464
Guide to Pharmacology: sparfloxacin
Citations:
  • https://pubmed.ncbi.nlm.nih.gov/11549783/
  • https://pubmed.ncbi.nlm.nih.gov/15917145/

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