Compound ID | 2041

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Sparfloxacin

Synonym(s): Zagam  |  AT-4140

Class: Fluoroquinolone

Agent Type: Synthetic; Small molecule; Direct acting;
Spectrum of activity: Gram-positive & Gram-negative
Mechanism of action: DNA synthesis inhibitor. Binds to type II topoisomerases, gyrase and topoisomerase IV to inhibitor DNA cleavage and ligation reactions; bacterial topoisomerase inhibitor
Description: Synthetic quinoline derivative.
Institute where first reported: Mylan
Year first mentioned: 1985
Highest development stage: Approved by FDA in 1996
Development status: Withdrawn
Reason dropped: Safety concerns; 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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