ofloxacin   Click here for help

GtoPdb Ligand ID: 10918

Synonyms: DL-8280 | Exocin® (eye drops) | Floxin® | HOE-280 | OFX | Tarivid®
Approved drug
ofloxacin is an approved drug (FDA (1990), UK (1992))
Compound class: Synthetic organic
Comment: Ofloxacin is a second generation fluoroquinolone antibacterial.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 2
Topological polar surface area 75.01
Molecular weight 361.14
XLogP 3.7
No. Lipinski's rules broken 0
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Canonical SMILES CN1CCN(CC1)c1c(F)cc2c3c1OCC(n3cc(c2=O)C(=O)O)C
Isomeric SMILES CN1CCN(CC1)c1c(F)cc2c3c1OCC(n3cc(c2=O)C(=O)O)C
InChI InChI=1S/C18H20FN3O4/c1-10-9-26-17-14-11(16(23)12(18(24)25)8-22(10)14)7-13(19)15(17)21-5-3-20(2)4-6-21/h7-8,10H,3-6,9H2,1-2H3,(H,24,25)
1. Barnard FM, Maxwell A. (2001)
Interaction between DNA gyrase and quinolones: effects of alanine mutations at GyrA subunit residues Ser(83) and Asp(87).
Antimicrob Agents Chemother, 45 (7): 1994-2000. [PMID:11408214]
2. Dotson CD, Zhang L, Xu H, Shin YK, Vigues S, Ott SH, Elson AE, Choi HJ, Shaw H, Egan JM et al.. (2008)
Bitter taste receptors influence glucose homeostasis.
PLoS One, 3 (12): e3974. [PMID:19092995]
3. Gellert M, Mizuuchi K, O'Dea MH, Nash HA. (1976)
DNA gyrase: an enzyme that introduces superhelical turns into DNA.
Proc Natl Acad Sci U S A, 73 (11): 3872-6. [PMID:186775]
4. Kondo H, Taguchi M, Inoue Y, Sakamoto F, Tsukamoto G. (1990)
Synthesis and antibacterial activity of thiazolo-, oxazolo-, and imidazolo[3,2-a][1,8]naphthyridinecarboxylic acids.
J Med Chem, 33 (7): 2012-5. [PMID:2163456]