7-fluoro-2-methyl-6-(4-methylpiperazin-1-yl)-10-oxo-4-oxa-1-azatricyclo[7.3.1.0^{5,13}]trideca-5(13),6,8,11-tetraene-11-carboxylic acid

• ChemBase ID: 1036
• Molecular Formular: C18H20FN3O4
• Molecular Mass: 361.3675032
• Monoisotopic Mass: 361.14378436
• SMILES: Fc1c(N2CCN(CC2)C)c2OCC(n3c2c(c1)c(=O)c(c3)C(=O)O)C
• Canonical 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)
• InChIKey: GSDSWSVVBLHKDQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-fluoro-2-methyl-6-(4-methylpiperazin-1-yl)-10-oxo-4-oxa-1-azatricyclo[7.3.1.0^{5,13}]trideca-5(13),6,8,11-tetraene-11-carboxylic acid; 7-fluoro-2-methyl-6-(4-methylpiperazin-1-yl)-10-oxo-4-oxa-1-azatricyclo[7.3.1.0^5,^1^3]trideca-5(13),6,8,11-tetraene-11-carboxylic acid
• IUPAC Traditional name: 7-fluoro-2-methyl-6-(4-methylpiperazin-1-yl)-10-oxo-4-oxa-1-azatricyclo[7.3.1.0^5,^1^3]trideca-5(13),6,8,11-tetraene-11-carboxylic acid; ofloxacin
• Brand Name: Akilen; Baccidal; Bactocin; Danoflox; Effexin; Exocin; Exocine; Flobacin; Flodemex; Flotavid; Flovid; Floxal; Floxil; Floxstat; Fugacin; Inoflox; Kinflocin; Kinoxacin; Liflox; Loxinter; Marfloxacin; Medofloxine; Mergexin; Novecin; Nufafloqo; O-Flox; Obide; Occidal; Ofcin; Oflin; Oflocee; Oflocet; Oflocin; Oflodal; Oflodex; Oflodura; Oflox; Ofloxin; Ofus; Onexacin; Operan; Orocin; Otonil; Pharflox; Praxin; Puiritol; Qinolon; Qipro; Quinolon; Quotavil; Rilox; Sinflo; Tabrin; Taravid; Tariflox; Tarivid; Telbit; Tructum; Uro Tarivid; Viotisone; Zanocin; Floxin
• Synonyms: 9-Fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic Acid; Floxil; Monoflocet; Ocuflox; Mefoxacin; Oflocin; Ofloxacin; Oflocet; Ofloxacine; Oxaldin; Tarivid; Visiren; 9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-3,7-dihydro-2H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid; Ofloxacin; DL-8280; HOE-280; Exocin; Flobacin; Floxin; 氧氟沙星

Database IDs

• CAS Number: 82419-36-1
• MDL Number: MFCD00226105
• PubChem SID: 24860450; 46507574; 160964499; 24278613
• PubChem CID: 4583

CALCULATED PROPERTIES

JChem

• Acid pKa: 5.4470572
• H Acceptors: 7
• H Donor: 1
• LogD (pH = 5.5): 0.616237
• LogD (pH = 7.4): -0.2825112
• Log P: 0.65427977
• Molar Refractivity: 94.9359 cm^3
• Polarizability: 34.82272 Å^3
• Polar Surface Area: 73.32 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.02
• LOG S: -2.4
• Solubility (Water): 1.44e+00 g/l

PROPERTIES

Physical Property

• Solubility: 28.3 mg/mL; Chloroform; DMSO
• Apperance: Off-White Solid
• Melting Point: 270-275°C
• Hydrophobicity(logP): 2.1

Safety Information

• Storage Condition: -20°C; -20°C Freezer; Room Temperature (15-30°C)
• RTECS: UU8815500
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 2
• Risk Statements: R:40-20/21/22-42/43
• Safety Statements: S:22-26-45-36/37/39
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C; room temp

Pharmacology Properties

• Target: topoisomerase
• Gene Information: human ... CSNK2A1(1457), KCNH1(3756)rat ... Gabra1(29705)
• Mechanism of Action: DNA gyrase inhibitor

Product Information

• Grade: certified reference material; VETRANAL™, analytical standard
• Salt Data: Free Base
• Packaging: pkg of 1 g
• Suitability: suitable for 1694 per US EPA
• Application(s): Antibacterial agent; Antiseptic; Shows broad spectrum of activity against gram-positive and -negative bacteria
• Pharmacopeia Traceability: traceable to USP 1478108
• Empirical Formula (Hill Notation): C18H20FN3O4

DETAILS

MP Biomedicals - 02199018

Anti-bacterial Agent

DrugBank - DB01165

• Drug Groups: approved
• Description: A synthetic fluoroquinolone (fluoroquinolones) antibacterial agent that inhibits the supercoiling activity of bacterial DNA gyrase, halting DNA replication. [PubChem]
• Indication: For the treatment of infections (respiratory tract, kidney, skin, soft tissue, UTI), urethral and cervical gonorrhoea.
• Pharmacology: Ofloxacin is a quinolone/fluoroquinolone antibiotic. Ofloxacin is bactericidal and its mode of action depends on blocking of bacterial DNA replication by binding itself to an enzyme called DNA gyrase, which allows the untwisting required to replicate one DNA double helix into two. Notably the drug has 100 times higher affinity for bacterial DNA gyrase than for mammalian. Ofloxacin is a broad-spectrum antibiotic that is active against both Gram-positive and Gram-negative bacteria.
• Toxicity: LD₅₀=5450 mg/kg (orally in mice)
• Affected Organisms: Enteric bacteria and other eubacteria
• Biotransformation: Hepatic
• Absorption: Bioavailability of ofloxacin in the tablet formulation is approximately 98%
• Half Life: 9 hours
• Protein Binding: 32%
• Elimination: Elimination is mainly by renal excretion. Between 65% and 80% of an administered oral dose of ofloxacin is excreted unchanged via the kidneys within 48 hours of dosing. Four to eight percent of an ofloxacin dose is excreted in the feces. This indicates a small degree of biliary excretion of ofloxacin.
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Selleck Chemicals - S1463

Research Area: Infection
Biological Activity:
Ofloxacin is a synthetic chemotherapeutic antibiotic of the fluoroquinolone drug class. Ofloxacin is a broad-spectrum antibiotic that is active against both Gram-positive and Gram-negative bacteria. It functions by inhibiting DNA gyrase, a type II topoisomerase and topoisomerase IV, which is an enzyme necessary to separate replicated DNA, thereby inhibiting cell division. [1]

Sigma Aldrich - O8757

Other Notes
Nalidixic acid analog with broad-spectrum antibacterial activity.
Application
Ofloxacin is a synthetic fluoroquinolone with broad-spectrum antibacterial activity. It is a nalidixic acid analog. It is given to patients before undergoing retinal reattachment surgery1. It is used to study pneumococcal cell wall-degrading virulence factors2.
Biochem/physiol Actions
Ofloxacin inhibits bacterial DNA gyrase and topoisomerase IV, which haults DNA replication and cell division. Ofloxacin has been shown to convert LytA from the inactive E-form to the active C-form2. It is a chiral molecule that inhibits pneumococcal cell wall-degrading virulence factors2.

Sigma Aldrich - 33703

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 33703.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Sigma Aldrich - PHR1168

General description
This certified reference material (CRM) is produced and certified in accordance with ISO/IEC 17025 and ISO Guide 34.
Other Notes
Values of analytes vary lot to lot.

Toronto Research Chemicals - O245750

Fluorinated quinolone antibacterial.

REFERENCES

• http://www.rxlist.com/floxin-drug.htm
• Monk, J.P., et al.: Drugs, 33, 346 (1987)
• Drlica, K., Curr. Opin. Microbiol. 2, 504 (1990)
• Sato, K. et al., Antimicrob. Agents Chemother., 1982, 22, 548, (pharmacol)
• Eur. Pat., 1982, Daiichi Seiyaku, 47 005; CA, 97, 55821b, (synth, pharmacol)
• Hayakawa, I. et al., Antimicrob. Agents Chemother., 1986, 29, 163, (resoln, props)
• Egawa, H. et al., Chem. Pharm. Bull., 1986, 34, 4098, (synth)
• Monk, J.P. et al., Drugs, 1987, 33, 346, (rev)
• Mitscher, L.A. et al., J. Med. Chem., 1987, 30, 2283, (synth, activity)
• New Gener. Quinolones, 1990, (Eds. Siporin, C. et al), M. Dekker (see Infect. Dis. Ther. v5 1990), 1990, (book)
• The 4-Quinolones: Antibacterial Agents in Vitro, (Ed. Crumplin, G.C.), Springer-Verlag, London, 1990, (book)
• Todd, P.A. et al., Drugs, 1991, 42, 825, (rev)
• Tunkel, A.R. et al., Infect. Control Hosp. Epidemiol., 1991, 12, 549, (activity, rev)
• Atarashi, S. et al., J. Het. Chem., 1991, 28, 329, (synth)
• Sanders, C.C., Clin. Infect. Dis., 1992, 14, 526, (rev)
• Lamp, K.C. et al., Clin. Pharmacokinet., 1992, 22, 32, (pharmacokinet, rev)
• Davis, R. et al., Drugs, 1994, 47, 677, (rev)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 7th edn., Akademie-Verlag, 1994, 6400; 6401, (synonyms)
• Hashimoto, K. et al., Acta Cryst. C, 1995, 51, 519
• Kitaoka, H. et al., Chem. Pharm. Bull., 1995, 43, 649, (cryst struct, props)
• Langtry, H.D. et al., Drugs, 1998, 56, 487-515; 895-928, (rev)
• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 221; 233
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, OGI300