CAS 82419-36-1|Sinflo|Fugacin|Uro Tarivid|Oflox|Loxinter|Nufafloqo|Ofloxacin|Operan|Floxal|Rilox|Oflodex|Kinflocin|Ofcin|Tructum|Ofus|Quinolon|Kinoxacin|Flotavid|Exocine|Akilen|Marfloxacin|Bactocin|...

General Information

Structure

Molecular Formula

C₁₈H₂₀FN₃O₄

Molecular Mass

361.3675032

Exact Mass

361.14378436

Charge

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

Canonic Smiles

CN1CCN(CC1)c1c(F)cc2c3c1OCC(n3cc(c2=O)C(=O)O)C

Isomeric Smiles

Fc1c(N2CCN(CC2)C)c2OCC(n3c2c(c1)c(=O)c(c3)C(=O)O)C

Calculated Properties

JChem

Acid pKa

5.4470572

H Acceptors

H Donor

LogD (pH = 5.5)

0.616237

LogD (pH = 7.4)

-0.2825112

Log P

0.65427977

Molar Refractivity

94.9359

Polarizability

34.82272

Polar Surface Area

73.32

Rotatable Bonds

Lipinski's Rule of Five

true

ALOGPS 2.1

Log P

-0.02

LOG S

-2.4

Solubility (Water)

1.44e+00 g/l

Data Source

Names and Identifiers

Brand Name

NufafloqoMarfloxacinBactocinRiloxOflodexOfusFugacinSinfloUro TarividOperanOfcinTructumTabrinFloxalKinflocinKinoxacinFlotavidExocineLoxinterAkilenQuinolonOfloxFlodemexExocinFloxinOccidalEffexinPuiritolOflocinOnexacinQinolonTaravidBaccidalOfloduraMergexinPharfloxOflocetFlobacinOtonilTarifloxFloxstatZanocinOfloceePraxinQuotavilOflinObideOfloxinFlovidMedofloxineOflodalFloxilInofloxDanofloxOrocinLifloxTarividO-FloxNovecinViotisoneQiproTelbit

Synonyms

OfloxacinOflocet9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-3,7-dihydro-2H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acidTarividVisirenOfloxacineOxaldin氧氟沙星OfloxacinFloxinFlobacinExocinDL-8280HOE-280OcufloxMonoflocetFloxil9-Fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic AcidMefoxacinOflocin

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[7.3.1.0⁵,¹³]trideca-5(13),6,8,11-tetraene-11-carboxylic acid

IUPAC Traditional name

ofloxacin 7-fluoro-2-methyl-6-(4-methylpiperazin-1-yl)-10-oxo-4-oxa-1-azatricyclo[7.3.1.0⁵,¹³]trideca-5(13),6,8,11-tetraene-11-carboxylic acid

Names and Identifiers

Registration numbers

PubChem SID

160964499248604504650757424278613

PubChem CID

4583

CAS Number

82419-36-1

MDL Number

MFCD00226105

Registration numbers

Properties

Pharmacology Properties

Target

topoisomerase

Gene Information

human ... CSNK2A1(1457), KCNH1(3756)rat ... Gabra1(29705)

Mechanism of Action

DNA gyrase inhibitor

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

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]

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]

MP Biomedicals

02199018

Anti-bacterial Agent

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.

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.

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.

TRC

O245750

Fluorinated quinolone antibacterial.

Molecule Details

References

PubChem Literature

From Data Sources

• http://www.rxlist.com/floxin-drug.htm

• Drlica, K., Curr. Opin. Microbiol. 2, 504 (1990)

• Monk, J.P., et al.: Drugs, 33, 346 (1987)

• Hayakawa, I. et al., Antimicrob. Agents Chemother., 1986, 29, 163, (resoln, props)

• 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)

• 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)

• Kitaoka, H. et al., Chem. Pharm. Bull., 1995, 43, 649, (cryst struct, props)

• Sato, K. et al., Antimicrob. Agents Chemother., 1982, 22, 548, (pharmacol)

• Sanders, C.C., Clin. Infect. Dis., 1992, 14, 526, (rev)

• Egawa, H. et al., Chem. Pharm. Bull., 1986, 34, 4098, (synth)

• Mitscher, L.A. et al., J. Med. Chem., 1987, 30, 2283, (synth, activity)

• Negwer, M., Organic-Chemical Drugs and their Synonyms, 7th edn., Akademie-Verlag, 1994, 6400; 6401, (synonyms)

• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 221; 233

• Hashimoto, K. et al., Acta Cryst. C, 1995, 51, 519

• Todd, P.A. et al., Drugs, 1991, 42, 825, (rev)

• Monk, J.P. et al., Drugs, 1987, 33, 346, (rev)

• Eur. Pat., 1982, Daiichi Seiyaku, 47 005; CA, 97, 55821b, (synth, pharmacol)

• Langtry, H.D. et al., Drugs, 1998, 56, 487-515; 895-928, (rev)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, OGI300

• Davis, R. et al., Drugs, 1994, 47, 677, (rev)

• Lamp, K.C. et al., Clin. Pharmacokinet., 1992, 22, 32, (pharmacokinet, rev)

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Brand Name

Synonyms

IUPAC name

IUPAC Traditional name

ofloxacin 7-fluoro-2-methyl-6-(4-methylpiperazin-1-yl)-10-oxo-4-oxa-1-azatricyclo[7.3.1.0⁵,¹³]trideca-5(13),6,8,11-tetraene-11-carboxylic acid

Registration numbers

PubChem SID

160964499248604504650757424278613

PubChem CID

CAS Number

MDL Number

Molecule Details

S1463

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

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

External Links

• [Wikipedia]

• [RxList]

• [PDRhealth]

• [Drugs.com]

MP Biomedicals

02199018

Anti-bacterial Agent

Sigma Aldrich

O8757

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.

33703

TRC

O245750

Fluorinated quinolone antibacterial.

References

PubChem Literature

From Data Sources

• http://www.rxlist.com/floxin-drug.htm

• Drlica, K., Curr. Opin. Microbiol. 2, 504 (1990)

• Monk, J.P., et al.: Drugs, 33, 346 (1987)

• Hayakawa, I. et al., Antimicrob. Agents Chemother., 1986, 29, 163, (resoln, props)

• 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)

• 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)

• Kitaoka, H. et al., Chem. Pharm. Bull., 1995, 43, 649, (cryst struct, props)

• Sato, K. et al., Antimicrob. Agents Chemother., 1982, 22, 548, (pharmacol)

• Sanders, C.C., Clin. Infect. Dis., 1992, 14, 526, (rev)

• Egawa, H. et al., Chem. Pharm. Bull., 1986, 34, 4098, (synth)

• Mitscher, L.A. et al., J. Med. Chem., 1987, 30, 2283, (synth, activity)

• Negwer, M., Organic-Chemical Drugs and their Synonyms, 7th edn., Akademie-Verlag, 1994, 6400; 6401, (synonyms)

• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 221; 233

• Hashimoto, K. et al., Acta Cryst. C, 1995, 51, 519

• Todd, P.A. et al., Drugs, 1991, 42, 825, (rev)

• Monk, J.P. et al., Drugs, 1987, 33, 346, (rev)

• Eur. Pat., 1982, Daiichi Seiyaku, 47 005; CA, 97, 55821b, (synth, pharmacol)

• Langtry, H.D. et al., Drugs, 1998, 56, 487-515; 895-928, (rev)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, OGI300

• Davis, R. et al., Drugs, 1994, 47, 677, (rev)

• Lamp, K.C. et al., Clin. Pharmacokinet., 1992, 22, 32, (pharmacokinet, rev)

Bioactivity

PubChem BioAssay

Properties

Pharmacology Properties

Target

topoisomerase

Gene Information

human ... CSNK2A1(1457), KCNH1(3756)rat ... Gabra1(29705)

Mechanism of Action

DNA gyrase inhibitor

Molecule

ID:1036