Ofloxacin

Structural formula
1: 1 mixture of ( R ) -isomer (top) and ( S ) -isomer (bottom)
General
Non-proprietary name	Ofloxacin
other names	( RS ) -9-Fluoro-3-methyl-10- (4-methylpiperazin-1-yl) -7-oxo-2,3-dihydro-7 H -pyrido [1,2,3- de ] [1, 4] benzoxazine-6-carboxylic acid ( IUPAC ) Ofloxacinum ( Latin )
Molecular formula	C 18 H 20 FN 3 O 4 (Ofloxacin) C 18 H 20 FN 3 O 4 HCl (Ofloxacin hydrochloride)
External identifiers / databases
CAS number 82419-36-1 [( RS ) -ofloxacin] 118120-51-7 [( RS ) -ofloxacin · hydrochloride ] EC number 680-263-1 ECHA InfoCard 100.205.209 PubChem 4583 ChemSpider 4422 DrugBank DB01165 Wikidata Q411447
Drug information
ATC code	J01 MA01 S01 AX11
Drug class	Fluoroquinolone - antibiotic
Mechanism of action	Gyrase inhibitors
properties
Molar mass	361.37 g · mol -1 [( RS ) -Ofloxacin] 397.83 g · mol -1 [( RS ) -Ofloxacin · hydrochloride]
Physical state	firmly
Melting point	250–257 ° C (decomposition)
pK s value	6.05; 8.22
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed GHS labeling of hazardous substances no GHS pictograms H and P phrases H: no H-phrases P: no P-phrases
Toxicological data	3590 mg kg −1 ( LD 50 ,  rat ,  oral ) 208 mg kg −1 ( LD 50 ,  mouse ,  iv )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Ofloxacin is an antibiotic from the group of fluoroquinolones that was patented by Daiichi Sankyō in 1982 .

Clinical information

Application areas (indications)

General medicine

Ofloxacin is at bacterial infections of the respiratory tract , of the ear-nose-throat region , of the gastrointestinal tract including the bile ducts , the genital organs (including gonorrhea ), the kidneys and the urinary tract , of the skin , of soft tissues and bones used .

Ophthalmology

In ophthalmology, ofloxacin is used as an eye ointment or eye drop for bacterial infections of the anterior segment of the eye, such as the cornea or corneal ulcers, and of the soft ocular appendages (adnexa), such as the conjunctiva ( conjunctivitis ), the edge of the eyelid ( blepharitis , stye ) or those that merge Infections ( blepharoconjunctivitis ) up to infections of the tear sac . It has been on the WHO list of essential drugs for these applications since 2013 .

Important sensitive pathogens (selection)

• Aerobic gram positive microorganisms
  • Staphylococcus aureus (methicillin sensitive); Streptococcus pyogenes ;
• Aerobic gram-negative microorganisms
  • Chlamydia trachomatis ; Enterobacter cloacae ; Haemophilus influenzae ; Klebsiella aerogenes ; Klebsiella oxytoca ; Moraxella catarrhalis ; Proteus mirabilis ; Proteus vulgaris ; Serratia marcescens

Type and duration of application

General medicine

The duration of treatment with ofloxacin and the dosage depend on the type, location and severity of the infection, with 3 to 10 days of treatment being usual. In the case of severe infections, treatment is also possible for 1–2 months. The tablets containing ofloxacin are taken orally with plenty of fluids, with an interval of two hours between antacids and mineral supplements . Another drug form is an infusion solution, which is mostly used in clinics.

Ophthalmology

For eye treatment, ofloxacin-containing eye drops and ointments are available, which are used in the eye as well as on the eyelid and on the edge of the eyelid.

Contraindications (contraindications)

The active ingredient must not be used in:

• Patients with epilepsy or a lowered seizure threshold, since therapy reduces the seizure threshold in the CNS
• Children and adolescents up to the age of 18 years, since joint cartilage damage cannot be excluded with certainty
• during pregnancy and breastfeeding (for reasons see there )
• Tendon disease / damage that has occurred in connection with previous ofloxacin treatment

Drug interactions

A serious interaction is the simultaneous intake with gastric acid agents ( antacids ) or mineral supplements, as these complex the active ingredient and thus the absorption and availability is no longer guaranteed. Pretreatment with coumarin derivatives increases the bleeding tendency, which necessitates close coagulation control. The situation is similar when taking glibenclamide at the same time , which increases the risk of hypoglycaemia and therefore the need for frequent blood sugar measurements. In connection with the administration of drugs that prolong the QT interval , such as: B. certain antiarrhythmics , antidepressants , neuroleptics , macrolides and anti- malarials , therapy is only indicated after strict indication and great caution.

Use during pregnancy and breastfeeding

Animal experiments have shown no evidence of teratogenic effects, but damage to the articular cartilage during the growth phase has been demonstrated. Sufficient experience with the use in humans is not available. Ofloxacin crosses the placental barrier and can be detected in maternal serum. It is not known whether ofloxacin is excreted in breast milk. For these reasons, drugs containing ofloxacin should not be given to pregnant or breastfeeding women.

Special patient groups (diabetics, kidney patients and liver patients)

Since ofloxacin is mainly eliminated through the kidneys, the dosage needs to be adjusted in patients with impaired renal function. Correspondingly, caution should be exercised in the case of severe kidney disorders . Kidney and liver function as well as blood values ​​should be checked regularly during long-term therapy. The Qo value of ofloxacin is low (Q = 0.1). In patients with impaired liver function, the biotransformation and subsequent elimination of ofloxacin may be reduced, so that the daily dose should be adjusted accordingly. For diabetics and cardiovascular patients, it is important to pay particular attention to interactions .

Adverse effects (side effects)

In addition to adverse reactions such as allergies , drowsiness, nausea and vomiting , severe cases can lead to epilepsy-like seizures, which then represent an emergency. Circulatory-related problems such as dizziness , drop in blood pressure and headaches are also possible. Since there is a possibility of reactions caused by UV light , excessive exposure to the sun should be avoided. In rare cases, the Achilles tendon can rupture . This is more likely to affect the elderly and those who take corticoids. As an allergic reaction to the drug, potentially life-threatening skin rashes Stevens-Johnson syndrome are possible. Side effects can be delayed, persist after discontinuation, intensify over time, and cause permanent disability. Compared to other common antibiotics, fluoroquinolones are responsible for most of the permanent disabilities.

Dosage forms

The active ingredient is available in the form of tablets in strengths of 100 mg, 200 mg and 400 mg and as an infusion solution. For therapy directly on the eye, there are eye drops and eye ointment with a strength of 3 mg / ml.

Pharmacological properties

Mechanism of action (pharmacodynamics)

Ofloxacin interferes with the replication of the bacterial DNA, the topoisomerases II & IV ( gyrases ) and thus makes reproduction impossible and thus has a bactericidal effect . Ofloxacin exists as a racemate , of which the (S) - (-) - enantiomer levofloxacin has the double effect of the mixture.

Absorption and distribution in the body (pharmacokinetics)

The active ingredient is quickly absorbed from the gastrointestinal tract and is then 25% bound to plasma proteins. The half-life in the organism is approx. 5–7 hours and the apparent volume of distribution is 120 liters.

toxicology

In the event of overdosing and poisoning, the expected reciprocal effects and side effects may occur more intensely, so that intensive medical care or monitoring may be indicated. A specific antidote is not available. The administration of calcium and magnesium containing antacids after an oral overdose of ofloxacin can delay the absorption due to the formation of poorly soluble complexes.

Other Information

The fluorescence spectrum of a 51 mg / l aqueous solution of ofloxacin, excited by UV light with a wavelength of 275 nm.

Opiate tests performed can be false positive. In addition, ofloxacin is a fluorescent dye that fluoresces blue-green when exposed to UV light. The fluorescence can be quenched with copper ions .

Trade names

Monopreparations

Floxal eye drops (D, A, CH), Gyroflox (D, except sales), Tarivid (D, A, CH), Uro-Tarivid (D), various generics (D, A)

Web links

• Ofloxacin entry at Vetpharm, accessed on August 5, 2012.
• FDA Text of Labeling for FLOXIN® Otic (ofloxacin otic solution) (PDF; 174 kB)
• Medicinal products approved in Germany with the active ingredient ofloxacin

literature

• Hermann J. Roth: Medicinal Chemistry: Targets and Drugs; 157 tables . German Apotheker-Verlag, Stuttgart 2005, ISBN 3-7692-3483-9
• W. Forth, D. Henschler, W. Rummel: General and special pharmacology and toxicology . 9th edition. URBAN & FISCHER, Munich 2005, ISBN 3-437-42521-8 .
• Vyas et al. Quinolone-associated rupture of the Achilles' tendon. New England Journal of Medicine 2007; 357 (20): 2067.
• McGarvey et al. Partial Achilles tendon ruptures associated with fluoroquinolone antibiotics: a case report and literature review. Foot Ankle Int. 1996 Aug; 17 (8): 496-8. PMID 8863030

Individual evidence

1. ↑ ^{a b c d e f} Entry on Ofloxacin. In: Römpp Online . Georg Thieme Verlag, accessed on July 13, 2019.
2. ↑ ^{a b} Datasheet ofloxacin from Sigma-Aldrich , accessed on May 13, 2017 ( PDF ).
3. ↑ ^{a b c d e f g h i j k} Technical information on Tarivid from Sanofi-Aventis.
4. ↑ ^{a b} Technical information on Floxal from Bausch & Lomb.
5. ↑ Dose adjustment in case of renal insufficiency with Dosing ( Memento of August 21, 2007 in the Internet Archive ).
6. ↑ Vyas et al. Quinolone-associated rupture of the Achilles' tendon. New England Journal of Medicine 2007; 357 (20): 2067.
7. ↑ McGarvey et al. Partial Achilles tendon ruptures associated with fluoroquinolone antibiotics: a case report and literature review. Foot Ankle Int. 1996 Aug; 17 (8): 496-498. PMID 8863030 .
8. ↑ http://www.apotheken-umschau.de/Medikamente/Beipackoppel/Ofloxacin-Ophtal-1959242.html
9. ↑ Drug Safety and Availability - FDA Drug Safety Communication: FDA updates warnings for oral and injectable fluoroquinolone antibiotics due to disabling side effects ( en ) Retrieved January 10, 2018.
10. ↑ FDA: FDA / CDER Drug Information Webinar - Fluoroquinolone Safety Labeling Changes. In: www.fda.gov. FDA, April 2017, accessed January 22, 2019 . 
11. ^ Ruß, Endres, Arzneimittelpocket Plus 2008, 4th edition Oct. 2007, ISBN 978-3-89862-287-5 .
12. ^ E. Batard, F. Jamme, S. Villette, C. Jacqueline, MF de la Cochetière, J. Caillon, M. Réfrégiers: Diffusion of oxacin in the endocarditis vegetation assessed with synchrotron radiation UV fluorescence microspectroscopy. In: PLOS ONE . Volume 6, number 4, 2011, p. E19440, doi : 10.1371 / journal.pone.0019440 , PMID 21559378 , PMC 3084860 (free full text).
13. Jump up ↑ B. Pan, X. Han, M. Wu, H. Peng, D. Zhang, H. Li, B. Xing: Temperature dependence of oxacin fluorescence quenching and complexation by Cu (II). In: Environmental Pollution . Volume 171, December 2012, pp. 168-173, doi : 10.1016 / j.envpol.2012.07.046 , PMID 22922456 .

This article is about a health issue. It is not used for self-diagnosis and does not replace a diagnosis by a doctor. Please note the information on health issues !