Ofloxacin
[CAS# 82419-36-1]

Identification

• Classification: API >> Synthetic anti-infective drugs >> Quinolone
• Name: Ofloxacin
• 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; OFLX; Floxin; (+/-)-Ofloxacin
• Molecular Formula: C₁₈H₂₀FN₃O₄
• Molecular Weight: 361.37
• CAS Registry Number: 82419-36-1 (83380-47-6)
• EC Number: 680-263-1
• SMILES: CC1COC2=C3N1C=C(C(=O)C3=CC(=C2N4CCN(CC4)C)F)C(=O)O

Properties

• Solubility: 10 mM (DMSO)
• Melting point: 218-220 ºC

Safety Data

• Hazard Symbols: GHS07;GHS08 Danger
• Hazard Statements: H302-H312-H317-H332-H334-H341-H361
• Precautionary Statements: P203-P233-P260-P261-P264-P270-P271-P272-P280-P284-P301+P317-P302+P352-P304+P340-P317-P318-P321-P330-P333+P317-P342+P316-P362+P364-P403-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin sensitization	Skin Sens.	1	H317
Acute toxicity	Acute Tox.	4	H332
Respiratory sensitization	Resp. Sens.	1	H334
Acute toxicity	Acute Tox.	4	H302
Skin irritation	Skin Irrit.	2	H315
Reproductive toxicity	Repr.	2	H361
Eye irritation	Eye Irrit.	2	H319
Germ cell mutagenicity	Muta.	2	H341
Acute toxicity	Acute Tox.	3	H311
Carcinogenicity	Carc.	2	H351
Acute toxicity	Acute Tox.	4	H312

Discovory and Applicatios

Ofloxacin is a synthetic antibiotic belonging to the fluoroquinolone class, widely used to treat a variety of bacterial infections. Discovered and developed in the 1980s, ofloxacin has become an important tool in the management of infections due to its broad-spectrum antibacterial activity, effective against both Gram-positive and Gram-negative bacteria.

Ofloxacin works by inhibiting bacterial DNA gyrase and topoisomerase IV, enzymes critical for bacterial DNA replication, transcription, and repair. By disrupting these processes, ofloxacin prevents bacterial cells from multiplying, ultimately leading to their death. This mechanism of action makes ofloxacin effective in treating a wide range of infections, including respiratory tract infections, urinary tract infections (UTIs), skin infections, and certain sexually transmitted infections.

The discovery of ofloxacin was part of the ongoing development of fluoroquinolones, which aimed to create antibiotics with enhanced potency, a broader spectrum of activity, and improved pharmacokinetic properties. Ofloxacin was introduced as an advanced generation fluoroquinolone with better tissue penetration and a longer half-life, allowing for more convenient dosing schedules compared to earlier antibiotics.

Ofloxacin is available in various forms, including oral tablets, ophthalmic solutions, and topical preparations. This versatility in formulation allows it to be used in different clinical settings. For example, oral ofloxacin is commonly prescribed for UTIs, bronchitis, pneumonia, and certain gastrointestinal infections. The ophthalmic solution is used to treat bacterial infections of the eye, such as conjunctivitis, while the topical form is used for skin infections.

One of the significant advantages of ofloxacin is its broad-spectrum activity, which makes it a valuable option when the specific causative bacteria are unknown or when infections are caused by multiple bacterial species. Additionally, its favorable pharmacokinetic profile, including good oral bioavailability and tissue distribution, contributes to its effectiveness in treating both systemic and localized infections.

However, the use of ofloxacin, like other fluoroquinolones, is associated with certain risks and side effects. Common side effects include gastrointestinal disturbances such as nausea, diarrhea, and abdominal pain. Of greater concern are the potential serious side effects, including tendonitis, tendon rupture, peripheral neuropathy, and central nervous system effects such as seizures. These risks have led to more cautious use of ofloxacin, especially in populations such as the elderly or those with certain underlying conditions.

Moreover, the increasing problem of antibiotic resistance has impacted the use of ofloxacin. Bacteria can develop resistance to fluoroquinolones through various mechanisms, such as mutations in the target enzymes or changes in drug efflux systems. As a result, the use of ofloxacin and other fluoroquinolones is now often reserved for cases where other antibiotics are ineffective or unsuitable.

Despite these challenges, ofloxacin remains a critical antibiotic in the treatment of bacterial infections, particularly when broad-spectrum coverage is needed. Its role in managing a wide range of infections, combined with its pharmacokinetic properties, ensures that it continues to be an important option in clinical practice.

References

1991. Enhancement of antibiotic concentrations in gastric mucosa by H2-receptor antagonist. Implications for treatment of Helicobacter pylori infections. Digestive Diseases and Sciences, 36(1).
DOI: 10.1007/bf01300082

1990. The metabolism of ofloxacin in humans. Drug metabolism and disposition: the biological fate of chemicals, 18(11).
DOI: 10.1016/s0090-9556(25)08675-1

1987. Activity of ofloxacin and pefloxacin against Mycobacterium leprae in mice. Antimicrobial Agents and Chemotherapy, 31(4).
DOI: 10.1128/aac.31.4.671