Indobufen
[CAS# 63610-08-2]

Identification

• Classification: API >> Blood system medication >> Anticoagulant and antiplatelet drugs
• Name: Indobufen
• Synonyms: 4-(1,3-Dihydro-1-oxo-(2H)-isoindol-2-yl)-alpha-ethylbenzeneacetic acid
• Molecular Formula: C₁₈H₁₇NO₃
• Molecular Weight: 295.34
• CAS Registry Number: 63610-08-2
• EC Number: 264-364-4
• SMILES: CCC(C1=CC=C(C=C1)N2CC3=CC=CC=C3C2=O)C(=O)O

Properties

• Density: 1.3±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.630, Calc.^*
• Boiling Point: 518.1±50.0 ºC (760 mmHg), Calc.^*
• Flash Point: 267.1±30.1 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302
• Precautionary Statements: P264-P270-P301+P317-P330-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315

Discovory and Applicatios

Indobufen is a nonsteroidal anti-inflammatory drug (NSAID) primarily used for its antiplatelet and anti-inflammatory properties. The chemical structure of Indobufen consists of a substituted indole ring system, which is central to its pharmacological activity. It is commonly used to prevent blood clot formation in conditions where thrombosis is a concern, such as in stroke prevention, and for the management of inflammatory conditions like arthritis. Indobufen's mechanism of action primarily involves inhibiting the enzyme cyclooxygenase (COX), which plays a key role in the biosynthesis of prostaglandins, mediators of inflammation and pain.

The discovery of Indobufen dates back to the 1980s when researchers in the field of pharmacology were actively investigating new compounds with dual antiplatelet and anti-inflammatory properties. The compound was developed as an alternative to traditional NSAIDs that could provide therapeutic benefits without some of the side effects commonly associated with other drugs in this class. Indobufen was introduced to the market in the early 1990s and gained attention for its selective inhibition of COX-1 and COX-2, two enzymes responsible for the production of prostaglandins.

One of the major applications of Indobufen is in the prevention of thrombosis, which can lead to conditions such as deep vein thrombosis (DVT), pulmonary embolism, and stroke. Its ability to inhibit platelet aggregation makes it effective in reducing the risk of blood clots forming in the arteries and veins. Indobufen is often used in patients who have undergone surgery, particularly orthopedic surgeries, or those who are at high risk for cardiovascular events due to underlying health conditions such as hypertension or diabetes. The compound is sometimes prescribed in combination with other antiplatelet agents for enhanced therapeutic effects.

Indobufen also has applications in the management of inflammatory conditions such as rheumatoid arthritis and osteoarthritis. Its anti-inflammatory effects help to alleviate pain, reduce swelling, and improve joint function. By inhibiting the production of inflammatory prostaglandins, Indobufen reduces the inflammation associated with these conditions, thereby improving the quality of life for patients suffering from chronic pain and disability caused by joint inflammation. It is often used when conventional treatments like ibuprofen or aspirin are not effective or when patients experience adverse reactions to other medications.

Another significant application of Indobufen is its potential use in preventing complications in individuals undergoing coronary artery bypass grafting (CABG) and other cardiovascular procedures. Postoperative thrombotic complications are a major concern after such surgeries, and Indobufen’s role in reducing platelet aggregation can help mitigate the risk of clot formation, enhancing patient recovery and reducing the likelihood of major cardiovascular events.

Although Indobufen is generally well-tolerated, its use requires careful monitoring, especially in patients with a history of gastrointestinal ulcers, renal dysfunction, or bleeding disorders. Like other NSAIDs, Indobufen may increase the risk of bleeding and gastrointestinal side effects such as ulcers and gastrointestinal bleeding, especially when used in high doses or for prolonged periods. Therefore, healthcare providers must assess the potential benefits and risks when prescribing this medication to ensure its safety and efficacy for each patient.

In summary, Indobufen is a versatile chemical substance with applications primarily in the prevention of thrombosis and the treatment of inflammatory conditions. Its discovery as a dual-action antiplatelet and anti-inflammatory agent has made it an important drug in the management of cardiovascular and inflammatory diseases. By inhibiting COX enzymes and reducing the production of pro-inflammatory prostaglandins, Indobufen helps to prevent blood clots, reduce inflammation, and manage pain. Ongoing research may expand its therapeutic uses, particularly in the fields of cardiovascular medicine and inflammation-related disorders.

References

1979. Pharmacokinetic, bioavailability and pharmacodynamic study of indobufen (K 3920), an inhibitor of platelet aggregation, after a single dose in man. European Journal of Clinical Pharmacology.
DOI: 10.1007/bf00558435

2023. Comparison of the prophylactic antithrombotic effect of indobufen and warfarin in patients with nephrotic syndrome: a randomized controlled trial. Renal Failure.
DOI: 10.1080/0886022x.2022.2163505

2023. Indobufen or Aspirin on Top of Clopidogrel After Coronary Drug-Eluting Stent Implantation (OPTION): A Randomized, Open-Label, End Point-Blinded, Noninferiority Trial. Circulation.
DOI: 10.1161/circulationaha.122.062762