6-Aminocaproic Acid: Structure, Uses, and Safety

6-Aminocaproic acid (often abbreviated as EACA) is a synthetic derivative of the amino acid lysine, widely recognized for its antifibrinolytic properties. It plays a critical role in medicine, particularly in controlling bleeding during or after surgical procedures.

What is 6-Aminocaproic Acid?

• Chemical Formula: C₆H₁₃NO₂

• Molecular Weight: 131.17 g/mol

• IUPAC Name: 6-Aminohexanoic acid

• Synonyms: ε-Aminocaproic acid, Amicar (brand name)

This compound consists of a six-carbon chain terminating in a carboxylic acid group on one end and an amino group on the other — structurally resembling lysine but lacking a second amino group on the side chain.

Key Properties

Property	Description
Appearance	White crystalline powder
Solubility	Freely soluble in water
pKa (amino group)	~10.5
pKa (carboxyl group)	~4.4
Melting Point	~205–208°C
Stability	Stable under standard conditions

 

Mechanism of Action

6-Aminocaproic acid is an antifibrinolytic agent, meaning it prevents the breakdown of blood clots. It works by inhibiting plasminogen activation, a crucial step in fibrinolysis (the process by which the body breaks down clots).

By blocking plasminogen from converting into plasmin (the enzyme that degrades fibrin), EACA stabilizes clots and prevents excessive bleeding.

Applications

1. Medical Use

EACA is most notably used in:

• Surgical settings (e.g., cardiac, orthopedic, and liver surgery) to reduce blood loss

• Dental procedures in patients with bleeding disorders

• Treatment of hereditary angioedema and hemophilia

• Heavy menstrual bleeding (occasionally, off-label)

It’s available in oral and intravenous forms, often under the brand name Amicar.

2. Biochemical Research

EACA is sometimes used to inhibit proteases, particularly plasmin, in lab settings during protein purification and analysis.

3. Veterinary Medicine

It is occasionally used in veterinary applications to control bleeding in animals during surgery or trauma.

Dosage and Administration

Typical human doses range from 2.5 to 15 grams per day, depending on the condition and severity of bleeding. Always follow a physician's instructions, as overuse can lead to complications like thrombosis.

Safety and Side Effects

Common Side Effects:

• Nausea or vomiting

• Muscle weakness

• Hypotension (especially with IV administration)

Serious Risks:

• Thrombosis (blood clots)

• Rhabdomyolysis (muscle breakdown)

• Seizures (rare, but reported with high doses)

Contraindications include:

• Active intravascular clotting

• Disseminated intravascular coagulation (unless under close medical supervision)

Drug Interactions:

• May interact with oral contraceptives, tranexamic acid, and anticoagulants

Always review a patient’s medical history and medications before prescribing.

Storage and Handling

• Store at room temperature (15–30°C)

• Protect from moisture and light

• Keep tightly sealed

Conclusion

6-Aminocaproic acid is a vital drug in the control of bleeding, especially in surgical and hematological contexts. Its ability to inhibit fibrinolysis makes it a lifesaving therapy in many clinical settings. While generally safe when used appropriately, care must be taken to monitor for rare but serious side effects such as thrombosis.

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