Aminocaproic acid

Aminocaproic acid
Systematic (IUPAC) name
6-aminohexanoic acid
Clinical data
Trade names Amicar
AHFS/Drugs.com monograph
MedlinePlus a608023
Legal status
Legal status
  • ℞ (Prescription only)
Pharmacokinetic data
Metabolism Renal
Biological half-life 2 hours
Identifiers
CAS Number 60-32-2 YesY
ATC code B02AA01 (WHO)
PubChem CID 564
IUPHAR/BPS 6574
DrugBank DB00513 YesY
ChemSpider 548 YesY
UNII U6F3787206 YesY
KEGG D00160 YesY
ChEBI CHEBI:16586 YesY
ChEMBL CHEMBL1046 YesY
NIAID ChemDB 018631
Chemical data
Formula C6H13NO2
Molar mass 131.173 g/mol
Physical data
Melting point 205 °C (401 °F)
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Aminocaproic acid (also known as ε-aminocaproic acid, ε-Ahx, or 6-aminohexanoic acid) is a derivative and analogue of the amino acid lysine, which makes it an effective inhibitor for enzymes that bind that particular residue. Such enzymes include proteolytic enzymes like plasmin, the enzyme responsible for fibrinolysis. For this reason it is effective in treatment of certain bleeding disorders, and it is marketed as Amicar. Aminocaproic acid is also an intermediate in the polymerization of Nylon-6, where it is formed by ring-opening hydrolysis of caprolactam.

Clinical use

Aminocaproic acid is used to treat excessive postoperative bleeding, especially after procedures in which a great amount of bleeding is expected, such as cardiac surgery. It can be given orally or intravenously. A meta-analysis found that lysine analogs like aminocaproic acid significantly reduced blood loss in patients undergoing coronary artery bypass grafting.

Aminocaproic acid can also be used to treat the overdose and/or toxic effects of the thrombolytic pharmacologic agents tissue plasminogen activator (commonly known as tPA) and streptokinase.

Bleeding due to elevated fibrinolytic activity

Aminocaproic acid is used for the treatment of excessive bleeding resulting from systemic hyperfibrinolysis and urinary fibrinolysis. In life-threatening situations, fresh whole blood, fibrinogen infusions, and other emergency measures also may be required.[1]

Aminocaproic acid is used in systemic hyperfibrinolysis associated with surgical complications following heart surgery (with or without cardiac bypass procedures) and portacaval shunt; in carcinoma of the lung, prostate, cervix, or stomach; in abruptio placentae; and in hematologic disorders such as amegakaryocytic thrombocytopenia accompanying aplastic anemia (reduces the need for platelet transfusions).[1][2]

Aminocaproic acid is used in urinary fibrinolysis associated with complications of severe trauma, anoxia, and shock, and as manifested by surgical hematuria especially following prostatectomy and nephrectomy, or in nonsurgical hematuria accompanying polycystic or neoplastic disease of the GU tract.

Aminocaproic acid is used in conjunction with heparin therapy in patients with acute promyelocytic leukemia. Use is not currently included in the labeling approved by the US Food and Drug Administration. It is used as initiate therapy when plasma α2-antiplasmin (α2-plasmin inhibitor) levels have decreased to <40% of normal levels.[3]

Ocular hemorrhage

Aminocaproic acid has been used effectively for the prevention of secondary ocular hemorrhage in patients with nonperforating traumatic hyphema (Use is not currently included in the labeling approved by the US Food and Drug Administration.).[4] Designated an orphan drug by FDA for topical treatment of traumatic hyphema.[5]

Hereditary hemorrhagic telangiectasia

Aminocaproic acid has been used orally for the management of hereditary hemorrhagic telangiectasia.[6] This use is not currently included in the labeling approved by the US Food and Drug Administration.

Side effects include Confusion, Vision decrease, Vomiting, Headache, Convulsions, Malaise, Muscle weakness, Dizziness, Tinnitus, Nausea, Bradycardia, Thrombosis, Edema, Hypotension, Stroke, Syncope, Intracranial hypertension, Peripheral ischemia, Pulmonary embolism, Dyspnea, Congestion, Diarrhea, Abdominal pain, Leukopenia, Agranulocytosis, Coagulation disorder, Dry ejaculation, Injection site reactions (pain/necrosis), Pruritus, Rash, Renal failure, Anaphylaxis, and risk for myalgia.

References

  1. 1 2 Xanodyne Pharmaceuticals. Amicar (aminocaproic acid) injection, syrup, and tablets prescribing information. Florence, KY; 2004 Sep.
  2. ↑ Gardner FH, Helmer RE III (1980). "Aminocaproic acid: use in control of hemorrhage in patients with amegakaryocytic thrombocytopenia". JAMA 243 (1): 35–37. doi:10.1001/jama.1980.03300270023023. PMID 6965311.
  3. ↑ Schwartz BS, Williams EC, Conlan MG; et al. (1986). "Epsilon-aminocaproic acid in the treatment of patients with acute promyelocytic leukemia and acquired alpha-2-plasmin inhibitor deficiency". Ann Intern Med. 105 (6): 873–877. doi:10.7326/0003-4819-105-6-873. PMID 3465267.
  4. ↑ Gharaibeh A, Savage HI, Scherer RW, Goldberg MF, Lindsley K (2011). "Medical interventions for traumatic hyphema". Cochrane Database Syst Rev 1: CD005431. doi:10.1002/14651858.CD005431.pub2. PMC 3437611. PMID 21249670.
  5. ↑ Food and Drug Administration. Orphan designations pursuant to section 526 of the Federal Food and Cosmetic Act as amended by the Orphan Drug Act (P.L. 97-414) to June 28, 1996. Rockville, MD; 1996 Jul.
  6. ↑ Saba HI, Morelli GA, Logrono LA (1994). "Brief report: treatment of bleeding in hereditary hemorrhagic telangiectasia with aminocaproic acid". N Engl J Med 330 (25): 1789–1790. doi:10.1056/NEJM199406233302504. PMID 8190155.

Further reading


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