関: 6-aminohexanoic acid、epsilon-aminocaproic acid

WordNet

street name for lysergic acid diethylamide (同)back breaker, battery-acid, dose, dot, Elvis, loony toons, Lucy in the sky with diamonds, pane, superman, window pane, Zen
any of various water-soluble compounds having a sour taste and capable of turning litmus red and reacting with a base to form a salt
having the characteristics of an acid; "an acid reaction"

PrepTutorEJDIC

酸性の / 酸味のある,すっぱい(sour) / (言葉・態度などが)厳しい,しんらつな / 酸 / すっぱいもの / 《俗》=LSD

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/05/02 03:06:03」(JST)

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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

^ ^a ^b Xanodyne Pharmaceuticals. Amicar (aminocaproic acid) injection, syrup, and tablets prescribing information. Florence, KY; 2004 Sep.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.

UpToDate Contents

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1. 血栓溶解異常による血栓性および出血性疾患 thrombotic and hemorrhagic disorders due to abnormal fibrinolysis
2. 成人における慢性難治性免疫性血小板減少症（ITP） chronic refractory immune thrombocytopenia itp in adults
3. 血小板輸血療法に対する不応性 refractoriness to platelet transfusion therapy
4. フィブリノゲンの異常 disorders of fibrinogen
5. 外傷に伴う凝固障害 coagulopathy associated with trauma

English Journal

Fractal Kinetic Behavior of Plasmin on the Surface of Fibrin Meshwork.

Varjú I, Tenekedjiev K, Keresztes Z, Pap AE, Szabó L, Thelwell C, Longstaff C, Machovich R, Kolev K.
Biochemistry.Biochemistry.2014 Sep 15. [Epub ahead of print]
Intravascular fibrin clots are resolved by plasmin acting at the interface of gel-phase substrate and fluid-borne enzyme. The classic Michaelis-Menten kinetic scheme cannot describe satisfactorily this heterogeneous-phase proteolysis, because it assumes homogeneous well-mixed conditions. A more suit
PMID 25222106

Efficacy and Safety of Tranexamic Acid Versus ϵ-Aminocaproic Acid in Cardiovascular Surgery.

Falana O1, Patel G2.
The Annals of pharmacotherapy.Ann Pharmacother.2014 Sep 11. pii: 1060028014549558. [Epub ahead of print]
BACKGROUND: Blood conservation is a major concern in the management of surgical patients because of transfusion-related complications, limited supply, and health care costs. Tranexamic acid (TXA) and ϵ-aminocaproic acid (ϵACA) are lysine analogue antifibrinolytics used to reduce surgical bleeding
PMID 25214649

The effect of tranexamic Acid on hemoglobin levels during total knee arthroplasty.

Pachauri A1, Acharya KK, Tiwari AK.
American journal of therapeutics.Am J Ther.2014 Sep-Oct;21(5):366-70. doi: 10.1097/MJT.0b013e318250f85a.
The aim of this study was to evaluate the efficacy of perioperative administration of 1,4-amino-carboxylic acid (tranexamic acid) in reducing the intraoperative and postoperative blood loss in patients undergoing total knee replacement (TKR). Tranexamic acid is an antifibrinolytic agent that is 7-10
PMID 23917458

Japanese Journal

Novel Biodegradable Copoly(amino acid)s Based on 6-Aminocaproic Acid and L-Proline

ZHANG Weipeng
Chemistry letters 37(11), 1142-1143, 2008-11-05
… Novel biodegradable copoly(amino acid)s based on 6-aminocaproic acid and L-proline were prepared by melt polycondensation and characterized by IR and 1H NMR. …
NAID 10024397028

安全な 6-ナイロンの合成 : 6-アミノカプロン酸によるε-カプロラクタムの開環重合

井上正之
化学と教育 49(5), 292-293, 2001-05-20
NAID 110008592232

Protective Effect of N-Acyl Amino Acids (NAAs) on Cephaloridine (CER) Nephrotoxicity in Rabbits.

Hirouchi Yasukuni,Naganuma Hideo,Kawahara Yukinori,Okada Ryuzo,Kamiya Akira,Inui Ken-ichi,Hori Ryohei
The Japanese Journal of Pharmacology 63(4), 487-493, 1993
… Simultaneous treatment with several NAAs (at dosages of 100, 200 mg/kg, etc., i.v.), such as N-benzoyl-β-alanine (NBBA), N-benzoyl-6-aminocaproic acid, and Nα, ε-dibenzoyl-D, L-lysine, remarkably suppressed the histopathological damage in the kidney induced by CER. …
NAID 130000840473

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★リンクテーブル★

リンク元	「epsilon-aminocaproic acid」「6-アミノカプロン酸」「6-aminohexanoic acid」
関連記事	「aminocaproic acid」

「epsilon-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
ATC code	B02AA01 (WHO)
PubChem	CID 564
IUPHAR/BPS	6574
DrugBank	DB00513
ChemSpider	548
UNII	U6F3787206
KEGG	D00160
ChEBI	CHEBI:16586
ChEMBL	CHEMBL1046
NIAID ChemDB	018631
Chemical data
Formula	C6H13NO2
Molar mass	131.173 g/mol
	SMILES C(CCC(=O)O)CCN ;
	InChI InChI=1S/C6H13NO2/c7-5-3-1-2-4-6(8)9/h1-5,7H2,(H,8,9) ; Key:SLXKOJJOQWFEFD-UHFFFAOYSA-N ;
Physical data
Melting point	205 °C (401 °F)
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