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Aminocaproic acid information


Aminocaproic acid
Skeletal formula
Ball-and-stick model of the zwitterionic form of the molecule found in the crystal structure[1][2]
Clinical data
Trade namesAmicar
AHFS/Drugs.comMonograph
MedlinePlusa608023
License data
  • US DailyMed: Aminocaproic_acid
Routes of
administration
By mouth
ATC code
  • B02AA01 (WHO)
Legal status
Legal status
  • US: ℞-only[3]
  • In general: ℞ (Prescription only)
Pharmacokinetic data
MetabolismKidney
Elimination half-life2 hours
Identifiers
IUPAC name
  • 6-aminohexanoic acid
CAS Number
  • 60-32-2 checkY
PubChem CID
  • 564
IUPHAR/BPS
  • 6574
DrugBank
  • DB00513 checkY
ChemSpider
  • 548 checkY
UNII
  • U6F3787206
KEGG
  • D00160 checkY
ChEBI
  • CHEBI:16586 checkY
ChEMBL
  • ChEMBL1046 checkY
NIAID ChemDB
  • 018631
CompTox Dashboard (EPA)
  • DTXSID0020070 Edit this at Wikidata
ECHA InfoCard100.000.427 Edit this at Wikidata
Chemical and physical data
FormulaC6H13NO2
Molar mass131.175 g·mol−1
3D model (JSmol)
  • Interactive image
Melting point205 °C (401 °F)
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) checkY
  • Key:SLXKOJJOQWFEFD-UHFFFAOYSA-N checkY
  (verify)

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 sold under the brand name Amicar.[3] Aminocaproic acid is also an intermediate in the polymerization of Nylon-6, where it is formed by ring-opening hydrolysis of caprolactam. The crystal structure determination showed that the 6-aminohexanoic acid is present as a salt, at least in the solid state.[4]

  1. ^ G. J. Reiss (2010). "CSD Communication AMCAPR11: 6-Aminohexanoic acid". Cambridge Structural Database: Access Structures. Cambridge Crystallographic Data Centre. doi:10.5517/ccv38nv. Retrieved 18 August 2021.
  2. ^ Bodor G, Bednowitz AL, Post B (1967). "The crystal structure of ε-aminocaproic acid". Acta Crystallographica. 23 (3): 482–490. doi:10.1107/S0365110X67003019.
  3. ^ a b "Amicar- aminocaproic acid solution Amicar- aminocaproic acid tablet". DailyMed. 9 October 2020. Retrieved 11 November 2020.
  4. ^ Reiss GJ (2011), "Crystal Structure", CCDC 777717: Experimental Crystal Structure Determination, Cambridge Crystallographic Data Centre, doi:10.5517/ccv38nv, retrieved 24 October 2019

and 24 Related for: Aminocaproic acid information

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Aminocaproic acid

Last Update:

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...

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Antifibrinolytic

Last Update:

inhibitors of fibrinolysis. Examples include aminocaproic acid (ε-aminocaproic acid) and tranexamic acid. These lysine-like drugs interfere with the formation...

Word Count : 184

Tranexamic acid

Last Update:

Tranexamic acid has roughly eight times the antifibrinolytic activity of an older analogue, ε-aminocaproic acid.[citation needed] Tranexamic acid also directly...

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Caprolactam

Last Update:

described in the late 1800s when it was prepared by the cyclization of ε-aminocaproic acid, the product of the hydrolysis of caprolactam. World demand for caprolactam...

Word Count : 771

Fibrinolysis

Last Update:

breakdown in the clot. Antifibrinolytics, such as aminocaproic acid (ε-aminocaproic acid) and tranexamic acid are used as inhibitors of fibrinolysis. Their...

Word Count : 1060

Cryoprecipitate

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intravascular coagulation Uremic bleeding tendency Reversing tpa (with aminocaproic acid) Adverse effects reported with the usage of cryoprecipitate include...

Word Count : 745

Hyphema

Last Update:

(antifibrinolytic agents [oral and systemic aminocaproic acid, tranexamic acid, and aminomethylbenzoic acid], corticosteroids [systemic and topical], cycloplegics...

Word Count : 996

Allysine

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to give a peptide containing the 6-hydroxynorleucine (6-hydroxy-2-aminocaproic acid) residue, which (unlike allysine) is stable to proteolysis. Luna C...

Word Count : 404

Aprotinin

Last Update:

that, compared to other antifibrinolytic drugs (epsilon-aminocaproic acid and tranexamic acid) aprotinin may increase the risk of death. On October 29...

Word Count : 2912

Radioimmunoprecipitation assay buffer

Last Update:

leupeptin, aprotinin, pepstatin, 1-5 mM EDTA, 0.5-1 mM EGTA, 5 mM aminocaproic acid) or commercial protease inhibitor cocktail (use according to the manufacturer's...

Word Count : 322

Angiodysplasia

Last Update:

First-line options include the antifibrinolytics tranexamic acid or aminocaproic acid. Estrogens can be used to stop bleeding from angiodysplasia. Estrogens...

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Angioedema

Last Update:

nonhistaminergic angioedema, antifibrinolytics such as tranexamic acid or ε-aminocaproic acid may be effective. Cinnarizine may also be useful because it blocks...

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Thromboelastography

Last Update:

and may be treated with an antifibrinolytic, such as tranexamic acid or aminocaproic acid, in the appropriate clinical setting. A single, modified TEG assay...

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Streptokinase

Last Update:

activator (tPA). Overdose of streptokinase or tPA can be treated with aminocaproic acid. Any prior intracranial hemorrhage Known structural cerebral vascular...

Word Count : 1615

Yunnan Baiyao

Last Update:

Nakamura, Reid K. (2016-09-26). "Use of Yunnan Baiyao and epsilon aminocaproic acid in dogs with right atrial masses and pericardial effusion". Journal...

Word Count : 2783

Coagulation

Last Update:

increasingly popular in the treatment of major bleeding. Tranexamic acid and aminocaproic acid inhibit fibrinolysis and lead to a de facto reduced bleeding rate...

Word Count : 5970

Plasmin

Last Update:

"A mechanism for hereditary angioedema caused by a lysine 311-to-glutamic acid substitution in plasminogen". Blood. 139 (18): 2816–2829. doi:10.1182/blood...

Word Count : 1821

Plastic

Last Update:

(1975). "Utilization of a Cyclic Dimer and Linear Oligomers of E-Aminocaproic Acid by Achromobacter Guttatus". Agricultural and Biological Chemistry...

Word Count : 11611

Complement deficiency

Last Update:

Haemophilus infections can be prevented via immunization. Epsilon-aminocaproic acid could be used to treat hereditary C1-INH deficiency, though the possible...

Word Count : 1260

ATC code B02

Last Update:

which follows the WHO version. B02AA01 Aminocaproic acid B02AA02 Tranexamic acid B02AA03 Aminomethylbenzoic acid B02AB01 Aprotinin B02AB02 Alfa1 antitrypsin...

Word Count : 305

Elmer Keiser Bolton

Last Update:

had been made from ε-aminocaproic acid was due to cyclization reactions, so he replaced ε-aminocaproic acid with 9-aminononoic acid which would not cyclize...

Word Count : 2229

Sumire Uesaka

Last Update:

with an Amagami Sister as Yae Amagami Eyedrops (2016) as Epsilon-Aminocaproic Acid Cute Executive Officer (2021–2023) as Yuki Karuizawa Ganbare Dōki-chan...

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AHX

Last Update:

airline American History X, a 1998 film Aminohexanoic acid (Ahx), also known as Aminocaproic acid Renault AHx, a range of light/medium trucks Vehicle registration...

Word Count : 92

Haemophilia

Last Update:

may be used in those with mild haemophilia A. Tranexamic acid or epsilon aminocaproic acid may be given along with clotting factors to prevent breakdown...

Word Count : 6728

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