:Aminocaproic acid

{{Drugbox

| Watchedfields = changed

| verifiedrevid = 476999776

| image = 6-Aminocaproic acid.png

| alt =

| image2 = Aminocaproic-acid-from-xtal-3D-bs-17.png

| alt2 =

| caption2 = Ball-and-stick model of the zwitterionic form of the molecule found in the crystal structure{{ Cite journal | url = https://dx.doi.org/10.5517/ccv38nv | title = CSD Communication AMCAPR11: 6-Aminohexanoic acid | author = G. J. Reiss | year = 2010 | website = Cambridge Structural Database: Access Structures | publisher = Cambridge Crystallographic Data Centre | doi = 10.5517/ccv38nv | access-date = 18 August 2021 }}{{ cite journal | journal = Acta Crystallographica | volume = 23 | issue = 3 | pages = 482–490 | title = The crystal structure of ε-aminocaproic acid | vauthors = Bodor G, Bednowitz AL, Post B | year = 1967 | doi = 10.1107/S0365110X67003019 | bibcode = 1967AcCry..23..482B }}

| tradename = Amicar

| Drugs.com = {{drugs.com|monograph|aminocaproic-acid}}

| MedlinePlus = a608023

| DailyMedID = Aminocaproic_acid

| pregnancy_AU =

| pregnancy_AU_comment =

| pregnancy_category=

| routes_of_administration = By mouth

| ATC_prefix = B02

| ATC_suffix = AA01

| ATC_supplemental =

| legal_US = Rx-only

| legal_US_comment = {{cite web | title=Amicar- aminocaproic acid solution Amicar- aminocaproic acid tablet | website=DailyMed | date=9 October 2020 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=2238c70f-b0b5-4755-896b-45b28777b217 | access-date=11 November 2020}}

| legal_status = Rx-only

| bioavailability =

| protein_bound =

| metabolism = Kidney

| elimination_half-life = 2 hours

| IUPHAR_ligand = 6574

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 60-32-2

| PubChem = 564

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB00513

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 548

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = U6F3787206

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D00160

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 16586

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 1046

| NIAID_ChemDB = 018631

| IUPAC_name = 6-aminohexanoic acid

| C=6 | H=13 | N=1 | O=2

| smiles = C(CCC(=O)O)CCN

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C6H13NO2/c7-5-3-1-2-4-6(8)9/h1-5,7H2,(H,8,9)

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = SLXKOJJOQWFEFD-UHFFFAOYSA-N

| melting_point = 205

}}

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. 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.{{Citation| vauthors = Reiss GJ |title=CCDC 777717: Experimental Crystal Structure Determination|date=2011|chapter-url=http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccv38nv&sid=DataCite|publisher=Cambridge Crystallographic Data Centre|doi=10.5517/ccv38nv|access-date=24 October 2019|chapter=Crystal Structure}}

Medical use

Aminocaproic acid (Amicar) is FDA-approved for use in the treatment of acute bleeding due to elevated fibrinolytic activity. It also carries an orphan drug designation from the FDA for the prevention of recurrent hemorrhage in patients with traumatic hyphema.{{cite web | title=Aminocaproic acid Orphan Drug Designations and Approvals | website=U.S. Food and Drug Administration (FDA) | date=6 January 1995 | url=https://www.accessdata.fda.gov/scripts/opdlisting/oopd/detailedIndex.cfm?cfgridkey=83294 | access-date=11 November 2020}}{{dead link|date=May 2025|bot=medic}}{{cbignore|bot=medic}}{{cite journal | vauthors = Crouch Jr ER, Williams PB, Gray MK, Chames M | title = Topical aminocaproic acid in the treatment of traumatic hyphema | journal = Archives of Ophthalmology | volume = 115 | issue = 9 | pages = 1106–1112 | date = September 1997 | pmid = 9298049 | doi = 10.1001/archopht.1997.01100160276001 }} In clinical practice, aminocaproic acid is frequently used off-label for control of bleeding in patients with severe thrombocytopenia,{{cite journal | vauthors = Bartholomew JR, Salgia R, Bell WR | title = Control of bleeding in patients with immune and nonimmune thrombocytopenia with aminocaproic acid | journal = Archives of Internal Medicine | volume = 149 | issue = 9 | pages = 1959–1961 | date = September 1989 | pmid = 2774776 | doi = 10.1001/archinte.1989.00390090039008 }} control of oral bleeding in patients with congenital and acquired coagulation disorders,{{cite journal | vauthors = Lucas ON, Albert TW | title = Epsilon aminocaproic acid in hemophiliacs undergoing dental extractions: a concise review | journal = Oral Surgery, Oral Medicine, and Oral Pathology | volume = 51 | issue = 2 | pages = 115–120 | date = February 1981 | pmid = 6782532 | doi = 10.1016/0030-4220(81)90025-6 }} control of perioperative bleeding associated with cardiac surgery,{{cite journal | vauthors = Lu J, Meng H, Meng Z, Sun Y, Pribis JP, Zhu C, Li Q | title = Epsilon aminocaproic acid reduces blood transfusion and improves the coagulation test after pediatric open-heart surgery: a meta-analysis of 5 clinical trials | journal = International Journal of Clinical and Experimental Pathology | volume = 8 | issue = 7 | pages = 7978–7987 | date = 1 January 2015 | pmid = 26339364 | pmc = 4555692 }}{{cite journal | vauthors = Chen RH, Frazier OH, Cooley DA | title = Antifibrinolytic therapy in cardiac surgery | journal = Texas Heart Institute Journal | volume = 22 | issue = 3 | pages = 211–215 | date = 1 January 1995 | pmid = 7580358 | pmc = 325256 }} prevention of excessive bleeding in patients on anticoagulation therapy undergoing invasive dental procedures,{{cite journal | vauthors = Patatanian E, Fugate SE | title = Hemostatic mouthwashes in anticoagulated patients undergoing dental extraction | journal = The Annals of Pharmacotherapy | volume = 40 | issue = 12 | pages = 2205–2210 | date = December 2006 | pmid = 17090725 | doi = 10.1345/aph.1H295 | s2cid = 33961815 }} and reduction of the risk of catastrophic hemorrhage in patients with acute promyelocytic leukemia.{{cite journal | vauthors = Wassenaar T, Black J, Kahl B, Schwartz B, Longo W, Mosher D, Williams E | title = Acute promyelocytic leukaemia and acquired alpha-2-plasmin inhibitor deficiency: a retrospective look at the use of epsilon-aminocaproic acid (Amicar) in 30 patients | journal = Hematological Oncology | volume = 26 | issue = 4 | pages = 241–246 | date = December 2008 | pmid = 18613223 | pmc = 3496178 | doi = 10.1002/hon.867 }}

:Aminocaproic acid

Medical use

References

Further reading