Misplaced Pages

:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Aminocaproic acid: Difference between pages - Misplaced Pages

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
(Difference between pages)
Page 1
Page 2
Content deleted Content addedVisualWikitext
Revision as of 13:18, 15 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 472533540 of page Aminocaproic_acid for the Chem/Drugbox validation project (updated: 'DrugBank').  Latest revision as of 05:26, 1 July 2024 edit Citation bot (talk | contribs)Bots5,409,294 edits Added bibcode. | Use this bot. Report bugs. | Suggested by Whywhenwhohow | #UCB_webform 63/1421 
Line 1: Line 1:
{{Short description|Chemical compound}}
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}}
{{refimprove|date=June 2016}}
{{Use dmy dates|date=March 2024}}
{{Drugbox {{Drugbox
| Verifiedfields = changed | Watchedfields = changed
| verifiedrevid = 456688274 | verifiedrevid = 476999776
⚫ | IUPAC_name = 6-aminohexanoic acid
| image = 6-Aminocaproic acid.png | image = 6-Aminocaproic acid.png
| alt =
| caption = ]
| image2 = Aminocaproic-acid-from-xtal-3D-bs-17.png
| alt2 =
| caption2 = ] of the ]ic form of the molecule found in the ]<ref>{{ Cite journal | url = https://dx.doi.org/10.5517/ccv38nv | title = CSD Communication AMCAPR11: 6-Aminohexanoic acid | author = G. J. Reiss | year = 2010 | website = ]: Access Structures | publisher = ] | doi = 10.5517/ccv38nv | access-date = 18 August 2021 }}</ref><ref>{{ cite journal | journal = ] | 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 }}</ref>


<!--Clinical data--> <!--Clinical data-->
| tradename = Amicar | tradename = Amicar
| Drugs.com = {{drugs.com|monograph|aminocaproic_acid}} | Drugs.com = {{drugs.com|monograph|aminocaproic-acid}}
| MedlinePlus = a608023 | MedlinePlus = a608023
| DailyMedID = Aminocaproic_acid
⚫ | pregnancy_category =
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
⚫ | legal_status =
| pregnancy_AU_comment =
⚫ | routes_of_administration =
⚫ | pregnancy_category=
⚫ | routes_of_administration = ]
⚫ | ATC_prefix = B02
⚫ | ATC_suffix = AA01
⚫ | ATC_supplemental =

| legal_US = Rx-only
| legal_US_comment = <ref name="Amicar FDA label">{{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}}</ref>
⚫ | legal_status = Rx-only


<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
| bioavailability = | bioavailability =
| protein_bound = | protein_bound =
| metabolism = ] | metabolism = ]
| elimination_half-life = 2 hours | elimination_half-life = 2 hours


<!--Identifiers--> <!--Identifiers-->
| IUPHAR_ligand = 6574
| CASNo_Ref = {{cascite|correct|CAS}}
| CAS_number_Ref = {{cascite|correct|??}} | CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 60-32-2 | CAS_number = 60-32-2
⚫ | ATC_prefix = B02
⚫ | ATC_suffix = AA01
⚫ | ATC_supplemental =
| PubChem = 564 | PubChem = 564
| DrugBank_Ref = {{drugbankcite|changed|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00513 | DrugBank = DB00513
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
Line 40: Line 52:
| ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1046 | ChEMBL = 1046
| NIAID_ChemDB = 018631


<!--Chemical data--> <!--Chemical data-->
⚫ | IUPAC_name = 6-aminohexanoic acid
| C=6 | H=13 | N=1 | O=2 | C=6 | H=13 | N=1 | O=2
| molecular_weight = 131.173 g/mol
| smiles = O=C(O)C(N)CCCC | smiles = C(CCC(=O)O)CCN
| InChI = 1/C6H13NO2/c1-2-3-4-5(7)6(8)9/h5H,2-4,7H2,1H3,(H,8,9)
| InChIKey = LRQKBLKVPFOOQJ-UHFFFAOYAT
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C6H13NO2/c7-5-3-1-2-4-6(8)9/h1-5,7H2,(H,8,9) | StdInChI = 1S/C6H13NO2/c7-5-3-1-2-4-6(8)9/h1-5,7H2,(H,8,9)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = SLXKOJJOQWFEFD-UHFFFAOYSA-N | 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 ] ], which makes it an effective ] for ]s that bind that particular residue. Such enzymes include ] enzymes like ], the enzyme responsible for ]. For this reason it is effective in treatment of certain ], and it is sold under the brand name '''Amicar'''.<ref name="Amicar FDA label" /> Aminocaproic acid is also an intermediate in the polymerization of ], where it is formed by ring-opening hydrolysis of ]. The crystal structure determination showed that the 6-aminohexanoic acid is present as a salt, at least in the solid state.<ref>{{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}}</ref>

==Medical use==
Aminocaproic acid (Amicar) is FDA-approved for use in the treatment of acute bleeding due to elevated fibrinolytic activity.<ref name="Amicar FDA label" /> It also carries an ] designation from the FDA for the prevention of recurrent hemorrhage in patients with traumatic ].<ref>{{cite web | title=Aminocaproic acid Orphan Drug Designations and Approvals | website=U.S. ] (FDA) | date=6 January 1995 | url=https://www.accessdata.fda.gov/scripts/opdlisting/oopd/detailedIndex.cfm?cfgridkey=83294 | access-date=11 November 2020}}</ref><ref>{{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 }}</ref> In clinical practice, aminocaproic acid is frequently used off-label for control of bleeding in patients with severe thrombocytopenia,<ref>{{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 }}</ref> control of oral bleeding in patients with congenital and acquired coagulation disorders,<ref>{{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 }}</ref> control of perioperative bleeding associated with cardiac surgery,<ref>{{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 }}</ref><ref>{{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 }}</ref> prevention of excessive bleeding in patients on anticoagulation therapy undergoing invasive dental procedures,<ref>{{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 }}</ref> and reduction of the risk of catastrophic hemorrhage in patients with acute ].<ref>{{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 }}</ref>

== References ==
{{Reflist}}

== Further reading ==
{{refbegin}}
* {{cite journal | vauthors = Alkjaersig N, Fletcher AP, Sherry S | title = xi-Aminocaproic acid: an inhibitor of plasminogen activation | journal = The Journal of Biological Chemistry | volume = 234 | issue = 4 | pages = 832–837 | date = April 1959 | pmid = 13654273 | doi = 10.1016/S0021-9258(18)70185-3 | doi-access = free }}
* {{cite journal | vauthors = Kang Y, Lewis JH, Navalgund A, Russell MW, Bontempo FA, Niren LS, Starzl TE | title = Epsilon-aminocaproic acid for treatment of fibrinolysis during liver transplantation | journal = Anesthesiology | volume = 66 | issue = 6 | pages = 766–773 | date = June 1987 | pmid = 3296855 | pmc = 2965586 | doi = 10.1097/00000542-198706000-00010 }}
{{refend}}

{{Antihemorrhagics}}
{{Portal bar | Medicine}}

]
]