Misplaced Pages

:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Alcaftadine: 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 05:03, 17 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 457806376 of page Alcaftadine for the Chem/Drugbox validation project (updated: 'ChEMBL', 'KEGG', 'StdInChI', 'CAS_number').  Latest revision as of 21:09, 17 July 2024 edit IntentionallyDense (talk | contribs)Extended confirmed users, New page reviewers34,444 edits →Pharmacokinetics: Removing unsourced content 
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.}}
{{Use dmy dates|date=May 2024}}
{{Drugbox
{{cs1 config |name-list-style=vanc |display-authors=6}}
{{Infobox drug
| Verifiedfields = changed | Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 457805189
| verifiedrevid = 477316420
| IUPAC_name = 2-(1-Methylpiperidin-4-ylidene)-4,7-diazatricyclotetradeca- 1(14),3,5,10,12-pentaene-6-carbaldehyde
| image = Alcaftadine.svg | image = Alcaftadine.svg
| width = 200 | width =
| alt = | alt =
| imagename = <!-- else may use drug_name -->
| drug_name = Alcaftadine


<!--Clinical data--> <!-- Clinical data -->
| tradename = | pronounce =
| tradename = Lastacaft
| Drugs.com = {{drugs.com|CDI|alcaftadine-drops}}
| Drugs.com = {{drugs.com|monograph|alcaftadine}}
| MedlinePlus = a611022 | MedlinePlus = a611022
| DailyMedID = Alcaftadine
| licence_EU = <!-- EMA requires brand name -->
| licence_US = Lastacaft
| DailyMedID = <!-- preference to licence_US -->
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_AU_comment =
| pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_category = | pregnancy_category =
| routes_of_administration = ]
| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
| class =
| ATC_prefix = S01
| ATC_suffix = GX11
| ATC_supplemental =

<!-- Legal status -->
| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled -->
| legal_AU_comment =
| legal_BR = <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C4, C5, D1, D2, E, F -->
| legal_BR_comment =
| legal_CA = <!-- OTC, Rx-only, Schedule I, II, III, IV, V, VI, VII, VIII --> | legal_CA = <!-- OTC, Rx-only, Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_CA_comment =
| legal_UK = <!-- GSL, P, POM, CD, CD Lic, CD POM, CD No Reg POM, CD (Benz) POM, CD (Anab) POM or CD Inv POM -->
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> | legal_DE = <!-- Anlage I, II, III or Unscheduled -->
| legal_status = | legal_DE_comment =
| legal_NZ = <!-- Class A, B, C -->
| dependency_liability =
| legal_NZ_comment =
| routes_of_administration = Topical
| legal_UK = <!-- GSL, P, POM, CD, CD Lic, CD POM, CD No Reg POM, CD (Benz) POM, CD (Anab) POM or CD Inv POM / Class A, B, C -->
| legal_UK_comment =
| legal_US = OTC
| legal_US_comment = <ref name="Lastacaft FDA label" /><ref>{{cite web | title=Lastacaft- alcaftadine solution/ drops | website=DailyMed | date=10 August 2022 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=a3002410-4bf1-4182-9d7c-8193eb7cd215 | access-date=20 May 2024}}</ref>
| legal_EU =
| legal_EU_comment =
| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV -->
| legal_UN_comment =
| legal_status = <!-- For countries not listed above -->


<!--Pharmacokinetic data--> <!-- Pharmacokinetic data -->
| bioavailability = | bioavailability =
| protein_bound = | protein_bound =
| metabolism = | metabolism =
| metabolites =
| onset =
| elimination_half-life = ~2 hrs | elimination_half-life = ~2 hrs
| excretion = | duration_of_action =
| excretion =


<!--Identifiers--> <!-- Identifiers -->
| CAS_number_Ref = {{cascite|changed|??}} | CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = <!-- blanked - oldvalue: 147084-10-4 --> | CAS_number = 147084-10-4
| CAS_supplemental = | CAS_supplemental =
| ATCvet = | PubChem = 19371515
| ATC_prefix = None | IUPHAR_ligand = 7587
| ATC_suffix =
| ATC_supplemental =
| PubChem =
| PubChemSubstance =
| IUPHAR_ligand =
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB06766 | DrugBank = DB06766
Line 53: Line 69:
| UNII = 7Z8O94ECSX | UNII = 7Z8O94ECSX
| KEGG_Ref = {{keggcite|changed|kegg}} | KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = <!-- blanked - oldvalue: D06552 --> | KEGG = D06552
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 71023
| ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = <!-- blanked - oldvalue: 1201747 --> | ChEMBL = 1201747
| synonyms = | NIAID_ChemDB =
| PDB_ligand =
| synonyms =


<!--Chemical data--> <!-- Chemical and physical data -->
| IUPAC_name = 2-(1-Methylpiperidin-4-ylidene)-4,7-diazatricyclotetradeca- 1(14),3,5,10,12-pentaene-6-carbaldehyde
| chemical_formula =
| C=19 | H=21 | N=3 | O=1
| C=19 | H=21 | Ag= | As= | Au= | B= | Bi= | Br= | Cl= | Co= | F= | Fe= | Gd= | I= | K= | Mn= | N=3 | Na= | O=1 | P= | Pt= | S= | C= | Se= | Sr= | Tc= | charge =
| SMILES = CN1CCC(=C2c3ccccc3CCn4c(C=O)cnc24)CC1
| molecular_weight =
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| smiles = CN1CCC(=C2c3ccccc3CCn4c(C=O)cnc24)CC1
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C19H21N3O/c1-21-9-6-15(7-10-21)18-17-5-3-2-4-14(17)8-11-22-16(13-23)12-20-19(18)22/h2-5,12-13H,6-11H2,1H3 | StdInChI = 1S/C19H21N3O/c1-21-9-6-15(7-10-21)18-17-5-3-2-4-14(17)8-11-22-16(13-23)12-20-19(18)22/h2-5,12-13H,6-11H2,1H3
| StdInChI_comment =
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = MWTBKTRZPHJQLH-UHFFFAOYSA-N | StdInChIKey = MWTBKTRZPHJQLH-UHFFFAOYSA-N
| density = | density =
| melting_point = | density_notes =
| melting_high = | melting_point =
| melting_notes = | melting_high =
| boiling_point = | melting_notes =
| boiling_notes = | boiling_point =
| solubility = | boiling_notes =
| specific_rotation = | solubility =
| sec_combustion = | sol_units =
| specific_rotation =
}} }}

'''Alcaftadine''', sold under the brand name '''Lastacaft''', is an ] used to help prevent itching of the eyes.<ref name="Lastacaft FDA label" /> It is an H1 histamine receptor antagonist.<ref name="Lastacaft FDA label" /> It is given as an ] in the ].<ref name="Lastacaft FDA label" />

It was approved for medical use in the United States in July 2010.<ref name="Drug Approval Package: Lastacaft">{{cite web | title=Drug Approval Package: Lastacaft (alcaftadine) Ophthalmic Solution NDA #022134 | website=U.S. ] (FDA) | date=24 December 1999 | url=https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022134s000TOC.cfm | access-date=10 June 2020}}</ref> It is available as a ] and as an ].<ref>{{cite press release | title=Now Available Over the Counter, Lastacaft Provides Eye Allergy Itch Relief in Minutes that Lasts Through 16 Hours | website=PR Newswire | date=15 March 2022 | url=https://www.prnewswire.com/news-releases/now-available-over-the-counter-lastacaft-provides-eye-allergy-itch-relief-in-minutes-that-lasts-through-16-hours-301501288.html | access-date=18 May 2024}}</ref>

== Medical uses ==
Alcaftadine is ] for the prevention of itching associated with allergic conjunctivitis.<ref name="Lastacaft FDA label" />

==Pharmacology==
Alcaftadine is an ] of histamine receptor 1.<ref name="Lastacaft FDA label">{{cite web | title=Lastacaft- alcaftadine solution/ drops | website=DailyMed | date=1 August 2015 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=17d37e8d-7825-424b-b6ca-0a85d0bf4694 | access-date=10 June 2020}}</ref> By blocking the receptor, alcaftadine has been shown to reduce itching and redness of the eyes, and to reduce recruitment of ] after exposure to an allergen.<ref name="Greiner">{{cite journal | vauthors = Greiner JV, Edwards-Swanson K, Ingerman A | title = Evaluation of alcaftadine 0.25% ophthalmic solution in acute allergic conjunctivitis at 15 minutes and 16 hours after instillation versus placebo and olopatadine 0.1% | journal = Clinical Ophthalmology | volume = 5 | pages = 87–93 | date = January 2011 | pmid = 21339800| pmc = 3037035 | doi = 10.2147/OPTH.S15379 | doi-access = free }}</ref> Alcaftadine reduces the number of eosinophils compared to olopatadine 0.1%, and in animal models, alcaftadine 0.25% decreased the expression of the epithelial protein ] compared to placebo. Reducing E-cadherin decreases junctions that lead to the progression of allergic conjunctivitis.<ref>{{cite journal | vauthors = Ono SJ, Lane K | title = Comparison of effects of alcaftadine and olopatadine on conjunctival epithelium and eosinophil recruitment in a murine model of allergic conjunctivitis | journal = Drug Design, Development and Therapy | volume = 5 | pages = 77–84 | date = February 2011 | pmid = 21340041 | pmc = 3038998 | doi = 10.2147/DDDT.S15788 | doi-access = free }}</ref>


==Adverse effects==
In studies comparing the effectiveness of olopatadine to alcaftadine, there was not a dose-response increase of adverse effects as alcaftadine doses increases for 0.05% to 0.1% to 0.25%. The most common seen side effect of alcaftadine administration was irritation or a stinging sensation at the administration site.<ref name="Greiner" />

==Pharmacokinetics==
Because alcaftadine is administered at low concentrations and at a local site (the eye), it appears to have minimal systemic effects, and the low absorption of alcaftadine results in minimal systemic accumulation.<ref>{{cite web | title = Alcaftadine |url= https://www.fda.gov/downloads/drugs/developmentapprovalprocess/developmentresources/ucm223817.pdf | work = Office of Clinical Pharmacology Review | publisher = U.S. Food and Drug Administration | date = 17 November 2009 }}</ref>

== History ==
When alcaftadine was tested against placebo and ], only alcaftadine 0.25% showed a clinically significant reduction in conjunctival redness scores 7 and 15 minutes after administration. Alcaftadine 0.05%, 0.1%, and 0.25% all reduced lid swelling, conjunctival redness, and ocular itching/tearing compared to placebo.<ref name="Greiner" />

== Society and culture ==
=== Economics ===
] began selling alcaftadine under the trade name Lastacaft after it was approved by the US ] in July 2010.<ref>{{cite web | title=Drug Approval Package: Lastacaft (alcaftadine) Ophthalmic Solution NDA #022134 | website=U.S. ] (FDA) | date=24 December 1999 | url=https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022134s000TOC.cfm | access-date=10 June 2020}}</ref> By March 2012, 139,000 prescriptions had been written for 104,000 unique patients, and alcaftadine exceeded the sales of ] (Elestat).<ref>{{cite web | title = Lastacaft (alcaftadine ophthalmic solution 0.25%) | url = https://www.fda.gov/downloads/AdvisoryCommittees/CommitteesMeetingMaterials/PediatricAdvisoryCommittee/UCM317430.pdf | archive-url = https://web.archive.org/web/20170215193100/https://www.fda.gov/downloads/AdvisoryCommittees/CommitteesMeetingMaterials/PediatricAdvisoryCommittee/UCM317430.pdf | archive-date = 15 February 2017 | work = Drug Use Review | publisher = U.S. ] (FDA) | date = 21 June 2012 }}</ref>

=== Legal status ===
Alcaftadine was approved for medical use in the United States in July 2010.<ref name="Lastacaft FDA label" /><ref name="Drug Approval Package: Lastacaft" />

== References ==
{{Reflist}}

{{Antihistamines}}
{{Histamine receptor modulators}}
{{Portal bar | Medicine}}
{{Authority control}}

]
]
]
]