Alcaftadine
Chemical compound
title: "Alcaftadine" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["h1-receptor-antagonists", "mast-cell-stabilizers", "drugs-developed-by-abbvie", "ophthalmology-drugs"] description: "Chemical compound" topic_path: "general/h1-receptor-antagonists" source: "https://en.wikipedia.org/wiki/Alcaftadine" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0
::summary Chemical compound ::
::data[format=table title="Infobox drug"]
| Field | Value |
|---|---|
| Verifiedfields | changed |
| Watchedfields | changed |
| verifiedrevid | 477316420 |
| image | Alcaftadine.svg |
| image_class | skin-invert-image |
| tradename | Lastacaft |
| Drugs.com | |
| MedlinePlus | a611022 |
| DailyMedID | Alcaftadine |
| pregnancy_AU | |
| routes_of_administration | Eye drops |
| ATC_prefix | S01 |
| ATC_suffix | GX11 |
| legal_AU | |
| legal_BR | |
| legal_CA | |
| legal_DE | |
| legal_NZ | |
| legal_UK | |
| legal_US | OTC |
| legal_US_comment | |
| legal_UN | |
| legal_status | |
| elimination_half-life | ~2 hrs |
| CAS_number_Ref | |
| CAS_number | 147084-10-4 |
| PubChem | 19371515 |
| IUPHAR_ligand | 7587 |
| DrugBank_Ref | |
| DrugBank | DB06766 |
| ChemSpiderID_Ref | |
| ChemSpiderID | 14201635 |
| UNII_Ref | |
| UNII | 7Z8O94ECSX |
| KEGG_Ref | |
| KEGG | D06552 |
| ChEBI_Ref | |
| ChEBI | 71023 |
| ChEMBL_Ref | |
| ChEMBL | 1201747 |
| IUPAC_name | 2-(1-Methylpiperidin-4-ylidene)-4,7-diazatricyclo[8.4.0.0(3,7)]tetradeca- 1(14),3,5,10,12-pentaene-6-carbaldehyde |
| C | 19 |
| SMILES | CN1CCC(=C2c3ccccc3CCn4c(C=O)cnc24)CC1 |
| StdInChI_Ref | |
| 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 |
| StdInChIKey_Ref | |
| StdInChIKey | MWTBKTRZPHJQLH-UHFFFAOYSA-N |
| :: |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 477316420 | image = Alcaftadine.svg | image_class = skin-invert-image | width = | alt =
| pronounce = | tradename = Lastacaft | Drugs.com = | MedlinePlus = a611022 | DailyMedID = Alcaftadine | pregnancy_AU = | pregnancy_AU_comment = | pregnancy_category = | routes_of_administration = Eye drops | class = | ATC_prefix = S01 | ATC_suffix = GX11 | ATC_supplemental =
| legal_AU = | legal_AU_comment = | legal_BR = | legal_BR_comment = | legal_CA = | legal_CA_comment = | legal_DE = | legal_DE_comment = | legal_NZ = | legal_NZ_comment = | legal_UK = | legal_UK_comment = | legal_US = OTC | legal_US_comment = | legal_EU = | legal_EU_comment = | legal_UN = | legal_UN_comment = | legal_status =
| bioavailability = | protein_bound = | metabolism = | metabolites = | onset = | elimination_half-life = ~2 hrs | duration_of_action = | excretion =
| CAS_number_Ref = | CAS_number = 147084-10-4 | CAS_supplemental = | PubChem = 19371515 | IUPHAR_ligand = 7587 | DrugBank_Ref = | DrugBank = DB06766 | ChemSpiderID_Ref = | ChemSpiderID = 14201635 | UNII_Ref = | UNII = 7Z8O94ECSX | KEGG_Ref = | KEGG = D06552 | ChEBI_Ref = | ChEBI = 71023 | ChEMBL_Ref = | ChEMBL = 1201747 | NIAID_ChemDB = | PDB_ligand = | synonyms =
| IUPAC_name = 2-(1-Methylpiperidin-4-ylidene)-4,7-diazatricyclo[8.4.0.0(3,7)]tetradeca- 1(14),3,5,10,12-pentaene-6-carbaldehyde | C=19 | H=21 | N=3 | O=1 | SMILES = CN1CCC(=C2c3ccccc3CCn4c(C=O)cnc24)CC1 | StdInChI_Ref = | 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 = | StdInChIKey = MWTBKTRZPHJQLH-UHFFFAOYSA-N | density = | density_notes = | melting_point = | melting_high = | melting_notes = | boiling_point = | boiling_notes = | solubility = | sol_units = | specific_rotation =
Alcaftadine, sold under the brand name Lastacaft, is an antihistamine used to help prevent itching of the eyes. It is an H1 histamine receptor antagonist. It is given as an drops in the eye.
It was approved for medical use in the United States in July 2010. It is available as a generic medication and as an over-the-counter medication.
Medical uses
Alcaftadine is indicated for the prevention of itching associated with allergic conjunctivitis.
Pharmacology
Alcaftadine is an antagonist of histamine receptor 1. By blocking the receptor, alcaftadine has been shown to reduce itching and redness of the eyes, and to reduce recruitment of eosinophils after exposure to an allergen. 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 E-cadhedrin-1 compared to placebo. Reducing E-cadherin decreases junctions that lead to the progression of allergic conjunctivitis.
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.
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.
History
When alcaftadine was tested against placebo and olopatadine, 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.
Society and culture
Economics
Allergan, Inc. began selling alcaftadine under the trade name Lastacaft after it was approved by the US Food and Drug Administration in July 2010. By March 2012, 139,000 prescriptions had been written for 104,000 unique patients, and alcaftadine exceeded the sales of epinastine (Elestat).
Legal status
Alcaftadine was approved for medical use in the United States in July 2010.
References
References
- (10 August 2022). "Lastacaft- alcaftadine solution/ drops".
- (24 December 1999). "Drug Approval Package: Lastacaft (alcaftadine) Ophthalmic Solution NDA #022134".
- (15 March 2022). "Now Available Over the Counter, Lastacaft Provides Eye Allergy Itch Relief in Minutes that Lasts Through 16 Hours".
- (1 August 2015). "Lastacaft- alcaftadine solution/ drops".
- (January 2011). "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%". Clinical Ophthalmology.
- (February 2011). "Comparison of effects of alcaftadine and olopatadine on conjunctival epithelium and eosinophil recruitment in a murine model of allergic conjunctivitis". Drug Design, Development and Therapy.
- (28 November 2009). "Alcaftadine". U.S. Food and Drug Administration.
- (24 December 1999). "Drug Approval Package: Lastacaft (alcaftadine) Ophthalmic Solution NDA #022134".
- (21 June 2012). "Lastacaft (alcaftadine ophthalmic solution 0.25%)". U.S. [[Food and Drug Administration]] (FDA).
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