Identification
- Summary
Alcaftadine is a H1 histamine receptor antagonist for ophthalmic use to prevent itching associated with allergic conjunctivitis.
- Brand Names
- Lastacaft
- Generic Name
- Alcaftadine
- DrugBank Accession Number
- DB06766
- Background
Alcaftadine is a H1 histamine receptor antagonist indicated for the prevention of itching associated with allergic conjunctivitis. This drug was approved in July 2010.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Alcaftadine (DB06766)
- Weight
- Average: 307.3895
Monoisotopic: 307.168462309 - Chemical Formula
- C19H21N3O
- Synonyms
- Alcaftadina
- Alcaftadine
- Alcaftadinum
- External IDs
- R 89674
- R-89674
- R89674
Pharmacology
- Indication
For the prevention of itching associated with allergic conjunctivitis.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Symptomatic treatment of Allergic conjunctivitis •••••••••••• •••••••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Following bilateral topical ocular administration of alcaftadine ophthalmic solution, 0.25%, the mean plasma Cmax of alcaftadine was approximately 60 pg/mL and the median Tmax occurred at 15 minutes. Plasma concentrations of alcaftadine were below the lower limit of quantification (10 pg/mL) by 3 hours after dosing. The mean Cmax of the active carboxylic acid metabolite was approximately 3 ng/mL and occurred at 1 hour after dosing. Plasma concentrations of the carboxylic acid metabolite were below the lower limit of quantification (100 pg/mL) by 12 hours after dosing.
- Mechanism of action
Alcaftadine is a H1 histamine receptor antagonist and inhibitor of the release of histamine from mast cells. Decreased chemotaxis and inhibition of eosinophil activation has also been demonstrated.
Target Actions Organism UHistamine H1 receptor antagonistHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
The protein binding of alcaftadine and the active metabolite are 39.2% and 62.7% respectively.
- Metabolism
The metabolism of alcaftadine is mediated by non-CYP450 cytosolic enzymes to the active carboxylic acid metabolite.
- Route of elimination
Based on data following oral administration of alcaftadine, the carboxylic acid metabolite is primarily eliminated unchanged in the urine.
- Half-life
The elimination half-life of the carboxylic acid metabolite is approximately 2 hours following topical ocular administration.
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
Pathway Category Alcaftadine H1-Antihistamine Action Drug action - Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareBedaquiline The risk or severity of QTc prolongation can be increased when Alcaftadine is combined with Bedaquiline. Citalopram The risk or severity of QTc prolongation can be increased when Alcaftadine is combined with Citalopram. Clozapine The risk or severity of QTc prolongation can be increased when Alcaftadine is combined with Clozapine. Encorafenib The risk or severity of QTc prolongation can be increased when Encorafenib is combined with Alcaftadine. Etrasimod The risk or severity of QTc prolongation and torsade de pointes can be increased when Etrasimod is combined with Alcaftadine. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Lastacaft Solution / drops 2.5 mg/1mL Ophthalmic Allergan, Inc. 2010-11-01 Not applicable US 
Lastacaft Solution 2.5 mg/1mL Ophthalmic Vistakon Pharmaceuticals, LLC 2010-08-15 2010-10-13 US Lastacaft Solution / drops 2.5 mg/1mL Ophthalmic Rebel Distributors 2010-11-01 Not applicable US Lastacaft Solution / drops 2.5 mg/1mL Ophthalmic Physicians Total Care, Inc. 2011-08-19 Not applicable US - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Alcaftadine Solution / drops 2.5 mg/1mL Ophthalmic Aurohealth LLC 2023-06-23 Not applicable US Lastacaft Solution / drops 2.5 mg/1mL Ophthalmic Allergan, Inc. 2021-12-01 Not applicable US
Categories
- ATC Codes
- S01GX11 — Alcaftadine
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as benzazepines. These are organic compounds containing a benzene ring fused to an azepine ring (unsaturated seven-membered heterocycle with one nitrogen atom replacing a carbon atom).
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Benzazepines
- Sub Class
- Not Available
- Direct Parent
- Benzazepines
- Alternative Parents
- Carbonylimidazoles / Azepines / Aryl-aldehydes / Piperidines / N-substituted imidazoles / Benzenoids / Heteroaromatic compounds / Trialkylamines / Azacyclic compounds / Organopnictogen compounds show 2 more
- Substituents
- Aldehyde / Amine / Aromatic heteropolycyclic compound / Aryl-aldehyde / Azacycle / Azepine / Azole / Benzazepine / Benzenoid / Heteroaromatic compound show 13 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- piperidines, tertiary amino compound, aldehyde, imidazobenzazepine (CHEBI:71023)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 7Z8O94ECSX
- CAS number
- 147084-10-4
- InChI Key
- MWTBKTRZPHJQLH-UHFFFAOYSA-N
- InChI
- InChI=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
- 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
- SMILES
- CN1CCC(CC1)=C1C2=NC=C(C=O)N2CCC2=CC=CC=C12
References
- General References
- Mahvan TD, Buckley WA, Hornecker JR: Alcaftadine for the prevention of itching associated with allergic conjunctivitis. Ann Pharmacother. 2012 Jul-Aug;46(7-8):1025-32. doi: 10.1345/aph.1Q755. Epub 2012 Jul 17. [Article]
- Simons FE, Simons KJ: Histamine and H1-antihistamines: celebrating a century of progress. J Allergy Clin Immunol. 2011 Dec;128(6):1139-1150.e4. doi: 10.1016/j.jaci.2011.09.005. Epub 2011 Oct 27. [Article]
- Hussar DA, Samuel J: Vilazodone hydrochloride, linagliptin, and alcaftadine. J Am Pharm Assoc (2003). 2011 Jul-Aug;51(4):557-9. doi: 10.1331/JAPhA.2011.11534. [Article]
- External Links
- Human Metabolome Database
- HMDB0015670
- KEGG Drug
- D06552
- PubChem Compound
- 19371515
- PubChem Substance
- 99443288
- ChemSpider
- 14201635
- 1000082
- ChEBI
- 71023
- ChEMBL
- CHEMBL1201747
- ZINC
- ZINC000011726211
- PharmGKB
- PA165958399
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Alcaftadine
- FDA label
- Download (146 KB)
- MSDS
- Download (567 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Treatment Allergic Conjunctivitis (AC) 3 4 Unknown Status Treatment Allergic Conjunctivitis (AC) 1 4 Unknown Status Treatment Allergic Conjunctivitis (AC) / Rhinoconjunctivitis 1 3 Completed Treatment Allergic Conjunctivitis (AC) 4 3 Completed Treatment Healthy Volunteers Eligible for Study; Drug Being Developed for Allergic Conjunctivitis 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Solution Ophthalmic 250000 mg Liquid Ophthalmic 2.5 mg/1ml Solution Ophthalmic 2.5 mg/1mL Solution Ophthalmic 2.500 mg Solution / drops Ophthalmic 2.5 mg/1mL Solution / drops Ophthalmic 0.25 % Solution Ophthalmic 2.5 mg/mL Solution Ophthalmic 2.5 mg - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US8664215 No 2014-03-04 2027-12-23 US US5468743 No 1995-11-21 2016-04-20 US US10617695 No 2020-04-14 2027-03-19 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source boiling point (°C) 556.247 °C at 760 mmHg. # http://www.lookchem.com/Product_842767/CasNo_147084-10-4/Alcaftadine.html#.UXtC3Ct5N_k water solubility slightly solubility FDA Label logP 3.202 # http://www.lookchem.com/Product_842767/CasNo_147084-10-4/Alcaftadine.html#.UXtC3Ct5N_k - Predicted Properties
Property Value Source Water Solubility 0.333 mg/mL ALOGPS logP 2.09 ALOGPS logP 2.17 Chemaxon logS -3 ALOGPS pKa (Strongest Basic) 7.76 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 38.13 Å2 Chemaxon Rotatable Bond Count 1 Chemaxon Refractivity 102.88 m3·mol-1 Chemaxon Polarizability 34.68 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.9745 Caco-2 permeable + 0.5974 P-glycoprotein substrate Substrate 0.8775 P-glycoprotein inhibitor I Inhibitor 0.8923 P-glycoprotein inhibitor II Inhibitor 0.7024 Renal organic cation transporter Inhibitor 0.7448 CYP450 2C9 substrate Non-substrate 0.7517 CYP450 2D6 substrate Non-substrate 0.7096 CYP450 3A4 substrate Substrate 0.613 CYP450 1A2 substrate Inhibitor 0.6525 CYP450 2C9 inhibitor Non-inhibitor 0.6685 CYP450 2D6 inhibitor Non-inhibitor 0.6573 CYP450 2C19 inhibitor Non-inhibitor 0.7002 CYP450 3A4 inhibitor Non-inhibitor 0.8498 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.6381 Ames test Non AMES toxic 0.561 Carcinogenicity Non-carcinogens 0.9681 Biodegradation Not ready biodegradable 0.969 Rat acute toxicity 2.7266 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.6292 hERG inhibition (predictor II) Inhibitor 0.5603
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-03di-0290000000-89e154e3d89dbad02320 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-004i-0093000000-7cb833b09753cc1dcef7 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4i-0009000000-de5205a1f15a03693498 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0a4i-0398000000-edb494308159bb64284b Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4i-0029000000-e58a340384a448dad69d Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0h01-0390000000-8b56e4eda763f4002aa5 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0udi-1190000000-9e3803cf168a805edaab Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 185.9379667 predictedDarkChem Lite v0.1.0 [M-H]- 186.1347667 predictedDarkChem Lite v0.1.0 [M-H]- 170.28722 predictedDeepCCS 1.0 (2019) [M+H]+ 187.0204667 predictedDarkChem Lite v0.1.0 [M+H]+ 186.9383667 predictedDarkChem Lite v0.1.0 [M+H]+ 172.64522 predictedDeepCCS 1.0 (2019) [M+Na]+ 186.4249667 predictedDarkChem Lite v0.1.0 [M+Na]+ 186.7997667 predictedDarkChem Lite v0.1.0 [M+Na]+ 178.73836 predictedDeepCCS 1.0 (2019)
Targets
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Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- Histamine receptor activity
- Specific Function
- In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamin...
- Gene Name
- HRH1
- Uniprot ID
- P35367
- Uniprot Name
- Histamine H1 receptor
- Molecular Weight
- 55783.61 Da
References
Drug created at September 14, 2010 16:21 / Updated at February 21, 2021 18:52