ALCAFTADINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C19H21N3O
Molecular Weight	307.3895
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1CCC(CC1)=C2C3=NC=C(C=O)N3CCC4=C2C=CC=C4

InChI

InChIKey=MWTBKTRZPHJQLH-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C19H21N3O
Molecular Weight	307.3895
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22348913 | https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022134s004lbl.pdf

Alcaftadine is a broad-spectrum antihistamine displaying a high affinity for histamine H1 and H2 receptors and a lower affinity for H4 receptors. It also exhibits modulatory action on immune cell recruitment and mast cell stabilizing effects. Alcaftadine is an inhibitor of the release of histamine from mast cells. Decreased chemotaxis and inhibition of eosinophil activation has also been demonstrated. LASTACAFT® (alcaftadine ophthalmic solution) indicated for the prevention of itching associated with allergic conjunctivitis.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Histamine H1 receptor 316 Target ID: CHEMBL231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22348913	Antagonist 2849	3.1 nM [Ki]
Histamine H2 receptor 46 Target ID: CHEMBL1941 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22348913	Antagonist 2849	58.0 nM [Ki]
Histamine H4 receptor 20 Target ID: CHEMBL3759 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22348913	Antagonist 2849	2.9 µM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Itching associated with allergic conjunctivitis 5 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022134s004lbl.pdf https://www.ncbi.nlm.nih.gov/pubmed/26185412	Preventing		Approved 8583	LASTACAFT Approved Use LASTACAFT® is an H1 histamine receptor antagonist indicated for the prevention of itching associated with allergic conjunctivitis. LASTACAFT® is an H1 histamine receptor antagonist indicated for the prevention of itching associated with allergic conjunctivitis. Launch Date 2010

C_max

Value	Dose	Co-administered	Analyte	Population
0.05 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21314437/	1 drop single, intraocular dose: 1 drop route of administration: Intraocular experiment type: SINGLE co-administered:		ALCAFTADINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
0.04 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21314437/	1 drop single, intraocular dose: 1 drop route of administration: Intraocular experiment type: SINGLE co-administered:		ALCAFTADINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21314437/	1 drop single, intraocular dose: 1 drop route of administration: Intraocular experiment type: SINGLE co-administered:		ALCAFTADINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
60.8% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21314437/	1 drop single, intraocular dose: 1 drop route of administration: Intraocular experiment type: SINGLE co-administered:		ALCAFTADINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
1 drop 1 times / week multiple, ophthalmic Recommended Dose: 1 drop, 1 times / week Route: ophthalmic Route: multiple Dose: 1 drop, 1 times / week Sources: https://clinicaltrials.gov/ct2/show/NCT00889330	unhealthy, 37.8 Health Status: unhealthy Age Group: 37.8 Sex: M+F Sources: https://clinicaltrials.gov/ct2/show/NCT00889330	Sources: https://clinicaltrials.gov/ct2/show/NCT00889330

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946 inhibitor 2252	substrate 1193	substrate 1388 inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP2A6 879 CYP2C8 1057 CYP2E1 1060 CYP4A 20	CYP1A2 1197 CYP2A6 626 CYP2C8 810 CYP2C19 1119 CYP2E1 729

Drug as perpetrator

Target	Modality	Activity
CYP1A2 2333	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022134s000PharmR.pdf#page=47; https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022134s000clinpharm.pdf#page=25 Page: 46-48, (ClinPharm) 23-26	no
CYP2A6 911	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022134s000PharmR.pdf#page=47; https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022134s000clinpharm.pdf#page=25 Page: 46-48, (ClinPharm) 23-26	no
CYP2C8 1117	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022134s000PharmR.pdf#page=47; https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022134s000clinpharm.pdf#page=25 Page: 46-48, (ClinPharm) 23-26	no
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022134s000PharmR.pdf#page=47; https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022134s000clinpharm.pdf#page=25 Page: 46-48, (ClinPharm) 23-26	no
CYP2E1 1146	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022134s000PharmR.pdf#page=47; https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022134s000clinpharm.pdf#page=25 Page: 46-48, (ClinPharm) 23-26	no
CYP3A4 2633	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022134s000PharmR.pdf#page=47; https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022134s000clinpharm.pdf#page=25 Page: 46-48, (ClinPharm) 23-26	no
CYP4A 34	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022134s000PharmR.pdf#page=47; https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022134s000clinpharm.pdf#page=25 Page: 46-48, (ClinPharm) 23-26	no

Drug as victim

Target	Modality	Activity	Clinical evidence
CYP1A2 1197	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022134s000PharmR.pdf#page=46; https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022134s000clinpharm.pdf#page=25 Page: 46-48, (ClinPharm) 23-26	likely
CYP2A6 626	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022134s000PharmR.pdf#page=46; https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022134s000clinpharm.pdf#page=25 Page: 46-48, (ClinPharm) 23-26	no
CYP2D6 1388	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022134s000PharmR.pdf#page=46; https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022134s000clinpharm.pdf#page=25 Page: 46-48, (ClinPharm) 23-26	no
CYP2E1 729	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022134s000PharmR.pdf#page=46; https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022134s000clinpharm.pdf#page=25 Page: 46-48, (ClinPharm) 23-26	no
CYP2C8 810	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022134s000PharmR.pdf#page=46; https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022134s000clinpharm.pdf#page=25 Page: 46-48, (ClinPharm) 23-26	unlikely
CYP2C9 1193	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022134s000PharmR.pdf#page=46; https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022134s000clinpharm.pdf#page=25 Page: 46-48, (ClinPharm) 23-26	unlikely
CYP2C19 1119	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022134s000PharmR.pdf#page=46; https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022134s000clinpharm.pdf#page=25 Page: 46-48, (ClinPharm) 23-26	yes
CYP3A4 1946	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022134s000PharmR.pdf#page=46; https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022134s000clinpharm.pdf#page=15; https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022134s000clinpharm.pdf#page=25 Page: 46-48, (ClinPharm) 15, 23-26	yes	no (co-administration study) Comment: Human liver microsomes (10 donors/patients); Following 2 mg oral dose of alcaftadine, co-administered ketoconazole (a CYP3A4 inhibitor) was found not to inhibit the in vivo metabolism of alcaftadine as there was no changes in the plasma concentrations of alcaftadine and the AUC of the metabolite R90692 increased 10% following co-administration of ketoconazole. Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022134s000PharmR.pdf#page=46; https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022134s000clinpharm.pdf#page=15; https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022134s000clinpharm.pdf#page=25 Page: 46-48, (ClinPharm) 15, 23-26

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022134s000PharmR.pdf#page=19 Page: 19.0

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:71023	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:71023
ChemicalBook	CB21011726	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB21011726
MolPort	MolPort-023-219-144	https://www.molport.com/shop/molecule-link/MolPort-023-219-144
ZINC	ZINC000011726211	http://zinc15.docking.org/substances/ZINC000011726211

PubMed

Title	Date	PubMed
Alcaftadine for the prevention of itching associated with allergic conjunctivitis.	2012-07-20	22811343
Histamine and H1-antihistamines: celebrating a century of progress.	2011-12	22035879
Vilazodone hydrochloride, linagliptin, and alcaftadine.	2011-07-15	21752782

Patents

Sample Use Guides

In Vivo Use Guide

Instill one drop in each eye once daily. Ophthalmic solution containing alcaftadine, 0.25% (2.5 mg/mL).

Route of Administration: Other

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:32:14 GMT 2025` Edited by `admin` on `Mon Mar 31 18:32:14 GMT 2025`
Record UNII	7Z8O94ECSX
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

LASTACAFT

Preferred Name

English

ALCAFTADINE

Official Name

English

ALCAFTADINE [VANDF]

Common Name

English

ALCAFTADINE [USAN]

Common Name

English

R 89674

Code

English

Alcaftadine [WHO-DD]

Common Name

English

ALCAFTADINE [JAN]

Common Name

English

ALCAFTADINE [MART.]

Common Name

English

11-(1-Methylpiperidin-4-ylidene)-6,11-dihydro-5H-imidazolo[2,1-b][3]benzazepine-3-carbaldehyde

Systematic Name

English

5H-IMIDAZO(2,1-B)(3)BENZAZEPINE-3-CARBOXALDEHYDE, 6,11-DIHYDRO-11-(1-METHYL-4-PIPERIDINYLIDENE)-

Systematic Name

English

R-89674

Code

English

ALCAFTADINE [ORANGE BOOK]

Common Name

English

4-(1-METHYL-PIPERIDIN-4-YLIDENE)-9,10-DIHYDRO-4H-3,10A-DIAZA-BENZO(F)AZULENE-1-CARBALDEHYDE

Common Name

English

alcaftadine [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C257