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

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	MOL RATIO 1 MOL RATIO (average)

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

Description

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 315	Antagonist 2,778	3.1 nM [Ki]
Histamine H2 receptor 46	Antagonist 2,778	58.0 nM [Ki]
Histamine H4 receptor 20	Antagonist 2,778	2.9 µM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Itching associated with allergic conjunctivitis 5	Preventing		Approved 8,429	LASTACAFT

C_max

Value	Dose	Co-administered	Analyte	Population
0.05 ng/mL	1 drop single, intraocular		ALCAFTADINE plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
0.04 ng × h/mL	1 drop single, intraocular		ALCAFTADINE plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.1 h	1 drop single, intraocular		ALCAFTADINE plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
60.8%	1 drop single, intraocular		ALCAFTADINE plasma	Homo sapiens

Doses

Doses

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Dose	Population	Adverse events
1 drop 1 times / week multiple, ophthalmic Recommended	unhealthy, 37.8 n = 30

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1,737 inhibitor 1,587	substrate 1,037	substrate 1,217 inhibitor 1,852	inhibitor 1,612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1,524 CYP2A6 707 CYP2C8 911 CYP2E1 882 CYP4A 19	CYP1A2 1,054 CYP2A6 543 CYP2C8 693 CYP2C19 991 CYP2E1 667

Drug as perpetrator

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Target	Modality	Activity
CYP1A2 1,692	inhibitor 3,277	no
CYP2A6 739	inhibitor 3,277	no
CYP2C8 965	inhibitor 3,277	no
CYP2D6 1,891	inhibitor 3,277	no
CYP2E1 970	inhibitor 3,277	no

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Drug as victim

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Target	Modality	Activity
CYP1A2 1,054	substrate 3,367	likely
CYP2A6 543	substrate 3,367	no
CYP2D6 1,217	substrate 3,367	no
CYP2E1 667	substrate 3,367	no
CYP2C8 693	substrate 3,367	unlikely

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Tox targets

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Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1,647	inhibitor 1,626

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Sourcing

Sourcing

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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

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PubMed

Title	Date	PubMed
Vilazodone hydrochloride, linagliptin, and alcaftadine.	2011 Jul-Aug	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
Record UNII	7Z8O94ECSX
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ALCAFTADINE

Official Name

English

ALCAFTADINE [VANDF]

Common Name

English

ALCAFTADINE [USAN]

Common Name

English

LASTACAFT

Brand Name

English

R 89674

Code

English

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Classification Tree

Code System

Code

Analgesic and Antipyretic

NCI_THESAURUS

C257

Immunotherapeutic Agent

NCI_THESAURUS

C29578

Established Pharmacologic Class

NDF-RT

N0000175587

Other antiallergics

WHO-ATC

S01GX11

Other antiallergics

WHO-VATC

QS01GX11

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Code System

Code

Type

Description

CAS

147084-10-4

PRIMARY

ChEMBL

CHEMBL1201747

PRIMARY

EPA CompTox

DTXSID80598455

PRIMARY

FDA UNII

7Z8O94ECSX

PRIMARY

NCI_THESAURUS

C72686

PRIMARY

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Related Record

Type

Details


					7Z8O94ECSX

ALCAFTADINE

EXCRETED UNCHANGED

Comments:

Based on data following oral administration of alcaftadine (1 mg, at day 8), the carboxylic acid metabolite is primarily eliminated unchanged in the urine.

Interaction Type:

MAJOR

Qualification:

URINE

Amount:

60.1 % [54.8 to 65.4] (average)


					PUO0521HZV

CYTOCHROME P450 3A4

METABOLIC ENZYME -> NON-SUBSTRATE


					6D53G0FD0Z

PLASMA PROTEIN FRACTION (HUMAN)

BINDER->LIGAND

Interaction Type:

BINDING

Amount:

39.2 % (average)


					28XBT591QG

HISTAMINE H1 RECEPTOR

TARGET -> AGONIST

Comments:

Alcaftadine is a H1 histamine receptor antagonist and inhibitor of the release of histamine from mast cells.

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Related Record

Type

Details


					JWC6JV6KKL

11-(1-METHYL-4-PIPERIDYLIDENE)-5,6-DIHYDROIMIDAZO(1,2-C)(3)BENZAZEPINE-3-CARBALDEHYDE

METABOLITE -> PARENT

Interaction Type:

MINOR


					N3S879Z8ZC

ALCAFTADINE-N-OXIDE

METABOLITE -> PARENT

Interaction Type:

MINOR


					T50E484899

ALCAFTADINE CARBOXYLIC ACID

METABOLITE -> PARENT

Comments:

by one or more cytosolic enzymes

Interaction Type:

MAJOR

Qualification:

PLASMA

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Related Record

Type

Details


					7Z8O94ECSX

ALCAFTADINE

ACTIVE MOIETY

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Name	Property Type	Amount	Parameters
Biological Half-life	PHARMACOKINETIC	2 hours (average)

Tmax	PHARMACOKINETIC	15 minutes (average)	topical administration of 0.25% alcaftadine ophthalmic solution

SMILES

InChI

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Tox targets

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound

Drug as perpetrator