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Details

Stereochemistry ACHIRAL
Molecular Formula C19H21N3O
Molecular Weight 307.3903
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ALCAFTADINE

SMILES

CN1CCC(=C2c3ccccc3CCn4c(cnc24)C=O)CC1

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 307.3903
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
3.1 nM [Ki]
58.0 nM [Ki]
2.9 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
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

1.28027525E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
0.05 ng/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
0.04 ng × h/mL
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1.1 h
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
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
60.8%
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

Doses

DosePopulationAdverse 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:
unhealthy, 37.8
n = 30
Health Status: unhealthy
Condition: Allergic Conjunctivitis
Age Group: 37.8
Sex: M+F
Population Size: 30
Sources:
Overview

OverviewOther

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
no
no
no
no
no
no
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
likely
no
no
no
unlikely
unlikely
yes
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.
Page: 46-48, (ClinPharm) 15, 23-26
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Histamine and H1-antihistamines: celebrating a century of progress.
2011 Dec
Vilazodone hydrochloride, linagliptin, and alcaftadine.
2011 Jul-Aug
Alcaftadine for the prevention of itching associated with allergic conjunctivitis.
2012 Jul-Aug
Patents

Sample Use Guides

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 Sat Jun 26 07:46:09 UTC 2021
Edited
by admin
on Sat Jun 26 07:46:09 UTC 2021
Record UNII
7Z8O94ECSX
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ALCAFTADINE
DASH   INN   MART.   ORANGE BOOK   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
ALCAFTADINE [VANDF]
Common Name English
ALCAFTADINE [USAN]
Common Name English
LASTACAFT
Brand Name English
R 89674
Code 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
ALCAFTADINE [WHO-DD]
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
Created by admin on Sat Jun 26 07:46:09 UTC 2021 , Edited by admin on Sat Jun 26 07:46:09 UTC 2021
NCI_THESAURUS C29578
Created by admin on Sat Jun 26 07:46:09 UTC 2021 , Edited by admin on Sat Jun 26 07:46:09 UTC 2021
NDF-RT N0000175587
Created by admin on Sat Jun 26 07:46:09 UTC 2021 , Edited by admin on Sat Jun 26 07:46:09 UTC 2021
WHO-ATC S01GX11
Created by admin on Sat Jun 26 07:46:09 UTC 2021 , Edited by admin on Sat Jun 26 07:46:09 UTC 2021
WHO-VATC QS01GX11
Created by admin on Sat Jun 26 07:46:09 UTC 2021 , Edited by admin on Sat Jun 26 07:46:09 UTC 2021
Code System Code Type Description
CAS
147084-10-4
Created by admin on Sat Jun 26 07:46:09 UTC 2021 , Edited by admin on Sat Jun 26 07:46:09 UTC 2021
PRIMARY
ChEMBL
CHEMBL1201747
Created by admin on Sat Jun 26 07:46:09 UTC 2021 , Edited by admin on Sat Jun 26 07:46:09 UTC 2021
PRIMARY
EPA CompTox
147084-10-4
Created by admin on Sat Jun 26 07:46:09 UTC 2021 , Edited by admin on Sat Jun 26 07:46:09 UTC 2021
PRIMARY
FDA UNII
7Z8O94ECSX
Created by admin on Sat Jun 26 07:46:09 UTC 2021 , Edited by admin on Sat Jun 26 07:46:09 UTC 2021
PRIMARY
NCI_THESAURUS
C72686
Created by admin on Sat Jun 26 07:46:09 UTC 2021 , Edited by admin on Sat Jun 26 07:46:09 UTC 2021
PRIMARY
INN
8707
Created by admin on Sat Jun 26 07:46:09 UTC 2021 , Edited by admin on Sat Jun 26 07:46:09 UTC 2021
PRIMARY
RXCUI
1000082
Created by admin on Sat Jun 26 07:46:09 UTC 2021 , Edited by admin on Sat Jun 26 07:46:09 UTC 2021
PRIMARY RxNorm
EVMPD
SUB37833
Created by admin on Sat Jun 26 07:46:09 UTC 2021 , Edited by admin on Sat Jun 26 07:46:09 UTC 2021
PRIMARY
WIKIPEDIA
ALCAFTADINE
Created by admin on Sat Jun 26 07:46:09 UTC 2021 , Edited by admin on Sat Jun 26 07:46:09 UTC 2021
PRIMARY
DRUG CENTRAL
4165
Created by admin on Sat Jun 26 07:46:09 UTC 2021 , Edited by admin on Sat Jun 26 07:46:09 UTC 2021
PRIMARY
IUPHAR
7587
Created by admin on Sat Jun 26 07:46:09 UTC 2021 , Edited by admin on Sat Jun 26 07:46:09 UTC 2021
PRIMARY
DRUG BANK
DB06766
Created by admin on Sat Jun 26 07:46:09 UTC 2021 , Edited by admin on Sat Jun 26 07:46:09 UTC 2021
PRIMARY
MESH
C557708
Created by admin on Sat Jun 26 07:46:09 UTC 2021 , Edited by admin on Sat Jun 26 07:46:09 UTC 2021
PRIMARY
PUBCHEM
19371515
Created by admin on Sat Jun 26 07:46:09 UTC 2021 , Edited by admin on Sat Jun 26 07:46:09 UTC 2021
PRIMARY
Related Record Type Details
EXCRETED UNCHANGED
Based on data following oral administration of alcaftadine (1 mg, at day 8), the carboxylic acid metabolite is primarily eliminated unchanged in the urine.
MAJOR
URINE
METABOLIC ENZYME -> NON-SUBSTRATE
BINDER->LIGAND
BINDING
TARGET -> AGONIST
Alcaftadine is a H1 histamine receptor antagonist and inhibitor of the release of histamine from mast cells.
Related Record Type Details
METABOLITE -> PARENT
MINOR
METABOLITE -> PARENT
by one or more cytosolic enzymes
MAJOR
PLASMA
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Tmax PHARMACOKINETIC topical administration of 0.25% alcaftadine ophthalmic solution