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Alcaftadine

Alcaftadine structure

CAS No:
147084-10-4
Formula:
C19H21N3O
Chemical Name:
Alcaftadine
Synonyms:
5H-Imidazo[2,1-b][3]benzazepine-3-carboxaldehyde,6,11-dihydro-11-(1-methyl-4-piperidinylidene)-;6,11-Dihydro-11-(1-methyl-4-piperidinylidene)-5H-imidazo[2,1-b][3]benzazepine-3-carboxaldehyde;R 89674;Alcaftadine;Lastacaft;11-(1-Methylpiperidin-4-ylidene)-5,6-dihydroimidazo[2,1-b][3]benzazepine-3-carbaldehyde
Categories:
Pharmaceutical Intermediates > Ophthalmic Agents

Description

ChEBI: An imidazobenzazepine that is 6,11-dihydro-5H-imidazo[2,1-b][3]benzazepine substituted at position 3 by a formyl group and at position 11 by a 1-methylpiperidin-4-ylidene group. An antihistamine used for treatment of allergi conjunctivitis.Alcaftadine, a histamine H1/H2 receptor antagonist, was approved in the United States in 2010 for the prevention of itching and redness associated with allergic conjunctivitis.

Solid

Alcaftadine is an imidazobenzazepine that is 6,11-dihydro-5H-imidazo[2,1-b][3]benzazepine substituted at position 3 by a formyl group and at position 11 by a 1-methylpiperidin-4-ylidene group. An antihistamine used for treatment of allergic conjunctivitis. It has a role as a H1-receptor antagonist and an anti-allergic agent. It is an aldehyde, a member of piperidines, an imidazobenzazepine and a tertiary amino compound.|Alcaftadine is a H1 histamine receptor antagonist indicated for the prevention of itching associated with allergic conjunctivitis. This drug was approved in July 2010.|Alcaftadine is a Histamine-1 Receptor Antagonist. The mechanism of action of alcaftadine is as a Histamine H1 Receptor Antagonist.

Alcaftadine Basic Attributes

Molecular Weight：

307.395

Exact Mass：

307.39

EC Number：

1308068-626-2

UNII：

7Z8O94ECSX

DSSTox ID：

DTXSID80598455

ATC Code：

S - Sensory organs

Characteristics

PSA：

38.1

XLogP3：

1.7

Appearance：

Solid

Density：

1.24

Boiling Point：

556.247

Flash Point：

290.2±32.9 °C

Refractive Index：

1.663

Water Solubility：

H2O: slightly solubility

Toxicity

Protein Binding：

The protein binding of alcaftadine and the active metabolite are 39.2% and 62.7% respectively.

Drug Information

Drug Indication：

For the prevention of itching associated with allergic conjunctivitis.|FDA Label

Pharmacology：

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.

MeSH：

Drugs that selectively bind to but do not activate histamine H1 receptors, thereby blocking the actions of endogenous histamine. Included here are the classical antihistaminics that antagonize or prevent the action of histamine mainly in immediate hypersensitivity. They act in the bronchi, capillaries, and some other smooth muscles, and are used to prevent or allay motion sickness, seasonal rhinitis, and allergic dermatitis and to induce somnolence. The effects of blocking central nervous system H1 receptors are not as well understood. (See all compounds classified as Histamine H1 Antagonists.)

Absorption：

Based on data following oral administration of alcaftadine, the carboxylic acid metabolite is primarily eliminated unchanged in the urine.

Metabolism/Metabolites：

The metabolism of alcaftadine is mediated by non-CYP450 cytosolic enzymes to the active carboxylic acid metabolite.

Biological Half-Life：

The elimination half-life of the carboxylic acid metabolite is approximately 2 hours following topical ocular administration.

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.

MeSH Entry Terms：

alcaftadine

Alcaftadine Use and Manufacturing

Uses

Alcaftadine is a H1 histamine receptor antagonist. Alcaftadine is used to prevent eye irritation and treat the signs and symptoms of allergic conjunctivitis.

Use Classification：

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:307.4
XLogP3:1.7
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:307.168462302
Monoisotopic Mass:307.168462302
Topological Polar Surface Area:38.1
Heavy Atom Count:23
Complexity:479
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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CAS No.: 147084-10-4

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CAS No.: 147084-10-4

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