Human Metabolome Database: Showing metabocard for Alcaftadine (HMDB0015670)

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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

enzymes (1) Show 1 protein

Record Information

Version

4.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2017-12-31 16:51:26 UTC

HMDB ID

HMDB0015670

Secondary Accession Numbers

HMDB15670

Metabolite Identification

Common Name

Alcaftadine

Description

Alcaftadine is only found in individuals that have used or taken this drug. It 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 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.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
Alcaftadina	ChEBI
Alcaftadinum	ChEBI
Lastacaft	ChEBI

Chemical Formula

C₁₉H₂₁N₃O

Average Molecular Weight

307.3895

Monoisotopic Molecular Weight

307.168462309

IUPAC Name

2-(1-methylpiperidin-4-ylidene)-4,7-diazatricyclo[8.4.0.0³,⁷]tetradeca-1(14),3,5,10,12-pentaene-6-carbaldehyde

Traditional Name

alcaftadine

CAS Registry Number

147084-10-4

SMILES

CN1CCC(CC1)=C1C2=NC=C(C=O)N2CCC2=CC=CC=C12

InChI Identifier

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

InChI Key

MWTBKTRZPHJQLH-UHFFFAOYSA-N

Chemical Taxonomy

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

Substituents

Benzazepine
Azepine
Imidazole-4-carbonyl group
Aryl-aldehyde
N-substituted imidazole
Piperidine
Benzenoid
Imidazole
Azole
Heteroaromatic compound
Tertiary aliphatic amine
Tertiary amine
Azacycle
Organic oxide
Amine
Organooxygen compound
Organonitrogen compound
Aldehyde
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

piperidines (CHEBI:71023 )
tertiary amino compound (CHEBI:71023 )
aldehyde (CHEBI:71023 )
imidazobenzazepine (CHEBI:71023 )

Ontology

Disposition

Route of exposure:

Parenteral:

Dermal

Biological location:

Biofluid and excreta:

Subcellular:

Process

Naturally occurring process:

Biological process:

Biochemical pathway:

Alcaftadine H1-Antihistamine Action

Role

Industrial application:

Drug

Pharmaceutical industry:

Pharmaceutical

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.33 g/L	ALOGPS
logP	2.09	ALOGPS
logP	2.17	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Basic)	7.16	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	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-0290000000-89e154e3d89dbad02320	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0039000000-edbab9f942994bcdc834	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a6r-2095000000-99aa3370392cde3889c1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0909-4290000000-9455884b1ad78d19deb8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0019000000-f9c0d18e0b95b14486cc	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0096000000-07fa6dab65a51dd3e0ae	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0w5d-9030000000-4a0dbea890140ccf214e	View in MoNA

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Location

Not Available

Pathways

Name	SMPDB/Pathwhiz	KEGG
Alcaftadine H1-Antihistamine Action		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified		Not Available	Not Available	Taking drug identified by DrugBank entry DB06766	21059682	details
Urine	Expected but not Quantified		Not Available	Not Available	Taking drug identified by DrugBank entry DB06766	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB06766

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

14201635

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Alcaftadine

METLIN ID

Not Available

PubChem Compound

19371515

PDB ID

Not Available

ChEBI ID

71023

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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. [PubMed:22035879 ]
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. [PubMed:21752782 ]
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. [PubMed:22811343 ]

Enzymes

Enzyme Details

1. Histamine H1 receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
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 catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system
Gene Name:: HRH1
Uniprot ID:: P35367
Molecular weight:: 55783.6

Showing metabocard for Alcaftadine (HMDB0015670)

Structure for HMDB0015670 (Alcaftadine)

Enzymes